Archive of Our Own ^beta

Chapter Text

Christopher’s phone rang and he excused himself to take the call. Rory turned around, and then she saw him. Jess was standing there under a tree, a lone figure in a warm jacket on a sunny summer day at the wedding he wasn’t invited to, in the town where he didn’t belong. And yet there he was, standing there looking her way. Rory thought she would never see him again after that time she went to visit him in New York, so she couldn’t help the nervous knots in her stomach when she noticed him in the distance. She came over to him and asked. “What are you doing here?”

“Hello to you too,” he responded in his typical Jess manner.

“Is everything okay?” her mind was reeling with all the possible scenarios and reasons why he would be here again.

“You look nice,” he complimented her instead.

“Thank you,” she exhaled softly. She was suddenly glad she spent a certain amount of time on getting ready.

“What are you doing here?” she asked fidgeting. He was making her nervous, not giving her a single response to her actual questions.

“I moved back.”

“What?”

“I moved back,” he shrugged.

“But… why?”

“Just … wanted to,” he was looking at her with those warm brown eyes that had specks of green in them in this lighting, and something just snapped in her. The longing for him that has been a permanent resident in her thoughts since he left, the butterflies in her stomach that turned into pterodactyls at the sight of him, the rush of some weird restless energy, all of it made this moment feel crucial somehow, and she felt the powerful urge to do something, anything. And so she did. She launched forward and kissed him, her arms clutching at his sides. He stumbled at little, but responded immediately, taking her face in his palms, deepening the kiss. Rory’s head was spinning like she was in a roller coast cart that just started descending, when your heart skips a bit and you can’t hear anything except for blood pumping in your ears. He felt amazing, his lips moved against hers expertly, he sucked on her lower lip a little, and she opened her mouth yearning for more. When he slipped the tip of his tongue in her mouth to meet hers, she knew she lost it. It was officially the best kiss she’s ever head. She was so overwhelmed by all of those wonderful sensations, she didn’t register when her own arms snaked around his torso, when his arms wrapped around her pulling her closer to him. She couldn’t catch her breath, and she didn’t want to. The rest of the world disappeared into a white noise and concentrated in a single point in time and space where their mouths connected. She moaned softly into his lips. He took it as a sign of encouragement and went on to pepper kisses along her jaw moving to her earlobe and down her neck. Every kiss he planted on her neck caused a minor firework explosion in her core. She didn’t even realize her neck was so sensitive. It felt like all of the nerve endings there were wired straight to her lower belly, where every touch echoed with a hot pulsating thump. She has never felt that before. It was so new and overwhelming she didn’t know what to do, so she just stood there, desperately clutching onto his back and letting him do whatever he pleased. When she felt his tongue dart out of his mouth and latched onto her pulse point, she let out his name in a whimper.

That had a major effect on Jess. He imagined, pictured the moment when she would say his name like that a hundred times, maybe more, but the real thing was so much better than his wildest fantasies. He felt his dick twitch at that. There was nothing he wanted to do more than to press her body to his tightly, to make her feel his growing hard-on, to let her know what she did to him, but he knew it would scare her away, so he didn’t dare. The way Rory smelled, the way her skin tasted and the way she felt in his arms, under his lips, it was messing with his head, he was losing all connection to reality. He was pretty sure he’s never felt this way before. Even though he was no stranger to sex, and had his fair share of conquests, this kiss with Rory somehow felt completely different from anything he’s ever experienced. He kept kissing her neck gently, careful not to leave any marks on her delicate skin, relishing in a way she trembled in his arms, in the way her chest was rising and falling rapidly against him, in the way her breathing seemed to hitch every time he touched her with his tongue leaving damp trails from the chords in her neck to her collar bones.

Something loud happened in the distance and the sound was enough to snap Rory out of her lust-induced trance. Her eyes flew open and she froze. He lifted his head from the juncture between her neck and shoulder where he was currently nipping on to a particularly sensitive spot, and looked at her. He saw her eyes wide and dark blue filled with desire and something else, confusion and then fear. He was thankful at least there was no regret in her stare. She took a step back staggering a little in her heels on the grassy hill, still drunk on his kisses.

“Oh my God,” she gasped taking another step away.

“Rory-“ he tried to follow her.

“Oh my God…” she looked positively panicked now. “I have to go.”

“Rory-“ he called softly.

“Don’t say a word!” she warned him.

“Okay,” he nodded.

“I have to go,” she turned away and ran, and then as an after-thought, she added “Welcome home.”

Jess was so shocked it happened he couldn’t move for a second. She kissed him. Rory kissed him! She let that happen, she initiated it. Maybe moving back here wasn’t such a bad idea after all.

~XXX~

Rory’s mind was a jumbled mess. She just kissed Jess! She did. He didn’t trap her, didn’t attack her, didn’t take her by surprise. She did it, herself, because she wanted it. And boy did it feel amazing! It was exhilarating! He made her whole body tremble with desire. She has never ever experienced it before. Sure, kissing Dean felt nice, but it never felt as intense, as urgent. She didn’t want Jess to stop. In fact, if he tugged on her dress, she probably would’ve taken it off letting him explore her skin with that glorious mouth of his even more. That thought scared her. Did it… did it mean she was ready for more…for sex? With Jess?

The thought about having sex with Dean never even crossed her mind, not even once! And they were together for almost two years, for God’s sake! Then a sinking feeling settled in her stomach. Dean… She just cheated on Dean… he didn’t deserve it. Just because she didn’t have the same feelings for him anymore like she used to, didn’t mean she had a right to cheat on him. What kind of a horrible person was she? She felt like crying, but she couldn’t, not now. It was Sookie’s wedding, so she had to be there, standing next to her mom, and then face Dean… how was she supposed to do that knowing she just cheated on him? Knowing she let some other guy suck all over her neck? That thought made a tiny throb of arousal pulse in her nether regions again. Guilt overwhelmed her. This was so wrong. What was she supposed to do?

She couldn’t tell Dean though, but she should… Shouldn’t she? Finally, she figured there would be time to dissect every single emotion later. Now she had to put her game face on and get through that wedding somehow.

~XXX~

Kissing and running. That seems to be her thing. Hasn’t she learnt anything at all? She’s been in a relationship with Dean for almost two years for crying out loud! But her first kiss with Dean was so different from this kiss with Jess. She was just a naïve girl back then, running away, stealing cornstarch in the process. This time around though, she officially became a cheater. Kissing was the only thing they did with Dean, they didn’t go any further, so kissing someone else seemed like a pretty big deal. It could be categorized as cheating for sure.

Then why would she do that? Why would she act like that? So unlike herself? Probably for the same reason she went to New York to see Jess without telling anyone about it. Dean still didn’t know about that little stunt she pulled. She denied it so furiously when Lorelai suggested it, that she was falling for Jess. And maybe she would be able to continue lying to herself, pretending like this whole thing never happened, if he didn’t come back. If only he just stayed in New York… She could think about it as a fluke, a minor mishap in her perfect little world. But he came back, and she could no longer deny it. She had fallen for Jess Mariano, and she has absolutely no idea what to do about it.

Chapter Text

Everything is happening so fast, like someone is fast forwarding the VHS tape that has Rory’s life recorded on. One moment Paris calls her on Dean’s cell to tell her they won that stupid election she didn’t want any part of. Meaning she has to go to Washington D.C. for six weeks, spending a good part of her summer in another state away from her mom, her town and Dean, doing God knows what with Paris of all people! Next thing she knows, her dad promises he’s here to stay, they could finally be a real family like Rory always secretly wanted but already started losing hope. Then she sees Jess who came back without telling her why. She throws herself at him and they share the most mind-blowing kiss she’s ever had. Then her mom drops the ‘Sherry’s pregnant’ bomb on her head. Rory’s mind went into overdrive; she can’t seem to take a grasp on reality. Her entire world is spinning out of control. She needs to think, to slow down for a minute to catch her breath. So she sneaks away from the wedding, from everyone and goes to hide in the shed she and Lorelai used to live in before the Crapshack. Rory doesn’t know how much time she’s been sitting there for, minutes, maybe hours? Finally she decided to exit and go home to make a list of all the things she needs to pack for her six weeks in D.C.

The departure date comes pretty soon after. She doesn’t even have time to talk to Jess to tell him she’s going away. Lorelai had a fight with Luke about the car accident, and they still hadn’t made up, so the Gilmores don’t go to the diner anymore. She doesn’t have any excuse to go seek Jess. Dean is trying to cram as much time with her as possible until she leaves, and as she’s feeling guilty for cheating on him, she barely denies his company. Lorelai is upset about Christopher, Rory can tell, and her imminent departure doesn’t help matters. Rory feels like telling her mom about Jess would be only adding fuel to the fire, so she keeps it to herself. Paris is calling her non-stop about the program, so by the time they have to leave Rory’s already sick of her, mad she agreed to be dragged into this mess in the first place. She didn’t even have time to talk to Lane properly without the ever-present Mrs. Kim. This way not even her best friend knows about the kiss. Rory is beyond frustrated and snappy.

When the plane takes off and Paris falls asleep, it is the first time Rory can catch a breath. She can’t believe she left like that without talking to Jess. On the other hand, she has no clue as what she would say. She couldn’t date two guys at the same time, she had to choose. But then again, she kissed him, she initiated it, not the other way around. Sure, he didn’t push her away, quite the opposite, but that didn’t necessarily mean he wanted to date her. What if he thought it was just a spur of the moment thing, that she didn’t want to date him? Did she though? Did he? All those questions swirling in Rory’s head the entire flight ridding her of rest. When they finally got to their living quarters and Paris claimed the bed still talking without stopping, Rory plopped on the mattress with an irritated sigh. This is going to be a long summer.

~XXX~

After their passionate make out session Jess stood there for a moment not able to make a move, elated and puzzled at the same time. What the hell was that? What did it mean for him, for her, for them? Luke said she was still with Dean. He could see the tall shape of the bag boy from the distance when he first approached the venue. If Rory was still dating that moron, why did she kiss him? Was it an indication she wanted to be with him? He figured he would get back to the diner and talk to her later. When he called her the next day though the line was busy, he couldn’t get through. He thought since she kissed him first, she should be the one to seek him out. After all, if there was an explanation to what happened she was the one who had it.

He noticed Lorelai didn’t show up at the diner at all the next day or the day after. When he asked his uncle about it, he didn’t give him an answer but alluded to the fact they had a nasty fight after the accident, and they still weren’t on the speaking terms. Seemed like Luke took his side and Lorelai got pissed at him for it. Jess felt a pang of guilt like he really was the one screwing everything up, but at the same time he couldn’t help the strange satisfaction creeping up his entire being, knowing someone stood up for him, maybe for the first time in his life.

When Rory hadn’t come to the diner the day after the wedding or the next day or the next one, he started to worry the kiss might have caused a rift between them he couldn’t fix. A week went by, still no sign of Rory until he decided to go to her place and talk to her himself. He was approaching the Crapshack from a side street to avoid the gossip factory which was Babette, when he saw Rory standing at the back door with Dean. They were talking and then he leaned in and kissed her. It seemed pretty innocent compared to what they did, but it was enough to make Jess’s stomach churn. He stopped abruptly only to turn on his heels and walk away fuming. So that’s how that is, huh? She’s still with the beanstalk, looks like he doesn’t even know what his precious little girlfriend did behind his back! At first Jess had a nasty urge to go back there and confront her about the kiss right in front of Dean, make the giant see things as they really were. But after a moment of consideration he decided against it.

It pained him though, to know he was some dirty little secret for her. The anger and hurt made him go to the bridge and smoke an entire pack of cigarettes in one go.

After a couple of days he accidentally (God bless Babette) found out Rory left to spend the summer in Washington D.C. because she got involved in some political program in her fancy school. A part of him still hoped she would contact him somehow to shed some light on their situation. He was eager to pick up the phone every time it rang, which earned him a few sarcastic remarks from Luke. She was never the caller.

Then one day Kirk stepped into the diner wearing a mailman uniform. Jess wasn’t surprised anymore by the older guy’s antics. Apparently now he was the one responsible for correspondence around here. Grace wasn’t one of Kirk’s attributes though, so when he came in he tripped over the threshold and his messenger back fell out of his arms sending its contents flying everywhere. Luke told Jess to help Kirk pick everything up; otherwise it would take the poor man all day. Kirk being intimidated by Jess didn’t object, much. While gathering the mail Jess came across a standard white envelope with D.C. stamps on it. His heart skipped a beat in hope of finally getting his answers when he saw the name of the sender – Rory Gilmore. But all those hopes evaporated a millisecond later, when his eyes landed on the name of the receiver – Dean Forester. He went through all other contents of Kirk’s bag despite his protests, only to find a single envelope for the diner’s address – some food bill for Luke, and nothing, absolutely nothing for Jess Mariano. He guessed he’s got his answer after all.

~XXX~

Meanwhile in Washington

Rory has been tossing and turning for good two hours before she gave up trying to fall asleep and decided to give herself a break. Jess was the only thing she could think about since the wedding. Their kiss kept replaying in her mind on repeat every waking minute. And when she finally does fall asleep it gets even worse. She’s been having dreams about him ever since she left for D.C. The more time passes, the more frustrated she gets, the racier the dreams become. Last night was a particularly dirty one. They were standing there under the tree, but this time Jess was not just kissing her. He was pressing her back to the tree, his lips sucking on a sensitive spot on her neck, while his palms were gliding up her thighs and under her skirt, until they reached her underwear. Only to tug it down revealing her most intimate parts to his hot touch. When his fingers went to brush her folds, her breathing hitched. She felt like the molten lava flooded her nether regions and something exploded. She woke up with a start panting hard, a sneaking suspicion creeping in her mind that she just had an orgasm in her sleep. She was mortified… she could not just have had her first ever climax dreaming about a guy who wasn’t even her guy! Whom she couldn’t bring herself to write to, because she just couldn’t gather her wits about her.

Tonight she couldn’t fall asleep anyway, so she quietly got up from the bed and turned her desk lamp on. She opened a blue folder with a stack of paper in it, the first page said ‘Dear Jess’ and then nothing. She didn’t know how to start. It’s been ten days since she left. And she couldn’t for the life of her figure out what to write him. She’s exchanged a couple of letters with Dean already, but they were quite ordinary, just telling him about mundane details of her trip, complaining on living with Paris, the assignments she had to do, that kind of stuff. She couldn’t send such a letter to Jess, not after she kissed him and ran away. She knew she had to address that situation, she just didn’t know how.

But tonight she was beyond frustrated. She came to a conclusion that she probably won’t be able to send him anything anyway, so why even bother picking the right words, if she can just ramble like in a diary. Nobody sends their diary entries to anyone, right? So, she took a pen and started to pour all of her frustrations and thoughts on the page. Her fantasies came alive on the pages filled with her neat hand-writing. She decided she would be as forward as she can be, since it’s the only way for her to communicate her secret desires. No one knew about their kiss, not Lane, not even her mom. So she is forced to go over it in her head over and over again without an outside perspective. It’s driving her insane, slowly but surely. She writes a letter to Jess every night until she comes to a conclusion fantasizing about him this much is probably not healthy. That is why being the ever studious girl as she was, she decided to explore these novel feelings and thoughts she was having the only way she knew how. She decided to read about it.

A few days later she managed to pry herself away from Paris, who thankfully was occupied by working on an assignment with Jaime, a student from Princeton. This guy seemed to like her, though Paris was completely oblivious to the notion. This worked in Rory’s favor, as she finally had some time alone. She excused herself and headed for the vast Washington library all of the participants were encouraged to use. In the peace and quiet of this literal haven Rory browsed the shelves for a particular topic she was eager to explore. She felt uncomfortable at first. It seemed like a sacrilege of sorts to use the sacred space of the library for a purpose she went in having. But then again, library was the only friend that never let her down, so Rory hoped it wouldn’t abandon her in this time of need as well.

Finally she came across the section devoted for everything sex-related. Rory looked around nervously, checking for intruders. She was afraid someone she knew from the program, or even worse – Paris, might find her here. There was no way of explaining what she was doing in this particular part of the library, since it had nothing to do with politics. She brushed her fingers across the spines on the shelf, taking a few out to read the descriptions until she found something she thought might be the most fitting one, at least for now. It was called ‘Sexual happiness for women. A practical approach’. The description said the book may serve as a guide on the way to exploring female sexuality. Rory looked through the pages to find there were a few questionnaires in the beginning regarding different topics like sexual awareness, prior experience and the like. She blushed bright red when further exploring revealed the book had lots of illustrations on various sex positions meant for a better understanding of the act itself. A very practical approach indeed.

Rory would not be caught dead checking out a book like that, so she slipped it in a journal on modern politics she picked beforehand, and went to find an alcove in the farthest wall with a few chairs littered around the area to read in peace. She chose the one located in the nook behind a stack of shelves, so she couldn’t be seen right away and began to read.

She answered all of the questionnaires first to reveal her sexual profile. She found out that despite her vast knowledge on all sorts of subjects, sex was not her forte. She didn’t know much about physical reactions and the like. Even though Lorelai considered herself a cool mom, and the topic of where the babies come from was breached fairly early on in Rory’s life, the pleasurable aspects of sex was something Rory knew nothing about. Deep down she knew Lorelai was scared Rory would repeat her path getting pregnant at sixteen, so Rory tried to act like a perfect obedient child who had no physical desires of her own. It wasn’t hard to pull off though. When she was with Dean she didn’t feel any sexual urges at all. Sometimes she wondered if it was the reason why her mom liked him so much. If she, in fact, knew nothing of the sort would happen, that he was a safe boyfriend in that regard. Was it the reason why she hated Jess so much? Was she afraid he was some sort of a sex equivalent of a big bad wolf, who would devour her little innocent daughter and lead her to the world of heady lust, unlocking the mysteries of physical love? Dean respected Lorelai and probably wouldn’t make a move on Rory. She wondered if she made a move on him, would he reciprocate? He was a guy after all… But then again, she didn’t feel that way about him, which she now realized she probably should have. Otherwise, what’s the point of having a boyfriend if not daydreaming during class about having a sexy romp with him?

The answers she gave to the survey in the book made her realize that even though she was familiar with the medical aspect of sex, she was not at all in tune with her sexuality, her own desires and sensuality. The book promised to fix that. It took her a couple of hours to finish the entire thing, and by the last page her head was buzzing with information. The one thing she decided after she closed the book what that she needed to explore her body first, before she dived into anything physical with any guy, be it Dean or hopefully Jess. She has never masturbated before, which now seemed like a good idea to try. She could feel the tension in her lower belly all the time from daydreaming about Jess constantly, and masturbating looked like a key to relieve that tension. She skimmed through the self-discovery section of the book once again to memorize the steps and decided to give it a go tonight, when Paris falls asleep. She carefully put the book back on the shelf looking left and right making sure nobody saw her. Then she went on to browse for a couple of books on her latest assignment to check them out front and bring back as an alibi. She did not feel like discussing her new findings with anyone, especially not with Paris. She didn’t consider them enemies anymore, but they definitely weren’t friends. At least not in a sense to discuss such intimate topics. Rory once again felt a pang of loneliness. She was completely on her own in this. Paris was out of the question both because of her prying nature and lack of experience. The latter ruled out Lane too. And her mom would probably have a heart attack knowing her precious little girl was finally developing some adult desires, even though it was bound to happen. After all, Rory would turn eighteen this fall, and Lorelai already gave birth at sixteen, meaning her sexuality was awake long before it happened to Rory. But still, Rory thought she couldn’t discuss it with her mother, which kind of sucked, since they were supposed to tell each other everything. Apparently, ‘everything’ did not include a topic like this.

Rory had this prickly sensation all over her body all day after she returned from the library, anticipating and dreading what she was about to do. She had all sorts of apprehensions. What if she doesn’t feel a thing? What if she’s frigid, like some women described in the book? What if it hurts? What was she supposed to think about during that experiment? What if Paris wakes up and catches her in the act?

Later that night Rory was lying in her bed listening intently to her roommate’s breathing. Finally it evened out indicating she fell asleep. Rory stayed still for excruciating additional fifteen minutes, building up her courage. The mere idea of what she was about to do made her hot and then cold, her heart was hammering in her chest, throat dry. ‘Hey, it’s just you, nobody has to know if you fail,’ she thought to herself in a futile attempt to ease her nerves. ‘It’s gonna be okay, baby steps.’

She carefully covered her right breast with her delicate palm. She was wearing a thin t-shirt to bed with no bra on to make her quest easier. She rubbed her breast softly, experimentally. It made her realize touching her nipple felt really pleasant. Rory kept rubbing at it through the thin cotton, the nipple hardened under her fingers and she tugged on it unsure. The sudden sensation made her jerk lightly. ‘Wow, that felt good,’ she thought. She started doing the same thing to her other breast setting her left hand in motion. Then she lifted her shirt up revealing her chest to the touch, and grazing the nipples without any barrier made her gasp. She immediately looked over at Paris, afraid she might have been too loud. Her roommate stayed the way she was, undisturbed. Seeing as the coast was clear, Rory continued her exploration by sliding her palms down her stomach, which made her skin tingle. She wondered what she would feel if Jess touched her like this, if it were his hands. She admitted to herself a long time ago that she liked looking at his hands. Just something about the shape of his palms and fingers gave off the impression he was good with everything that required a hands-on approach. Rory had no doubt in her mind his fingers would be nimble and expert not only in fixing a toaster and flipping book pages, but also at touching her in various places. She blushed furiously, the very thought about that boy changed this experience to the more exquisite somehow. Rory slid her hand down between her legs and gave her center a timid rub. She remembered the drawing of a woman’s genitals in the book, and tried to picture if hers look like that as well. She never looked at herself, but thought that maybe now was the time to do that, just like the book suggested. Not tonight, of course, but later, when she learns how to touch herself first. She decided to forego her PJ bottoms completely for a better access. Sliding out of her cotton shorts she felt weird somehow. She was still covered with a blanket, but feeling her skin bare against the sheets made her feel exhilarated. Rory never slept naked at home, she always wore pajamas to bed, or sweatpants or just underwear if the weather was exceptionally hot. She found the soft material of the sheets against her bare skin strangely arousing. Spreading her legs under the covers she set to continue her path of self-discovery. At first she just put her palm flat against her core to get used to the sensation of something being there, she quite liked what she felt. Then following the commentary from the book she went to search for her clit. It was easy to find even though she’s never done that before. She knew in an instant it was the thing she was looking for, as the pleasant feeling shocked her entire body. The moment her fingers came into contact with that little nub she understood why people masturbated in the first place. She proceeded to rub the bundle of nerves, timidly at first, growing more confident by the second, as the pleasure grew. Then she remembered the kiss with Jess and something inside of her started pulsating, she kept feeding that need in her core, her constant companion for the last two weeks, by increasing the speed of her movements. The faster she went, the better it felt, and soon she couldn’t stay still, her hips jerked on its own volition as if she was searching for something, for some action she couldn’t quite get, for someone who wasn’t there. She used her other hand as the book instructed to go lower and found her entrance. By the time she did that, her slit was already wet and inviting. She choked on a small moan when her fingers landed on her lower lips and rubbed the juices all over. In the heat of the moment she slipped the tip of her index finger inside and that combined with the rhythmic circles she drew on her clit sent her over the edge. The only thing she was capable of thinking in that moment was Jess’s face and lips against hers on the warm summer day.

She slumped down exhausted, but feeling incredibly relaxed and content. For the first time in two weeks she slept well without any dreams at all.

The next night she painted the picture of this new experience in another letter to Jess she would never send. She does that every single night she’s in Washington from now on. Every night after Paris falls asleep Rory gets up and writes her letter to Jess, denoting her discoveries, her fantasies, feelings, emotions, throwing something book related in between. Then she goes back to bed, masturbates and falls asleep. It’s a nice routine that keeps her sane during her time in D.C. away from him. She goes to the library every other day slowly going through the contents of the sex books shelf. She tries different things while pleasuring herself, creating new fantasies as her book knowledge expands, describing every new experience and idea in detail. By the time the trip is over and it’s time for Rory to go home, her blue folder is filled to the brim with unsent letters to Jess documenting her entire sexual journey.

It’s nice; it’s a relief in a way. Sure, she doesn’t intend to show him any of those letters ever, but it’s good to have a reprieve, however fake one. It’s not the same as talking to someone about it, but it’s better than keeping all those emotions bottled up. In those letters/diary she can be herself, she can be bold, she can reveal everything without the fear of rejection, without being judged, with no inhibitions. It never even crossed her mind that while she’s here, he’s there, with no clue about where she is and how she feels, and someone else gets a taste of his crooked mouth and an explicit touch from his perfect nimble fingers.

~XXX~

He has seen it. The letter with the address in her neat hand-writing – from Rory Gilmore to Dean Forester. And nothing for Jess Mariano. His stomach felt like it was full of bricks, heart racing, palms sweating. She writes to Dean, but not to him. It got Jess so angry! He stormed out of the diner without another word, he knew he would flip and break something if he stayed. He needed a smoke desperately. Going through his pockets he found a pack, picked one cigarette out and lit it up taking a long drag. He felt so stupid! Of course she wouldn’t break up with Dean! No matter what he did, no matter how explosive their chemistry was, no matter how good their conversations were, she still wouldn’t break up with Dean! He even moved back to this crack-pot town in the middle of nowhere because of her. Of course he wouldn’t admit it, but he secretly liked living with Luke too. Only going back to New York after the accident, and getting a taste of life with Liz again made him realize how much he actually grew to like his uncle. Their bantering and bickering, their work dynamic in the diner, the fact that he actually made an effort in expanding his living space to accommodate him, that he asked him where he was going and when he was coming back. As annoyed as it sometimes made him feel, Jess recognized it for the signs that Luke cared about him. The way nobody else, not even Liz ever did. It felt nice. So after Rory came to visit him in New York moving back to Luke was a no brainer. And then she kissed him, and it was fucking amazing. He thought that maybe it meant something, maybe she would dump her gigantic dumbass boyfriend and they would be together, but no-o… Seems like she didn’t even consider the possibility. Playing with his feelings like that, like he was some small town hill Billy to sit around and wait! He wasn’t a fucking guard dog waiting for a master to come home. Fuck this! Fuck her! Fuck you, Rory Gilmore!

The next day was no better. His usual less than friendly demeanor changed into snappier less tolerable version of himself. Luke tried asking, but Jess wouldn’t say anything, disappearing late in the evening coming back God knows when.

One night Jess was walking around town aimlessly, lazily scouting for new places to read or just be away from the crazy townsfolk, when he stumbled upon a huge bonfire near the edge of town close to some woodsy area. It was organized by some people from his school, as he was able to recognize some of them from his classes and the fact most of them were teenagers. He stopped a few steps away to observe the scene. There was a keg of beer with guys and girls around it in various states of inebriation. There was a boom box blaring with the hottest current pop track on the radio. Some people were dancing to it, mostly girls in some skimpy outfits. Then he noticed a group of girls who were all staring at him, talking and giggling. He didn’t recognize any of them, but they all looked about his age. One of the girls was looking at him a lot more intently than the others. She had short blonde hair that was all curly and frilly. He couldn’t make out the color of her eyes from the distance, but a skin tight dress didn’t leave much to imagination. She had a hot body; he had to give her that. She noticed he was looking at her and smiled seductively. Oh, he knew that look. She definitely puts out, great. Maybe this night wouldn’t be as awful as the previous ones. He smirked at her, and she stepped away from her girlfriends and headed towards him. He took out the cigarette pack to keep his hands busy, only to find it was empty. When did he manage to smoke all of his cigarettes? This town was definitely getting on his nerves more than usual lately. The blonde came up to him and purred.

“Hey.”

“Hey yourself,” he looked her in the eyes; they were brown, a little like his. She looked nothing like Rory. Perfect.

“You’re the new guy, from New York, right?” she asked.

“I’ve been living here for a year, not sure it qualifies me as new anymore,” he shrugged.

“Well, I haven’t seen you much in class. I’m Shane Matthews,” she extended her hand, he took and shook it.

“Jess Mariano.”

“Mmm, Mariano, is that Italian?” she smirked at him. “I hear Italians are great lovers.”

Jess remembered Liz once told him Jimmy, his father, was the third generation of Italian immigrants from Cecily no less. That’s why Jess always felt some sort of connection to all those Italian mafia movies like The Godfather and Good fellas. It was his only source on the subject, since he never met Jimmy.

“Yeah, it is Italian. Why, you’d like to see if there’s any truth to that statement?” he smirked at her suggestively. Hey, she said it first. If talking about lovers is not a mating call, then Jess didn’t know what was.

“What if I do?” she licked her lips and looked at his mouth, than back to his eyes.

“Let’s get outta here,” he took her hand and led her away from the fire and people into the woods. Shane was trembling in anticipation and excitement. She has seen him in school, although not very often since he didn’t bother to show up every day. But from the very first day she saw him she was attracted to him. He had this devil-may-care attitude to him, a hot body, a swag in his step, and he didn’t take shit from anyone. Combine that with brown eyes, olive skin and a nice shiner he plastered on Chuck Presby’s face, and you get exactly Shane’s kind of guy. She wanted to make a move on him, but he was almost never at school, they didn’t have any classes together, and she didn’t want to do that in the diner in front of his uncle. This bonfire appeared to be a perfect opportunity, and Shane was a go-getter, so she wouldn’t let a chance like this slip away. Her hand was now clasped firmly in his, as he led her away from the potential audience. Soon they stopped and he pressed her back to a huge tree attacking her lips with a hungry kiss. Her mouth instantly opened responding in kind, and she felt arousal pooling in between her legs almost immediately. The kiss was passionate, hot and a little aggressive, but she liked it. For some reason she didn’t expect anything less from him.

Jess wasn’t new to sex. Back in New York he had a few girls he could casually hook up with, but since moving to Stars Hollow that was not an option. The town was small, everybody saw him as some sort of delinquent, and so it was not exactly playing in his favor with the ladies. He didn’t go to school often, so he didn’t have a chance to check the ones who would fall for a bad boy, and then there was Rory. He liked her instantly. As soon as she turned around and said her name he got lost in her blue eyes, and after she called him Dodger something clicked in him. He wanted to get her. And of course she had a boyfriend, which made a scavenger hunt for her heart all the lot more interesting. But while doing so he completely missed out on other opportunities, and judging by this Shane girl he still had some. So it’s been a while for him and getting laid never seemed as great as it did now.

Her arms wrapped around his neck pulling him closer. She responded to his kiss pressing her whole body into him. He squeezed her hips and pulled her even closer letting her feel his growing hard-on. She moaned lustfully into his mouth in anticipation. He went down her neck and bit on her shoulder, making her let out a husky exhale. Good thing she seemed to like it rough, because that what exactly what he wanted. To fuck all of his frustrations out of his system, to fuck all thoughts of Rory out of his head with a girl who looked nothing like the youngest Gilmore.

Shane’s hands were gliding up and down his body, she was moaning as he dragged the straps of her dress down along with her bra to latch his mouth onto her nipple. She had one of her nipples pierced, and the metal in his mouth strangely aroused him further. He bunched the hem of her dress up to get to her underwear. When he cupped her center with his hot palm, her panties were already soaked through. She bucked herself against his hand desperate for friction. He tugged her underwear down and probed her folds expertly. She was wet and ready for him. Jess took a wallet out of his back pocket to retrieve a condom. Good thing he always had a couple on him at all times. You never know when you get lucky. He always kept them up to date, even though he didn’t get any for the last several months. Quickly pulling the rubber on he turned Shane around, her back to him, and pulled her hips to his and entered her all the way in, burying himself deep inside in one swift motion. She moaned out loud. He was so much bigger than she anticipated, but it only made her enjoy it even more. He started thrusting hard and deep from the start, hips snapping, wet slapping sounds echoing in the woods. She felt the pleasure building up in waves. His dick felt so good stretching her, she couldn’t get enough. His hands were gripping her hips firmly as he was fucking her from behind mercilessly, forcefully, hitting all the right spots. He felt her walls tightening and knew she was close. He increased the rhythm and it made her see stars. She came around him hard with a long husky moan and he followed suit. So far he was the best lay she’s ever had.

Chapter Text

Jess and Shane kept fooling around after their initial encounter in the woods. She tried to make him do the ‘dating’ stuff, like movies and going out to eat. For the lack of better things to do he obliged, but it soon made him realize her mouth was a lot better equipped for sucking him off rather than talking. It wasn’t that she wasn’t nice to him, but they had absolutely nothing in common, and she made it even more painfully obvious when she kept making up new words that had perfectly good already existing equivalents. It was so annoying Jess started kissing her just to shut her up every time she did that. This only fueled her idea that he just couldn’t get enough of her. A few weeks went by and the differences between them grew even more apparent, but Rory still hasn’t contacted him, he was still angry, and Shane was just as good of a distraction as any. He didn’t want to spend so called ‘quality time’ with her though, so when she tried suggesting anything that didn’t include sex, he usually said he was busy working. He didn’t even have to lie about it all that much, since he found a summer job at Wal-Mart. He wanted to save money to buy a car, and Luke’s diner wages alone couldn’t cover it. He didn’t know how Shane felt about him, and frankly he didn’t care. It’s not like he wanted to marry her or anything. They never labeled the relationship they had, and it was fine by him. Not one for commitment, he didn’t see anything wrong with the situation. Thankfully, Shane didn’t prod, and hot summer weeks went by filled with passionate making out sessions in public places, and even more passionate rolling between the sheets in their beds.

This fling with Shane didn’t help Jess get over Rory though, not completely. Sure, for the briefest moments when Shane was moaning under him, or on top of him, he could dive into the heady lust, shutting the rest of the world out, but as soon as it was over and he rolled off to have a smoke, the reality came crushing down again. The color of her eyes, her hair, and the way she smelled and tasted, all screamed back at him that she wasn’t Rory. Jess couldn’t even understand why he was so hung up on someone he hadn’t even had sex with. How did this innocent looking, virginal Stars Hollow princess of all people manage to get so deeply under his skin? He was never tender with Shane, not during, not afterwards. It was always rough, fast, steamy. Never slow and gentle. He never cuddled with her, and didn’t let her make any affectionate gestures towards him after the condom went off into trash. He didn’t want her to get any ideas. She didn’t seem to mind. Maybe her lack of intelligence stopped her from putting two and two together, at least for now. And now was enough for Jess, he definitely wasn’t planning on having any kind of future with the girl the last name of whom he couldn’t even recall.

Lorelai and Luke were still in a fight, so she didn’t come in for her coffee fix of the day, hence no latest updates on Rory. That limited Jess’s sources of information to occasional diner visits from Babette, the biggest town gossip and Gilmore’s neighbor. But the only thing he knew for sure, that Rory is not going to be back for at least three more weeks or so. He started questioning his decision coming back here. Was life in New York really that bad? Was it worse than this crazy town? At least back in New York nobody knew who he was. He could go around the block undetected, nobody would gossip about the way his hair was styled or what facial expression he had at any waking moment of the day. Sure, Luke was way better than Liz. As far as he knew, she was still a drunk, still smoked pot and still brought home one jerk after another. She hasn’t called him in months. He wasn’t expecting her to, and honestly, it didn’t bother him, not anymore. He was going to turn eighteen in August, and if anything, he wouldn’t have to stay in this godforsaken place any longer. Not even Luke could tell him what to do. He saved a pretty decent amount of cash, and in a couple of more weeks he would be able to afford a car – his plan B, his means for an easy getaway. Until then, he had to stay put, interacting with Luke, having fun with Shane, working all the extra shifts he could get at Wal-Mart and trying to get over Rory Gilmore.

~XXX~

It was Rory’s last day in Washington. Jamie finally asked Paris on a date, and she being the oblivious one didn’t even realize it. Rory helped her get ready for the big event, and talking about compatibility between boys and girls made her mind wonder. All the reasons why two people can make a great couple she named, strangely made her think about Jess. When Paris finally left, making Rory hide in the closet first, she sat there with her blue folder perched on her knees, and the painful realization hit her right in the chest. She did not think of Dean as the most compatible person for her. All those nights she spent fantasizing about Jess had to mean something. Yes, she was attracted to him on a physical level, but all the reasons she mentioned to Paris were not sexual, but intellectual. It could not get any clearer to Rory. She wanted to be with Jess. She wanted to actually date him. Which meant one thing – she had to break up with Dean first. The very thought made her heart ache. She’s been with him for almost two years. He’s been a constant part of her daily life; he was her first kiss, first boyfriend. She couldn’t just throw that away. Conflicting emotions made her weepy. She cried sitting there in the closet, thankful nobody can hear or see her like this. Saying goodbye to Dean would be like letting go of a huge part of herself too. And even if Jess didn’t want to be with her, the notion she tried not to think about, it would not be fair to string Dean along. He was a great first boyfriend, and she really did love him, but sometimes people grow out of relationships and friendships, it’s inevitable, it’s a circle of life. She was just the first one to realize she grew out of her relationship with Dean. Being with him when she didn’t feel a thing would be unfair to him and painful to her.

Earlier in the evening when he called right in the middle of Paris’s freak out and she forced Rory to hang up, he said ‘I love you’ as a way of goodbye, and she couldn’t bring herself to say it back. She just couldn’t make her tongue move in her mouth to utter those words. Thank God this trip is over and tomorrow she would be home. Dean was coming back from Chicago on a later flight than her, so hopefully she would still have time to find Jess and tell him about her new revelation about feelings towards him. And then she would have to master up her courage and break up with Dean.

~XXX~

The First Annual Stars Hollow End of Summer Madness Festival, another one of Taylor’s crazy ideas, was in a full swing. Lorelai was chatting incessantly about one thing or the other while they were walking around the square. Rory opted for a dress for this outing, and managed to successfully avoid Lorelai’s questions on who she was trying to impress. She seemed to believe her daughter dressed up for Dean.

Rory was looking around searching the area hoping to catch a glimpse of a certain someone, when she finally spotted the one she was looking for. Her heart squeezed painfully in her chest, and she immediately felt a dead weight settling in her stomach. Jess was standing there under a huge tree sucking face with some blonde girl Rory didn’t recognize. Rory’s knees went weak with a mix of despair, anger, jealousy and hurt. There he was, tucking his beautiful hands into the girl’s back pockets, squeezing her ass, pulling her closer to him. He was wearing a t-shirt that revealed his magnificent arms in all their glory, those toned arms Rory dreamt about every night in D.C., those amazing arms were now firmly wrapped around some girl who most definitely wasn’t Rory. His eyes were closed, and by the way he was touching her, and how she leaned into him, it was obvious they were well acquainted with each other’s bodies. How long has he been seeing her? Was it serious? Did Jess love this blonde? What about the kiss at Sookie’s wedding? How could he do that? All those questions circling in Rory’s brain a mile a minute. She thought their kiss was special, she thought he liked her enough to move back to Stars Hollow. And now he was kissing this… this skank (!) as explicitly as he kissed Rory.

She felt hurt and betrayed and also embarrassed about all the fantasies she had about him during the summer. It hurt so much to realize he was hooking up with someone, most definitely having fun, while she was tortured by all those dreams and sexual frustration over there in D.C. this entire time. He didn’t have even the slightest idea about her turmoil. Rory felt so stupid and humiliated, her cheeks flushed and Lorelai finally noticed her daughter wasn’t listening to her rambling, facing away staring at something.

“Rory, what are you looking at?” she questioned.

“Nothing,” Rory recoiled with a pouty expression on her face. Lorelai followed the direction of Rory’s gaze and saw Jess making out with a girl against a tree.

“Oh, well, looks like he's got his ‘what I did this summer' essay all researched and ready to go. Guess you dodged a bullet there, huh?” This comment made Rory avert her eyes uncomfortably. Lorelai saw that change and concluded that Rory was upset, which she did not fail to inform her daughter about. A few more minutes of bickering and Rory went on to give Lorelai an edited version of what happened at the wedding. Even though the two simple words ‘we kissed’ didn’t even come close to covering what transpired between her and Jess. Lorelai got that angry and disappointed look on her face, as expected. Every time it came to Jess she had this sour look, like she was doing a Nickolas Cage impression or something. Rory was sick of it. She was getting pretty tired defending Jess all the time in front of the entire town, and especially her mom. Was it so hard to believe Luke’s nephew wasn’t actually a spawn of Satan sent to destroy the Earth? Lorelai, on the other hand, couldn’t fathom Rory’s distress because she had no idea about Rory’s feelings for Jess that have been developing for the last two months, and the letters she wrote, and her decision to break up with Dean nobody knew about yet. If she found out about the letters, she would have a field day for sure. Rory didn’t understand how their mother-daughter connection, this close friendship they had, which was developing for almost two decades now, immediately became unstable with a mere mention of Jess, who’s been in their lives for less than a year. Weren’t they supposed to be above that? How couldn’t she understand? So, of course, they had another argument about it. It seemed like Lorelai, who kept constantly saying how smart Rory was, completely backtracked and basically called her the most stupid person in the world as soon as Jess got involved into the situation.

And now they were standing in the middle of a town square arguing about her confused emotions about a guy who was currently swapping spit with another girl in the background, while Rory still dated another guy who had no clue he got a real competition.

“Look, kid, you have gotta make up your mind. Jess, Dean, Jess, Dean, it's enough already. If you want Jess, that's fine, go get him, there he is. If you think that's the great love of your life, then great... grab a liver treat and a squeaky toy and run to him. Don't worry about that girl because I'm sure he will have moved onto somebody else in about an hour. But do something. Dean has been sweet and supportive and incredibly patient, and now you are officially treating him like dirt, and I'm sorry, but not only is that not you, he doesn't deserve that. God, I wish they knew another song!” Lorelai finally took a breath finishing her rant. “Okay, listen, if you don't wanna be with Dean anymore, cut him loose. Let him find someone who does because this is just so… wrong!” Rory knew what she was doing was wrong, and Lorelai just voiced all of her apprehensions and basically gave her permission to break up with Dean, which Rory suddenly realized she needed. She was still dependent on her mother’s opinion, and a huge part of her pain when she thought about ending things with Dean, was the guilt about wanting to let go of someone who her mom liked so much in favor of being with someone she hated.

They would’ve continued arguing, if Dean hasn’t approached. Rory didn’t expect to see him so soon. She was thinking about breaking up with him the entire summer because she could no longer deny her affection for Jess. In her perfect little fantasy world she would wear a cute dress to impress Jess. He would look at her in awe. She would smile at him showing him how much she liked him. He would smile back in understanding. Then she would break up with Dean as gently as possible so they could still be friends. Then she would go back to find Jess. They would go to the bridge and this time he would kiss her first, and it would feel just as amazing, no, better than the last time, and they would be together. But all those fantasies came crushing down when she saw Jess making out with some blonde bimbo, Lorelai yelling at her and Dean coming earlier than he was supposed to in the worst possible moment. She didn’t have time to come off the shock of seeing Jess with someone else, to regroup, to make a pro-con list, to process everything. She couldn’t bring herself to break up with Dean now. There was no Jess to turn to, so she just hugged Dean instead. Good, reliable, sweet Dean. Perfect first boyfriend. Perfectly dull and boring. She didn’t feel anything from their embrace. It was like hugging a relative. It made her want to cry, but just like at Sookie’s wedding, she couldn’t afford to bawl this exact moment, she had to get through this somehow. She can decide what to do about it later when she gets home.

~XXX~

Rory was mostly quiet while she walked through the Festival with Dean hand in hand. She kept asking him questions about his family and his summer, nodding occasionally, and smiling when he was looking down at her, but refrained from telling him anything about herself. Since Lorelai went to the Friday Night Dinner to her grandparents, that left Rory to fend for herself. Dean suggested they go for pizza, and she agreed. When finally Dean asked her the reason why she wasn’t her usual chatty self, she told him she was just tired from her trip and all that time she had to spend with Paris. Not long after that she excused herself and went back home. He walked her to the Crapshack and gave her a sweet kiss which she returned, but again, didn’t feel anything at all. The movements of her tongue against his were mechanical, like she was just going through the motions. Thankfully, Dean didn’t seem to notice. After he left, she went inside straight to her room, and wrote an angry letter to Jess. It didn’t ease the pain, and her conflicted emotions finally resurfaced in a form of hot angry tears. They were stinging her eyes and cheeks, but she couldn’t stop wailing. All of her hopes and dreams, those tentative feelings that were building and growing for six weeks shattered in one second when she saw Jess with another girl. She didn’t want to talk to her mother today, so she took a shower and went to bed before Lorelai came home. She switched off all the lights and pretended she was asleep. But no matter how tired she was she couldn’t fall asleep until far well into the night. When she finally drifted off, she dreamed of Jess, but it wasn’t sexy or pleasant like it used to. He was just standing there with an evil smirk on his face and a half-naked leggy blonde in his arms.

~XXX~

Jess would not be caught dead in another stupid shindig this town had to offer, especially not the one called ‘The First Annual Stars Hollow End of Summer Madness Festival’. But he figured it was around the time Rory was supposed to get back from D.C. and there was a high chance she might be there, so when Shane dragged him, he didn’t object much. He tried to placate himself in his mind that he was going just because there was nothing better to do, and making out with Shane was never a bad thing, but deep down he knew the real reason. He missed Rory. No matter the fact she didn’t contact him at all this summer, he still missed her like crazy. He missed talking to her, discussing whatever topics they could come up with. She was probably the only person in this town who could hold a conversation, who didn’t let him get away with anything, who treated him as a person. Shane was only good for one thing, and it was not profound conversations. He missed the way Rory smiled when she thought she came up with a witty comeback to something he said. He missed the way her blue eyes lit up when she was excited about a new book. He missed the way she put a stray hair behind her ear when she was nervous. He just missed her.

He threw an arm over Shane’s shoulders while they were walking through various stands and vendors in the town square. Shane got a kick out of him messing with Kirk, so he sent him a few menacing glares, making the poor guy drop the souvenirs he was holding. The useless objects flew everywhere, making Kirk stumble and stutter. They got a couple of nasty stares from Taylor, but the guy was in a wheelchair, what could he possibly do? They walked around once and seeing no Rory, Jess tugged Shane to the nearest tree and covered her mouth with a kiss. She told him a few times he was a good kisser. It was not news to him; he knew he was good at physical stuff. She seemed to enjoy it a lot, not shy of some heavy PDA, she leaned into him, pressing her whole body to his as the kiss deepened. A few more minutes going like this and he knew, she would lead him away to find some secret hideout to have a steamy quickie. He liked those the most. He didn’t have to worry about Luke coming in on them above the diner, and they didn’t even have to take all of their clothes off. He could never imagine doing something like this with Rory though. She would probably want scented candles, silk sheets and rose petals every time. Although he had a feeling, there might be a secret side to Rory Gilmore nobody, not even herself, knew about. She might not be as willing as Shane in the beginning, but if a guy could find a way to push her buttons right, who knows, maybe she could be the wild one, if that kiss at Sookie’s wedding was any indication.

The band Taylor hired was playing the same song over and over again, which started to get on Jess’s nerves. He wanted to leave already, but something kept him rooted in place. After a while Shane pulled away from the kiss and asked him to go somewhere quiet. The song got to her as well. When they broke apart and he wrapped his arm around her waist to stir her away from the festival he saw her. Rory was standing in the middle of the square with the bag boy glued to her face. The sight made the bile rise up in his throat. He clenched Shane’s side roughly and nodded his head away from the masses.

“Wanna get outta here?”

“Fuck yes!” she responded with a sultry glint in her eyes.

~XXX~

A week goes by, and Rory is still not over the fact Jess has a girlfriend. She’s seeing them in the diner all the time, shamelessly making out in front of everyone. It makes her lose her appetite, which gets her noticeably cranky. Paris keeps calling her about either Franklin or their presidency positions, and for the umpteenth time Rory regrets her decision to run for vice-president in the first place. The only thing keeping her from quitting is the fact it’s going to look good on her Harvard application. She sees Dean, but not as often as he would’ve liked. She blames it on Lorelai, who missed her a lot during her absence and needs to make up for the lost time with movie marathons and shopping sprees. Dean’s upset, but seems to buy her excuse. She can’t bring herself to care at this point. Lorelai seems happy, Rory didn’t make any rush decisions and didn’t break up with Dean, which only makes her guilt run deeper. She can’t help but feel like she’s a fraud, like she’s faking her own life for the sake of everyone else’s happiness. And on top of it all, Christopher comes to the Friday Night Dinner that week, they have a nasty fight, and she lets out all of her frustrations and bad mood on him. At least, it looks justified. No one has to know, that her angry outburst is only partially her father’s fault. She’s mad at Jess, mad at Dean and more importantly, she’s mad at herself for not being able to do anything about anything important in her life. And after this horrible horrible night, the last thing she needed was a confrontation with Jess. But that is exactly what happened, when she went to buy supplies for the movie night with her mom. She saw Jess between the aisles and decided to ignore him completely, but he had the audacity to approach her and accuse her of giving him a cold shoulder. Which turned into a heated argument about him being with that skank, whose names was Shane, and about her not calling him, or sending him any mail. Her cheeks heat up at the mentions of written correspondence. If he only knew what she kept in a secret folder in her desk drawer under the pile of other notepads and school stuff. But the final straw was when he asked her if she was still with Dean. She didn’t want to answer, but knew she had to. She did not break up with him after all. And even if she did, it wouldn’t change anything, seeing how Jess was dating this Shane girl. So finally she admitted “Yes, I'm still with Dean, yes!”

“Glad to hear it,” came his angry reply.

“Glad to tell you.”

“See you around.”

“Whatever.”

“Right back at ya,” with that Jess stormed off fuming.

Tired, Rory walked out of the market and met her mom ready to go home and forget this awful day, stuffing her face with an unhealthy amount of sugary treats.

Chapter Text

Another week went by, and it was finally Saturday. Rory planned on hanging out with Dean for a bit, and then have a movie marathon with her mom, but her plans were not meant to be fulfilled that day. A very frantic Michel called, and Lorelai had to rush to the Inn because of some pipe emergency. She called Rory an hour later saying she would most likely be stuck at work for most of the day. Rory was actually upset; she really counted on that movie marathon to serve as a distraction from her jumbled thoughts. Even though she went to Luke’s for breakfast every day after her fight with Jess, and saw him there a lot, they didn’t talk at all. He didn’t even acknowledge her presence, like they were complete strangers. It hurt, but Rory didn’t want to give him the satisfaction, so she ignored him as best as she could, only allowing her true feelings on the paper when she wrote another letter to him. She kept seeing Dean, but she was not fully in it. Sometimes she wondered whether he could tell something was wrong, or was he completely dense and didn’t notice anything amiss.

This Saturday when he came over as they agreed earlier, he seemed delighted when she told him her mom wouldn’t be home for quite a while. He kept smiling at her and telling her how he missed her this week. She gave him a strained smile in response, because she couldn’t say the same. She felt awful for not missing her boyfriend one bit, but it’s not like she could say it to his face. So the only way out of it she could think of was kissing him, which he returned with fervor he hadn’t expressed before. They were in her room when he responded to her timid kiss. He was deepening the kiss and his arms came to wrap around her small frame. Rory didn’t protest when he lowered himself on her bed pulling her with him. She was sitting beside him and he was slowly but surely moving her to lie down on her back. They’ve never made out on her bed, and alarming bells chimed in her head. But she decided to ignore them for now. She remembered how Jess kissed Shane, how passionate their kiss looked, and bitter thoughts of him choosing that blonde over her returned. So she tried to forget that feeling of rejection by immersing herself in this battle of tongues with Dean. She desperately wanted to feel something, anything, so when Dean came to lie on top of her supporting his weight on one arm, she didn’t protest. But no matter how frenzied their encounter was getting, her neither regions remained cool and impassive. She was almost angry at herself for not being able to sense anything at all. This was Dean, her boyfriend, her sweet caring boyfriend. Why the hell wasn’t her vagina working at all?

They were making out on her bed for a while, and Dean was getting turned on by the feel of her body underneath his. She was so small, so pliant in his arms. He couldn’t hold back his urges and slowly lowered his hand down her side and underneath the hem of her shirt, finally touching her bare skin. She didn’t seem to mind this time. Usually she stopped him at this point. They never had a skin on skin contact. Encouraged by her reaction he continued his exploration and glided his palm up her side towards her breast. She was wearing a soft cotton bra with no padding, so when his hand came to cover her breast, he could feel a bump of her nipple underneath the fabric. He rubbed at it. His kisses grew hungrier. As his fingers pinched her nipple, Rory realized she couldn’t pretend anymore. She couldn’t pretend she wanted to be with Dean. She couldn’t pretend she wanted to get physical with him, when everything inside of her was screaming she wanted to stop. She didn’t feel anything at all, no anticipation, no tingles, no butterflies, nothing. His touch on her breast did not feel pleasant, and she wanted him to get off of her and leave. The tears welled up in her closed eyes. She just wanted to feel sexy, desirable for once in her life. And if Jess didn’t want her that way, Dean certainly did. But it didn’t make her feel good. Somehow it was gross; she felt violated and just plain horrible. She didn’t want to be a jerk to Dean, but she didn’t want him to touch her intimately in any way, shape or form. She would not be able to go all the way with Dean, when his mere touch repulsed her. She wouldn’t want to have sex with him, not now, not ever. So when he tried to go further and get under her bra she pushed him away.

“Rory? What’s wrong?” she heard concern in Dean’s voice, and it filled her with guilt. It really wasn’t his fault she didn’t feel the same anymore. “Rory?” he called again sitting up. She sat up too.

“I can’t… I can’t do this,” she heaved.

“Hey, hey, Rory, it’s okay. We don’t have to do anything tonight, it’s fine.” He tried to reassure her, but she wouldn’t listen.

“No, it’s not just tonight. I don’t want to do this, ever,” tears were not streaming down her face freely, she choked, “I’m sorry.” The confusion written on Dean’s face made her cry even harder.

“I don’t understand. What does that mean, Rory? I know you’re scared of getting pregnant, but we’re going to use protection, we’re gonna be safe, Rory. Rory?” she shook her head no. “What is it? We don’t have to do anything you don’t want to. Rory?”

“It’s not that… I …. I….” she sniffled. It was now or never. “I think we should break up.”

“What?” he frowned in disbelief. “Is this about sex? I told you, I’m not gonna hurt you. We don’t have to…” but she interrupted him.

“No, Dean! I don’t want you like that… I’m sorry, I don’t want to have sex with you… I’m sorry,” she pleaded. He jumped off the bed and looked at her hurt and angry.

“We’ve been together for two years! Two fucking years, Rory!” She flinched at his choice of words. She never heard him swear before. “And I was remarkably patient! I never tried anything your mother wouldn’t approve! And now when I finally touched your skin for the very first time, you’re breaking up with me? How fucked up is that?” He was straight up yelling at her now. Rory was scared. She’d never seen him like this, so riled up and aggressive, not even the first time they broke up or when he caught Jess and Paris having dinner at her house.

“I’m sorry,” she whispered.

“Is it because of Jess?” his eyes bore into hers, full of hatred. She scooted back unconsciously.

“What?” she asked when his words registered in her brain.

“Are you breaking up with me because of him? You like him, don’t you? Well, news flash, Rory! He has a girlfriend!” A small part of her knew there was no way Dean could’ve known about her feelings for Jess or about the letters. He was just being jealous and irrational, so she couldn’t give herself away and show him he was in fact right about everything.

“This has nothing to do with Jess!” she shouted back. “I haven’t spoken to him since the accident! How can he possibly have anything to do with this? No, this is about us, about me! I want to break up because… because I don’t love you anymore!” this stunned them both into silence. She was afraid to voice this even in her head, still not wanting to believe it was true. But here, now, those words rang between them, and they both knew there was no going back from that. She took a calming breath. “I’m sorry, Dean, I really am, but it’s unfair to be dating when we are not on the same page.” The look of hurt and betrayal crossed his features.

“What happened, Rory? We were happy… Did something happen in Washington?” his voice suddenly quiet and tired.

“No, nothing happened in Washington. I don’t know Dean. I’m sorry.”

“But I love you!” he tried again. “We’ve been together for two years! Did you lie to me when you said you loved me?”

“No! I didn’t lie. I really did love you… I just…”

“Just what, Rory?” he snapped.

“I just don’t… not anymore…” she sighed sadly. She really didn’t mean to hurt him. Dean’s anger reared its ugly head again. He wanted to hurt her just as badly as she hurt him.

“You know what, maybe it’s for the best! I can finally find someone who’s not a frigid virginal ice queen like you!” he spat. She gasped in shock, hurtful tears stinging her blue eyes. “What’s wrong, Rory? Don’t like hearing the truth? We are seventeen! All the other normal girls have their needs and desires too! But not you! Your mother brainwashed you so hard, you can’t even think straight by yourself! Not every sex ends up with pregnancy!” Rory choked up on a sob at his venomous words. This could not be happening. Her voice barely above the whisper as she managed to say, “Get out.”

“Gladly!” he yelled and stormed off. She heard the front door slammed shot behind him rocking the entire house.

All of her strength suddenly left her, she slumped on the bed drained and exhausted. Violent sobs wrecked her entire body. She’d never felt this horrible in her life. It physically hurt to breathe, her heart clenched in pain, and Rory wailed so desperately, so broken like never before in her seventeen years of existence.

~XXX~

Shutting the door gave a little bit of relief, but it still wasn’t enough. Dean ran down the steps of her porch onto the lawn. Rory didn’t follow. A small part of him wanted her to run after him saying it was a mistake, that she didn’t mean it. But deep down he knew it was not going to happen. A sense of finality has settled in his mind. He knew this was it. It was truly the end. She seemed off ever since she came back from Washington. She was distant and distracted. It looked like she was forcing herself to spend time with him, and when they said their goodbyes for the day she seemed almost relieved. That left him hurt and confused every time.

He wondered why she acted that way. Did something happen in D.C.? He has known her for two years, so he could tell when something was bothering her. He didn’t want to push her, so he waited for her to open up on her own, but two weeks passed and she never did. To an outsider everything seemed fine, but he could tell something was not right. So when he came over earlier today and they started making out, he thought maybe Rory got over whatever it was she was going through, and they can finally get back to normal, but it appeared he was wrong.

She broke up with him. This time around she did it. And it felt terrible to be on the receiving end of things. He yelled at her, which he would probably feel sorry for later, but not now. Right now he was fuming, his heart beating rapidly, muscles tensed, he felt like punching something so badly. He turned to walk away from the Crapshack towards his own house, his strides long and determined a scowl fixed on his face. Then his phone rang. For a brief second he hoped it was Rory, but when he checked the caller ID he saw it was his mom. He took a deep breath trying to calm down, hoping his mother wouldn’t pick up on his emotions. He clicked the green button trying to sound even.

“Hey mom, what’s up?”

“Hey sweetie, I’m sorry to bother you during your date with Rory, but I just remembered that Clara ran out of her vitamins and I wouldn’t be able to buy them myself today. So can you please pick them up in the pharmacy on your way back?” his mom’s voice sounded a bit apologetic. She liked Rory. If she only knew what had just transpired.

“Okay mom, I’ll get them,” he pinched the bridge of his nose. He really wanted to be alone right now, and visiting a pharmacy where Mrs. Preston, the chatty cashier, would no doubt grill him on every single detail of his life was the last thing he needed.

“Thanks sweetie. I love you! Bye.”

“Love you too mom, bye.” He replied automatically and turned the other way to run the newly assigned errand.

~XXX~

Dean reached the drug store a few minutes later. The short walk didn’t help to dissipate the anger brewing inside. He walked through the aisles towards the vitamin section when he stopped dead in his tracks noticing Jess. The diner boy was standing in front of the sex products shelf, his eyes skimming through various packs of condoms. His stance was confident. He didn’t look awkward or embarrassed at all, like some other teenagers would. When he spotted what he was looking for he traced his fingers over the packages until he found the biggest one containing the maximum amount of condoms. He picked it out easily from the stack and sauntered towards the register, not a single muscle betraying any sort of discomfort. He looked like he’s done that a hundred times before. You don’t get to act this expertly if you’re new to sex, or even worse… a virgin. Jess didn’t see Dean looking at him all throughout his purchase. Jess’s face was neutral and he didn’t react when Mrs. Preston gave him a wry look. He just paid and left his stride as confident as ever.

A strange wave of envy washed over Dean. He had seen Jess around with that blonde chick from their school, Shannon or Shane, or something. They didn’t dial down their PDA no matter who was around them. But as annoying as it was, Dean had to admit they looked like they knew what they were doing. There was no doubt about the nature of their relationship, and Dean just got a firsthand confirmation. Jess was having sex with his girl, while Dean was still a virgin, and as of now didn’t even have a girl to call his.

Dean instantly disliked Jess when he first appeared in Stars Hollow. The punk defied all of the town’s rules and norms, he was rude and infuriating. But the worst part was that Rory seemed to like him. He often spotted them talking about music and books he had never even heard of, and it made him nervous and insecure. He felt inadequate compared to Jess who clearly had a lot more in common with Rory than Dean had. And then that delinquent got her into a car accident, crashed the car Dean spent months on building, and bailed. Dean thought it was all over when Jess went back to New York, but after a while he returned, and uneasy feeling settled in Dean’s stomach again. But Rory didn’t seem to be bothered by the fact Jess was back. She was too busy packing and getting ready for the trip to Washington. A summer later Jess had a girlfriend and apparently moved on from his crush on Rory. So it seemed like Dean had nothing to worry about in that regard. Until his girlfriend broke up with him out of the blue, telling him she didn’t want him, physically that is. That part stung the most. They were together for two years and he was incredibly patient this entire time. He understood where she was coming from. She was scared she might end up like her mother – pregnant at sixteen. He respected Lorelai, so he didn’t give them both any reason to worry. But slowly it was taking its toll on him. He was a teenage guy after all, and Rory was really beautiful. The fact all of his friends were already doing it, and he was the only virgin in the group didn’t help matters. He wanted to have sex, he wanted to go all the way with Rory, he wanted to see her innocent face flush with desire, but she rejected him. Two years of waiting for nothing. That was a serious blow to his male pride. That is why seeing Jess buying condoms like a pro only fueled his anger. Why did that jerk have to be better at this? Why does he have to better at everything? Why was he getting all the sex while Dean wasn’t getting any? The girls like Shane were easy, she was definitely jumping Jess’s bones all the time and didn’t need any convincing, and Rory… Rory kicked Dean out when he just made an attempt to touch her breast for the first time.

He was standing there behind the aisles, his breathing heavy, he clenched and unclenched his fists trying to regain his composure. He didn’t want to let it all out on Mrs. Preston. After all, it wasn’t her fault Dean was having a shitty day.

~XXX~

It was almost 10 PM when Lorelai got back.

“Honey, I’m home!” she yelled from the hall kicking her shoes off. When she didn’t hear any response from her offspring, a nagging feeling of worry crept up her mind. “Rory, sweet daughter of mine, where are you?” she called again, nothing. Until she heard muffled sounds from behind Rory’s bedroom door. She hurried towards the room and swung the door open to see Rory lying on her side hugging a stuffed animal close to her chest, she was curled into a ball and her body was shaking with silent sobs.

“Rory, honey, what’s wrong?” she immediately sat on the bed beside her daughter. Rory didn’t answer, just choked on a sob and wiped at her cheeks. “Sweetie, you’re scaring Mommy, please tell me what happened? Are you hurt? Should I call a doctor?” Rory shook her head ‘no’ in reply to her mother’s concerned voice. “What is it then? Did you have a fight with Dean?” she must’ve hit a nerve, as a new wave of crying came over Rory. “I’m sure he’ll come around and you make up, c’mon honey, don’t cry.”

“No, we won’t,” Rory’s voice hoarse from crying for hours. “We broke up.”

“What? Why?? What happened?” Lorelai’s hand came to pet Rory’s back soothingly.

“He.. he.. tried to… I said no…” the youngest Gilmore hiccupped. “He got mad and yelled at me,” she hiccupped again. “Horrible, horrible things…” a new portion of violent sobs crashed her.

“Rory, honey, you’re making Mommy freak out, what did he try? Rory?” her insides clenched in suspicion, she really hoped she was wrong, but Rory looked really distressed. “Did he try to go further than you’re used to?”

Rory nodded and hid her face into the fake fur of the toy. Lorelai’s lips pressed into a thin line, she was an inch away from going into a mama-bear mode and ripping Dean a new one, when Rory started speaking again.

“We were kissing… and he tried to touch my breast… and I let him, but I didn’t feel anything…” she gulped nervously. “So I pushed him away… and he got really mad and said I was… “ She started crying again, sniffling, her vision blurred, so she missed the pained look on her mom’s face. “He said… he said I was a frigid ice queen…” she wailed. “He said you brainwashed me into thinking I’ll get pregnant…. He said I wasn’t normal because I didn’t want to have sex with him…” the tears were streaming down her face with renewed force. Somewhere in the back of her mind she idly registered how odd it was, she thought she couldn’t cry any more from spending the entire day in bed disposing all of the Kleenex she had. Lorelai’s heart clenched seeing how much her daughter was hurting, her precious little girl. She’d never seen her like this and it was breaking her heart. She didn’t know what to do. She liked Dean a lot, so it came as a shock he would say something like this, something so cruel and spiteful.

“And that is why you broke up?” Lorelai prodded gently.

“I told him I didn’t want to have sex with him and that I wanted to break up… I told him I didn’t love him anymore and he freaked…” A sneaking suspicion crawled up into Lorelai’s brain and she just couldn’t let it go, the thought came unbidden, she remembered how Rory told her she kissed Jess at Sookie’s wedding and how upset and jealous she was seeing him with another girl. Before she could stop herself, she blurted out. “Did you break up with Dean because of Jess?”

Rory’s head whipped into her direction so fast she felt dizzy.

“Why do you automatically blame Jess? Why?? Jess has nothing to do with this! Didn’t you hear a single word I just said?” she spat at her mom angrily.

“Rory, sweetie, you told Dean you didn’t love him anymore. You were together for two years!”

“Thanks for the recap, Dean did that already!”

“How come everything was fine until one day you kiss another guy, and then suddenly you break up with your long-term boyfriend?” Lorelai questioned in a high pitched voice.

“Because he tried to make me have sex with him! And I didn’t feel a single thing!” Rory yelled back. “Or what? Should I just have braced myself and just push through it, so you would be happy I’m still dating this so-called perfect boyfriend?! You know what, maybe he is right, and I am frigid! Because you grilled this idea that I get pregnant just like you did so deep inside my head, my genitals are not working anymore!”

Lorelai gasped in shock. She didn’t know how to respond. Rory was never like this. She was always a perfect child, someone who didn’t get into any trouble, someone who was grown up beyond her years, someone who was responsible and sensible. So hearing these hurtful things from her only kid felt like being stabbed in the guts.

“Honey, I get that you’re upset, and break up is a hard thing to go through, so how about we talk about this in the morning, okay? I’ll be in my bedroom if you need anything.” She slowly stood up and went to the door, a muffled ‘whatever’ was the only response she got.

~XXX~

The next morning Rory woke up with a terrible headache from crying all day before. She slowly got up and went to look in the mirror. As expected she looked like crap. Her eyes bloodshot and puffy, the usual blue of her irises was now some dull shade she didn’t recognize. Her cheeks blotchy with a pillow print on one side, her hair all tangled and messy. She let out a groan and went to the bathroom. After a long hot shower she finally felt like a human being again. Lorelai was already in the kitchen making coffee. She glanced up at her carefully reading Rory’s expression, who gave her a clipped smile in return.

Rory felt horrible about the way she yelled at her mom, they were best friends after all. She could probably help her through the situation, but then again, there was this Jess issue Rory was not sure was smart to discuss with Lorelai.

After she got dressed, she exited her room and came to sit at the kitchen table. Lorelai put a plate with a pop tart on it and a steaming mug of coffee in front of her daughter.

“How are you-“

“Look, mom-“

They started at the same time and chuckled awkwardly. “You go first,” Lorelai said.

“Mom,” Rory sighed preparing for the inevitable conversation. They had to have it at some point, and now seemed like as good time as any. “I’m sorry I yelled at you last night, I was really upset, and I wasn’t thinking clearly. Please forgive me?”

“Aw, honey, I’m sorry too. I shouldn’t have pounced at you the way I did. Can you forgive mommy too?” she pouted in an attempt to diffuse the tension.

“Mutual forgiveness then?” Rory gave her mother a timid smile in response.

“Mutual forgiveness,” Lorelai nodded with a cheerful smile on her face that still looked a little fake.

“Mom… I think I have to tell you something, but you have to promise me you won’t get mad.”

“Wow, that is not the most promising start of the conversation. It’s kinda freaking me out already,” Lorelai said.

“Mom, please. You know you’re my best friend and I really need my best friend right now. So please, I need to tell you something, and you have to promise you let me finish before commenting on it. Please?”

“Okay, I promise,” Lorelai exhaled in defeat.

“Thank you. Well… the things Dean said last night… it hurt a lot to hear that, especially from someone who supposedly loved me for two years. But at the same time, I think I can’t really blame him for what happened….” Rory fidgeted in her seat and continued. “I already told you about the kiss at Sookie’s wedding, and it did something to me, you know… “

“I knew it was Jess’s fault after all-“

“Mom!” Rory cut her off voice rising. “I asked you to let me finish!”

“Okay okay, sorry,” she huffed.

“I know you hate Jess, this is why it makes me feel twice as horrible telling you this, because I can’t shake off this guilt for liking someone you don’t approve! But we agreed you’re my best friend at this moment, not my mom, so please, don’t judge me on this, at least once!”

“I’m sorry, please continue.”

“Anyway, I know I’ve been dating Dean for a long time, and I’m going to turn eighteen soon, so naturally people at this age think about getting more … intimate with their partners… But the thing is, Dean and I, we never really talked about it, and the thought of... well... sleeping with him never even crossed my mind. When he kissed me, sure it felt nice, but… But it wasn’t something that would make me think about… about something more…” Rory took a sip of her coffee trying to placate her nerves and continued. “And then I kissed Jess, and it was… it was like I was lethargic for ages and then suddenly woke up. I’ve never felt that way with Dean. And then, when I went to Washington I kept thinking about that kiss, about Jess… and it made me realize I actually like him...” Rory looked up afraid of what she might see in her mother’s face. Lorelai was frowning and it was evident she tried really hard not to say anything. Rory was thankful for that attempt. “The entire summer I was thinking that I should break up with Dean, because you were right, you know, about cutting him loose, because it wasn’t fair to string him along. And I totally agree with you because I was thinking about the same thing. And I was going to do that as soon as I got back, because breaking up over a letter would just be awful. And when I came back I saw Jess with Shane, and it felt like I was punched in the gut, you know? And then you and I had this fight, and then Dean came earlier than I expected, and I don’t know, I was just so confused about everything. So I stayed with Dean even though I didn’t want to, but you seemed happy about it, and especially with that dad situation I didn’t want to upset you even more, and I just…”

“Honey, you didn’t have to stay with someone just because of what I said!” Lorelai felt guilty for not noticing how unhappy her daughter has been the last few weeks, and it seemed like it was for her sake, and it made her feel even worse.

“Mom, you promised not to interrupt,” Rory warned her mom who immediately closed her mouth and made a zipping motion with her fingers. “Anyhow, I realized that I like Jess, but I obviously can’t be with him because he doesn’t even want to be with me, he has a girlfriend now, and I guess I wanted to feel… wanted, needed by someone, so when Dean came over last night and started what he started, I let him because I was hoping that kiss with Jess was just a fluke, and that I can actually feel the same with Dean, but I didn’t. And he said all those horrible things, and it made me so upset. But the thing is, I’m not frigid, as he said. I just don’t feel anything for him specifically. But I couldn’t tell him that! It would only hurt him even more. And I should feel a lot more upset about it but, quite honestly, I don’t blame him. I should’ve broken up with him the first chance I got, but I waited instead, and this happened, and I don’t know… I feel terrible… what do I do?” she looked at her mother with hope in her blue eyes, needing her to understand where she’s coming from and not to judge. Lorelai sighed. The situation was not ideal, obviously, her daughter fell for the worst possible guy in town just like she suspected since her impromptu trip to New York. It surprised her to see how long it took for her daughter to actually come to terms with her feelings for Jess. She had a sneaking suspicion he would be the one to deflower her baby girl, to take her away from her mommy, and break her heart. But it was snowballing since Jess first got here, and apparently she couldn’t do anything to stop it at this point. A heart wants what it wants, and in Rory’s case it was this James Dean wannabe with horrible manners and a crooked smirk.

“Honey, there’s nothing really you can do. You broke up with Dean, which was a fair thing to do, because you shouldn’t be in a relationship with someone you don’t love any longer. Jess has a girlfriend, so you can’t do anything about that. I guess, now you just have to get over the break up, wallow, eat tons of ice cream and watch a bunch of really sad movies. It’ll take some time, but it will get better. And then you’ll know what to do.” She reached for her daughter’s hand over the table and squeezed her fingers.

“I guess you’re right… thanks mom.” She gave her a small smile.

“You’re welcome, sweets. So… I guess it’s wallowing time today. How about I go pick up some movies and some supplies, so we could have the saddest movie day-slash-night ever?” Lorelai tried to sound cheerful, that was the least she could do.

“Sounds great, thanks mom,” this time Rory’s smile was a little wider and a little less sad.

~XXX~

Some time into the 4^th movie Rory turned to Lorelai. “Hey, mom?”

“Yeah?”

“Promise me you won’t blame Jess for my break up with Dean? It’s not his fault, he doesn’t even know about my feelings. So, please, don’t give him a hard time?” she looked at her mom with a hopeful expression. Lorelai’s face was sad when she turned to look at Rory. The logical part of her brain knew it wasn’t right to date someone you don’t love anymore, so breaking up with Dean was a pretty reasonable thing for Rory to do. But her animosity to Jess couldn’t be eliminated in a short few moments after Rory’s confession, because it was building for months based on his behavior and how he treated Luke. She remembered the time she promised Rory she would give him a chance, and they had lunch the day he was cleaning their rain gutters, and they even had a somewhat nice conversation. And then everything went to hell when she caught Jess in Rory’s room, yelled at him for stealing the bracelet and he yelled back. She didn’t know if there was anything left to salvage in her ‘relationship’ with Jess. They clearly couldn’t stand each other. But here she was, sitting on the coach looking at her only daughter, her face illuminated by the TV glow, she was looking at her with those big innocent blue eyes Rory inherited from her, and she couldn’t just smash her hopes. Rory just confessed something big to her, something she kept inside the entire summer. Lorelai couldn’t help but feel like she was losing her daughter, because she stopped sharing every single thing with her, she started keeping things from her ever since Jess showed up. Lorelai realized every secret her daughter kept was somehow related to Jess. So the very fact she finally told her how she felt about the boy was apparently a big deal. And if she wanted Rory to be open and tell her things in the future, she would have to find a way to pretend she’s okay with Jess. Otherwise Rory would just close up and they would grow apart, and that was the last thing Lorelai wanted. So she took a deep breath and gave Rory a small smile.

“Okay, I’ll do my best.”

“That’s all I’m asking,” Rory smile back timidly and turned her attention back at the TV.

Chapter Text

The next day she met up with Lane, and told her about the break up, but she left out the ‘having-feelings-for-Jess’ part. It was hard enough to share it with her mom. She still hasn’t come to terms with the fact she was more upset about Jess dating Shane than her own split from Dean.

After her separation from Dean she stopped going to the diner as often as she did, because she couldn’t stand to be around Jess shamelessly making out with Shane in front of everyone, but also because she didn’t feel like eating most of the time. Luke even noticed and one day asked Lorelai about it. She told him Rory was just upset about the break up. Rory really was eating a lot less than she used to. She just didn’t feel hungry. She tried to compartmentalize her emotions in order to prepare for her last year at Chilton, but she was still very sad most of the time. Her usual banter with Lorelai was not up to par, and Rory didn’t seem too excited when Lane told her about the band she got in as a drummer. She couldn’t understand why she was feeling this way, she was the one doing the dumping, shouldn’t she be more confident about it and hurting less?

Everything was so mixed up in her head, the spiteful words Dean said kept replaying in her mind, and combined with her jealousy over Shane, it made her feel very insecure. She really was an inexperienced virgin, while Shane seemed pretty skilled. It made her question everything from her appearance to the way she dressed. Suddenly, all of the things she had in common with Jess didn’t seem to matter, because he chose sex over thought-provoking conversations. He was a guy, after all. Every morning Rory looked in the mirror and found a new reason why she could never be with Jess or anyone else for that matter, because in her own eyes she looked stupid, hideous, Bambi-like, unattractive, unsexy, and not desirable at all. Her letters to Jess were no longer racy, because she felt really dumb for writing those in the first place. She wrote about her musings on his relationship with Shane instead.

One day when Lane decided to rebel against her mother’s dictatorship in a form of dyeing her hair purple, Rory was helping her with the process. Lane was talking about the band and Dave, and admitted she was in love with him. She kept gushing on how cute and perfect Dave was and on her newfound feelings, when she let a phrase slip that made Rory freeze.

“I finally have a first love, like what you and Dean have,” she instantly knew it was a wrong thing to say because Rory’s hands stopped moving applying the dye on her hair. “Oh my God, I’m so sorry, Rory! I didn’t mean to say it, it just slipped,” Rory interrupted her.

“It’s fine, Lane, really.”

“No, it’s not! I am so sorry! It’s just… you guys dated for so long and the idea of you not being together anymore is kinda weird. I promise I won’t talk about him ever again!”

“It’s okay, Lane, you can talk about him, after all, you go to school together.”

“No, it’s not okay! I’m a terrible friend! I mean how insensitive am I to go on and on about my love for Dave when you just went through a break up, and to say stuff like you were still together, I’m a horrible person, I’m sorry!” Lane kept berating herself.

“Lane, just forget about it. It’s nothing.” She tried to shake it off, but her friend wouldn’t budge.

“No, it’s not nothing, that was very awful of me. Please, forgive me?”

“There’s nothing to forgive, it’s fine, I’m fine.”

“Are you though? I mean, you look really dejected most of the time…” Lane tried carefully.

“Gee, thanks, I thought I was doing a better job at hiding my feelings,” Rory got upset over Lane’s comment. She didn’t want the entire town to know how miserable she felt.

“Sorry! Sorry! Again! God, I just keep sticking a foot in my mouth, don’t I?” Lane let out a frustrated groan.

“It happens, now don’t move, you’ll drip.” A few minutes of silence followed. But then Lane decided to break it again.

“How are you, really?”

“Honestly? Not great… I mean, I know I was the one who broke up with him, so I probably shouldn’t feel as despondent as I do, I don’t know why I do though…” she trailed off.

“Well, like I said, you’ve been together for a long time. He was a big part of your life for two years, and suddenly he’s not there anymore, it’s like a part of you just died.” Lane suggested.

“Yeah, I guess…”

“And grieving is a natural way to process loss. So don’t beat yourself up for it, grieve, be sad, it’s fine. You’ll get over it eventually.” Lane reassured her.

“Yeah, I guess you’re right. Thanks Lane.”

~XXX~

A while later Lane freaked out about her hair being purple and the fact she couldn’t let her mother see her like that. So Rory suggested dying her hair back into her natural color. Since Lane couldn’t go outside without anyone noticing her new look, Rory volunteered to go to the beauty store to buy some black hair dye. Shane was still there working, and now without Lane distracting her with her enthusiastic ramblings Rory couldn’t help but paid attention to the girl behind the counter. While Rory was strolling down the aisles in search of the product she came in here for, she overheard Shane’s phone conversation with someone. When she heard the name of a certain someone her ears perked up.

“Who? Jess? Oh, he’s fantastic! Fucks like you wouldn’t believe,” she told her friend. “Big dick too.” She added with a sultry purr. Her friend on the other end of the line said something that was apparently funny as Shane giggled and said matter-of-factly. “Well, he is Italian.” It made Rory sick to her stomach as the realization that Jess is having sex with the blonde hit her like a ton of bricks. It was one thing to suspect they were doing it, without the actual confirmation it might still have been not true, but knowing it for a fact was a completely different thing. At the same time, the dick remark sent her mind into overdrive. Rory wondered if her comment had anything to do with Mario Puzo’s novel The Godfather about Italian mafia, where one of the characters – Sonny Corleone, was known for having a huge penis. Although she doubted Shane read anything except for celebrity gossip magazines. When she came up to the register to pay she was really rude to Shane, making a few snarky comments about her less than stellar grammar and the general level of intellect. Rory couldn’t explain what possessed her to act like that, when she was usually very nice and polite, but the very fact this girl was currently not only dating Jess, but also sleeping with him irked her too much.

After she came back to Lane’s and finished with her hair, they took a walk down the street discussing her new look. They ran into Jess and Shane walking together in the opposite direction, and Rory heard Shane saying ‘That girl is a freak’ to Jess. He looked over his shoulder and caught her eye. His expression was blank, and Rory’s heart broke into million pieces once again at the realization he is someone else’s boyfriend and he couldn’t care less about what happened between them at Sookie’s wedding.

Even though she despised Shane immensely, she couldn’t stop thinking about what she said on the phone. When she came home that night she fished out her copy of The Godfather from under the bed and kept re-reading the scene where Sonny Corleone fucks Lucy Mancini against the door until she got so hot and bothered a mere touch to her clit through her pants made her orgasm on the spot. That night the erotic dreams about Jess came back and she woke up in the middle of the night sweating and panting. She pushed her face into the pillow with a groan. Not again! While she was in Washington such dreams were a welcome distraction from her mundane routine, but now knowing Jess was having sex with someone else, it only hurt her and made her pining over him that much harder. When she woke up the next day she wrote another letter to Jess about Shane’s comment and about her feelings about it.

She kept having dreams about Jess, and it only made her more miserable in the morning. She had the urge to write about those dreams, but at one point she decided it was not healthy for her to be writing those letters anymore, since it only fueled her unrequited crush and just kept her hung up on him. So a week later she wrote her last letter, and decided to turn the page, start a new chapter of her life Jess-free, no matter how much it hurt.

~XXX~

School started on the 4^th of September marking the beginning of the Senior Year. Since Luke basically kicked Jess out of the diner so that he wouldn’t be late for his first day at school, Jess got there early. He was contemplating bailing all together, but haven’t for some reason. Even though Luke was a tad bit too overbearing for Jess’s liking, still he was the only person who cared about him. They had another ‘talk’ about school last night. Luke reminded him again that one of the conditions of him staying was graduating, which meant actually attending, to a certain extent at least. That meant Jess had to cut his shifts at Wal-Mart too. It was unfortunate in Jess’s opinion, since he was already very close to buying a car. The diner wages alone wouldn’t cover that. He needed that second job, but it would contradict with his classes too much as the school started.

The first period was English. Jess vaguely remembered his teacher from the last semester. He could make the most interesting books sound like medical records. Needless to say Jess was not looking forward to the lesson. He sighed and pulled out a battered copy of Slaughterhouse Five from his back pocket before slumping in a seat in the back of the class.

Closer to the bell the room started filling up. He barely glanced around, though he noticed Frankenstein’s monster aka Dean was in this class with him, again, joy.

A few minutes before the bell rang a woman in her mid-thirties entered the class. She had short blond hair, an angular face and gray eyes. She wasn’t tall, but she held herself with confidence indicating she was used to commanding the room. Jess thought she kind of looked like Buttercup from Princess Bride, if Buttercup had an edge to her. She was carrying a stack of folders and went to her desk to spread them in some order. When the bell rang, everyone settled and looked at the new teacher with interest. Jess saw from his seat in the back how a few guys in the front exchanged glances, the ones indicating they thought the new teacher was hot.

“Hello everyone! My name is Carol Wilson, and as you’ve probably guessed I’m going to be your new English teacher this year,” she glanced around the room seeing thirty pairs of eyes directed at her. “I know, the first day of school I’m supposed to collect your summer reading essays, but since I wasn’t here last semester, and wasn’t the one who assigned them, I thought maybe we start this year differently. Mr. Krepinski left me his notes on what material you covered last year, but I want to get to know you better. And what a better way to do that, then read a piece of your writing? You could still submit the summer reading essays if you have them with you, but I won’t hold it against you if you don’t. I would much rather read about the books you found impressive. So, you are to prepare a two thousand words essay on a book that impacted you the most till next Wednesday.” The collective groans filled the room. They were hoping for a lenient teacher, and she already assigned them a writing task less than five minutes into the class. Jess knew most of the students in his class didn’t read anything apart their required syllabus, most of them didn’t even read that to full extent, meaning such an assignment would be an absolute nightmare for them. He, on the other hand, was intrigued. Mrs. Wilson continued.

“It doesn’t have to be recent, it doesn’t have to be your favorite, it could even be something you covered in class in previous years, but it has to be something that made you think about things, maybe question stuff you already knew, maybe dare I say it, change your life in some way. It can even be something your mom read to you when you were a kid. It has to be personal, not something you copied from an online source. Also, don’t write something you think I want you to write. I won’t grade this essay, so don’t be afraid to express yourself. There’s no failing or acing this assignment. I want to get to know you.” She was met with the doubtful looks on the students’ faces. What kind of assignment is that, if it’s not graded? It’s a senior year for God’s sake, they have to prepare for college, improve their GPA and whatnot. She continued.

“Since I want to get to know you, it’s only fair that you get to know me.” She came to stand in front of her desk and leaned on it. “I am thirty six years old, and I moved to Starts Hollow from New York. My husband inherited some business here, so we moved to settle down in this town. I graduated Columbia University, and have over a decade of teaching experience. The assignment may seem weird right now, but trust me, I know what I’m doing. Now to this year’s syllabus…”

Jess zoned out after she started talking about their acquired reading. He looked through the list beforehand and it turned out he already read all of it. He wanted to return to his paperback, but for some reason, his mind kept going back to this assignment. How was he supposed to choose just one book that impacted him? There were so many out there. He could probably write a thesis-worth of the amount of words on the subject. But then again, why would he do that for something that wasn’t even going to get him a grade? He had to admit, that part intrigued him the most. She said she was from New York, but he never had a teacher like that in his old schools. There was something different about her. Call him crazy, but Jess had an inkling she was actually genuine when she said she wanted to get to know them. Some teachers might pretend like they wanted to know their students better, but it was just a ruse most of the time. Jess had yet to see if this one was just like the rest of them he encountered in all the schools he ever attended. But she had an honest face. He didn’t trust authority figures easily, if ever, but maybe he might test her, humor himself. It was something to do, and definitely less boring than listening to Mr. Krepinski droning on and on about Twain. Jess couldn’t put a finger on it, but there was this gut feeling, like he had to make an effort with that essay.

~XXX~

Jess never really struggled with learning when he actually paid attention. But the problem with school for him was that everything seemed too scripted. The teachers tried to drill some information into the students’ heads without actually teaching them how to think and analyze. That frustrated and bored Jess to no end. But at least now he had Shane, so he had someone to make out with during breaks. It made school a little more bearable. After third period he was on his way to her locker where they agreed to meet when he saw Dean standing in the end of the hallway, leaning against his own locker talking with some blonde chick in a cheerleader uniform. She was clearly flirting with him putting her hand on his arm, smiling, twirling her pony tail. Dean was smiling back at her and was apparently responding to her advances. Jess frowned. As much as he couldn’t stand Dean, he didn’t think the guy was a cheating type. He couldn’t really fathom how someone who had the luxury of dating Rory Gilmore could actually cheat on her. He kept watching the oaf and the blonde. She was leaning closer and closer, she was basically throwing herself at him, and Dean took the bait. He lifted his hand to fix a stray hair behind the girl’s ear and grazed her cheek with his thumb. The girl giggled and bit her lip. The anger welled up in Jess’s chest. Un-freaking-believable! That moron just didn’t cherish what he had.

Even though Jess worked at the diner where one can learn about every new hottest piece of gossip, the one about Rory and Dean breaking up completely escaped him for some reason. Therefore, Jess was under the impression those two were still dating. That is why seeing Dean blatantly flirting with some floozy from the cheerleading squad got him so riled up. Jess turned away and headed outside. Suddenly, the idea of smoking was more appealing than making out with Shane.

~XXX~

A week later on Wednesday Jess submitted his essay for the new teacher. On Friday Mrs. Wilson asked him to stay after class. Jess huffed in irritation and held back waiting for the rest of the class to leave the room.

“Mr. Mariano, I wanted to talk to you about your essay,” she said fishing a paper out of the pile on her desk.

“What about it?” he tried to look indifferent, but his defenses were already up. Not this, not again. It wasn’t even supposed to be graded, how the hell could she fail him, when he actually put some effort into writing the damn paper?

“Maybe it’s not very ethical of me to say, but I have to admit, that it impressed me, more than any other work.”

“Huh,” that was so not what he was expecting to hear.

“Yes. The way you analyzed Hemingway prose was unique and refreshing. It was college level work.” She looked at his guarded face keeping eye contact, trying to convey her message. “The way you expressed your opinion, the word choice, everything about your writing indicates talent. That is why I have a proposition for you.” He raised an eyebrow, suspicion written on his face.

“The AP English literature and composition class is not full for this year, so you can still sign up for it.” She looked at him imploringly. “The quality of your essay gives me the confidence in your ability to keep up with a work load and requirements of an AP class. And it would look good on your college application.”

“Pass,” he shrugged. Mrs. Wilson raised her eyebrows. She didn’t expect him to agree instantly, but she was hoping he would at least consider it. She didn’t lie when she said she was impressed by his essay. Reading his paper made her curious about this bright young man. That is why she requested his file, read the transcripts from his previous schools, and asked a few teachers here in Stars Hollow High about him. All of them said he was inattentive at best, always read in class, and didn’t pay much attention to the material actually taught, when he attended at all, that is. She found out he was a New Yorker just like her, and judging by his previous schools wasn’t from a good neighborhood. She knew it was wrong of her to assume anything about him, since she didn’t actually know him, but she couldn’t help but think he reminded her of herself at that age.

“May I ask why?”

“I’m not going to college, so it wouldn’t make any difference.”

“I saw you reading Slaughterhouse Five during class. That book is on the AP Lit syllabus.”

“So?”

“So, if you wrote a paper on how Hemingway novels impacted your life which you’ve read at the age of twelve, I’m pretty sure you’ve read everything on a regular English syllabus. If you take AP class you would read what you would’ve read anyway, and you’d be graded for it. C’mon, at least you wouldn’t be bored to death.” She gave him a small knowing smile. “Just think about and get back to me before October 4th.”

He just shrugged noncommittally. “Can I go now?”

“Sure. Oh, and consider taking creative writing as one of your electives. I’m going to be teaching it. You have real talent. And I’m asking you this so that I wouldn’t be bored to death.” A small smirk playing on her lips.

He gave her one last look and walked out the door.

Could she be for real? No one ever told him he had talent before. Maybe it could have something to do with the fact Liz moved them around a lot, from one shithole apartment to another when she couldn’t pay rent. From one dickhead boyfriend to the next, when the previous one kicked them out. Jess didn’t really have many chances to prove himself constantly switching schools, always being the new kid adjusting to the curriculum. When he got older, their whole living situation did not make him a happy-go-lucky kind of guy. He had so much anger and resentment towards Liz he began acting out. When he was thirteen he was kicked out of school for the first time because of something he did, not because Liz uprooted him yet again. He started pulling pranks, get into fights. Less than stellar neighborhoods they lived in also meant he was attending public schools with metal detectors on every exit, where teachers were underpaid and depressed. The majority of them didn’t even try to see their students for what they really were. Hence, Jess was written off as a hoodlum, as someone who stirs the pot, as trouble. Jess did not disappoint living up to that reputation. He spent more time in detention than in class, never did his homework, and barely passed the tests not to be kicked out permanently. The fact of the matter was, he was smart enough to know how many questions he had to answer correctly to pass. When he was fifteen Liz married Ronny, husband number four, and they moved to a new neighborhood. During one of her clean streaks she enrolled him in a new school. Jess got cornered by the local gang of cool guys on the first day, but he was perfectly capable to hold himself in a tussle, so they accepted him. And for the first time his life became more or less stable. He had a group of people he could call friends. He attended school at the reasonable amount not to get expelled. He wasn’t putting any effort in his studies, but he was doing alright. That was before husband number four got comfortable enough to show his violent nature. He was beating Liz up on a regular basis, Jess tried to intervene but she always screamed at him to mind his own business. That was until one day Ronny got too drunk and decided to add another step to his beating routine – Jess. That was the last straw, Jess punched back. And Liz took her husband’s side in this, telling him he was an awful son who didn’t care about her happiness, the one she should’ve never had. Next thing Jess knew, he was on the bus to Stars Hollow, to live with his estranged uncle indefinitely.

The whole situation made him so angry and resentful. His whole life he never had stability because of Liz, and when he finally found some ground, she had to ruin it yet again.

The things she said when she kicked him out… She never once told him he was talented. She didn’t care enough to get to know anything about her son. Jess was convinced she didn’t even know how old he was, because she only remembered his birthday four times in his entire life.

That is why hearing this teacher, this woman who didn’t know him at all, telling him he’s got talent was weird, unsettling. Jess couldn’t quite describe how that made him feel. No other teacher ever told him that. He didn’t know how to deal with all of this. And taking creative writing? Was she serious? AP class… yeah, right…

He stopped at the bridge to smoke and clear out his head.

~XXX~

Rory was walking from the bus stop to her house. She just got back from school and was looking for her phone she shoved into her backpack earlier in the day. She forgot to turn it on after her classes ended, but now she needed to call her mom. Finding an object as small as a cell in her seemingly bottomless backpack was no mean feat. She had tons of stuff in it, it was filled almost to the brim with books and notepads and everything else. She was so engrossed in the process she wasn’t really looking at the path in front of her. So it wasn’t very shocking when she walked right into someone, her backpack falling out of her clutch on an impact, its contents flying everywhere. With a muttered ‘sorry’ she kneeled down without even looking up at the person she collided with to retrieve her belongings. The other party was none other than Jess. He was walking down the street reading as he went as usual without paying much attention to his surroundings, when he bumped into Rory. He saw it was her and froze for a second. They haven’t talked in days, so this little run-in was the closest thing to an interaction they had in a while. He sat down on his hunches to help her collect her stuff. The nearest thing to him was a blue folder that opened when it fell. Normally he wouldn’t have given it a second thought, but he saw his name in it, it said ‘Dear Jess’ and had a date written next to it marking the time she was still in D.C. Jess glanced at Rory who turned away to catch some pens and pencils that rolled all over the pavement, so she didn’t notice him looking at the folder. He quickly took the folder and put it in his back pocket before she had a chance to catch him in the act. When she finally turned around and realized who she just bumped into, she blushed and shoved all of her things into her backpack hastily. He didn’t dare to say anything and just gave her the other notepads he picked up. She nodded awkwardly in thanks, and walked away from him as fast as she could without actually running.

Jess’s blood was pumping in his veins, heartbeat accelerated. He had a feeling he just stumbled upon a big secret, and he couldn’t wait to find out what it was all about. He walked straight to the diner, book long forgotten. It wasn’t his shift today, so when he arrived to Luke’s he headed straight upstairs. Thankfully his uncle was busy with the customers so he didn’t follow him into the apartment, and judging by the amount of patrons in the diner, he probably wouldn’t come up in a while. Meaning Jess had an hour or two for himself. With sweating hands he reached into his back pocket and retrieved the folder. It was plain blue with no décor and no writing on the cover. He came to lie down on his bed and opened the folder. There it was, ‘Dear Jess’ on the very first page, just like the one in the middle that he saw back outside when it fell. He skimmed through the pages and the sight made his heart get caught in his throat. Letters. To him. The entire pad was filled with Rory’s letters to him. The dates marking summer months she spent in Washington. So she was writing to him this entire time, but didn’t send a single letter. The question was why? With trepidation he began to read.

Chapter Text

Dear Jess,

I know it’s been a while and I probably should’ve sent you something way earlier, so now seems kind of pointless to try. So I won’t. This is something I’ll never send, and it’s better this way. I guess what I wanted to say was, I can’t take it anymore! I constantly think about you, about that kiss. I keep replaying it in my head over and over again. It’s like you’ve been living in my head rent-free and there’s no one I can complain about it. That kiss… it did something to me… I don’t know what it is, but I’ve never felt this way before, not when I kiss Dean and not when I kissed Tristin. There’s just something about you that makes my heart race, and my whole body tingles, and I realize I could’ve put those sensations into more eloquent words, as I’m sure you know, I’ve always been quite articulate, but I can’t. When I think about that day my mind turns into a hormone-flavored jelly and I can’t come up with anything smart to say.

It’s getting worse though. I started having dreams about you, and they’re awfully realistic too. It’s like I can actually feel your lips and hands on me all over again. Last night though I hit rock bottom. I had a dream about you touching me there, while pressing me against a tree, and I woke up from an orgasm. I think guys call it a ‘wet dream’. I’m not sure if it’s the same name for when a girl has it, but I guess I could say that I had a wet dream about you, Jess. My first ever wet dream, might I add… and the first ever orgasm, for that matter… Gosh, this is so stupid… Why does it have to be you? I’m still with Dean, but he hasn’t crossed my mind all that much. I feel guilty. I shouldn’t feel this way about you, but I do. What am I going to do? I feel so lost… I can’t even talk to anyone about it since nobody knows about the kiss. It’s 3 in the morning, I have to get up early, but I can’t fall asleep because you keep haunting my dreams. I wish I could kiss you right now.

Rory

Dear Jess,

I went to a library yesterday pretending I’m going to do some research on the assignment I was given, but what I was actually doing research on was sex. I’m blushing even writing this word down. Anyway, I wanted to know if my thoughts about you are normal. I was convinced I was obsessed and not in a good way. I don’t believe fantasizing about a guy this much is healthy. I found a few books on the subject. One of them had pretty realistic and detailed drawings of different sex positions. Looking at them I couldn’t help but imagine us together like that, and it turned me on so much I felt so hot and out of breath, the old lady next to me noticed and gave me a questioning look. I guess I was panting out loud or something. Good thing I disguised the book by putting it inside a journal on politics, otherwise the lady would’ve had a heart attack. Note to self, public library is probably not the best place to review books on sex.

Anyway, there was this chapter on masturbation… God, I can’t believe I’m actually writing to you about this. Good thing you’ll never see this letter. Anyhow, that chapter gave a pretty detailed description on the act. It also postulated that it’s completely healthy from a medical stand point. It said that pleasuring yourself helps with easing the tension, helps one relax and also learn stuff about your body. So I decided to try it. I mean, it’s not like I wasn’t familiar with the concept, but I never had the urge to do it. I’ve always thought it was something boys do and very rarely girls. But there was a description on how to do it for women. So, anyway, I tried it last night. I couldn’t fall asleep, again. Paris was already out and I gave it a go. It felt a little weird at first. I mean touching myself in places I only touch when I shower. I felt quite stupid doing it, but then I started to think about our kiss again, and it didn’t feel as weird anymore.

I have to confess; when I touched my breasts I imagined your hands instead of mine. I like your hands a lot. I can’t count the times when I caught myself staring at your hands when you worked in the diner. There’s just something about the shape of your palms, and your long fingers. And that wrist watch of yours is so sexy. I love it when you roll up your sleeves to reveal your forearms. I like how toned they look, the color of your skin, the shape of your biceps… I remember only one time I saw you in a t-shirt, it was that ugly one with a Metallica logo. Even though the shirt itself was hideous, it had one perk to it – showing off your biceps. It’s a shame you always wear so many layers of clothing. Although living in Connecticut I guess I can’t blame you. Anyway, I’m rambling again. So, I was thinking about your hands on my breasts. For some reason, I feel like you would know exactly what to do with them, and your fingers would circle around my nipples perfectly.

Anyhow, I kept picturing you the entire time when I was touching myself, down there too. As soon as I found my clitoris, I knew why people do that so often, it felt incredible! If it feels the same way for boys when they have sex, no wonder they like it so much. I was thinking about our kiss and my fantasies and dreams I had about you, my vulvar lips were so wet, all because of you. I even pushed a finger inside, just a tip, but it was enough for me to climax. It is official now, you’ve claimed my first ever masturbation orgasm. I don’t know how I feel about this, to be honest. I can’t help but want you to touch me there, like you did in my dreams and in my fantasies. I’d give anything for you to think about me the same way.

Love,

Rory.

Dear Jess,

Just so you know, I kept -rereading that book and a few others I found on that shelf. I think I memorized the positions and how they’re supposed to feel to boot. Also there was this chapter on oral sex… with pictures… the commentary said that women might have reservations about doing it, but I was strangely aroused by the concept… probably because I was thinking about you… I’ve seen the penises in all those pictures and it made me wonder how yours looks like… I bet it’s beautiful, just like everything about you. Okay, here, I said it. I think you are supremely attractive. Everything from your crooked smile and fingers to the way you walk is just so hot. I wish I had your picture… Wow, that’s just creepy. Scratch that. Besides, I have plenty of visual images to haunt my memory anyway.

I’ve never wanted to see any guy naked before, but you, shirtless, is the only thing I can think about these days. It’s so strange to me. I’ve never had such thoughts about Dean. I still don’t. What is wrong with me? I am supposed to want my boyfriend of almost 2 years, but I don’t. I feel bad for not wanting him, as if I’m obligated to do that. It’s like you turned my entire world upside down when you moved to Stars Hollow. I wish I could tell you all of this in person, but I would be too embarrassed. I’m thinking about breaking up with Dean, because I’m obviously not as invested in our relationship as I’m supposed to be. It’s just unfair to string him along. It’s not his fault I don’t feel for him anything even remotely close to what I feel to you. But I don’t want to do it over a letter. I don’t want to be a jerk to him. He’s been pretty great to me. Sorry, you don’t want to hear about how great Dean was.

Anyway, I touch myself every night thinking of you. I guess I’m getting pretty good at this masturbating thing, as it ends in orgasm every single time. I wish you could be the one touching me like that.

Kisses,

Rory

Dear Jess,

Last night I had a dream about you going down on me. It keeps me wondering if you ever done that before. I mean, in New York, you probably had tons of girlfriends, I mean with how good you look and considering what an amazing kisser you are… I think you most definitely had sex before, whereas I’m still a virgin. Would you ever be able to want me if I don’t have any experience at all? If we ever found ourselves in a situation like that with no clothes on, as much as I’d like to see you naked, I wouldn’t know what to do… I’d probably be so disappointing. Argh, I’m such a mess.

The thing is, my fantasies about you, they kind of progressed… I often think about you on top of me with your penis inside or me on top of you riding you, with your mouth kissing my breasts. In that book there was also this position called ‘doggy style’ when a woman is standing on all fours and a man is entering her from behind. It’s kind of primal and natural because of the location of genitalia against each other. The commentary said some women don’t like that position because it makes them feel submissive and way too animal-like, as if they don’t have a say in the matter. I wonder if I liked that. What if I did? Would that make me less of a feminist?

Thinking about you giving me oral also made me insecure. What if we ever did that and you didn’t like my taste or smell or how I looked down there? Today I closed up in the bathroom and examined my lower lips in a compact mirror like the book suggested. I don’t have anything to compare it to except for that image in the book, but everything seems normal, in place… Have you ever watched porn? There are probably tons of genitalia of all shapes and sizes. Not sure I can look it up here though; they probably monitor traffic and web activity here. Don’t want to get busted by CIA or something for watching porn. Anyway, that’s all for today.

Yours,

Rory

Dear Jess,

I’ve been having this dream about your head between my legs for a few nights in a row. It’s also a recurring fantasy of mine when I touch myself. So tonight after I took a shower, I mastered up my courage and… tasted myself. I dipped my finger inside and then licked it. The taste is okay I guess, not off-putting. At least I hope so. I wonder what you taste like…

Kisses,

Rory

Dear Jess,

Remember that chapter on oral sex in that book I told you about? Well, I think it finally caught up to me, because I’ve been having very racy dreams about it lately. It made me feel like I just want to come up to you, pull your pants down and suck your dick until you can’t cum anymore. It’s wild, crazy, but I like it. In my dreams there’s nothing standing in our way, no inhibitions, just you and me, naked loving each other.

I found a chapter in one of the books denoted to different kinks and stuff. So, there was this paragraph on dirty talk, and it got me thinking. You read so much, you’re good with words, would you be just as good at dirty talk? Do you make any noises during sex or are you the silent type? There’s this whole image of you in my mind of what you might be like in bed. I wonder if the real you is any close to that image I created. Tell me, Jess, what kind of lover are you? Do you have a favorite position? What is it? What do you like about it? Do you like it rough or sweet and slow? Would you mind being my first? Have you ever been with a virgin before? How old were you when you lost your virginity? How was it? There are so many things I don’t know about you! But I want to know them; I want to get to know you better, Jess Mariano.

I wonder if you let me.

Yours,

Rory

Dear Jess,

Today I was helping Paris to prepare for her first date. A guy from the program asked her out. She kept asking me questions about relationships, and how do you know if a person is right for you. While I kept answering I realized I had you in mind the entire time. That was some wake up call. I think I want to be with you, Jess. And not just physically. Although I’m sure that part would be amazing. But in general too. I want to be your girlfriend. I want to be able to go out with you, hold your hand, kiss you whenever I feel like it. I want to read together quietly and then discuss books with you, I want to go see movies and our favorite bands live. I want road trips and laughing and picnics and everything in between. I want to be with you. But what if it’s too late, and you don’t want to be with me? Did you even want to be with me? Why did you move back to Stars Hollow, Jess? Do you like me? Because I like you, I really do. I think I started to like you since the day you gave me my copy of ‘Howl’ with those notes in the margins. But I didn’t want to admit it, couldn’t because of Dean. But that kiss… it finally opened my eyes, and I can confess that I like you. I really really do, so much! God, this trip can’t be over soon enough, good thing it’s the last day. Tomorrow I’m coming home. Hopefully I will see you.

Love,

Rory

Jess went through those letters one by one. There were more. He checked the dates, she wrote to him every single day she was in D.C. starting from two weeks after her arrival. Not all of her letters contained such explicit details, sometimes she just wrote about her day, the books she read and wanted his opinion on or thought he might be interested in reading. Somehow that made his heart clench in longing even more. That was so Rory, even in the midst of lusty confessions she still wanted to talk to him, her brain called to the intellectual part of him, not only the physical one that was currently strained by his pants. Tens of different emotions swirled in Jess’s mind. He was shocked to the core to find out about this side of Rory, the side he wasn’t quite sure existed. He had a feeling there was more to her than meets the eye. With the entire intellectual prowess she possessed, she couldn’t just be that quiet and naïve blue-eyed Bambi he met on his first day in Stars Hollow. The saying also went that the quiet ones snap the loudest. Judging by the letters Rory wrote her own snap would be as loud as the nuclear explosion. Jess suspected as much, but now he knew that for a fact. He only wondered if he would be lucky enough to be the one to detonate this secret passionate side of Rory, to make her combust.

As he finished with the D.C. portion of the letters, he noticed the few last ones were dated when she was already back to Stars Hollow. They were distinctly shorter, and he thought he knew why.

Dear Jess,

I can’t believe I was so stupid! Writing all those letters to you, feeling the way I did while you’ve been playing a tonsil hockey with that blonde skank the entire time! How could you do this? I thought our kiss meant something for you. I guess I was wrong. You know what, fine, have a nice life with your blondie! I hope you two are happy together!

Not yours,

Rory

Dear Jess,

I guess I can’t blame you. I know you and what’s-her-face are having sex. I overheard her talking about it on the phone with some friend. She said you had a big dick. I hate that it makes me feel so hurt. I hate that it makes me feel jealous, but most of all, I hate that this piece of information about your penis still managed to arouse me.

I hate that I still want you.

I hate that you’re with her.

I hate that I can’t do anything about it.

Dear Jess,

It pains me to see you with her, but I can kind of guess what you see in her. As much as it pains me to admit, she’s beautiful, her body is gorgeous, and she’s obviously experienced. I don’t have any of that, there’s literally nothing I can offer you in that regard. I’ve always been too gangly and ungraceful. Her boobs are bigger than mine and she’s blonde. I guess you’re into blondes, huh? Would you like me better if I dressed differently? If I wore tighter jeans, lower cuts, crop tops? It just sucks that you’re with her.

Rory

Dear Jess,

It’s over… with Dean… he came over today and he was talking about how much he missed me, how beautiful I was. I let him go further than we usually do. I guess I wanted to feel desirable like Shane. At least by someone. So Dean tried to go all the way, but when he kissed me, I didn’t feel anything at all. I didn’t feel a single thing that I did when you kissed me or when I was fantasizing about you in D.C. It made me so sad. I started crying and told him I don’t want him, and that it’s better if we break up. He got really furious and left. So that’s it. I am officially single, but the only guy I want doesn’t want me back.

Rory

The realization dawned on Jess, suddenly Dean flirting with that cheerleader made sense. Rory broke up with him, and apparently the beanstalk didn’t mind finding himself a little rebound.

Dear Jess,

I guess I should stop writing these letters. You hate me, we don’t even talk, so what’s the point? It only makes me feel worse. Because I know that there’s no possibility for us to be together. I should probably just start a diary or something, rather than continue with this.

I loved our time together though. So goodbye Imaginary Jess, you’ve been a real help on my journey through my sexual awakening and self-discovery.

I need to move on somehow.

Goodbye,

Rory

His heart clenched, he felt knots of anxiety in his stomach. No! No way, this can’t be a goodbye. He didn’t want it to be a goodbye! He had to do something, but he wasn’t sure what. Even though he’s been dreaming about pretty much the same things she wrote about almost the entire summer, he still couldn’t let go of the anger he felt about the fact she didn’t send him any note indicating she was interested. If she had, things would’ve been so different. He wouldn’t have slept with Shane. Of course, it would’ve been a pretty dry summer that way, filled with lots and lots of jerking off fantasizing about Rory’s lips, but at least he would have something to look forward to. He would even wait for her to come back, so she could break up with Dean properly. She stated it herself, that she wanted to end things between the bagboy and herself long before Shane came into the picture. The thought about Dean trying to force himself on Rory made Jess see red. Thankfully, nothing happened and he could relax. For some reason he felt strangely elated by the fact Rory was a virgin and he was the first one ever to evoke these emotions in her. He felt special somehow, to be the one responsible for her sexual awakening. Therefore, the mere thought about Dean getting his hands on her first irked him. To answer one of her questions, he not only wouldn’t mind being her first, he would love that, and he would be honored to be the first guy to show her all the possibilities of sexual pleasures. He was sure he was able to provide that for her. If their kiss was any indication, they had chemistry in spades, so his instincts would tell him what to do. The only question remained was, what was he supposed to do now that he had this secret knowledge on the inner workings of Rory Gilmore’s dirty side of mind?

~XXX~

The next few days he kept watching her closely when she came to the diner with Lorelai. He noticed she didn’t order her usual breakfast Luke called ‘heart attack on a plate’. She was just drinking coffee. She didn’t even eat a Danish, and on a Danish day no less. Lorelai was talking to her cheerfully in her usual speed, but Rory wasn’t engaging in the conversation as much as she usually did. He could tell the smile she was giving her mother wasn’t a genuine one; it was strained and didn’t reach her eyes. Something was definitely wrong, and after reading the letters he thought he had a pretty good idea of what it was. Jess was torn. His heart longed for her, he wanted to comfort her, to make her feel better, but he didn’t know how. Sure, she was single now, but the unhappy look on her face could indicate she was still not over Dean. He didn’t want to be a rebound. Plus he was with Shane. Even though it wasn’t serious, he didn’t want to cheat on her. If there was one rule Jess had on relationships it was a ‘no cheating’ policy.

 Shane kept coming to the diner and pulling him into heated kisses, but his heart just wasn’t in it anymore. More often than not he made excuses about having to work, so not to hang out with her. One time he went to her place and they were getting hot and heavy on her bed, but he couldn’t help thinking about the letters Rory wrote, and what she wanted him to do to her, and he just couldn’t bear to do the same things to Shane. He abruptly stopped kissing her and came up with another excuse of suddenly remembering he had an extra shift at Wal-Mart to come in for some guy who was sick. Shane looked at him with suspicion, but didn’t question him. He put his shirt back on and left. He headed to the bridge as usual to clear his head. Just like Rory wrote about their kiss doing something to her, these letters were doing something to Jess. He kept rereading the letters while Luke wasn’t in the apartment, he went through them so many times he memorized them all. He was still trying to wrap his mind about this passionate side of Rory. Under her unassuming innocent-looking exterior there was a fire burning bright. A fire he was now drawn to like a moth. After smoking almost half a pack of cigarettes on the bridge he still didn’t come close to any decision at all.

Chapter Text

The next day Jess was walking down the street reading without looking up, again, when he bumped into Rory, again. She was soaked from head to toe and Jess just couldn’t leave it alone. After a minute of questioning she finally gave in and explained what happened.

“This guy moved in across the way from us and we said we'd water his lawn and the grass can only be watered in ten minute increments, otherwise the lawn drowns, and the thing is stuck and it won't turn off and I have to find someone, Luke or Taylor or…” without letting her finish Jess started walking away in the direction she previously came from. “Where are you going? Jess!” she called after him but he didn’t even look back, so she had no choice but to follow him into her neighbor’s front yard.

“You don't have to do this. I didn't ask you to do this. I can just find someone else to do it,” despite all of her protests Jess turned the sprinkler off with a single move of his arm. “Aw, you made it look so easy.”

“Yeah, it was loose. You just had to press down and give it a good twist, that's all.” He gave her a small smile.

“Well, thank you,” Rory said shyly. He looked so cute with his hair all wet and sticking to his forehead instead of his usual gelled up-do. All of her feelings for him that she was trying to repress came crushing back again. She hasn’t talked to him in forever, and it felt so good to hear his voice again. She dared to look up at him and he was looking at her with what she thought was a somewhat hopeful expression, like he was waiting for something. Or was it just her?

“You're welcome. So things are good?” he asked looking at her, and she couldn’t help but look back getting lost in his hazel eyes immediately.

“Oh, yeah, good.” She nodded with a small smile breaking down on her face.

“School?” he kept asking.

“Good,” she answered, berating herself for not being able to come up with any other word.

“Still gonna do the Harvard thing?”

“Yeah.” She couldn’t look away. It felt like his eyes just drew her in closer. Suddenly she wasn’t annoyed with her neighbor anymore, and she didn’t even mind being all wet, as long as it kept her talking to Jess.

“Good.” He nodded.

“Yeah, good.” She agreed. They were looking into each other’s eyes, and Jess got lost in her blue orbs thinking she never looked as kissable as she did in this moment. It was like her eyes pulled him closer like a magnet. He remembered the first letter she wrote where she described what their kiss made her feel, and he wanted to repeat that, to make her feel that way again. He almost leaned in and kissed her, when she said, “So…?” the spell was broken and he took a small step back. In order to kiss her freely he had to take care of a few things first.

“I have to get back to the diner and change, Shane’s waiting.” He saw a flash of disappointment in her face, but she quickly plastered a fake smile to cover it.

“Right, Shane. Wouldn’t want to keep the girl waiting,” Rory shuffled her feet awkwardly.

“That we wouldn’t,” Jess agreed.

“Thanks for your help.”

“You’re welcome.” He nodded in goodbye and turned to walk away. She kept watching him until he disappeared from the view. She suddenly felt wet and cold again, and hurried to her house to change.

~XXX~

Later that day there was a knock on the front door. Rory came to see who it was, only to find no one standing on the porch. She glanced down and saw a package on the floor. Something rectangular was wrapped in a brown paper bag with her name written on it. It was just simple ‘Rory’ with nothing else. She picked up the package and came inside. The handwriting seemed familiar somehow, and by the time she closed the door to her room, the realization dawned on her. No. It couldn’t be! She tore the paper to see her blue folder inside. Her stomach sank, a sudden wave of nausea overcame her. Oh no. It was THE folder, with all the letters, and the only person that handwriting could belong to was the one who was not meant to read those letters ever, even though every single one of them were addressed to him.

When she realized she couldn’t find the folder anywhere, she tried to calm herself down; talking herself into thinking she just might have misplaced it somehow, maybe left it in her locker at Chilton or something. But the looks Jess had been giving her in the diner the last few days had her worried. Now she knew she was right. She had all the reasons to be worried, because apparently Jess somehow got the letters into his possession, meaning he’s read them, meaning he now knows everything. Her knees went weak, hands shaking, so she lowered herself on the bed. The sheer power of that realization hit her like a freight train. He read it ALL. Oh God… How was she supposed to look him in the eyes after this? At least, he was decent enough to return it anonymously. Otherwise she would be the laughing stock of the entire town! How embarrassing! She couldn’t imagine the scenario where all of the residents of Stars Hollow knew about her fantasies, and about whom? About a town’s hoodlum, no less! She would die on the spot for sure. She tried to even out her breathing and brushed her fingers over the spine of the folder. After a minute of consideration, she decided to read them again, to relive her embarrassment or to try to imagine what he might have thought about them, she wasn’t quite certain.

She slowly opened the folder and was met by a strange, but not unfamiliar sight. The page was filled with her neat handwriting, but there was something else there. All of the margins were marked with his small letters. Just like always when he read, he left some notes in the margins for her. She couldn’t help a sound escaping her throat, half a chuckle half a sob. She skimmed through the pages and saw that he had something to say on pretty much everything she wrote, and her heart beat sped up in fear and anticipation. Now instead of imagining what he might have thought, she had a firsthand opportunity of actually knowing that for a fact. He offered her a glance into his mind. With a slight trepidation she returned to the first page and began reading.

Dear Jess,

I know it’s been a while and I probably should’ve sent you something way earlier, so now seems kind of pointless to try. So I won’t. (You should’ve sent me something, anything).This is something I’ll never send, and it’s better this way. I guess what I wanted to say was, I can’t take it anymore! I constantly think about you, about that kiss. I keep replaying it in my head over and over again. (Makes two of us). It’s like you’ve been living in my head rent-free and there’s no one I can complain about it. That kiss… it did something to me… I don’t know what it is, but I’ve never felt this way before, not when I kiss Dean and not when I kissed Tristin. (Who the hell is Tristin?) There’s just something about you that makes my heart race, and my whole body tingles, and I realize I could’ve put those sensations into more eloquent words, as I’m sure you know, I’ve always been quite articulate, but I can’t. When I think about that day my mind turns into a hormone-flavored jelly and I can’t come up with anything smart to say.

It’s getting worse though. I started having dreams about you, and they’re awfully realistic too. It’s like I can actually feel your lips and hands on me all over again. (I’ve had those dreams too…) Last night though I hit rock bottom. I had a dream about you touching me there, while pressing me against a tree, and I woke up from an orgasm. I think guys call it a ‘wet dream’. I’m not sure if it’s the same name for when a girl has it, but I guess I could say that I had a wet dream about you, Jess. My first ever wet dream, might I add… and the first ever orgasm, for that matter… (are you serious? Wow….) Gosh, this is so stupid… Why does it have to be you? I’m still with Dean (of course, the ever present Dean), but he hasn’t crossed my mind all that much. I feel guilty. I shouldn’t feel this way about you, but I do. What am I going to do? I feel so lost… I can’t even talk to anyone about it since nobody knows about the kiss. It’s 3 in the morning, I have to get up early, but I can’t fall asleep because you keep haunting my dreams. I wish I could kiss you right now. (Same…)

Rory

Dear Jess,

I went to a library yesterday pretending I’m going to do some research on the assignment I was given, but what I was actually doing research on was sex. I’m blushing even writing this word down. Anyway, I wanted to know if my thoughts about you are normal. I was convinced I was obsessed, and not in a good way. I don’t believe fantasizing about a guy this much is healthy. I found a few books on the subject. (Of course you did) One of them had pretty realistic and detailed drawings of different sex positions. Looking at them I couldn’t help but imagine us together like that, (Care to elaborate on that, Miss Gilmore?) and it turned me on so much I felt so hot and out of breath, the old lady next to me noticed and gave me a questioning look. I guess I was panting out loud or something (I’d love to have seen that). Good thing I disguised the book by putting it inside a journal on politics (smart move), otherwise the lady would’ve had a heart attack. Note to self, public library is probably not the best place to review books on sex. (I bet you were blushing hardcore)

Anyway, there was this chapter on masturbation… God, I can’t believe I’m actually writing to you about this. Good thing you’ll never see this letter. Anyhow, that chapter gave a pretty detailed description on the act. It also postulated that it’s completely healthy from a medical stand point (That it is). It said that pleasuring yourself helps with easing the tension, helps one relax and also learn stuff about your body. So I decided to try it. I mean, it’s not like I wasn’t familiar with the concept, but I never had the urge to do it. (Not even once, ever?) I’ve always thought it was something boys do and very rarely girls. But there was a description on how to do it for women. So, anyway, I tried it last night. I couldn’t fall asleep, again. Paris was already out and I gave it a go. It felt a little weird at first. I mean touching myself in places I only touch when I shower. I felt quite stupid doing it, but then I started to think about our kiss again, and it didn’t feel as weird anymore. (I want you to show me how you do it, how exactly you touched yourself)

I have to confess; when I touched my breasts I imagined your hands instead of mine. I like your hands a lot. I can’t count the times when I caught myself staring at your hands when you worked in the diner. There’s just something about the shape of your palms, and your long fingers. And that wrist watch of yours is so sexy. I love it when you roll up your sleeves to reveal your forearms. I like how toned they look, the color of your skin, the shape of your biceps… I remember only one time I saw you in a t-shirt, it was that ugly one with a Metallica logo. Even though the shirt itself was hideous, it had one perk to it – showing off your biceps. It’s a shame you always wear so many layers of clothing. Although living in Connecticut I guess I can’t blame you. Anyway, I’m rambling again. So, I was thinking about your hands on my breasts. For some reason, I feel like you would know exactly what to do with them, and your fingers would circle around my nipples perfectly. (That they would. So would my lips)

Anyhow, I kept picturing you the entire time when I was touching myself, down there too. (Fuck!!) As soon as I found my clitoris, I knew why people do that so often, it felt incredible! If it feels the same way for boys when they have sex, no wonder they like it so much. I was thinking about our kiss and my fantasies and dreams I had about you (I want to hear them all), my vulvar lips were so wet, all because of you. (You have no idea what it just did to me) I even pushed a finger inside, just a tip, but it was enough for me to climax. It is official now, you’ve claimed my first ever masturbation orgasm. I don’t know how I feel about this, to be honest. I can’t help but want you to touch me there, like you did in my dreams and in my fantasies (I would love to do that). I’d give anything for you to think about me the same way. (Trust me, you wouldn’t have to give a lot, because I already think about you that way, maybe even too much)

Love,

Rory.

Dear Jess,

Just so you know, I kept rereading that book and a few others I found on that shelf. I think I memorized the positions and how they’re supposed to feel to boot. (That’s a good thing. You’ll need that information later) Also there was this chapter on oral sex… with pictures… the commentary said that women might have reservations about doing it, but I was strangely aroused by the concept… probably because I was thinking about you… I’ve seen the penises in all those pictures and it made me wonder how yours looks like… (You’ll just have to see for yourself to decide) I bet it’s beautiful, just like everything about you. Okay, here, I said it. I think you are supremely attractive. (Why, thank you, Miss Gilmore) Everything from your crooked smile and fingers to the way you walk is just so hot. I wish I had your picture… Wow, that’s just creepy. Scratch that. Besides, I have plenty of visual images to haunt my memory anyway.

I’ve never wanted to see any guy naked before, but you shirtless are the only thing I can think about these days. It’s so strange to me. I’ve never had such thoughts about Dean. I still don’t. What is wrong with me? I am supposed to want my boyfriend of almost 2 years, but I don’t. I feel bad for not wanting him, as if I’m obligated to do that. (Ouch, that’s harsh) It’s like you turned my entire world upside down when you moved to Stars Hollow (I won’t apologize for that). I wish I could tell you all of this in person, (I wish you did) but I would be too embarrassed. I’m thinking about breaking up with Dean, because I’m obviously not as invested in our relationship as I’m supposed to be. It’s just unfair to string him along. It’s not his fault I don’t feel for him anything even remotely close to what I feel to you. But I don’t want to do it over a letter. I don’t want to be a jerk to him. He’s been pretty great to me. Sorry, you don’t want to hear about how great Dean was.

Anyway, I touch myself every night thinking of you. (You’re not the only one, I do that thinking about you too) I guess I’m getting pretty good at this masturbating thing, as it ends in orgasm every single time. I wish you could be the one touching me like that. (I could be…)

Kisses,

Rory

Dear Jess,

Last night I had a dream about you going down on me. It keeps me wondering if you ever done that before. (I have) I mean, in New York, you probably had tons of girlfriends, I mean with how good you look and considering what an amazing kisser you are… I think you most definitely had sex before, whereas I’m still a virgin. Would you ever be able to want me if I don’t have any experience at all? (You have no fucking clue how much I want you, experienced or not, doesn’t matter) If we ever found ourselves in a situation like that with no clothes on, as much as I’d like to see you naked, I wouldn’t know what to do… I’d probably be so disappointing. (You would never be a disappointment for me) Argh, I’m such a mess.

The thing is, my fantasies about you, they kind of progressed… I often think about you on top of me with your penis inside, or me on top of you riding you with your mouth kissing my breasts. In that book there was also this position called ‘doggy style’ when a woman is standing on all fours and a man is entering her from behind. (You’re killing me…) It’s kind of primal and natural because of the location of genitalia against each other. The commentary said some women don’t like that position because it makes them feel submissive and way too animal-like, as if they don’t have a say in the matter. I wonder if I liked that. What if I did? (If you did, I’d fuck you like that as many times as you wanted) Would that make me less of a feminist? (It wouldn’t, don’t worry. A woman who knows how she likes her sex and not afraid to inform her partner about it, is definitely a feminist)

Thinking about you giving me oral also made me insecure. What if we ever did that and you didn’t like my taste or smell or how I looked down there? Today I closed up in the bathroom and examined my lower lips in a compact mirror like the book suggested. I don’t have anything to compare it to except for that image in the book, but everything seems normal, in place… (I bet you look and taste amazing, I would eat your pretty little pussy out until you couldn’t remember your own name) Have you ever watched porn? (Yes, what guy hasn’t?) There are probably tons of genitalia of all shapes and sizes. (There sure are) Not sure I can look it up here though; they probably monitor traffic and web activity here. Don’t want to get busted by CIA or something for watching porn. (No, we wouldn’t want that) Anyway, that’s all for today.

Yours,

Rory

Dear Jess,

I’ve been having this dream about your head between my legs (that can be arranged) for a few nights in a row. It’s also a recurring fantasy of mine when I touch myself. So tonight after I took a shower, I mastered up my courage and… tasted myself. I dipped my finger inside and then licked it. (That is so fucking hot, you have no idea how fucking hard it made me) The taste is okay I guess, not off-putting. At least I hope so. I wonder what you taste like… (Once again, no idea what you just did, fuck…)

Kisses,

Rory

Dear Jess,

Remember that chapter on oral sex in that book I told you about? Well, I think it finally caught up to me, because I’ve been having very racy dreams about it lately. It made me feel like I just want to come up to you, pull your pants down and suck your dick until you can’t cum anymore. (Fuck!!!!) It’s wild, crazy, but I like it. In my dreams there’s nothing standing in our way, no inhibitions, just you and me, naked loving each other. (We can do that)

I found a chapter in one of the books denoted to different kinks and stuff. So, there was this paragraph on dirty talk, and it got me thinking. You read so much, you’re good with words, would you be just as good at dirty talk? (Yes, if that’s what you’re into) Do you make any noises during sex or are you the silent type? (Depends on the location) There’s this whole image of you in my mind of what you might be like in bed. (I want to hear about it) I wonder if the real you is any close to that image I created. Tell me, Jess, what kind of lover are you? (I’d rather show you) Do you have a favorite position? What is it? (Cowgirl) What do you like about it? (Seeing a girl’s face and breasts while she sets the rhythm she likes, being able to touch her everywhere) Do you like it rough or sweet and slow? (Both) Would you mind being my first? (I would be honored) Have you ever been with a virgin before? (No) How old were you when you lost your virginity? (14) How was it? (Awkward) There are so many things I don’t know about you! But I want to know them; I want to get to know you better, Jess Mariano.

I wonder if you let me. (I want to….)

Yours,

Rory

Dear Jess,

Today I was helping Paris to prepare for her first date. A guy from the program asked her out. (Wow, he must be a brave man) She kept asking me questions about relationships, and how do you know if a person is right for you. While I kept answering I realized I had you in mind the entire time. That was some wake up call. I think I want to be with you, Jess. And not just physically. Although I’m sure that part would be amazing. But in general too. I want to be your girlfriend. I want to be able to go out with you, hold your hand, kiss you whenever I feel like it. I want to read together quietly and then discuss books with you, I want to go see movies and our favorite bands live. I want road trips and laughing and picnics and everything in between. I want to be with you. (What about Dean?) But what if it’s too late, and you don’t want to be with me? Did you even want to be with me? (Yes) Why did you move back to Stars Hollow, Jess? (It felt more like home than home in NY did…) Do you like me? (Yes) Because I like you, I really do. I think I started to like you since the day you gave me my copy of ‘Howl’ with those notes in the margins. But I didn’t want to admit it, couldn’t, because of Dean. But that kiss… it finally opened my eyes, and I can confess that I like you. I really really do, so much! God, this trip can’t be over soon enough, good thing it’s the last day. Tomorrow I’m coming home. Hopefully I will see you.

Love,

Rory

He also left comments on her less explicit letters where she asked him about books and other stuff. He was rather thorough in his annotating on those ones. When the D.C. letters came to an end there was a note written in larger letters, underlined a few times (Why didn’t you say anything???)

Rory bit her lip as the guilt overwhelmed her. If only she sent him something…. At the same time she couldn’t help the hot arousal that started throbbing in her core, spreading through her entire body, while she read all of his comments about how turned on her fantasies made him. He felt the same way. He pictured her just like she pictured him in all those sexy situations. He wants her, he likes her. She couldn’t believe it. Light-headed she stood up and paced for a little bit in her room trying to shake off the nervous energy. He likes her! But then she remembered he was still dating Shane, so she set down and proceeded reading further.

Dear Jess,

I can’t believe I was so stupid! Writing all those letters to you, feeling the way I did while you’ve been playing a tonsil hockey with that blonde skank the entire time! How could you do this? I thought our kiss meant something for you. I guess I was wrong. You know what, fine, have a nice life with your blondie! I hope you two are happy together!

Not yours,

Rory

After that letter he wrote an entire letter of his own.

(Are you fucking serious??? How the hell was I supposed to how what you felt? You just left! Bailed, without saying goodbye! Is that your revenge for me going back to NY after the car accident? I thought we cleared the air when you came to the city. Why didn’t you say anything? I saw you kissing Dean on the porch of your house before you left. How can you seriously expect me to sit around and wait, when you didn’t tell me you were leaving, when you still kissed the Jolly Green Giant? I am not responsible for what you felt and what you fantasized about when you were in Washington! You didn’t tell me any of these things! So you don’t have the right to get mad at me for going out with someone else. )

Dear Jess,

I guess I can’t blame you. I know you and what’s-her-face are having sex. I overheard her talking about it on the phone with some friend. She said you had a big dick. I hate that it makes me feel so hurt. I hate that it makes me feel jealous, but most of all, I hate that this piece of information about your penis still managed to arouse me.

I hate that I still want you.

I hate that you’re with her.

I hate that I can’t do anything about it. (Yes, you can)

Dear Jess,

It pains me to see you with her, but I can kind of guess what you see in her. As much as it pains me to admit, she’s beautiful, her body is gorgeous, and she’s obviously experienced. I don’t have any of that, there’s literally nothing I can offer you in that regard. I’ve always been too gangly and ungraceful. Her boobs are bigger than mine and she’s blonde. I guess you’re into blondes, huh? Would you like me better if I dressed differently? If I wore tighter jeans, lower cuts, crop tops? (It wouldn’t be you) It just sucks that you’re with her. (I like you just the way you are)

Rory

Dear Jess,

It’s over… with Dean… he came over today and he was talking about how much he missed me, how beautiful I was. I let him go further than we usually do. I guess I wanted to feel desirable like Shane. At least by someone. So Dean tried to go all the way, (He’s dead) but when he kissed me, I didn’t feel anything at all. I didn’t feel a single thing that I did when you kissed me or when I was fantasizing about you in D.C. It made me so sad. I started crying and told him I don’t want him, and that it’s better if we break up. He got really furious and left. So that’s it. I am officially single, but the only guy I want doesn’t want me back. (Not true)

Rory

Dear Jess,

I guess I should stop writing these letters. You hate me, (I don’t hate you) we don’t even talk, so what’s the point? It only makes me feel worse. Because I know that there’s no possibility for us to be together. (There could be if you wanted to…) I should probably just start a diary or something, rather than continue with this.

I loved our time together though. So goodbye, Imaginary Jess, you’ve been a real help on my journey through my sexual awakening and self-discovery.

I need to move on somehow.

Goodbye,

Rory

There was a little bit of space left on the page under the last letter. He used it to write one final note.

(Meet me at the bridge tonight at 8 pm, if you want to talk.)

Her heart was beating so fast in her chest she thought she was having a stroke. He wants to talk. He’s giving her a chance to talk about their situation. She couldn’t help but feel the hope blooming inside. Did he really mean it? That they have a chance to be together if she wanted to? Apparently there was only one way to find out. So at 7.50 PM she exited the house and headed for the bridge.

Every step was bringing her closer to her destination making her more nervous by the second. Her hopefulness was replaced by embarrassment and she started questioning her decision to see him. He has read all of her explicit letters, her deepest darkest fantasies and desires he was never supposed to find out about. What if he’s just going to mock her? What if he didn’t mean what he wrote? What if it’s all just a joke, an elaborate prank for him? To fool a small town virgin into thinking he, the big city hot badass, could actually want her? Her mouth went dry, she wanted to turn back and run to her house, but stopped herself from doing so every few seconds. He was already sitting there, his feet dangling over the water. He was twirling a cigarette between his long fingers, but didn’t light it up. She came on the bridge and set down two feet away from him. He didn’t look up when he asked, “Did you mean what you wrote?”

“Why does it matter? You’re with Shane, so it doesn’t matter anyway,” her answer came out bitter.

“I broke up with Shane.” She dared to look up at him for the first time. He was staring right back at her, his gaze dark, intense. She gulped.

“Do you still mean it?” He asked her in a low husky voice.

“Yes…” she whispered. She couldn’t take her eyes off of him hypnotized by his hazel orbs. Her blue ones were wide open, her breathing got heavier with anticipation of something, anything…

“Good,” he said and leaned in and kissed her, surprisingly gentle as if not to spook her. Her mouth opened on its own accord and she let out a small moan of pleasure, as she finally felt his tongue against hers again. He kissed her methodically, confidently and she leaned into him, wrapping her arms around his neck. He hugged her around her waist and pulled her into his lap. Their position was risky on the edge of the bridge but they didn’t care. They made out like that for what felt like hours. He kissed her behind her ear and she whimpered, then he went to kiss her down her neck just like he did at the wedding, and it’s there again, this incredible feeling like she’s tingling all over. She couldn’t help it and ground her hips against his unconsciously which made him groan lowly into her neck. This sound did something to her, it was raw and a bit animalistic, it awakened something primal in her and she grinded some more searching for friction, pressure and release. He halted her movements putting his hands on her hips.

“Rory,” he pulled away from her lips and questioned, his voice husky, “What is this?”

She blinked in confusion, her eyes still dazed and dark with desire. He almost gave in not wanting to talk, but he needed to know what’s going on, where they stand.

“What do you mean?” she asked breathless.

“What is this between us? What do you want from me?” he looked at her and saw the fog of lust starting to clear from her eyes, and suddenly she’s uncertain, vulnerable in his lap.

“I…” she gulped not knowing how to answer. “You already know what I want from you. You read all about it.” Her cheeks were flaming hot and it was showing in a form of a brilliant blush. She was embarrassed, he could tell.

“Is it for real though? It’s not just your fantasies that you would never dare to follow through?” he was still looking at her searching the truth in her eyes. She gulped again, her nerves making her throat dry. She wasn’t sure if she’s ready for this conversation. He wasn’t supposed to find out about the letters. But if he didn’t, he’d still be with Shane and Rory wouldn’t have a chance in hell with him, but now she does…

“It… it’s real… and….” She took in a shaky breath. “And I want to follow through, but maybe take it slow?” she finally dared to glance at him, eyes hopeful and a little insecure. He realized he was in the position of power in this situation, because she didn’t know all that much about his own feelings apart from the brief and not exactly informative notes he left for her in the margins. She might think he’s only in it for the sex.

“Okay, we can take it slow,” he answered with a thoughtful expression on his face.

“So…” she trailed off. “What does it mean?” she needed to know.

“That means we’re going on a date.”

“A date?” out of all the possible scenarios on how this could go this was not the one she envisioned.

“Yes, like a proper date. You wrote you wanted to date me, to be my girlfriend. Hence, the date. Knowing you, probably eating and a movie?” she couldn’t help a tiny smile.

“Sounds great.” Her eyes were gleaming in the dark, and he smirked at her.

“Okay then.”

~XXX~

When they finally parted ways, she was walking to her house still dazed from a passionate make out session they sealed their deal with. She couldn’t believe it was really happening. She’s going on a date with Jess! He dumped the skank to be with her! He feels the same way as she does. If the prominent bulge in his pants that was pressing into her core while she straddled him was any indication, he desired her just as badly as she did him. Rory still felt her vagina throbbing even after they separated. It was even better than in her fantasies. She couldn’t wait to explore everything with him. But first, she had to explain their date to her mom somehow. That put a damper on her mood. There was no way in hell she would tell Lorelai about the letters, so she had to come up with some other excuse why Jess wanted to see her at the bridge all of a sudden, when they haven’t talked for days. Finally she thought about the sprinklers and decided to use that situation to her benefit. Judging by the jeep in the driveway, her mother was already home, so it was time to face the music. Rory took a deep breath and walked inside.

Chapter Text

The next morning Rory and Lorelai came to the diner for breakfast. Lorelai was rambling to her daughter about something or other, Rory, again, wasn’t as responsive as usual, but this time it wasn’t because of the break up. This time it was because she was uncertain on her situation with Jess. Sure, they had a very steamy make out session last night at the bridge, so much so she was still dazed and disoriented when she got home, but they didn’t discuss their official status. He asked her out on a date, which was supposed to happen tomorrow, but today seemed like some sort of limbo, where she didn’t know where they stand. If she sees him at the diner, what was she supposed to do? Does she great him with a kiss like she did with Dean? The breakfast rush would probably be in full swing, so if she kissed him, it would surely be the talk of the town in less than two minutes. She didn’t want that until she knew exactly what it was between them. On the other hand, what if he ignored her completely? What if he wanted to keep it under wraps?

When Lorelai opened the door, and the bell jingled announcing their arrival to Luke’s, Rory’s stomach tied into knots. She quickly looked around the small room trying to be as discreet as possible. Jess was nowhere to be seen, and she couldn’t identify the emotion it caused. Was she relieved he wasn’t there to confront her about last night, or upset because she didn’t have the chance to see his handsome face before school?

Rory and her mom settled at the counter, Luke already pouring two large cups of coffee for them. Lorelai started her usual ‘bickering with Luke over breakfast’ routine, while Rory nervously glanced at the curtain leading upstairs every few seconds. Jess hasn’t showed up until they were done with their pancakes and it was time for Rory to head out.

When he sleepily tumbled out from behind the curtain, he stopped dead in his tracks when he saw her. She looked so cute in her Chilton uniform, the blue collar of her dress shirt bringing out her eyes. Did they become even bluer over night? His jaw slacked for a second. Then he cleared his throat and said “Hi.”

“Hi,” she responded. He turned to Lorelai and said ‘Hi’ to her and to Luke as well.

Then Rory chickened out and said “I have to get to school.”

“Yeah, me too,” he mumbled, which followed by the awkward ‘byes’ to everyone. Rory flew out the door and Jess headed back upstairs.

Luke turned to Lorelai, confused. “What was that?”

“It was Jess and Rory, the early years.”

“What does that mean?”

“Jess and Rory are together. Well, at least, he asked her out. See, now that she’s single, after the ‘Dean break up’ and all. They’re going on a date tomorrow.” Lorelai shrugged and sipped on her coffee.

“Wow… Rory and Jess? Jess and Rory?... Wow…” a pleased grin spread across Luke’s face. “That’s great!”

“You think?” Lorelai asked skeptically.

“Why, you don’t think it’s great?”

“I don’t know what to think anymore. I mean, she’s single, she can date whoever she wants. And I want her to be happy, and if she thinks Jess is gonna make her happy, then I’m gonna have to deal with that.”

“Listen, Lorelai, I know you didn’t start on the right foot with Jess, and he can be a little rough sometimes, but he likes Rory, and she’s a good kid. Maybe she’ll rub off on him.” Luke was clearly pleased with this turn of events. Lorelai couldn’t understand why it bothered her so much. She was fighting the ‘Jess thing’ for quite some time now, but Rory confessed to have feelings for him. She had to respect that. But Luke being on board with this was just weird… She couldn’t figure just how she felt about it yet.

“Well… we’ll see. Now can I get a coffee to go, please? I need to go to the Inn.”

“Sure.” He poured a to-go cup to the brim and handed it to her with a happy smile. “On the house.”

~XXX~

Luke didn’t have the chance to catch Jess before he left for school, but he intended to talk to him after classes. What he didn’t expect was Jess initiating the conversation instead.

“Hey, Luke?” Jess asked when Luke came upstairs to have a short break before the dinner rush.

“Oh good, you’re here, I actually wanted to talk to you about something.”

“Great. Can I go first?”

“Okay, go ahead.”

“Well, I need tomorrow off. I haven’t had weekends off in a while, so I wanna take my off day tomorrow.”

“Okay, sure.” Jess couldn’t understand why his uncle didn’t try to argue and agreed so fast. Also, he hasn’t looked so pleased in… well, a long time.

“You’re sure?” Jess asked suspiciously.

“Yes, why wouldn’t I be? You want Saturday off; you’ll have Saturday off.”

“Okaay… while you’re being so understanding, can I borrow your truck too?”

“What?” Luke snapped. “Why the hell do you need my truck for?”

“I just need your truck. Can I borrow it? Please?” He added for good measure.

“I need to know what you need my truck for. Also, can you even drive stick?”

“Yes, I can,” Jess rolled his eyes.

“Since when? You’re a New Yorker.”

“Geez, I worked in an auto repair shop since I was fifteen. Now, can I borrow the truck or not?”

“You worked at the auto repair shop? What? Just tell me why you need the truck!”

“I wanna take Rory out on date, okay!” Jess yelled, but the only thing his outburst caused was an even bigger shit-eating grin from Luke.

“You wanna take Rory out on a date,” Luke chuckled. “That’s amazing.”

“What?” Jess couldn’t believe what he was hearing.

“What? She’s a great girl, I think you two going out is amazing. You can borrow the truck, no problem.”

“Wow… okay, thanks.”

Luke just nodded in response and went downstairs whistling.

~XXX~

To say Lorelai was not thrilled about the prospect of her daughter going on a date with the town hoodlum was an understatement. But then again, when Rory returned from her rendezvous with Jess, she looked so radiant, so happy. Lorelai hasn’t seen her like this in weeks, possibly months, maybe even in her happiest times with Dean. It made her worried. She could tell Rory was falling hard and fast, but she couldn’t do or say anything about it without the risk of alienating her daughter, which she didn’t want. She thought Rory would need her more than ever, because this thing with Jess seemed serious, like adult content kind of serious, and Lorelai needed to be there for her daughter, in case things went south. So she decided to suck it up and find a way to be okay with this somehow.

They set their date for the upcoming Saturday, that way they both didn’t have school to worry about. Luke gave Jess the day off and even let him borrow his truck. The grumpy diner owner seemed strangely on board with his nephew going out with Rory. He was probably the only person in Star Hollow who actually rooted for the couple. Rory felt grateful, it made her feel even closer to Luke as she did before, their bond growing stronger. She still felt wary of her mother’s reaction. Rory could tell she wasn’t happy about it. So Luke seemed to be the only one she could express her genuine happiness about her date with. When she and Lorelai came to the diner late on Friday after the dinner with her grandparents, Luke was all smiling, attentive, and even gave them coffee on the house. It made Rory feel really good about her upcoming date with Jess. She could definitely count on Luke to be on their side. The man just hoped his nephew wouldn’t screw it up.

~XXX~

Finally, it was Saturday - the day of Rory’s first date with Jess. After agonizing about what to wear for about two hours, she settled on a pair of her favorite jeans that were the most tight-fitting and hugged her curves the best, and a cute dark blue top that made her eyes pop. She was contemplating wearing a dress or a skirt first, but none of those seemed to make her look beautiful in her eyes. Subconsciously she wanted to look not just pretty, but sexy. She wanted Jess to find her attractive. She wanted to look good for him. Maybe the top was a little too low cut than she usually wore, so what? It revealed a lot of skin, her neck and collarbones, which Rory knew she would love for him to kiss later into the date. They were going to the movies after all. The darkness of the theater was the perfect place to make out, and for the first time in her life she intended to use it to her advantage.

Jess parked Luke’s truck in front of her house, and waited for her outside the car leaning on the door. When she came out and headed towards him, he gave her such an appraising look her cheeks flushed. She stepped closer to him hesitantly. He took her hands in his, intertwining their fingers together. They looked into each other’s eyes for a bit, before he whispered “You look gorgeous.” She blushed again and mumbled “thanks.”

“So, shall we?” he opened the door for her, and she climbed in.

First they went to the movie theater in Hartford, because it was definitely better than the one in Start Hollow, and had wider variety of movies. September of 2002 wasn’t blessed with any significant premieres, so Jess and Rory had to go for whatever was in rotation in the cinema. Finally, their choice fell on the film called ‘Stealing Harvard’, which was about an uncle who went to commit a crime to be able to pay for his niece’s tuition in the Ivy League school.

“You do realize it’s most likely gonna suck, right?” Jess enquired with a raised eyebrow.

“Oh, I am 1000% sure, but the title seems fitting, considering I’m still going to do the Harvard thing, as you so eloquently put it the other day. Plus, it’s a guarantee to be a goldmine for mocking. I’m sure we’ll have fun.” She beamed. Having Lorelai for a mother prepared her for situations like this. She could ruthlessly mock anything and everything, especially having a company like Jess, who could keep up with her quips no sweat.

“Well, if you’re sure,” he went to the ticket booth and paid for the both of them. “Popcorn?”

“Do you even have to ask?”

Rory was surprised how at ease she felt with him. Sure, there was some lingering insecurity from knowing he read all of her letters, but other than that, it was always easy to be around him, to talk to him, joke with him. They were sitting at the very back of the room, and not many people wanted to see this movie in the first place, hence there were maybe ten more people besides them dispersed evenly in the rows in front of them. This way when Rory was whispering her comments into Jess’s ear about stupid things in the movie, or made her own jokes that were a million times better than the ones presented on the screen, no one scolded them and asked them to be quiet. A few times when she joked about something too loud and Jess bantered back, some people in the front rows laughed at their exchange of wits. It felt like a collective mocking session. The one she never had on dates with Dean. A couple of times Jess took advantage of their seats placement and pulled her in for a kiss when she leaned in to say something to him. She obliged eagerly. The kisses were even better than mocking, and better than popcorn. All in all, it was a great date so far. When the movie ended they exited the dark room holding hands.

“Sooo… did you like it?” Jess asked.

“As a cinematic creation – no. As a date – yes.” She smiled a looked at him. “You?”

“Same,” he leaned in and kissed her cheek. He was high on the fact he was now able to do that with no reservation. “Are you hungry?”

“I could eat.” He didn’t make fun of her eating habits and didn’t comment on the fact she just had a big bucket of popcorn, but led her to the doors out of the theater instead.

They found a clean looking diner not very far from the movies. It had lots of booths with red seats and checkered tables. They chose the one in the corner and both sat on one side facing the wall and away from the rest of the crowd. After they had their burgers and fries, and a milkshake, talking non-stop about the movie they just watched, the books they’ve read during the time they weren’t speaking and everything else under the sun, there was a brief pause in the conversation that Jess had to fill in.

“Rory, we have to discuss the letters at some point,” she blushed furiously at his comment. She already knew some of his thoughts on the matter from his notes in the margins, but they haven’t openly talked about it, not yet, and frankly Rory didn’t expect to have this conversation on the very first date. After all, they agreed to take it slow.

Jess continued. “You described some of your fantasies, very hot by the way, so how about I even it out a little and tell you one of mine?” she gulped and nodded. He moved on the fake leather seat, pulling Rory closer in his arms and whispered into her ear. “I like the way you look in your Chilton uniform. It’s kinda sexy. I want to put my hand between your legs while you’re still wearing that plaid skirt and see how wet you are, how fast I can make you cum on my fingers.” She could feel his hot breath on her ear, which made her shiver, his words affecting her more than she was willing to admit. There wasn’t one spot of her skin on her body that wasn’t blushing. He liked the way it crept up her neck. He leaned in and planted an open-mouthed kiss on her pulse point and she nearly jumped out of the booth. She was so tightly wound up she couldn’t think straight.

“We will have to recreate this fantasy sometime. What do you say?” he whispered in her ear. The fine hairs at the nape of her neck stood on end. This was too much, too intense. “Rory?” he called when she didn’t answer. How was she supposed to say anything when her mind turned into mashed potatoes.

“Uh-huh, yeah,” she mumbled.

“Great,” she could hear the smirk in his tone that no doubt played on his lips.

“C’mon, it’s not late yet, let’s go to the bookstore. How does that sound?” he suggested all nonchalant like he didn’t just turn her pussy into a hot spring.

“Great… Th-that sounds great,” she gulped and exhaled when he finally took his arms off from around her and stood up. They headed to the car, their fingers intertwined.

~XXX~

On their way back to Stars Hollow she kept sneaking glances at him, while he was focused on the road in front of them. Finally, he caught her staring, and she blushed a little. “What?”

“I… uh… nothing.”

“C’mon, Rory, what is it?”

“Jess… I… I know, it’s only been one date, but I think it went really well, so… I was thinking… and I need to ask you something…” He could tell she was nervous, so he decided against teasing her.

“What is it?”

“I wrote in one of the letters that I wanted to be your girlfriend, and that implies that you would be my boyfriend in that case. So… are you my boyfriend now?” she kept wringing her hands anxiously.

He decided that he doesn’t want to have this conversation while still being behind the wheel of a moving car. God knows she didn’t need any more accidents. He pulled over the first chance he got and turned to look at her.

“Do you really want me to be?”

“Yeah, I do.” She nodded, pink blush still evident on her cheeks.

“Okay,” he simply said.

“And we’re exclusive?” she felt the need to make sure after the first wave of elation subsided.

“Yeah, we are.” He smirked.

“Good, that’s good. Great! Uh, awesome,” she let out a nervous giggle.

“Rory?” he leaned closer.

“Yeah?” she whispered.

“Hush now,” he covered her lips with his, and they both got lost in the sensation for a while.

~XXX~

On Monday morning he waited for her at the bus stop with a to-go coffee cup from Luke’s. She was surprised to see him, as she thought he would be in school, but let him take a ride with her to Hartford nonetheless. They sat at the very back. He made her sit in the corner where the front row of chairs covered her from the view from the waist down. All of the other patrons were either napping or reading on this early morning bus. No one paid attention to the young couple in the back.

As the bus started moving Jess turned to Rory and captured her lips in a languid kiss. She relaxed into him, and he wrapped one arm around her back and the other around her front encircling her, leaning closer. Slowly his hand traveled down her waist to her thigh as they kissed. When his fingers crept under the hem of her skirt she jolted. “Jess!” she reprimanded him, flushed, breathless, “what are you…?”

“Shh… remember what we talked about the other night? I want to cash in on my school girl fantasy,” he shut down any possible protests with another kiss.

“What? No, not here, we can’t,” she stammered, weakly trying to pull away, her resolve quickly melting away as his tongue kept caressing hers in a sensual dance.

“No one’s looking,” his fingers went up her thigh, and she unconsciously spread her legs a little. He took that as an invitation and reached for her panties. The soft cotton was already soaked under his fingertips, and he hissed into the kiss. He didn’t expect her to be so responsive. Maybe doing this in a public place was not the best idea. He doubted his self-control was that strong.

He rubbed her carefully, searching for her clit. When he found it, she jolted in his arms and he covered her mouth with another kiss to keep her from alerting everyone on the bus. He then started a slow and steady rhythm, rubbing her clit in tight circles and felt her quiver in his arms. She was whimpering softly in his ear as her face was tucked into his neck, her eyes closed, breathing uneven. He kept going. She clutched his sweater between her fingers to do something with her hands. She was trembling and tingling all over. The feel of his fingers on her most intimate part, his smell – this mix of cologne, hair product he used, smoke and pure Jess was making her dizzy. She was completely consumed by this exquisite pleasure; she didn’t care about what was happening around her. His jeans were now getting painfully tight. He wanted nothing else but to fuck her right then and there, take her underwear off and plow into her, rumpling her plaid skirt, but he couldn’t do that here. As Rory’s legs spread wider on their own accord, he pushed her panties aside and probed her pussy, finding her entrance unbelievably hot and so wet he almost came then and there. When he touched her there she nearly gave them away with a startled mewl, but he silenced her in time with his mouth again. He pulled away from her mouth and looked into her eyes. They were so wide and round it almost made her look like an anime character. Her gaze hazy and dazed, she looked at him in bewilderment, like she just had some sort of Godly revelation dawned on her. He was watching her face while his fingertips gently grazed her slit. He could see her irises getting darker by the second, her lips parted, and bright pink blush colored her cheeks. She looked magnificent. When he pushed the tip of his forefinger inside, her jaw slacked in a silent scream, and he pressed his thumb to her clit. Teasing her sensitive entrance and rubbing her clit at the same time pushed her to orgasm. He was watching her cum, his finger coated with her juices, and he thought this was the most beautiful image he’s ever seen in his life. He kept moving his digits drawing out her climax until her eyes closed. Then he slowly withdrew his palm from between her legs and kissed her softly.

When they exited the bus at Hartford she looked frazzled, disoriented, staring at him in disbelief.

“I can’t believe you just did that,” she murmured.

“Did you enjoy it?” he asked.

“Yes,” her response barely above whisper.

“Good. Now go to school. You don’t wanna be late for all that knowledge.” She nodded dumbly and turned into direction of Chilton, still too shocked to comprehend what just happened.

When she wasn’t looking Jess took his fingers to his face and inhaled deeply. The scent of her arousal still lingering on his fingers echoed in his groin with a twitch of his dick. He licked his finger without any hesitation and his mind turned blank for a second. He couldn’t wait to eat her out properly. Her taste made his cock come alive again. He let out a heavy sigh and adjusted his pants. It’s going to be a long ride back.

~XXX~

“What’s wrong with you?” Paris looked at her, suspicion written all over her face.

“Huh?” Rory flinched at her friend’s attention.

“You look weird,” Paris still eyed her warily.

“No I don’t,” Rory could feel a hot blush rising up again. There’s no way she would admit to anyone what just happened between her and Jess on the bus. Especially not to Paris. Her brain was still processing their morning encounter, going over things again and again. Rory’s been daydreaming through an entire class, not comprehending a single word her teacher has said.

Jess just got her off for the very first time, for real, and on a bus of all places! That was so dirty, frisky… liberating. All those things she dreamed about doing with him while in Washington, all her fantasies of what it might be like being with him didn’t even come close to the real thing. Jess was so much better than she had imagined. Even in her wildest dreams she couldn’t anticipate the reaction she would have to his touch. Just the simplest gestures like hand holding sent all of her nerve endings ablaze. The mere touch of his fingers when he came to intertwine his digits with hers turned into an erotic act for her. When he brushed a stray hair out of her face and his fingertips brushed the shell of her ear, she was nearly jumping every time like she’s been zapped. It felt like her vagina had a mind of its own, and it wasn’t connected in any way to the rational part of her brain.

Today he gave her a glimpse into their sexual future, what it might feel like with him, and she thought she was in for a ride. They haven’t even seen each other naked yet, and he’s already managed to make her climax. Come to think about it, he gave her the first ever orgasm, and in a public place no less! When she thought about sex before, not having it with Dean, but as a general concept, she always pictured something resembling a setting from a romantic movie. Something like a nice bedroom with candles everywhere, maybe not necessarily rose petals, but it definitely wasn’t a back seat of a Hartford bus. Jess made her want things she never knew she was capable of wanting. He got her so turned on, she reached the point of not really caring about her surroundings. She even suspected that if he chose to fuck her then and there, she wouldn’t object too hard, or at the very least, she would seriously consider doing it. The thought scared her. They’ve only been on one date and he already had such a power over her. It didn’t seem right. She wished she could talk to someone about it, but there was literally no one she could trust with this information.

Now that she knew what his fingers felt like on her, what he could do to her, focusing on school was so much harder. She came out of her daze only after lunch, and realized she had to borrow someone’s notes from the first part of the day, because she doubted Jess’s hand movements would be on the test next week.

~XXX~

A week after their first date Jess came over to the Crap Shack. Rory had lesser amount of classes on Mondays than the rest of the week, so they wanted to take advantage of the time Lorelai was still at work to be alone together, away from the prying eyes of the townies.

Rory had already changed into her home clothes for comfort when Jess knocked on the back door to avoid the ever watchful Babette. They weren’t hiding their relationship in public, but Rory still felt a little bit awkward expressing her feelings for him in front of everyone. She wasn’t a big fan of PDA in the first place. Sure, she kissed Dean in public, but those were mostly just innocent pecks of hellos and goodbyes, and even the make out sessions they had outside were still pretty modest. His hands always stayed glued to her waist, not going any lower or higher, while her arms were statically wrapped around his neck. With Jess though…with him she didn’t trust herself to behave. As soon as his lips touched hers, her brain would short circuit, and she would lose all connection to reality. Their physical chemistry was too explosive for her to be able to handle in public. She didn’t want to be the talk of the town. She knew she would be eventually, but being talked about as the one who started dating the town hoodlum was a lot better than the one known for an indecent behavior. That is why while in public the only thing they did was holding hands, and occasional peck on the lips. No one needed to know that he already gave her the first orgasm of her life.

They were lying on her bed making out. The kisses were getting more heated by the minute. Soon they were both panting heavily, hands frantically roaming all over each other. Jess’s palm went down her front to the hem of her cardigan and slid underneath the thin fabric. His hot hand felt like it was leaving scorch marks on her skin everywhere he touched. Rory welcomed the sensation with a soft moan. Encouraged by her reaction his hand went further up until it came in contact with the wiring of her bra, and stopped there. Rory’s breathing hitched. She didn’t want him to stop, she wanted more, but wasn’t sure how to tell him that. He covered her breast with his hand carefully and looked at her as if reading her mind. She nodded and pushed into his palm, indicating she wanted it. This was so different from the same experience she had with Dean not long ago, on the day of their break up. The two could not be more dissimilar. While Dean’s touch made her feel icky, Jess’s made her crave more.

His fingers clenched her breast softly. She was wearing a padded bra, so she didn’t really feel anything; therefore, he slid his fingers under the garment and touched her nipple. Rory jerked at the sudden and intense sensation, her mind going blank for a second. The only thought present in the forefront of her brain that she wanted more. Jess looked into her eyes, seeing the desire in them and slowly reached for her bra clasp and undid it in one expert move. Rory’s heart was pumping with nerves and anticipation. They haven’t done that before. He’s never touched or seen her boobs, which was normal considering they’ve been only dating for a week. But already knowing her fantasies about the physical side of their relationship from her letters gave him the confidence to move a bit faster than he originally would have.

She wanted him to touch her breasts, but was insecure and scared he might not like what he saw. After all, she wasn’t heavily endowed in the chest department. Jess went to kiss her on the lips again, this time softly, soothingly. She hugged him closer and reached for the hem of his shirt as well, tugging it up his body. He was a little surprised at her boldness, but thought it was about time she saw him shirtless. She fantasized about it after all. He leaned back on his haunches and took his shirt off in one swift motion. Everything about that move was so sexy and masculine, Rory’s pussy clenched in longing. He wasn’t bulky, but rather lean and wiry. All the muscles were clearly defined. She noticed a star-shaped tattoo on his right bicep and made a mental note to ask him about it later. Right now she wanted to touch him. She sat up and traced her fingertips over his chest hesitantly. His skin was warm and smooth, she felt the sudden strong urge to kiss him all over. She kept dreaming about seeing him naked, kept imagining how he might look like shirtless, and she was really happy he more than lived up to her imagination. To her he looked perfect.

She raised her dazed eyes to look at him and saw an unfamiliar expression on his face. She thought he would look smug or cocky, maybe smirk knowingly, but his face was serious, solemn. She could feel his heart pumping underneath her palm and knew he was affected by this just like she was.

He didn’t know why he felt that way. He got undressed in front of girls hundreds of times before, but this somehow felt different. Maybe it was the fact she’d never done this before with any other guy, he was the first one she was seeing like this. Or maybe it was that reverent expression on her face when she reached out to touch him. He was a little apprehensive she might notice his scars he’s got over the years, especially the nasty one from when he was stabbed on the streets of his awful neighborhood. What if she sees that, and wouldn’t want to have anything to do with him? But no, she was looking him in the eyes, so trusting, so vulnerable. He inhaled sharply when she traced his abs. She was still looking in his eyes when she whispered “You’re beautiful.” That made his usual smirk appear and she blushed brilliantly.

“Why, thank you, Miss Gilmore,” the serious moment was broken and he got back to his usual teasing self. “You know how it goes, I show you mine, and you show me yours.”

She suddenly remembered her bra was undone, and he looked so hot, and also had seen tons of girls with much bigger boobs, and her insecurities came back. She hugged herself covering her front.

“Hey… Rory,” he reached for her and softly removed her arms from their position. He could feel her trembling. “You don’t have to do this, if you don’t want to. C’mere,” he pulled her closer into him and she wrapped her arms around his waist, hiding her face in the crook on his neck. The desire for him and her lack of confidence fought inside her head. She really wanted him to touch her, but was scared of his reaction to the way she looked.

“What are you afraid of?” he whispered softly, kissing her just below her ear. She once again wondered how he could read her so well.

“I… I’m not… What if…” she couldn’t finish any of her sentences.

“Shh… I just want to make you feel good. I want it so much…” he kept stroking her hair trying to soothe her nerves. “I want to touch you like you touched yourself that first time in D.C., the one you wrote about. Remember what you were thinking? That my hands would feel good around your nipples. I wanna show you just how good…”

She remembered the letter and her thoughts about him she had in the process. Finally, the desire won and she lifted her head to capture his lips in another kiss. He was so passionate, so giving. Every time he kissed her it felt like he was kissing her with his entire body. He pressed into her, his palms roaming over her back, slowly getting under her top. Soon she was breathless again and wanted nothing more than to feel him. He pulled away a little to unbutton her cardigan, his deft fingers working on each button methodically, increasing her anticipation. The folds of her shirt fell open revealing her loosely hanging bra. Jess gently pushed the top away from her shoulders and down her arms, the bra followed, and there she was. For a second there he stood frozen in place, looking at her, taking her in. Rory… her breasts weren’t too small or too big, just enough, perky, and her nipples were already hard, dark pink pebbles on her milky skin. She had a small brown freckle on the side of her right breast, and he knew in an instant that it’s going to be his favorite thing from now on. She fought the urge to cover herself when he didn’t say anything. But the look of complete adoration and fire in his eyes spoke more than any words.

He lifted his hand and traced his fingers over her collarbone down her breast softly, barely touching her, she held her breath. He gently flicked her nipple and it was there again, this amazing sensation she felt earlier, she couldn’t help but whimpered. The sound seemed to break him out of his revery and he attacked her lips again with a passionate kiss. She wrapped her arms around his neck and pressed herself to him. They moaned in unison at the skin-on-skin contact. He lowered her back on the bed and came to lie on top of her. Her hands traveled down his back, his muscles bulging under her touch. She was drowning in him, in the kiss, in the feel of his skin, in his taste and smell. She was completely lost to the outside world. There was only him. When he went down planting kisses down her neck to her collarbones she pressed harder into him savoring the moment. Her legs spread on their own accord, and he slotted between them naturally. He proceeded going lower, down her chest until his lips found her nipple, and she let out a loud moan. The sound startled her a bit. She didn’t even know she was capable of making such sounds at all. Jess didn’t think she would be a screamer. He pegged her more for a whining, whimpering kind, so her reaction to his actions pleasantly surprised him, even though he wouldn’t mind either way. He kept sucking her sensitive nub eliciting softer quieter moans out of Rory.

Her fingers were now in his hair and she seemed completely lost in the feeling. He covered her entire breast with open-mouthed wet kisses, and then moved to the other neglected one. She felt like this just might be heaven. What he was doing to her…. It was so wonderful, she was absolutely right about him, about wanting to try everything with him. She knew in that moment that he will definitely be her first. There’s no chance she could feel this way about anyone else.

“Jess,” she moaned, and it was the best sound he’s ever heard. He didn’t know if reaching into her pants would be pushing his luck at this point. He’s done that before, touched her pussy before he’s even seen her chest, but would it be okay to repeat the bus experience right now he wasn’t sure. His dick was painfully hard, but she didn’t seem to realize it was pressing into her thigh, too lost in lust he was inducing.

While he contemplated his next move, a knock on the front door came through her foggy brain. Someone was at the door. Oh God…

Rory pulled away from him, alarmed.

“Are you expecting anyone?” Jess asked.

“No, I’m not. It could be Lane though. Her schedule has been so hectic lately. I can’t keep up with her breaks from Mrs. Kim. I need to see who it is.” Rory answered sitting up. He passed her the cardigan silently. She hurried to button it up without putting her bra on as the knock repeated. Rory stood up from the bed and headed for the door, trying to fix her hair with her fingers hastily. If whoever asked, she could always say she took a nap after school. She opened the door to find Dean on the other side. He was holding a box in his hands.

“Hi,” he started.

“Hi… Dean.”

“I just thought I’d bring you this, you know, all of your things that I got over the years.” He nodded towards the box.

“Oh, okay. Thanks.” She tried to take the box out of his hands, but he wouldn’t let her.

“It’s pretty heavy. Lots of books. So, where should I put it? Kitchen?”

“Oh, it’s fine, just give it to me and-“

“I’ll just put it in the kitchen,” he tried to push through the doorway.

“No, Dean, it’s really not a good time right now, just give me the box.” She tried again.

“Why, is your mom home?”

“No, she’s not, but-“

“Listen, I also wanted to talk about what happened-“ he was looming over her, and she stepped back a little, which allowed him to cross the threshold, and he headed for the kitchen.

“Dean, it’s really not a good time-“

“Is there a problem?” Dean and Rory both looked back and saw a shirtless Jess leaning against the kitchen doorway.

“What the fuck?” Dean yelled. “Why is he naked in your house? Are you with him now?” He took a second look at Rory only now noticing her disheveled appearance. Her hair was mussed, and her cardigan was buttoned down wrong making one side longer than the other. “You said you didn’t wanna have sex with me, but you have no problem fucking him? I cannot believe you! You’re such a slut!” Rory gasped.

“Hey, watch it!” Jess warned.

“I can’t believe I came here to try and get back together. Tell me Rory, were you fucking him the whole time behind my back? Huh?”

“What? Dean, no!”

“You couldn’t hop into his bed fast enough!”

“Dean, stop, just stop!” Rory was on the verge of tears now, her face flushed.

“Listen, pal, you two are no longer together, and it’s none of your business what she does and whom she does it with. So why don’t you go back to flirting with the entire cheerleading squad and leave Rory alone.” Jess crossed his arms on his chest, his muscles becoming more prominent that way.

“Does Lorelai know about this?” Dean turned to Rory instead, ignoring Jess completely. She looked at him affronted. The audacity of this guy!

“Frankly, Dean, I’m with Jess on this one. It’s none of your business.” She crossed her arms over her chest too, if only to cover up the facts her buttons weren’t right.

“So, I take it she doesn’t. Interesting.” Dean had a nasty gleam in his eyes.

“So what, you’re gonna tell her? We’re not even together, and you still run to MY mom with your complaints. Unbelievable!” she cried.

“You can act offended all you like, Rory, but we both know she likes me more than him. And she’ll never like him, ever.” He spat.

“You know what, I don’t have to listen to what you have to say anymore. Thanks for bringing my stuff.” She pulled the box forcefully out of his clutch. “Have a good day, Dean. Goodbye.”

And once again he exited her house slamming the door shut with a bang. Rory’s legs suddenly felt weak, just like every time she had a confrontation with someone. That is why she never argued or fought with anyone. It made her feel sick and drained. She didn’t find any pleasure in scandals unlike some people, it wasn’t her way of blowing off steam. She kneeled to put the box on the floor and promptly collapsed next to it, her hands trembling, cheeks covered in red blotches, her guts twisting.

“Hey, you okay?” Jess kneeled in front of her, swiping her cheek gently with his thumb. “What a jerk, to attack you like that.”

“I’ll be fine,” she answered, her voice shaking. “God, this outburst kinda makes me thankful we’re not together anymore. I’m sorry he ruined our time.” She lifted her eyes to look at him, but he didn’t look annoyed, just concerned.

“Don’t worry about it.” He hugged her close and kissed her temple.

“You should probably get dressed. My mom would be home soon.”

“Yeah, I definitely don’t want her to find me in such a compromising position. After all, the bagboy was right about one thing, she’ll never like me the way she likes him. And being shirtless in your room unsupervised would definitely NOT earn me any brownie points from her.” He said bitterly.

“Hey, hey,” she stroked his cheeks. “Don’t let what he said get to you. I like you enough to compensate for my mom, alright?”

“If you say so,” he didn’t sound convinced.

“I do say so. I like you. A lot. So, you’ll have to deal with it, mister.” She smiled at him and pecked his lips.

“I’ll try,” he gave her a small smile in return.

If only it was so easy to believe.

Chapter Text

The next day Rory’s Harvard application arrived in the mail. She went to Luke’s for lunch after school and told Jess about it.

“So, what’s on your pro/con list for that one?” Jess asked filling her coffee mug to the brim.

“Oh, I worked it out a long time ago, I know what my essay subject would be and everything. I’m not nervous.” Rory beamed.

“Okay. What’s it gonna be about?”

“Hillary Clinton! She’s so smart and tough and nobody thought she could win New York but she did and she's doing amazing, and have you heard her speak? She's a great speaker, strong and persuasive with a wonderful presence, and even those suits of hers are getting better.”

“Huh,” was all he said with a raised eyebrow.

“What? You don’t think it’s a good essay subject?” Rory frowned.

“No, I’m just surprised, is all,” he shrugged.

“Why are you surprised?”

“Well, you’ve been talking about wanting to be the next Christiane Amanpour for so long, so I was kinda expecting you to write about her.” After seeing Rory’s pinched expression he continued. “But what would I know about application essays? Do what you think is right.” He pecked her on the temple and walked off to refill coffee mugs for other customers.

It got Rory thinking why she chose Hillary Clinton instead. When Jess came back to sit next to her, she was still contemplative.

“Hey, I didn’t mean to freak you out or anything. If you want to write about Hillary – do it.” She only pursed her lips.

“What’s on your mind, c’mon?” He nudged her knee with his.

“What about you?” she asked.

“What about me?”

“If you were applying, what would you write about?”

“I’m not applying.”

“But if you were?” she pressed.

“I have no clue,” he started getting fidgety. All these school talks really set him on edge.

“Oh, by the way, I’ve been meaning to ask you! Lane told me about a new English teacher in your school. She said she’s a New Yorker. Did you see her? Does she look like one?”

“Yeah, she’s my teacher as well.”

“Really?? How is she?” Rory’s eyes lit up in excitement. “Is she any better than Mr. Krepinski?”

“Anyone would be better than Krepinski,” Jess snorted. “Luke would be better than Krepinski. Even a bag of chips would be better than Krepinski.”

“Jess,” she admonished.

“What? I know you agree with me.”

“Well… Okay, maybe, he’s not the best teacher in the world, but I would never compare him to a bag of chips.”

“Maybe not out loud,” he quipped. She rolled her eyes, but he could see a flicker of amusement in her eyes.

“So, what’s she like?”

“I don’t know, seems cracked.” Jess shrugged noncommittally.

“How so?”

“For some bizarre reason she’s convinced I should take an AP English Literature and composition class, and she asked me to sign up for it,” he admitted reluctantly.

“What?” Rory’s eyes widened in surprise.

“Yeah, like I said – cracked.”

“Are you gonna do it?”

“Of course not,” he huffed.

“But why not? Jess, it’s an amazing opportunity.”

“Opportunity for what, I’m not going to college, it would be just a waste of time.”

“No, because it’s an opportunity to study something interesting for once! I got the list of books we’re gonna read for AP Lit, and they all seem so exciting! Some of them were on my ‘to read’ list for years, and I will finally have the chance to get to them. You’ve probably already read them before. I’d imagine you would have something similar on your AP list. Think of it this way, at least you wouldn’t be bored out of your mind in that class.” She smiled at him encouragingly.

“She said the same thing.”

“See, all the great minds think alike,” she smirked and tapped her temple with her index finger.

“I don’t know…”

“You have such a brilliant mind, Jess! Imagine coming across a challenging class where you can show what you’ve got. That AP teacher wouldn’t know what hit her,” she grinned. “And really, you have to go to school to graduate, and you would’ve read those books anyway, so why not get graded for something you would’ve done no matter what while you’re at it? It’s a win-win situation. Think about it.”

“You sound just like her.”

“Probably because it’s a pretty logical choice, and if she sees it like I do, then I already like her.” She said, and popped the last fry into her mouth. “Okay, I gotta go and study now. I’ll call you later, okay?” She stood up lifting her backpack.

“Okay,” he leaned in and pecked her lips in goodbye.

Jess kept working in the diner through the dinner rush, bringing orders from Caesar and serving customers, all the while thinking about what Rory have said. Even though begrudgingly, he had to admit, there was some logic in that proposition. Sitting through Krepinski’s English class was the purest form of torture. The way he talked about the books Jess has already read and loved was nauseating. He always came up with what seemed like the most moronic assignment ideas. They were most likely rather standard, but the way he interpreted them made Jess want to blow his brains out. As far as he could tell this Mrs. Wilson was far from dull, definitely a step up from Krepinski. Also he couldn’t really remember the last time he was genuinely curious about any school subject. This AP Lit class looked pretty stimulating. By the end of the shift he was almost convinced he will sign up.

~XXX~

The next day on the 2^nd of October, two days before the deadline of the AP student enrollment completion Mrs. Wilson heard a knock on her door followed by a head of gelled hair peaking inside.

“Mr. Mariano, how can I help you?”

Jess cleared his throat before speaking. “I’m here to sign up for AP Lit.”

“Oh, that’s great! Sit down please,” she started riffling through her papers to find the necessary ones. “I’m glad you decided to join. May I ask what changed your mind?”

“Well, I was offered an interesting class.” Jess offered.

“Then, you’re at the right place.” She smiled at him and gave him the papers to fill in.

When he left she couldn’t hold back a satisfied smirk.

~XXX~

A couple of days later Chilton was organizing a seminar for seniors called ‘The business of getting in’. Paris already managed to alienate the professor in charge, and told Rory about how all of his ideas and suits were outdated and asinine. Rory, for one, wasn’t having any of Paris’s complaints, as it was a useful seminar, and she was looking forward to it since the beginning of the school year.

Jim Romaine, admissions officer at Princeton University and Ivy-League college consultant, Rose Samuels, were invited for the panel to answer students’ questions about the applications. Paris asked the first question.

“Now, panel, you're addressing a group of kids just beginning the stressful process of applying to college. Question. What is the biggest mistake a person can make on his or her application? Mr. Romaine?”

“Well, forgetting to send it in would be the worst mistake, but perfunctory answers would be high on my list.”

“Explain,” Paris prodded.

“I'm talking about run of the mill responses, a lack of originality, particularly in the essay category. If I read one more over-adulating piece of prose about Hillary Clinton and her profound influence, my head will explode,” said Mr. Romaine. Rory froze at his words.

“I hear that. Sometimes a mistake like that comes from writing what one thinks an admission officer wants to read,” added Ms. Samuels.

“Big mistake,” Mr. Romaine chimed in.

“And sometimes it's just a lack of original thought,” Ms. Samuels continued.

“Just as big a mistake,” finished Romaine. All the while Rory was having an existential crisis, reeling, her stomach a lead weight, palms sweating. It was bad enough as it was, her chosen essay topic smashed to pieces by college consultants, but Paris just couldn’t not add her own five cents into the mix.

“Personal anecdote - when I was twelve and I was writing the first of my trial essays in practice for the day I'd write my real essay, I chose Hillary Clinton. Then I realized every braindead bint in a skirt would be writing about Hillary, but it was good to clear the pipes. Now, what are some other mistakes?”

“Well, small thing, but if your printing is bad, that is something we don't like. If your extracurriculars and volunteer activities are too by-the-book, that says something we don't like.” Mr. Romaine continued.

“Yes, those activities should have a personality behind them, a focus, a direction. I've seen applications where the student has circled every activity listed. Again, you're trying too hard there. One can't be interested in everything.” Ms. Samuels agreed.

Rory fidgeted in her seat. They were basically talking about her, she felt like the most generic person in the world. How was it possible? She was dreaming about this moment since she was in pre-school. Turns out, she wasn’t special and talented at all, she was thinking just like every other applicant there is. What were the chances of her actually getting into Harvard this way? If she was just as stereotypical as everybody else? How can the most competitive and prestigious school in the country, in the world even, accept her if she was no different from anyone else? The voices of Mr. Romaine and Ms. Samuels sounded distant, like she was hearing through a body of water, her brain taken over by a surge of anxiety.

“They're the ones who've had college paraphernalia on their walls their whole lives.”

“Too hungry, it's a little immature.”

When Paris turned to her and Rory saw her lips moving, she wasn’t comprehending what she was saying. “Interesting, interesting. Rory, do you wanna ask a question?”

“No.” How could she, if her entire world just went to hell? She didn’t want to hear anything else about how her thoughts lacked originality. She didn’t want to ask any more questions, she wanted this seminar to be over, she wanted to go home and freak out to her mommy. She wanted to curl into a ball under a blanket and pretend this whole thing never happened, if only for a moment.

“What?”

“No, thank you.” Rory repeated.

“Okay. So, how early should a student get an application in?” Paris addressed the panel once again.

“By the due date. Earlier makes no difference. It's a complete myth that there's a benefit to be derived from early admission. I do think it's important to talk about the interview process. I believe it's an opportunity to weed out the hyper-intense candidate.” Mr. Romaine went on.

The rest of the seminar went by in a blur. Rory couldn’t focus on anything else apart from the fact she’s apparently not going to Harvard.

~XXX~

After school Rory went to her grandparents’ house for dinner where she met with Lorelai, and they freaked out together in Richard’s office. Then after dinner she still wasn’t any closer to being calm. When she came home she called Jess and asked him to meet her on the bridge. She needed to talk to him about it.

When he plopped down next to her on the wooden planks she leaned into his side, and he wrapped his arms around her. She instantly felt better. There was something about his presence that soothed her.

“What’s up?” he asked her.

“I’m not getting into Harvard.”

“Whoa, what happened?” he squeezed her tighter.

“I have no original thoughts. My Hillary Clinton essay will be just like every other girl’s Hillary Clinton essay, I have the same GPA as everybody else, and give perfunctory run-of-the-mill responses.” Rory started to get fired up again, Jess could feel she was shaking in his arms.

“Slow down a bit. Where did you get all that crap?”

“We had a seminar today with Ivy League school consultants. When they listed all the most common mistakes the applicants make, they could’ve just said my name outright, because everything there is to get wrong about applying to college, I have done! I chose the most generic essay topic, I’m interested in too many things, and I have college paraphernalia on my wall, which apparently makes me too hungry and immature. I’m losing it!” she was almost hysterical.

“I can see that.”

“Apparently, I have zero original thoughts and my application will be just like everyone else’s application, it won’t stand out and I’ll never get into Harvard!” She went silent for a few minutes, while he kept stroking her hair, trying to calm her down. Finally, he said.

“Hey, can I ask you something?”

“Sure,” she sniffed.

“Why Harvard?”

“What do you mean?” she lifted her head to look at him.

“Why do you wanna get into Harvard so bad?”

“As I’ve told you, I’ve been dreaming about it since I was a kid.”

“Yeah, I know,” he cut her off. “But I mean, why Harvard specifically? I mean, as far as I know, kids don’t even know what Harvard is, not to mention want to apply when they grow up. Also, there’s what, like eight Ivy League schools in the country? Why Harvard? Why not Brown, or Columbia, or Yale for that matter? That one is even in Connecticut.”

Rory froze. This question, albeit so simple, for some reason sent her into a stupor. Harvard has been a dream for so long, she couldn’t even remember how it started.

“Well… I don’t know… I mean my mom and I used to dream about it, talk about it, we liked to imagine how it’s gonna be like when I get in,” Rory tried to answer.

“Sooo…. Whose dream is it then, yours or hers?” Jess asked.

Rory pulled away affronted. “Hey! It’s my dream, has been since forever.”

“Okay,” he said simply.

“It is!”

“Okay, I’m not questioning it.” He raised his hands in surrender.

She fell silent. After several minutes Jess dared to ask her another question.

“How did you decide you wanted to be an overseas correspondent?”

“Um… When I was little my mom left my grandparents and moved to Stars Hollow. She found a job at the Inn as a maid. We had no place to live, so Mia, the owner of the Inn let us stay in the potting shed behind the Inn. And since we lived at the same place as mom worked she used to take me with her on shifts when she cleaned the rooms. Often times she left me in the maids’ restroom, I was pretty quiet and self-sufficient. Give me a book, and I won’t bother you for hours kinda kid.” She chuckled at the memory. “So, there was this guy, Lorenzo, he was working at the Inn back then, and he liked to spend time in maids’ room because there was a TV. He used to watch CNN all the time, said he liked to stay current. Christiane Amanpour was on the screen a lot, and I was always mesmerized by her reporting style, and her passion, and bravery, and honesty. I thought she was so cool. I guess, that’s when it started.”

“Where did Christiane Amanpour graduate from?” he asked.

“University of Rhode Island.”

“So you don’t have to be an Ivy League school graduate to be a good journalist.”

“What’s your point?” she frowned.

“My point is, if you’re so freaked out about Harvard, have you thought about back-ups? Just in case?”

“Wow, look at you, Mister ‘I’m not applying to college’ actually giving a sound college advice.” She looked at him in awe.

“What? I hear that’s what people do. You know, not to put all the eggs in one basket or whatever.” He shrugged.

It reminded her of something someone else told her a while back.

“You know, I didn’t tell you about it, but when I was in D.C., our program included some college tours. And we went to Georgetown University. Our guide was a journalism major. Her name was Stephanie, and she was pretty cool, maybe too energetic for my liking, but she was a good guide. And she was talking about her college experience, and a lot of it stemmed from her major. And… I kinda liked it there… But I didn’t dwell on it, because, well, Harvard. After the tour we could ask questions, and I got a chance to talk to her. And she said something to me, that I brushed off at the time, but now it makes me think about it, and maybe she was right…” Rory trailed off.

“What was it?”

“When I told her I wanna go to Harvard, she asked me where else I was applying, and when I said just Harvard, she looked at me like I was the biggest idiot. And she said the same thing, about putting all the eggs in one basket. I remember I felt offended by her audacity, as it didn’t even occur to me that I might not get in, you know? Ever since I was a kid my mom encouraged my Harvard dream, and I always had good grades, and I liked reading, and I thought, I don’t know… It sounds so stupid and conceited now…”

“What?”

“I thought that I was… well…. Special, that I would get into Harvard just because I really want it, like it’s my destiny and it’s the only outcome there is… But now… Seeing as I am not special at all, and all my thoughts and ideas are so generic, I feel so stupid and naïve! Why haven’t I thought about back-ups? I was so sure I’d get in!”

“I’m no expert, but I think you still have time to pick out some back up options. And work on your Harvard application to improve it. At least now you know what to watch out for.”

“I guess you’re right…” she sighed.

“So, you know at least one school that has a journalism major – Georgetown.”

“Yeah, Georgetown is pretty cool…” Rory contemplated.

“What’s more important to you, the name of the school you go to, or the profession you acquire in the end?” Jess asked. He was genuinely curious about her reasoning behind wanting to go to Harvard since she told him about it.

“I… I don’t know… I haven’t thought about it like that, I guess…” Rory hugged herself feeling exposed somehow. “I feel like my whole world turned upside down today. I don’t know what to think anymore… and I don’t know how to tell my mom about it. She’s only gonna freak out and say I have to get into Harvard, and I will, because I’m special, like she always does… but… sometimes, I can’t help but feel like… I don’t know how to explain it, it’s gonna sound really cruel…”

“What is it?”

“I mean, she didn’t go to college herself, because she was pregnant with me. She dropped out too soon, and… well, she doesn’t know what it’s like to apply, to write this personal statement essay, it’s something ephemeral to her, you know? Like it’s just something that other people do, that she’s heard about, but haven’t done herself, so she doesn’t realize how grueling the process can be. Of course, raising a child at sixteen was not less grueling, but it’s still kinda different, you know? God, I’m a terrible person. I shouldn’t think something like this about my mom, much less say it.” She berated herself.

“It’s true though. Parents are not always right, and they don’t always know what to do. Don’t feel bad about it.” He reassured.

“But I do! I do feel bad! She’s my mom! I love her to pieces. She’s my best friend in the whole world. But sometimes I can’t help but think that maybe she doesn’t have all the answers. But I don’t wanna disappoint her, I don’t wanna fail her. So if I don’t get into Harvard, it’s like this major disappointment, the biggest failure I can possibly be. I can’t NOT get in. It would be like her not terminating the pregnancy and running away with me would be in vain. What if I don’t get into Harvard, Jess?”

“Look, I’m not the biggest Lorelai fan in the world, but I’m pretty sure she won’t love you any less. Despite all her flaws, she’s a decent mom, she loves you, Harvard or no Harvard.”

“I can’t even imagine telling her about back-ups.”

“Then don’t.” Jess shrugged.

“I can’t do that. We tell each other everything.” Rory objected.

“Oh jeez. I don’t know then. I have absolutely no experience in this parent-kid relationship department, so I don’t know what to say.”

Rory sighed.

“Okay, can we please not talk about it anymore? I don’t think I have the mental capacity for it left for today.”

“Okay,” he nodded and pulled her closer. She burrowed into his side, and they kept sitting there in a comfortable silence.

~XXX~

The following Sunday found Rory in Darren Springsteen’s house, Harvard alumni class of ’74. Headmaster Charleston was kind enough to arrange this meeting for Rory and Lorelai, so that Rory could ask him anything she wanted to know about the application process. On her quest for finding a bathroom, Rory stopped outside a bedroom on the second floor when she heard music inside. A girl rushed past her and went into the bedroom. After a brief discussion about Tom Waits and bunny ears Rory found out she just stumbled upon Carol, the third daughter of Mr. Springsteen, the one he and his wife didn’t feel like talking about.

“Are they on straight?” Carol asked after putting on the bunny ears for her costume she needed for her next job.

“I think so,” said Rory.

“Good. Who are you?” Carol asked, as if just now noticing she was talking to a stranger.

“I'm sorry, I'm Rory Gilmore.”

“You're one of the Harvard bound?”

“Yeah. At least, I hope so,” Rory fidgeted.

“Oh, trust me, you are. You've got that really good, straight, shiny Harvard hair,” said Carol pulling on her bunny costume. “Zip me up?” she turned her back to Rory,

“Can I ask you what exactly you are dressing up like this for?”

“Morgan Tanner's fourth birthday party.”

“You're kidding,” Rory stared back at her incredulously.

“Nope, this is my fifth birthday party this week. Great tips, all cash, and of course, there's cake.”

“So you're a waitress and a birthday bunny and you go to school. That's pretty amazing.” Rory said.

“I don't go to school.”

“Oh, sorry, I just assumed. I mean, your family…” Rory blushed.

“My brother and sister got stuck on that conveyor belt. I, however, escaped somewhere around the eleventh grade, thank God.”

“Huh,” Rory didn’t really know what to say.

“Oh, hey, but no offense. I mean, that's just me. If you like being on the conveyor belt, then good for you.” Rory couldn’t help but wonder, if that was what Jess thought about the whole education thing.

“I'm not on the conveyor belt,” she objected.

“Okay.”

“I'm not. I want this. I've dreamt of going to Harvard since I was a little girl,” Rory said somewhat indignantly.

“Yeah, a lot of four year olds dream of that. It comes right after meeting Harry Potter.” Carol noted sarcastically.

“Hey, I am not gonna justify myself to someone with a tail,” Rory tried to sound confident, but Jess’s word from the other night came to mind. Kids don’t even know what Harvard is.

“You're right, I'm sorry. It's just that around here the Harvard brainwashing starts in the womb. If you were to tell either of my siblings that there was another life choice outside of the Ivy League, I think their khakis would wrinkle.” Rory felt strangely offended by this. Was she brainwashed from the womb as well? Did her mom subconsciously try to ingrain the idea of Harvard into her head from the start?

“Well, maybe they really want it,” Rory tried to argue.

“Nope, my parents want it and they wanna please my parents. Have you seen a carrot?”

“Don't you wanna please your parents?” Rory questioned Carol.

“Yeah, but not at the expense of finding myself.” Somehow this random run-in with Carol was giving Rory more food for thought than all of the girl’s dad’s quiz questions did.

“Or your carrot.”

“You gotta have your carrot. So, tell me something, Harvard hair, how bad do you wanna please your parents?” Carol looked at her shrewdly.

“My mom, and really bad, but it's not hard to please my mom. She's okay with anything I do. As long as I'm happy, she's good.”

“You're sure?” Carol raised an eyebrow at her.

“I'm very sure,” Rory said, even though deep inside she wasn’t so sure. She kept questioning her Harvard dream and her mom’s influence in it since that conversation with Jess on the bridge.

“Then you're lucky.”

“Yeah, I am lucky.” Rory trailed off.

~XXX~

A couple of days later there was a message left on the Gilmore’s answering machine. Lorelai pressed ‘play’, and the room was filled with a Harvard alumni’s voice.

“Hello, Gilmores! This is Darren Springsteen, how are ya? I just wanted to let you know that I just finished going over Rory's records here, and no shock, they're perfect. Rory, you are tailor-made for Harvard. They're lucky to have you. As far as I'm concerned, you should pack your bags. I'm gonna tell all this to the people in admissions and I'll give your headmaster a call as well, so take care and we'll talk again. Bye-bye.”

Lorelai looked at Rory with barely concealed joy. “That's fantastic, honey!”

“Yeah.” Rory said meekly.

“You're in.”

“Well, not officially.” Rory tried to object. She didn’t want to get her mom’s hopes up.

“He said pack your bags.” Lorelai continued excitedly.

“Yeah, cool.”

“So what are you up to today? You have, uh, newspaper stuff to do, right?” it was clear Lorelai wanted to hang out with her, but Rory didn’t feel like it. There was a strange feeling gnawing on her insides, like something wasn’t right, like she was missing something.

“Yeah, a ton. I should better go work on it now,” Rory motioned her head in the direction of her room.

“Okay,” Lorelai wilted.

“I’ll see you later?”

“Sure,” her mom nodded.

Rory entered her room and leaned onto the closed door. Just because Mr. Springsteen said she was basically in, didn’t mean she would actually get into Harvard. It was the best university in States that admitted only about five percent of all the applicants after all. Also, the thought about back up schools already planted its seeds in her mind, and she couldn’t stop thinking about it. What if there was more out there than Harvard? Something more exciting than Ivy League? Something where she could thrive without killing herself over assignments?

She went to her desk, opened up her laptop and typed into the search engine ‘best journalism schools’.

Harvard was not on the list.

Chapter Text

Monday morning of October 7^th found Jess waking up five minutes before his alarm with a heavy feeling of uneasiness settled in his stomach. Today was supposed to be his first day in the new AP class, and he was surprised it made him feel this way. He never cared much about his studies, anxiety wasn’t his usual companion in the school related situations. It was reserved more to his home life. Is Liz going to be sober this time when he returns from school? Was it a good idea to go home now, or maybe he should’ve stayed longer at Vito’s instead? The auto repair shop he used to work back in the day was often times a lot safer place for him to be than his own home despite the seedy characters that used its service. What new guy was waiting for him in his living room while Liz was all over him, with a beer bottle in hand? But school, he was never nervous about that. He’s been a new kid way too many times to care at this point. He was pretty introverted by nature, so the desire to make new friends everywhere he went wasn’t the driving force behind his every action. He was perfectly content as long as he wasn’t bothered and had a good book in his back pocket.

What made today so different? What made him care?

Jess shuffled reluctantly through his morning routine, stalling for some unknown reason, yet he was still one of the first ones to show up in class. Maybe it was due to the fact this school was located right across the square from the diner, hence it was nearly impossible to be late, unless you really tried.

The classroom was slowly filling in, while he was hiding behind a book as usual. He finished Slaughterhouse five a long time ago, so now it was Mary Shelly’s Frankenstein, which was of course a re-read, but it was on this class study plan, so he decided to freshen up his memories of it.

Mrs. Wilson came in with a cheerful smile on her face. She was wearing another pant suit, and she seemed excited. Jeez.

When the bell rang and everyone was seated, Mrs. Wilson addressed the class.

“Good morning everyone! I’m happy to welcome you all in this Advanced Placement English literature and composition class. You’ve already been given the lesson plan when you signed up, so I hope you got acquainted with it by now. As you can see, it’s a pretty demanding schedule, which will require a lot of work. But I am fully confident that all of you would be able to meet the expectations and requirements of this class. In the end of the year you will have the opportunity to take the AP exam, which in case if you pass with a high score, will add one point to your GPA. Also, most colleges will award college credit for your successful completion of the examination. So I suggest you all to try your best, because it could give you a serious benefit.” She looked around the room. All of the students were listening attentively.

“As you can see, it’s a rather rigorous course that requires a lot of reading and writing. All the reading should be done beforehand. Make sure to make reading for this class your everyday routine. Without it you won’t be able to participate in class discussions, and that makes up a portion of an overall grade. This course also requires a lot of writing, both in class and at home. You are expected to complete all your assignments on time. We are going to have different types of projects, including group projects. For the final project of the course we’re going to be working on a short story. While you don’t have to have all the characters and plotlines figured out right now, keep in mind that you will have to do it in the next semester.” Mrs. Wilson paused gauging the reaction.

“Also, keep in mind that such an intense schedule requires attendance. So, if you have any part time jobs or anything else, make sure to plan your time accordingly. A missed class would be rather hard to compensate for. I don’t mean to sound like a monster, as I know that we all have our private lives and other obligations, but I’m warning you beforehand. Plan ahead. Please note that absence from class does not excuse you from turning in pre-scheduled assignments by the day they are due.” She clasped her hands together and smiled. “With all of that in mind, I want to point out that AP Literature and composition is my favorite class to teach, so I hope we all are going to have a great time together and learn something from each other, that we all going to benefit from in the end.” Some of the students smiled back at her. She really did seem enthusiastic.

“Now that we got all of that out of the way, I want to start with our first topic. I know it’s a little unconventional, but I want to start our very first unit with a group project. It’ll help you get to know each other better, make new friends from the get go, and adjust smoothly. At the very least, you would have someone to talk about me behind my back.” That earned her a few chuckles from the students. “Now, since there are precisely twenty-one of you, I’m going to divide you into nice little groups of three in the alphabetical order. When I call your name, raise your hand so that your groupmates would know who you are.” She started listing off the names. Jess was listening carefully.

Finally, she went with “Andrea Madsen, Jess Mariano and Scott McNally. Are you all present?” Mrs. Wilson looked up from the paper, and all three of them were raising their hands. Jess looked at his future partners. Both of them were sitting in the front row like total nerds. When the teacher finished dividing the groups, she prompted them to rearrange their desks to be able to sit in small circles to meet their partners. Jess took his stuff and went to the front of the room, since both Andrea and Scott already arranged the furniture for them. He plopped on the free seat.

“Hi, I’m Andrea, but everybody calls me Andy.” The girl was really pretty, she had long blonde hair that was pleated into a side braid. Her eyes were blue, but a shade darker than Rory’s, Jess noticed. She looked athletic, and she was wearing a plain blue hoodie with a Nike logo on the front, a pair of jeans and sneakers, nothing extravagant or revealing. She seemed outgoing and smart.

“Uh, nice to meet you, Andy.” The guy, Scott McNally, said. “I’m Scotty.” He gulped nervously. He looked like a typical nerd. Jess couldn’t even believe such prominent archetypes still existed. He looked like a caricature, almost cartoonish. He was scrawny and awkward, constantly fixing his big glasses that kept sliding down the tip of his freckled nose. When both Andy and Scotty looked at him expectantly he just said “Jess.” They nodded at him.

“Okay, so, Mrs. Wilson said that we have to meet up after class to work on this thing. I suggest we do it at someone’s house, because this school’s library is useless. Any suggestions?” Andy took charge. She seemed like the type, Jess figured. Come to think about it, he remembered seeing her a few times in the halls with a sports duffle, she must be on some team of something.

“Uhh, my room is kinda small, and my mom works from home, so it might not be ideal.” Scotty stuttered.
“I live above the diner, I don’t even have a room.” Jess found himself saying.

“Okay, my house it is then.” Andy concluded.

“Won’t your parents mind two guys in your room?” Scotty asked. ‘Jesus, what kind of environment he was raised in?’ Jess thought.

“Don’t worry, my parents are pretty chill. Also, I have three older brothers who have a lot of friends, so my parents are used to all kinds of boys hanging around the house at all times, it’s no biggie.” Andy shrugged. “Let’s exchange numbers and emails and set something up. Sound good?” Jess and Scotty nodded.

~XXX~

Later that day Rory plopped down on a stool at the diner counter with a groan. Jess already filling a mug with coffee for her just raised his eyebrows. Rory lowered her head on the countertop and groaned again.

“Who peed in your cornflakes?” Jess asked setting a mug in front of her, the divine smell of coffee wafting in her nostrils.

“Paris is driving me nuts!” She exclaimed after taking a huge gulp.

“What else is new,” Jess chuckled.

“She’s gonna drive me to an early grave, I swear to God! And this stupid feud they have going on with Francie about the hem lines is ridiculous. When I signed up for a student government I didn’t expect it to be so… so… high school!” Jess realized this amount of frustration would not be illuminated with just coffee, so he wrote an order for a burger with chili cheese fries for Ceasar and put it in place.

“I’m sorry, did you say hem lines?”

“Yes! Can you believe that? So this senior class president, Francie, wants Paris to approve the shortening of the girls’ uniform skirt length. Paris, of course, doesn’t want that. And Francie didn’t think of anything better than to yank me into the girls’ bathroom to have ‘a talk’ mafia style, trying to blackmail me to talk to Paris about it. Like, who does she think she is?”

“Isn’t Chilton supposed to be a serious private school where everyone’s going for Ivies, not for more leg?” Jess looked at her in disbelief.

“You would think that! But no. And you haven’t even heard about Louise yet,” Rory huffed.

“What’s up with her?”

“She’s my classmate who wants to have sex with pretty much everyone who has a penis. And a pulse.” That made Jess chuckle.

“Ah, those private school girls. I knew that fetish did not come from nothing,” the smirk playing on his lips made her blush, no doubt making her remember about them recreating the said schoolgirl fantasy on a bus a while ago.

“My point is,” she cleared her throat. “I did not expect this whole vice-presidency to come to this. Anyway, how was your day?”

“No mafia interactions for me,” he shrugged and placed a plate with the food in front of her.

“Don’t think for a second a burger can distract me from your evasive answer, mister. C’mon, Jess, tell me. Please? I really wanna know.” She made the best puppy eyes at him she could master. Of course, he caved in.

“I had my first AP class today,” he said with a sigh. Rory lit up immediately.

“Really? You signed up after all? Oh my God, that’s so great, Jess! I can’t wait to hear all about it!” Her eagerness was contagious, and he felt the urge to tell her everything, to spill every single little detail. That never happened before. No one was really interested in him enough to want to listen to even the serious stuff, not to mention the mundane details.

“We got assigned a group project right off the bat.” He shrugged like it was no big deal, but Rory kept looking at him with rapt attention munching on her fries.

“And?” she prodded.

“I got paired up with two people.”

“Oh, oh! Maybe I know them. Who were you partnered with?”

“Andy Madsen and Scotty McNally.”

“Hmm…. I think Andy was on a girls’ volleyball team, or something like that. But she had good grades, seemed nice. And I remember Scotty. We shared a chocolate bar in a science lab in middle school once. He’s really smart and sweet. But he was bullied for as long as I can remember by Chuck Presby and his goonies.” Rory contemplated.

“Huh,” Jess filed that information for later.

“Did you like the class?”

“It was alright. Too early to tell, I guess.” Jess shrugged again, and it seemed like he wouldn’t add anything else. Rory decided she would ask him again later, after he had more classes.

“Hey, so, listen… Tomorrow is my birthday. And since it’s a weekday my mom decided to throw me a little party on Saturday, but apparently she didn’t notify my grandma in time, and she got really pissed because she and grandpa already got some kind of an important trip booked for the weekend, so grandma kinda shanghaied me into having lunch with them tomorrow after school to celebrate. And later my mom wants to have a movie marathon, but I was thinking… maybe we could still meet up? Even for a little bit? To make out or something…” Rory asked sheepishly. She didn’t expect Jess to give her any presents because she wasn’t even sure he knew when her birthday was. She might’ve mentioned it once a long time ago, when he first moved to Stars Hollow, so she didn’t think he would remember. Also, the topic didn’t arise after they started dating, she didn’t know when his birthday was either. But she still wanted to hang out with her boyfriend on her birthday.

“To make out, huh?” he smirked. “Well, well, well, Miss Gilmore, do you only want me for my body?”

“Not only for it, but it’s definitely a plus,” she blushed, still not used to his teasing.

“Okay,” he said simply.

~XXX~

The next morning Rory woke up earlier than usual. She took a longer shower, did her make-up which she never did on regular days and put on a blazer part of her uniform that she really liked. It was dark blue and brought out her eyes a lot better than a grey cardigan. She couldn’t believe she turned eighteen today. Lorelai of course, sneaked into her room in the wee hours of the morning to rehash all the colorful details of her giving birth to Rory. The tradition never stopped, even if Rory could recite this story in her sleep by now.

They went to the diner together, both in a cheery mood. When they entered Lorelai immediately noticed a table in the corner with balloons floating above it, tied to a chair with a golden string, and a brown cake with two empty mugs next to it. Her heart melted. Luke seemed to care so much about her kid.

Rory greeted him happily and he wished her a happy birthday, nodding towards the table with a cake, informing her it was a coffee cake no less. She thanked him clapping her hands and went straight to it. Lorelai paused for a moment.

“Thank you, Luke. For doing it for Rory. It means a lot.” She said with a warm smile.

“It’s not a big deal,” Luke tried to shrug it off, but she placed a hand on his forearm and squeezed.

“It is a big deal, and we both appreciate it so much,” her eyes shone with something sincere and bright, Luke thought that maybe, just maybe there’s hope for him yet.

As soon as Rory sat at the table, her mug got filled with coffee by Jess, who seemed to appear out of nowhere. She turned to look at him and smiled at how cute he looked.

“Hi,” she whispered.

“Hi. Happy birthday,” he leaned in and kissed her on the lips. It was a sweet closed mouthed kind of kiss, both of them too aware of the audience. “Can you come out for a second after you finish here? I wanna give you something.” He fidgeted awkwardly, and Rory realized he was nervous.

“Okay, color me intrigued,” she smiled. The moment was interrupted by Lorelai, who came to sit next to her daughter.

“Jess,” she said in greeting.

“Ma’am,” he said just to mess with her. She glared at him, but he was already off to refill coffee for the others.

About fifteen minutes later they were both done with their pieces of cake. Lorelai kissed Rory on the forehead and rushed to the Inn. That left Rory looking around the diner, searching for Jess.

He came up to her from behind and leaned in, whispering in her ear “Come out the back with me.” She stood up and they both headed for the door that led to the back alley behind the diner.

As soon as they were outside, Jess attacked her lips with a searing kiss, pressing her back against the wall. She moaned into the kiss and her arms automatically went up to wrap around his neck. She could spend all day like this. But he slowed down the kiss and pulled away.

“Hey, happy birthday.”

“You said that already,” she smiled.

“I know. I have a present for you.” He said somewhat anxiously.

“Mmm, what is it? Is it as good as this kiss?”

“You think it was a good kiss?” he smirked, leaning in for more, planting an opened-mouthed kiss on her neck. Her breathing hitched.

“Oh yeah, so good,” her eyes closed and head fell back, revealing more skin for him to maul at. He kept caressing her neck for a bit before pulling away again.

“I hope you like it,” he said pulling something out of his back pocket. He gave her a shoddily wrapped rectangular package, which looked suspiciously like a book. If it was one, it was already a great present in Rory’s opinion. “Open it.”

She took the present and unfolded the paper. Inside she found a copy of The Fountainhead. She opened the book and riffled through the pages, seeing that the margins were filled with his messy handwriting. She looked up at him in awe. “You finished it?”

“Well, I promised you I’d give it a try. I had. Thought I’d put some notes in the margins for you. And don’t you ever make me read it ever again.” She laughed at the last part.

“Still not a fan?”

“Not in the slightest.” She then noticed there was some paper tucked in between the pages in the middle of the book. She opened it there and saw what can only be tickets to a concert.

“You got me tickets to Distillers show?” she asked in awe. “How did you get those? Weren’t they sold out?” He knew she liked the band, and when he saw they were having a show in Hartford on November 2^nd he just had to buy the tickets for her birthday. Even if it took tipping the guy at the club they were supposed to play to sell him the tickets he knew were reserved for last minutes sells.

“I have my ways,” he said. “Will you go with me?”

“Of course! Oh my God, Jess! This is amazing!!” she shook his shoulders in excitement. “Thank you, thank you, thank you!” She jumped a little before launching herself at him and kissing him passionately. It was truly an amazing gift, the book and the tickets! As cute as Dean’s bracelet was, it couldn’t even come close in comparison. Their make out session picked up from where it started until Rory suddenly pulled away.

“Crap! What time is it? I’m gonna miss my bus.” She took his wrist in her hand and turned it to look at his watch. “Damn, I really have to go. I’ll call you about tonight, okay? Thank you again, this is the best gift ever! Thank you!” she pecked his lips again, and again, punctuating each thank you with a kiss.  He couldn’t hide the tender smile. Finally, he squeezed her ass and nudged her away from him with a “beat it.” She beamed at him and stormed off back into the diner to grab her things and rushed to the bus stop.

~XXX~

Jess met Rory at the bridge later that day, after she returned from Hartford.

“So, how was the lunch?” he asked.

“It was kinda nice, I guess. Grandma gave me pearls.” Rory said burrowing into Jess’s side.

“Huh,” he wrapped his arms around her.

“Yeah, she said as I’m of age now, pearls are an appropriate and necessary girt for any young lady.”

“Okay.”

“And grandpa gave me a check and the second edition of Anna Karenina.” Rory added. He could tell by the tone of her voice that she liked the book a lot more than pearls.

“Cool.”

“Hey, I’ve been meaning to ask you, how did you know when my birthday was? I mean, Luke making me a cake and balloons would’ve been a giveaway, but you bought me tickets to the show, which should be bought in advance if you want a chance to actually get them. So, how did you know?” she looked up at him.

“You told me that last year, when you were paying for your burgers and some kid had a birthday hat on his head. You told me how cops shut down your party and the clown got arrested.” He shifted uncomfortably.

“And you remembered that?” she stared at him in awe. “I can’t believe you remembered that!”

“Well, it was a pretty interesting story. Not every day you hear about the cops shutting down an eight-year-old’s birthday party.”

“Wow, now I feel bad.” She wilted.

“What, why?”

“Because I don’t know when your birthday is. And we’ve know each other for a year! What kind of friend was I to you, to never even ask you about your birthday.” She looked really defeated with her head down and her hair falling over her face.

“Hey, it’s no big deal. It just never came up,” he rubbed her shoulder trying to soothe her.

“So, when is it?” Rory looked up at him.

“August 8^th.”

“Oh wow, we have the same date for our birthdays, that’s so cool!” She beamed at him. “You’re exactly two months older than me.” He just pecked her forehead.

“So… I already told you about my mom throwing me a birthday party this Saturday, and I know it’s a pretty short notice, and you’re probably busy, but I really want you to come.” She looked at him expectantly.

“Rory…” he sighed. “Your mom, and all of her friends, and me in the SAME room… I don’t think it’s a great idea.”

“But Jess, you’re my boyfriend now. She will play nice, I promise.” She made her puppy eyes at him again. Damn it.

“Do you really want me to come?”

“Of course I do! You’re my boyfriend, and I really want to have my boyfriend at my birthday party.”

“Well, I’ll come, but I can’t guarantee your mom won’t blow up at me.”

“I think as long as you don’t steal any beers, it’s gonna be fine,” she teased. “Besides, if it becomes really truly unbearable, you can always hide in my room and read.”

“Okay then,” he agreed. “Now, earlier you mentioned something about making out?” he smirked at her.

“Oh God, yes please!” she giggled and turned into him to kiss him properly.

~XXX~

Finally, Saturday came and Lorelai was busy decorating the house for the party. Without Emily and Richard’s presence looming on the horizon it promised to be a great Stars Hollow event, Gilmore style and everything. Lorelai thought it would be so fun, since she went all out on the decorations and food, which Sookie was currently making in the kitchen. Today promised to be a great day. Until Rory came to talk to her, that is.

“So, mom, I invited Jess to the party, and I wanted to ask you to be nice to him. Give him a chance. For me. Please?”

“You invited Jess?” Lorelai was thinking of a way to lift her jaw up from the floor. For some reason, it didn’t occur to her that her daughter seeing a new guy she didn’t like would also imply she would invite said guy to her party.

“Well, yeah, he’s my boyfriend, so of course I invited him.”

“Like you invited Dean last year.”

“Yeah…”

“Oh…”

“Mom?”

“Huh?”

“Why are you acting like this?”

“Like what?” Lorelai tried to fake a cheery tone.

“Like I invited a mass murderer to my party?”

“Well, you kinda did,” Lorelai muttered under her breath keeping the fake smile.

“Mom!” Rory cried.

“Well, what?”

“I don’t wanna fight you on this, on a day of my party no less. I’m just asking you to be civil with him, that’s it. Promise me?” she inquired urgently.

“Fine, I will,” Lorelai huffed. “As long as he’s nice too. If he’s acting out, I’m making no promises in that case whatsoever.”

“He will be nice. And thank you.” Rory nodded. When she was on the way to her room the phone rang. “I’ll get it,” she called out to Lorelai and picked up the device.

“Hello.”

“Hey,” she heard the familiar voice and smiled. She sneaked a look at her mom noticing she was turned the other way, and went to her room, closing the door behind her.

“What’s up?” she couldn’t keep the smile off her face and it showed in her voice. Their relationship was still so new, it made her giddy every time he called. There was just something about hearing him on the other end of the line.

“Not much. Just wanted to tell you that I might be a little late, Luke’s making me work the lunch shift.”

“Oh… But you’re still coming, right?”

“Yeah. Also, I wanted to make a request,” he continued.

“A request? What kind of request?” she sounded intrigued.

“Yeah, wear a skirt,” she could definitely hear him smirking.

“Why?” it made her blush for some reason.

“You’ll see,” the promise in his voice made a flock of butterflies erupt in her belly.

“Okay, I’ll see what I can do,” she replied a little breathless.

“Please do,” she heard some noise through the phone. “I gotta go. See you tonight.”

“See you.”

Now she really needed to work on her outfit. Better start now.

~XXX~

The party was in the full swing when Jess showed up. He slipped in the house quietly feeling awkward and out of place. He looked around noticing Rory in the center of the living room opening up her presents. She was wearing a sweater with the zipper in the front and a skirt he hasn’t seen before. He smirked in satisfaction.

“You should at least say hi, you know. It’s rude to sulk in the corner,” he heard a voice behind him say.

“Lane,” he nodded.

“Jess.”

They both shifted uncomfortably.

“So…. You’re dating my best friend now…” Lane started.

“Seems like it,” Jess quipped.

“Just so you know, if you ever hurt her, I’ll whoop your ass. And don’t let my small statue deceive you, I know stuff.”

“Okay,” Jess raised an eyebrow at her. Why was everyone so convinced he’s going to hurt her? He wanted to be with her since the first moment he saw her. Why would he hurt someone who he dreamed about for so long?

“Glad we understand each other.” Lane nodded. “Now, that we’ve got that out of the way. Rory told me you got her tickets to Distillers as a present. That’s so freaking awesome! I wish I could go to something like that. I bet it would be epic!” she rambled.

“It will,” Jess said.

“You’ve seen them before?”

“Yep, back in New York,” he confirmed with a nod.

“Oh my God, you’re like my new hero. Tell me absolutely everything!” Lane’s eyes lit up with almost manic excitement.

But before he could say a single word Rory noticed him and squealed “Jess!” Everyone turned to look at him. “You came!” She looked elated, which could not be said about the rest of the guests. Except for probably Miss Patty and Babette, who leaned closer expecting a new juicy piece of gossip.

“Of course I came,” he mumbled. Uncomfortable under everyone’s gaze.

“Come here, we’re about to eat the cake!” She pulled her arms out towards him inviting him to join her on the floor next to the coffee table, where all the presents were located. Lane gently pushed him towards Rory and followed.

“Help me put the presents away, Sookie is about to bring out the cake,” Rory asked Lane and Jess eagerly, and they helped her clear the table. Then Lorelai switched the lights off and Sookie came out of the kitchen with a huge cake with a whole bunch of candles. All of the guests started singing ‘Happy birthday’, and Miss Patty even hit a high note at the end, which made everyone laugh and applause. Rory was ecstatic. All of her favorite people AND a cake! What could be better.

“Make a wish, Hon,” Lorelai said when Rory leaned in and blew all of the eighteen candles out in one go. Everyone cheered and whistled in encouragement. Rory was beaming. Jess has never seen her so beautiful and happy, she was captivating, he couldn’t look away. She turned to him and got lost in his warm hazel eyes for a moment, which was soon broken by her mother and Sookie who started cutting the cake.

All in all, it was a good evening. Jess didn’t even feel like bolting, much. Rory was at his side at all times and held his hand under the table, or leaned her back into him, never giving him a chance to leave. It could’ve been annoying, but he somehow knew she didn’t do this just to glue him to the spot, but she just wanted to be with him, and tried to sooth him with her touch and presence.

When the party died down and almost everyone left, there was only Lane, Sookie, Lorelai and Jess remaining in the house. He helped cleaning up the living room, Lorelai did not attack him once, which seemed like a success.

After Lane and Sookie said their goodbyes and went home, it only left the three of them in the Crapshack. Jess tugged Rory by the hand and whispered in her ear. “Come for a walk with me?” She nodded and went to tell her mom she was going out for a while. Although Lorelai looked suspicious at first, Rory convinced her it was just a walk, and it’s Stars Hollow, nothing bad is going to happen.

Five minutes later they were strolling down the empty streets of the sleeping town.

“It wasn’t so bad, was it?” She asked him leaning into his side, making him wrap his arm around her shoulder.

“I guess not.”

“Thank you for coming.”

“You’re welcome.”

“Hey, why did you need me to wear a skirt?” she looked up at him, her brows furrowed. He just smirked at her.

“Jess!”

“Come to the diner with me.”

“What, why?”

“You’ll see,” he answered cryptically.

They entered the diner from the back alley. That door didn’t have a bell, so Luke wasn’t alerted to their presence. The lights in the diner and upstairs were both out. Jess learnt to navigate the place in the dark by now, so he easily led Rory by the hand to the store room. It had its own light which he switched on. He closed the door behind them and turned to Rory. She was looking at him expectantly.

“What are we doing here? Wouldn’t Luke look for you?”

“Luke’s out of it upstairs, he’s expecting an early shipment, so he won’t be up until his alarm goes off. Don’t worry. I wanna give you a present.” He said entwining their fingers together.

“But you already gave me my present,” Rory whispered, hushed by the realization they were alone together in a dark diner and no one knew where they were.

“I have another one,” he whispered back. “C’mere.” He pulled her in for a kiss, which she eagerly reciprocated. Making out with him was always so addictive, she couldn’t get enough. It was always such a bummer when they were interrupted. No interruptions this time.

His hands were rubbing her waist gently, while his tongue was caressing hers, making her breathless and dizzy. Her fingers ended up in his hair messing the careful updo he spent twenty minutes on in the morning. He didn’t seem to mind. Slowly his hands trailed up under her sweater and she whimpered when his calloused fingers came in contact with her skin. The sound made him squeeze her and pull her even closer. The kiss was getting more heated and her hands were travelling up and down his torso and back. One of her hands gliding underneath his shirt mimicking his actions. He pulled away from the kiss to lift her up and placed her on a sturdy looking wooden crate. She gasped at the sudden movement and the pang of arousal it caused. He took a moment to look at her, his eyes were completely dark in the dim light, lips parted. He looked so hot.

“Jess?...” she whispered.

“May I?” he placed his fingers at the zipper of her sweater and fiddled with it, waiting for permission. She gulped and nodded.

He pulled the zipper slowly revealing her skin. Her whole body was buzzing in anticipation. When the flaps of her sweater were opened he brushed them away and covered her breasts with his hands. She was glad she had a foresight to put on a pretty bra and a pair of matching panties. He tugged on the lace gently revealing her nipples and her inner muscles clenched in arousal. Fuck.

He went on to rub her nipples and they instantly became hard, she bit on her lower lip to swallow a moan. He was looking intensely at her, watching her reactions to his ministrations, studying what she liked. He wanted to get her really turned on for the thing he was hoping to try tonight. When he lowered his face to take her nipple in his mouth, she moaned softly and clenched his hair in between his fingers, pulling his head even closer.

“Jess…”

Taking that as a sign of encouragement, he kept on sucking on her nipples and breasts, going from the left to the right one, making her squirm in her sit. Her legs spread wider to accommodate his hips. Her skirt riding up allowing him to caress her legs softly. It was unusually warm for this time of the year, so Rory decided to wear stockings instead of tights, and now it was proving to be for Jess’s advantage. He was moving steadily up her thighs until he reached her panties. When he rubbed her core she moaned out load and immediately slapped her hand onto her mouth.

“Don’t worry, he won’t hear a thing,” Jess assured her as he kept going, rubbing circles around her clit, making her forget about the outside world once more. She clutched at his side underneath his shirt, needing to feel his hot skin, needing something to ground her, while he was doing these wonderful things to her. She looked up at him in confusion when he pulled back and kneeled in front of her.

“Jess?”

“Shh, here comes the present.” He whispered licking his lips.

“What?”

His hands went up her thighs again and pulled onto her panties. She subconsciously lifted her hips from the crate to help him take the garment off. And then the realization hit her. Oh.

“Jess? What are you doing?” she asked in alarm.

“What you were dreaming about all those nights in D.C. My head between your legs? Ring any bells?” he enquired smirking cockily. That was one of his favorite letters and he wanted to fulfil that fantasy for her since he read about it. And especially after he tasted her after he made her cum on the bus.

“Oh… but… Jess... I… huh?” her face pinched.

“Trust me,” he assured her and spread her legs gently, pushing her skirt up, revealing her most intimate parts to him. Her heartbeat was erratic, palms sweating, legs trembling. Oh God… he’s about to see her… All of her…. Does she want this?... Yes…. But so soon into their relationship… But she wanted it so bad… Just thinking about his skillful tongue and what it might do to her down there made her clit throb.

When he saw her he swore under his breath. She looked so perfect. So pink and pretty. Her lower lips swollen, her entrance glistening with her arousal. She had hands down the most beautiful pussy he’s ever seen. Her breathing was labored as she was waiting for the verdict. What if he didn’t like the way she smelled or tasted. She took a shower before the party, but it was a few hours ago, what if he finds her taste off-putting? Little did she know that he already tasted her after their bus encounter, and has been craving her ever since.

“Fuck, Rory…” he couldn’t wait any longer. Finally, her pussy was in front of him to feast at, just for him. He went right in and licked a long slick line from the bottom of her slit to her clit. She cried and jerked. He squeezed her thighs to steady her so she wouldn’t fall off the crate and began licking her. His tongue relentless, hungry, lapping at her, drinking all her juices, torturing her clit mercilessly.

Her knuckles turned white at how hard she was clutching the wood she was sitting on. One of her legs on Jess’s shoulder and the other spread wide hanging from the crate. Her lips were bitten to a pulp in her attempts to keep quiet.

She tasted so good he couldn’t get enough. Her pussy was so pretty he felt like he could stare at it all day. Her pink folds, soft like rose petals opening up for him, admitting his tongue where no other guy has been before. He knew her pussy was going to haunt him in his dreams now. Once he saw that, he couldn’t imagine not tasting her, not licking her. His cock was straining against the fabric of his underwear, he desperately wanted to let it out and rub it, but she hasn’t seen it yet, so maybe one sexual experience at a time was a better choice of action for tonight.

He was teasing her clit when she finally came. The tip of his tongue straining to be razor sharp, to deliver one last blow before she erupted in front of him. She couldn’t hold back her moans when she was shaking all over, her legs closed around his head, had thrown back, nipples hard in the cool air.

When she finished, she let go of his head, smiling sheepishly at him “Sorry.”

“It’s okay,” he looked up at her licking his lips like a sated cat, that made her blush even more.

“Wow…” was all that she managed to say.

"Wow, huh?” he smirked.

“Wow…” she said too tired to argue. So his ego would be inflated, so what?

He stood up and adjusted his pants. She only just now noticed his erection.

“Was it hot for you too?” she asked insecure.

“Are you kidding?” he looked at her incredulously. How could she even think it wouldn’t be? Instead of answering he kissed her deeply on the mouth. She could taste herself on his tongue and it strangely aroused her. “You have the prettiest pussy I’ve ever seen.” He said. She looked down shyly.

“Hey, look at me,” he put his finger under her chin and lifted it up to make her look at him. “I fucking wanna eat you out every day now.” He took her hand in his and placed it on his bulge. “See how crazy you make me?” She inhaled sharply. “You are so fucking hot, you have no idea.” His gaze was dark, intense. She couldn’t look away. “I would lick you every day if I could.”

“Oh…” her voice trembled. “Okay.”

“Okay.” He nodded. Right in that moment Rory’s cell rang and she hastily fished it out of her pocket.

“It’s my mom.” She said apologetically.

“Let me walk you home.” He adjusted his pants again while she answered, reassuring Lorelai they were just walking around town and she will be home soon.

While cold showers were definitely a thing, now that he had a full picture of how she felt, and looked and tasted down there, it would be so much harder to find solace in the cold stream.

~XXX~

Exiting school on the following Monday Rory heard Louise say “Hot guy alert.”

Louise shook Madeline’s forearm attracting her attention to someone in the Chilton parking lot. Rory and Paris were trailing behind them. Rory was putting her notepads in her backpack, so she didn’t see who peeked Louise’s interest yet. “Eight o’clock. Dark hair, jean jacket, leaning on a hood of a car.”

“Oh wow,” Madeline said in awe.

“His car needs work, but his physique certainly does not,” Louise purred. She was eyeing the guy like a three course meal with no shame at all. Then they were distracted by Paris’s voice.

“What’s Bukowski fanboy doing here?”

“What?” Rory finally raised her head, and saw who her friends were looking at.

Jess was standing in the parking lot leaning on the hood of a very crappy car she’s never seen before. He was wearing his usual denim jacket and looked really delicious indeed.

“I don’t know,” Rory frowned, confused.

“You know him?” Louise looked at her with a new found respect, like she was seeing Rory for the first time.

“Yeah, that’s my boyfriend.”

“Your boyfriend? Whatever happened to the tall one?” Louise asked.

“Uhh, we broke up.”

“Since when? You didn’t tell me you broke up,” Paris demanded. It was obvious from her tone she took it personally, as a jab to their friendship.

“Back in August,” Rory responded reluctantly. She did not feel like discussing her personal life at all.

“And you already replaced him with someone hotter? Nice one, Rory,” Madeline complimented her.

“Thanks,” Rory shifted from one foot to another uncomfortably. “I gotta go, see you guys tomorrow.” She waved at them and went to Jess.

As she was approaching Jess looked her up and down, appreciating her uniform.

“Hi,” Rory said a bit breathless. It was really good to see him.

“Hi,” he smiled and placed his hands on her waist pulling her closer, needing to touch her.

“What are you doing here? Also, whose car is it?”

“Mine. Thought I’d take it for a spin. I brought you coffee from Luke’s,” he said and then planted a kiss on her lips. “Shall we?”

“How? When?? What?” Rory struggled to choose the right question.

“C’mon, get in,” he tugged on her hand as he opened the door for her. She sat in the passenger seat and looked around. This car definitely has seen better days, but it had a stereo system, and a to-go cup was waiting for her in a cup holder. She took a sip gratefully.

“So?” she asked once Jess was inside.

“So what?”

“When did you get a car?”

“Yesterday.” He was succinct as always.

“Where did you buy it?”

“Gypsy’s.”

“With what money?”

“Jeez, I didn’t know I was in the episode of Law & Order. Is there a camera somewhere?”

“Jess,” she whined.

“I had a summer job. Plus Luke’s wages.”

“What summer job? You didn’t tell me you had a summer job.”

“Well, we weren’t exactly on speaking terms during the summer,” he pointed out. Rory cringed.

“Touché.” A brief silence fell, disturbed only by the sounds of Rory sipping her coffee.

“What was the summer job?” she finally asked, not being able to tolerate not knowing.

“Uhh, I’d rather not say.”

“Why not?” Was it just her, or did he actually blush a little?

“Because it’s a gigantic corporation that I hate with a passion, and it sucks the soul right out of you.”

“What did you do?” She looked at him, her curiously at its peak. Now she really wanted to know.

“I worked at Walmart,” he mumbled.

“Walmart?” she asked incredulously.

“Hey, it was good money,” he said somewhat defensively.

“Okay.”

“Are you done with the third degree? Can we go now?” she looked at him, but there was no aggression in his expression, just amusement.

“Sure,” she pushed her backpack in a back seat and put the seatbelt on. “Where to?”

“I know a place,” Jess smirked and started the engine.

~XXX~

The next day Louise and Madeline ambushed Rory at lunch.

“So, Rory, tell us everything about your new beau,” Louise leaned in closer conspiratorially.

“Uhh…” Rory almost choked on her sandwich.

“How long have you been together?” Madeline continued.

“Is he a good kisser? He looks like he is.”

“Did you sleep with him?”

“Are you going to?”

The girls bombarded Rory with questions, she couldn’t even comprehend them, looking at Madeline and then Louise back and forth helplessly.

“Can you think about literally anything else apart from boys?” Paris slammed her tray on the table next to Rory, she had an angry look on her face, well, angrier than usual.

“What else is there worth thinking about?” Louise retorted.

“So, is he a good kisser?” Madeline asked again. Rory blushed, but answered nonetheless.

“Uhh, yeah, he is.”

“I knew it!” Louise said with a satisfied smirk.

“Sooo, how far did you two get?” She leaned closer still.

“Uhh, not far,” Rory was now blushing harder. It was nice to finally be able to talk about Jess with someone who didn’t think he was Lucifer’s reincarnate or a town’s pariah, who could see at least one thing about him she liked, but at the same time, talking about something so private in a school cafeteria made Rory uncomfortable. She wasn’t sure she wanted them to know the details. The girls both had a lot of experience in the sex department, but Rory wasn’t really close with them, and now was not the time and place to discuss something like this.

“But you’re going to, right? I mean, c’mon, with how hot he is, I bet your panties would drop on their own accord.” Louise wiggled her eyebrows suggestively.

“I’m sure you know all about it,” Paris grumbled over her salad.

“You want him, do you?” Louise wouldn’t let up.

“Uhh, well yeah, I’ve thought about it.” Rory admitted reluctantly.

“About what?” Madeline who was temporary distracted by reading the amount of calories on her yogurt lost the line of the conversation a few questions ago.

“God, Madeline, how can you be so dense? She’s saying that before Bukowski showed up and got into the picture, her vagina was hibernating. Apparently, farmer John was not enough to set her loins on fire.” Paris snapped.

“Ohh, the jean jacket guy makes Rory’s kitty purr,” Madeline clapped her hands in delight.

“Oh my God, Madeline!” Rory exclaimed.

“Fucking-finally. I thought our virgin Mary would always stay the way she is,” Louise chimed in.

“I’m not having this conversation anymore.” Rory stood up to leave, but Louise tugged on her sleeve to stop her.

“Relax, we’re only teasing. There’s nothing wrong with wanting to get busy with a hot guy,” she winked at Rory. “Actually, you know what, I’m having a Halloween party on 26^th, you should come. Bring the hottie. You can fool around with him in any room you like, you have my permission.” She smiled at her suggestively. While the conversation itself was embarrassing, the possibility to be alone with Jess away from the prying eyes of every single person in Stars Hollow sounded very appealing.

“Uh, I’ll ask him,” Rory found herself saying.

“Awesome,” Louise smiled.

“And if you don’t have a costume, we can even go shopping together!” Madeline suggested excitedly. Rory noticed that even before, in her first and second year of Chilton, Madeline was always the most accommodating one, expressing interest in Rory’s friendship, wanting to hang out with her, always saying ‘hello’ to her, even when Paris forbade the girls to talk to her when they were fighting. Come to think about it, maybe, just maybe, Rory could get a new friend out of it. And maybe, she could even ask her some sex related questions. It could potentially be less embarrassing than asking her mom.

“That would be great actually,” Madeline let out a girly squeal at that making Rory smile.

“Shopping, yay!”

Rory noticed Paris did not seem thrilled at the prospect of the three of them going shopping together, but chose to ignore it for now.

~XXX~

Lane was just about to finish lacing her shoes after PE class when she heard voices in the girls’ locker room.

“Oh my God, Shane, you would not believe what I just found out!” the first voice said.

“What?” Lane heard the bubble gum popping. She was just about to stand up from the bench and leave, when she heard the name of her best friend and stopped to listen.

“You do know your ex, Jess, is dating this hoity toity private school chick, Rory Gilmore, that used to go here?” Shane of course has heard about it, and didn’t like it one bit. To be dumped by him actually hurt. She wasn’t in love or anything, but he was the best fuck she’s ever had, and losing that was less than pleasant. She already had sex with two guys after the break up, but they just weren’t up to par.

“Yeah, so?” she tried to sound nonchalant. Even her friend did not need to know that she still thought about him specifically, when she masturbated.

“So, before your ex she was dating this guy, Dean Forester. You know, the tall one from the hockey team?” her friend continued all excited, clearly not noticing Shane’s discomfort. Nothing could stop Vicky from sharing the hottest new gossip, manners and compassion be damned. “Well, Sydney Waller, the cheerleader, she had like this huge crush on him, but he didn’t pay her any attention while he was dating that Rory chick. Apparently they were together, since like sophomore year or something. Anyway, Nancy told me, that she heard from Brenda, who heard from Jane, who heard it from her boyfriend Brian, who heard it from Luke, who’s friends with Forester, that he told him Rory broke up with him because she didn’t wanna have sex! Imagine that!” Vicky’s eyes gleamed with wicked excitement.

“So, she’s what, like a virgin or something?” Shane asked.

“Apparently, yeah.”

“What a loser,” another pop of a bubble gum.

“I know, right?! Anyway, she dumps him over summer, and finally Sydney has a chance. So she was like, hitting on him hard, and he caved. And she took him to her place one night, and they had sex! But, hear this!” Vicky couldn’t contain the glee. “He was a virgin! And he came in like two seconds, and when he did, he called her Rory!”

Shane couldn’t deny that it was indeed a very hot piece of gossip. “No way!”

“I know, right?! So, like, Sydney gets mad, because she obviously didn’t cum, and he called her his ex’s name, so she kicked him out and slammed the door in his face.” Vicky finished with satisfaction.

“Wow…. What is it about this Rory chick that makes guys obsessed with her? Are virgins a thing these days? Is it like a trend or whatever?” Shane asked. She couldn’t deny it stung, knowing Jess dumped her for someone like that.

“I don’t know,” Vicky shrugged. “Maybe it won’t last.”

“Yeah, you’re right. It probably won’t. I mean, the way Jess fucks, no virgin could satisfy that,” she tried to convince herself. “He likes it rough, he likes to get his dick sucked and swallowed.”

“Oh wow, now I’m kinda jealous,” Vicky remarked with a slight envy in her voice.

“He’s probably in it for the chase. As soon as he realizes she’s not gonna lose her precious virginity to him, he’s gonna dump her and come back to me.”

“Oh, yeah, totally,” her friend nodded vigorously.

Lane heard the locker room door shut and everything went quiet. Wow…. She definitely needed to figure out a way to break down this information for Rory.

Chapter Text

The first unit of Jess’s AP class was devoted to short fiction. After Mrs. Wilson divided the class into groups for their projects, she approached each group with a hat filled with folded pieces of paper. Each group had to pull the paper out of the hat with a title of a short story written on it. Every group had a different story, so there wouldn’t be any copying or cheating. Jess’s trio got ‘The Cherry Orchard’ by Anton Chekhov, which Jess hadn’t read before. He was surprised to see such an unusual choice for the class. He expected something along the lines of Kate Chopin or maybe Hemingway. He had yet to get to the Russians. He instantly wondered if Rory read it, since she was so fond on those authors.

After each group received their stories Mrs. Wilson explained the task to them. They were to prepare a graphic organizer for a character of their choosing. The groupmates had to agree on a character first. The graphic organizer had to include textual details about a character, the character’s perspective, and the character’s motives. While reading the story each member of the group also had to list three quotations that resonated with them the most on notecards. On the back of each quotation card, students were to write the reason for their choice. Then all the group members had to discuss the relevance of the quotation, paying particular attention to diction, details, and syntax that reveal narrative perspective. And then they had to write a short essay using each other’s quotation regarding one of the problem described in the story. They had two weeks to complete the task, meanwhile they were given lessons on theory of short storytelling.

Andy suggested they read the story on their own separately and compile a list of characters they found the most interesting, so that they could meet up later and discuss which one they would choose for the graphic organizer. Then they were supposed to work on the organizer individually to meet up later and compare notes, see if anyone of them missed any valid points and such. And then they would share the quotations and decide whose cards go to whom to match their preferred essay topics better.

They set to meet up at Andy’s house one day, and Jess headed there straight after school. On the way there he met Scotty, who was walking from the other side of the street, so they approached the house together. Jess rang the bell. Andy opened the door and the guys stepped inside.

“I was thinking about where to study, and came to a conclusion that my room doesn’t have enough space for all of us and our study materials. So let’s go to the dining room. The table there is exactly the size we need.” Scotty and Jess nodded and went after her. They had to go through the living room. It was really spacious and cozy. Jess noted there were photo frames everywhere. The biggest one of them was hanging above the mantel. It portrayed three boys, a man and a girl all standing in line, each one of them holding a giant fish in their hands. The girl in the middle was obviously Andy, she looked a lot younger, maybe around seven or eight, she had a broad grin on her face, her front tooth was missing. The man was most likely their dad, and the boys must’ve been her brothers. Jess stopped for a bit to get a closer look. Andy noticed that and came to stand beside him.

“It’s my dad, my brothers and I at our fishing cabin. It’s the first and only time we caught this much fish,” she chuckled at the fond memory. Then she pointed to a smaller frame on the mantel that had a family portrait. All of the siblings were older, probably closer to their current age. Both of their parents were standing on either side of their kids smiling happily.

“These are my brothers. This is Marcus,” she pointed to the guy on the left next to her dad. “We call him Marky Mark. He hates it. He’s the oldest,” she then went to the next brother. “This is Whitney. My parents thought he was a girl, so they decided to name him after my grandmother. When he was born there was a big surprise for them, but they decided to keep the name anyway. And this is Montgomery, but we call him Monty. He’s surfing in Australia now. And this is yours truly,” she finished tapping a finger on her own face. All of them were tall and blonde, with an obvious Scandinavian origin. The next picture had Andy standing next to a tall and thin guy with shaggy auburn hair and green eyes.

“Is this your relative too?” Scotty asked. He walked over to them and was listening to Andy attentively.

“Oh, no. This is my boyfriend, Harry. He goes to Princeton,” Andy didn’t even try to hide the pride and affection in her tone.

“I think I remember him. Wasn’t he a valedictorian last year?” Scotty asked.

“Yes, he was,” Andy beamed proudly.

“You mentioned a dining table?” Jess asked.

“Oh yeah, sorry. Follow me.”

~XXX~

They were studying for about an hour now. Jess found the process a lot less annoying that he thought it would be. He never studied in groups before, but these guys didn’t seem to be slacking, and discussing his findings with them was actually quite interesting. Jess was surprised to see Scotty unload his backpack and putting a bunch of books on Russian history on the table. There was also a Chekhov’s anthology of his best works, commentary on social reforms of the nineteenth century Russia and a bunch of his own notes.

“I personally want to focus on the affect the Emancipation reform of 1861 had on society,” Scotty said. “It’s one of the main themes of the story. I studied it in detail, and it’s the most fascinating thing for me in this entire play,” when both Andy and Jess looked at him in surprise, Scotty blushed and added sheepishly. “I like history.”

“Okay, then you need to choose from our quotes something that can be used as evidence for your claim. I prepared extra, in case the quotes I chose won’t work for either of you,” Andy said shuffling through her cards. “What about you Jess?”

“Uhh, I was thinking I wanna focus more on the dual nature of the play, how Chekhov meant it as a comedy, but theatre production turned it into a tragedy. The balance between the farce and the tragic undertones.”

“Cool, I think I have just the right quotation for you,” she fished out one of the cards and handed to him. In that moment they heard a key jingling in the lock and the front door opened.

“Anybody home?” a male voice came through the hall.

“In here!” Andy shouted. A minute later a tall blonde man entered the dining room with two bags of groceries. Andy stood from her seat and came over to peck her father’s cheek in greeting.

“Hey dad!”

“Hi pumpkin,” he pecked her forehead.

“Let me help you with that,” she took one bag from his hand and went to the adjacent kitchen. “Hey dad, meet my new classmates. This is Jess and Scotty,” she motioned to the boys. “We’re studying for the AP English lit. Guys, this is my dad, Russell.”

“How you doing?” the man smiled broadly, his blue eyes twinkling. Then he turned to his daughter and pulled a brown paper bag out. “I bought you those chocolate chip cookies you like.”

“Aw, dad, I was just about to tell you I ate all of them last night,” she exclaimed.

“Yeah, I noticed that this morning, so I bought them for you.”

“Weston’s ones?” she asked hopefully.

“Of course.”

“Thank you!” she jumped excitedly and gave her dad a bear hug which he returned. Jess was looking at the scene with a weird feeling. After a second he realized what that pang in his chest was. Envy. Andy had a father who not only hadn’t left the day she was born, but he bought her favorite cookies, because he noticed she ran out of them. Liz didn’t even know whether he liked cookies at all, not to mention his favorite brand. And she definitely never went out of her way to buy something he liked from a specific bakery. Jess swallowed a lump in his throat and looked down at his notes trying to wrangle the anger storm in his heart.

Andy was still helping her dad with the groceries when another person entered the house.

“Honey, I’m hooome!!” a female voice shouted from the hall with a clear teasing undertone.

“In the kitchen,” both Andy and her dad shouted back in union, and then laughed. Jess figured it must be a thing they do. Then a tall blonde woman with high ponytail entered the room.

“We’re having guests?” she inquired, her smile was warm and kind when she turned to look at Jess and Scotty.

“Yeah, mom, these are my AP classmates, Jess and Scotty. Guys, this is my mom, Bridget.”

“Nice to meet you. Do you want anything to eat? I can whip something up,” she offered immediately.

“Oh, it’s fine, thank you,” Scotty stuttered.

“It’s fine mom, we’re about to be done soon, but maybe tea would be great,” she then turned to the guys and said. “Mom raised three boys, she knows they’re always hungry.” She winked at them and turned back to her parents noticing they were greeting each other in a special way.

“Ewww, get a room!” her parents who were just kissing pulled away from each other and laughed.

“Green is not your color, honey. When did you say you saw Harry last?” her mom retorted. Andy just rolled her eyes at that good-naturedly.

“Anyway, where were we in our study process?” she asked pointedly, and her parents promptly left the dining room.

The rest of their study date Jess was a bit distracted. He couldn’t figure out what he was feeling. Except for he desperately wanted to leave that house, that happy atmosphere. Andy was so lucky she had such an amazing family. Three brothers, both parents who were still together, and apparently still loved each other. Did she even realize how lucky she was?

Jess has never seen a family liked theirs. Even back in New York all of his friends’ families were fucked up in one way or the other. A lot of them had their parents divorced, on bad terms, or were raised by a single parent. One of the guys he knew had both mom and dad, but they were fighting all the time. No one had a nuclear family with a picturesque living situation, a metaphorical white fence and a dog.

Jess felt a longing for a family he hasn’t felt in a long time. He taught himself not to feel it anymore when he was around seven, when it was clear Liz was not going to be a better parent, and none of her partners would care about him. But this situation today with Andy, and her photo frames, and Russel and Bridget making out like teenagers, and huge dining room table big enough to fit all of her siblings, and the cookies, it was just too much for Jess. It opened the floodgates again. He felt that desperation again, that unquenchable desire to be loved, to belong. He remembered Luke bought him Frosted Flakes the first time he got to town. He used to love them when he was a kid. It was surprising Luke actually remembered considering he saw his nephew only a handful of times during his entire life. Was it the same as Andy’s dad remembering the exact kind of her favorite cookies? Jess didn’t know what to think. He headed for the bridge after their study session and spent a few hours there just sitting and staring at the water, for the millionth time wishing he didn’t quit smoking.

~XXX~

Rory looked at her calendar and realized that October 19^th was fast approaching, which meant she has been dating Jess for a month. They were about to have their first anniversary. The thought made her feel excited. Jess Mariano has been her boyfriend for a whole month. She tried to sum up the events that happened during the course of their short relationship, and realized they managed to cover some major ground during just four weeks. They went on their first date. He gave her two orgasms. He attended her birthday party and her mother and him didn’t even fight. She told him about her reservations about college. He saw her shirtless twice. She saw him shirtless once. He went down on her. The thought made Rory blush. He bought a car, and her classmates saw him, and thought he was hot. They had interesting conversations. She loved talking to him on the phone, hearing his voice. And they had numerous make out sessions that resulted in her having wet panties and naughty thoughts. But then she realized something else, and the thought made her a bit uncomfortable.

Conversations with Jess were always about books, or music, or some philosophical topics. They were interesting, challenging and Rory liked that about him, a lot. Conversations with Dean were always simple, but personal, what he had for breakfast, what his mom said to him, how Clara’s riding lessons go, how he felt when coach praised him in practice and stuff like that. They were never challenging, but they were sweet and familiar. After some reflection Rory realized that conversations with Jess, however stimulating, were never personal. They were together for a month, and she still didn’t know anything about him, anything of substance that is. But she wanted to know, she wanted to get to know him better. She wanted a glimpse behind his façade. Living in Stars Hollow pretty much guaranteed everyone knew everything about anyone in town, and living here he was inevitably going to find out all the details about her life, and she wasn’t exactly mute herself. The difference in knowledge about them suddenly weighed her down. It was concerning. She wanted to coerce him into talking to her, telling her something personal, but she didn’t know how to do it without being too forward. He wasn’t an easy nut to crack, and as tough as he seemed, he still needed a delicate approach. Something was telling her that trust was not something he gave easily and she had to earn it, no matter how strong their attraction was. How would she even start a conversation like that? Should she prod if he tries to deflect? Rory’s brows furrowed in concentration. She could at least try and ask him something. She wasn’t planning on going anywhere, so she figured she had to have patience.

A few days before their anniversary Rory mentioned it when talking to Jess on the phone. A silence followed. But then he suggested they go out of town to spend the day together. It would be very easy to pull off since he had a car now. No more asking Luke for his truck. Rory eagerly agreed. As much as she loved her home town, sometimes the attention and stares they got from the townies was too much even for her to handle. She also noticed he seemed a lot less tense and stiff when the Stars Hollow was nowhere near in their vicinity. Like when they went on their first date to Hartford, or when he picked her up from Chilton in his newly bought car. He seemed to be breathing easier, laugh more openly, talk more. His rants about book characters and certain music artists even rivaled Luke’s. And it also made Rory smile, to see the similarities between the two. So when the opportunity arose to get out of town to spend the entire day with Jess she happily jumped at it. It was decided they would go to Woodbridge.

Her mom of course pouted all day when she told her about it. Because weekend was supposed to be their time, where they could sit and mock movies all night or talk about anything and everything, but this weekend seemed like there would be no mother-daughter time, as Rory was going to be with Jess on Saturday, and she already agreed to go shopping with Madeline and Louise on Sunday. She still hasn’t asked Jess about the Halloween party, but she figured, she might as well look for something to wear to the Distillers concert, even if he doesn’t agree to go with her to Louise’s shindig.

Lorelai was complaining and whining about Rory abandoning her all through their ride to the Friday night dinner. But Rory firmly decided she would not feel guilty about it. After all, she had to have friends her age, and an anniversary with a new boyfriend was a big deal. Thankfully, Lorelai didn’t blurt anything out about Jess to Emily. Otherwise it would be a total shit storm. As much as Rory loved her grandparents, she wasn’t ready to tell them about Jess yet. She liked him too much to lose him so early into their relationship.

Finally, Saturday came and Rory woke up rather early. Jess suggested they leave town at 11 A.M. at the latest, to spend as much time together as they could, because they both had homework. And even though Jess wasn’t going to put much effort into anything else, this group project for AP class was not for only him to finish, he was in part responsible for other people’s grades now. As much as everyone liked to blame him for every single little thing, he could be responsible, and wasn’t going to let his groupmates down.

They were in his car, singing along to Nirvana. Jess was driving and Rory was sitting in the passenger seat bobbing her head happily up and down to the beat of the song. The farther they went away from Stars Hollow the freer she felt. When did her beloved home town became so stifling? She noticed Jess was getting more relaxed as well, with each passing mile his shoulders seemed to loosen up, his voice became louder as the song reached its chorus, and overall he just looked more opened.

Rory’s been to Woodbridge a long while ago, so she didn’t know the town all that well. But Jess seemed to know exactly where he was going, and she wondered how did he know that. They parked on a side street and exited the car.

“So, I’m not sure what a one-month anniversary date should look like, but I thought we could browse a book store for a few hours. They have a really good selection here, and then we can go grab something to eat and walk around or something,” Jess scratched the back of his neck, which Rory’s learnt was a sign of nervousness or uncertainty for him.

“That sounds like a great plan, actually!” She beamed. Bookstore, food and walking around without everyone staring at them seemed like a great date.

“Okay. Let’s go then,” he entwined his fingers with hers and led the way.

“Hey, while we’re on the subject, how do you know this town so well?” she asked looking at him.

“I used to come here often on my days off during the summer.”

“Too many Taylor-organized festivals?”

“You have no idea,” he rolled his eyes.

“Did you bring Shane here?” she didn’t know why she asked this, but for some reason it was important for her know.

“No,” he said simply.

“Oh.”

“Rory…” he sighed. “It wasn’t serious with Shane, I never wanted to spend more time with her than was strictly necessary to drown out Stars Hollow or my anger at you.”

“Oh,” she wilted, remembering how her not contacting him all summer must have affected him.

“It’s okay, now I know I wasn’t the only one who felt something after that kiss, so it’s fine, let’s move on from that, okay?” he stopped to look her in the eyes.

“Okay,” she glanced back at him and gave him a small smile. “I’m glad you didn’t bring her here.” He smirked.

“Let’s just find that bookstore. They have an amazing section of second-hand books. Maybe I’ll even convince you to buy a Hemingway,” he winked.

“Not a chance,” she giggled.

Jess was right, the bookstore was great. Woodbridge was approximately two times larger than Stars Hollow, and it reflected in the size of the bookstore. It was located in a two-storey building with a beautiful vintage staircase that had a round roof window right above it. Rory fell in love with the place immediately. On the second store there was a reading area with a big cozy couch and a couple of chairs. One part of the floor in the farthest corner was covered with a tarp. Jess told her they were going to remodel that part and turn it into a coffee shop, which got Rory excited. She wanted to come back here when they open to have a full coffee—books-couch experience.

They spent around three hours in the bookstore leaving with a bag full of books each. After they left their purchases in Jess’s car, and had lunch in a small diner, they went for a walk around town. He was holding her hand in his, swinging it occasionally, or pulling her closer for a quick kiss. Rory rarely got to see this soft side of Jess. The tender Jess, the clingy Jess, touchy-feely Jess. He wrapped his arm around her waist pulling her close into his side, and placed the other hand on her stomach where she put her hands and intertwined they fingers together. She was fully encircled by Jess and she loved it.

They were walking down a newer street when she noticed something unusual.

“Hey, look, they opened a tattoo parlor in Woodbridge,” she motioned with her head to the other side of the street where a bunch of balloons were hung up on the either side of a door that led to a tattoo shop.

“Huh. They’re gonna go out of business in about three months and lose all their money.”

“Why?”

“Think about it, how many people in Woodbridge, Connecticut actually want to have tattoos?” he looked at her pointedly. She sighed.

“Fair enough. Do you think we should get matching tattoos? You know, to commemorate our anniversary and help poor tattoo artists to keep their shop?” she looked at him grinning mischievously.

“Well, your mother will not be happy about that, but you’re eighteen now, so you don’t need a parent or legal guardian to write you a permission for a tattoo,” he said in mock seriousness. “What do you wanna get? Hearts? Skeletons? Or maybe books?”

“Oh, oh! I know! You should have a ‘I love Ayn Rand’ tattooed on your chest inside a ribbon, that is wrapped around a rose,” her grin was now threatening to split her face in half.

“Only after you get a ‘I heart Hemingway’ on your butt,” he smirked.

“Ewwww,” she scrunched her face, and he laughed.

“Don’t make deals you can’t keep, baby,” he pecked her on the temple.

“Hey, I’ve been meaning to ask you about your star tattoo. The one on your arm. When did you get it and why?” She noticed immediately that his face lost the carefree expression and turned serious, unreadable. She could practically see his walls building back around him, and didn’t like it one bit. And then it was there again, that thought that she doesn’t really know much about his life before Stars Hollow. This was a chance to find out at least something, and she wasn’t going to let it slip.

“Jess?” she questioned softly. He signed deeply and fell silent. She thought maybe he wouldn’t tell her, but after a long pause he said.

“I got it when I was sixteen, in a memory of a friend.”

“Oh… will you tell me about it?” she inquired as gently as possible, not wanting to spook him now as he started to open up.

“Do you really want to know?” he asked without looking at her.

“Yes,” she whispered and squeezed him tighter.

“Okay. When I was fifteen Liz got married, again, and we moved, again. I started going to a new school, again. And there I met a group of guys who kinda ruled the school. They tried to test me on the very first day, if I was a wimp or not. I kicked their leader’s ass before they outnumbered me. But it was a start of a beautiful friendship,” he mocked with a chuckle. “They kinda took me into their group after that. It was the first time I had a group of friends. One of them, Danny, even got me a job in his dad’s auto repair shop called Vito’s.” He felt the urge to smoke, his fingers playing with the lining inside of his jacket pocket, when he remembered that he quit. “Danny was a good kid, his dad liked me, I used to stay with them a lot when Liz was going through her phases. Around a year after I met him, Danny started messing with the wrong crowd. They got him hooked on drugs,” Jess inhaled deeply before continuing.

“I smoked pot once, but I didn’t like the experience, and also it reminded me way too much of Liz and her string of boyfriends. So I don’t drink or use, the very idea disgusts me to no end. But for Danny it was new, exciting. I don’t know when it happened, but he started using the heavy stuff…” Jess trailed off. His gaze became distant like he was reliving the moment from his past. They didn’t stop moving, and Rory realized they entered some park area by now.

“One day I came over to his place, knocked on his door. No one answered. I thought it was odd, because earlier we agreed to meet. I tried the door, it was opened. I went inside and found him in his room. He OD’ed….” Rory felt his arms clenched harder around her and squeezed back.

“I turned him on the side, called an ambulance, but it was too late. He was already cold. It was the first time I went to someone’s funeral. Vito was a wreck. I couldn’t come back to the auto shop…”

“At first he was the only Danny in our friends group, but then another Danny appeared, and we needed a way to distinguish between the too. Danny used to love Converse All Star shoes, wore them all the time, he said it was the best brand in the world, so we started calling him Danny Star, or just Star for short. The other Danny was the complete opposite of the Star. Six feet tall, buff, low voice, while Star was a scrawny little kid with thin arms and protruding ribs. He used to tease me about my biceps a lot,” Jess chuckled for the first time since he started telling his story. “I think he was just jealous. Anyway, when he died the big Danny and I decided to get tattoos in his memory. So I got a star on my bicep. Seemed fitting,” he trailed off again.

Rory’s stomach was in knots, heart beating fast. When she wanted him to open up about his past, she had absolutely no idea what she might find there. But losing a friend at sixteen to overdose was definitely not something she would’ve expected. The difference between their worlds seemed as wide as ever. While she lived this happy sheltered life in Stars Hollow where her biggest problems were Paris yelling at her or Taylor roping her into another town festival, Jess faced the things no kid has to face, ever.

Finally, Jess seemed to be woken from his trance. He looked around and noticed they were sitting on a bench in a very picturesque looking location, the sun was shining brightly, as if telling him it was not the place to rehash the harsh reality of his New York life. He shifted uncomfortably. Rory’s arms tightened around him. He looked down on her, and saw her eyes wide and bright with emotion.

“Hey, sorry, I didn’t mean to spring this all on you like this,” he looked away. He couldn’t even understand what came over him. Why did he tell her all of that all of a sudden? He never talked about this outside of his friends’ circle in New York. That was definitely not the story for Rory Gilmore, aka Miss Video-store Censorship, or miss Top-Three-Percent in her Chilton Class.

“It’s okay. I’m glad you told me about it,” she said softly. “I’m sorry about your friend.” She kissed him on the temple. “I want you to know, that I always wanna know stuff about you, you can tell me anything.”

“Are you sure?” he looked at her. “Half of it is not pretty.” Run, hide, save yourself until it’s too late, a voice inside of him screamed. He tried to convey that with his eyes. It’s just one month, it’s not too late to walk away from me.

“I don’t care if it’s pretty or not. I wanna get to know you, the real you. If you let me.” She whispered.

“Okay,” he nodded. The silence fell that neither of them dared to break. Their anniversary suddenly took a turn, but Rory was glad he talked to her, because that meant they were going somewhere together, in the direction of something real, a close bond with trust and acceptance.

~XXX~

The next day Rory took a bus to Hartford, and Louise picked her up at the bus station. Her shiny new BMW looked out of place next to a public transportation spot, but she didn’t seem to mind. Rory climbed in the back seat, since the front one was already occupied by a very excited Madeline.

“Hey Rory! I’m so glad you could come with us,” she offered as a greeting, and Rory couldn’t help but smile.

“Me too, actually,” she said back.

“Cool. Okay, so before we go to the mall, Rory, who do you wanna dress up as for Halloween?” Louise asked.

“Uhh… I’m not sure honestly. But I was hoping I could get an inspiration at the store,” Rory shrugged.

“Okay, sounds fair. Louise wants to be a slutty nurse this year,” Madeline provided.

“Yeah, I already was a slutty police officer last year. A slutty school girl sounds way too close to every day routine, I don’t wanna wear uniform outside of Chilton, you know what I mean.” Louise said to Rory. “Argh, that guy is an asshole,” she muttered under her breath honking at the car in front of her.

“Yeah, that would be no fun at all,” Rory agreed thinking every day was a Halloween for Louise since she was a school girl and a slutty one at that too.

“I think so too!” Madeline exclaimed. “I’m thinking about going as a cat or maybe a fox. There’s this store where they have the sexiest body suits, they are so tight, and you can choose any color. Pop on a pair of cat ears and you’re golden.”

“How are you gonna go to the bathroom in a body suit?” Rory asked, confused.

“Oh… well, you’d have to take the top off completely,” Madeline faltered.

“Every time?” Rory asked.

“Yeah… maybe it’s not such a good idea.” Madeline wilted.

“You can always buy a very tight pair of pants and a cute top instead,” Rory suggested feeling guilty for ruining Madeline’s potential costume plans.

“Yeah, I can do that,” Madeline smiled immediately.

“So, Rory, did you ask the hottie about the party?” Louise intervened.

“You can call him Jess instead of the hottie, you know.”

“I know, but where’s the fun in that?” The blonde gave Rory a predator smile in the mirror. “So, did you?”

“Not yet, but I will.”

“You better. I have a huge house. My step-father thought it was a good investment, so he bought this enormous mansion when he married my mom. I don’t know why since he’s always away on business, and mom is always away on SPA vacations. Last week she went to this resort in Hawaii, and she won’t return in at least two weeks.”

“Don’t you miss her?” Rory asked, thinking it would be a total nightmare if she and Lorelai got separated for that long.

“Miss her? Why would I miss her?” Louise looked at Rory like she said the dumbest thing ever.

“Aren’t you close with your mom?” Rory suddenly realized she was going to the same school as Louise for two years now, yet she didn’t know anything about her family life. Man, she really needed to expand her social circle.

“Me? Close with my mom? Of course not, Thank God.” Louise rolled her eyes. “Madeline, can you imagine me being close with my mom?” The brunette laughed at that.

“It would’ve been a total disaster.”

“Oh, okay,” Rory trailed off not knowing how to continue.

“Anyway, we’re here. Let’s go shopping ladies,” Louise purred.

~XXX~

They were going from one store to the other trying different outfits for a few hours now. They already had lunch and the girls were carrying three bags each, while Rory was walking empty handed.

“Okay, how about this one?” they entered another store, and Madeline took out a blouse from the rack.

“Ooh, I like it,” Louise snatched it from her hand.

“I was actually asking Rory.”

“Oh, it doesn’t seem very Halloweeny for me,” Rory shrugged.

“What kind of costume do you wanna get?” Louise looked at her pointedly. “We’ve been to a dozen stores already, and you didn’t buy anything at all.”

“I know, but I was thinking my mom can make something for me to wear.”

“Why did you even agree to come with us if you wanted your mom to make your costume all along?” Louise enquired.

“Well… I was actually thinking you could help me pick something out for a concert.”

“What concert?” Madeline asked.

“Jess bought me tickets to the Distillers show in November as a birthday present. And even though I love the band, my wardrobe doesn’t exactly scream rock’n’roll. I would’ve asked my best friend Lane to go with me, but her mom is very strict, so we never go shopping together. And my mom hates Jess, so it makes me uncomfortable even asking her to go shopping with me for the date with him.” Rory rambled. The other girls exchanged a knowing glance.

“Let me guess, you wanna dress sexy for that concert, because you wanna impress the hottie, but you don’t want your mom to know?” Louise suggested. Rory’s first instinct was to deny it, but then she gave up and agreed. “Well, then you’re in luck, my friend, because we know the best places for sexy outfits. C’mon,” the girls dragged Rory out of the store and led the way to another one on the other end of the mall.

“So, this concert, do you wanna wear a skirt or pants?” Louise asked while browsing the racks. The shop they were in was edgier and more modern, and to be completely honest, a bit outside of Rory’s price range.

“Uhh, I don’t know…”

“You know, Louise was really into this punk rock style last summer, so she knows everything about the right items,” Madeline said.

“Really?” Rory turned to Louise. “I would’ve never pegged you for someone into punk music.”

“I’m not. But a very cute guy moved a few blocks down the street from me last summer. And he was into that stuff. He looked like a good kisser, so I wanted to try him. I dressed like a punk chick and went for a walk when he was outside. He noticed me, I winked, he smiled, and the rest is history.” Louise reminisced fondly. “We fucked like horndogs, he was so amazing in bed, had a nice cock too. But he wanted to get me into that music scene, always dragged me to the shows. And that music is so trashy, I couldn’t stand it, so we had to end it eventually.” She sighed.

“Oh, I’m sorry,” Rory offered, while her ears were on fire. She wasn’t used to talk about sex, or hear someone talk about sex so openly and it made her uncomfortable.

“It’s fine. Hey, look at this jacket, it’s perfect!” Louise took a leather rocker style jacket out of the rack. “You should try it on.”

Rory took it and was immediately hit with a desire to have this thing. The leather was really soft, the lapels had metal rivets on them, there were zippers on the cuffs and it was artificially made to look worn out. It did look perfect. Beside her better judgement Rory went to the dressing room to try it on. The girls followed with their own stacks of clothing to try.

As soon as she put the jacket on Rory realized she fell in love with it. It looked so good on her, and she looked edgier, more mature, and, well, rock’n’roll. She wondered how would Jess react seeing her wearing it. She usually didn’t deviate from her style much. This jacket was a completely new look for her. She liked what she saw in the mirror. But as soon as she looked at the price tag, despair flooded her senses. She could never in a million years afford this thing. The downside of going shopping with Chilton girls was that the stores they chose to enter were not the places where she would go with Lorelai. They didn’t have a two-for-one sales and pretty much everything had some designer brand tag slapped on the inside. She sighed and took the jacket off, collected her things and exited the booth to wait for the girls on the couch just outside.

They were both in their respective changing rooms when Madeline’s phone rang. She answered.

“Uhh, I can’t right now, Paris. No. No. Because I’m not home. I’m at the mall with Rory and Louise, why? Paris-“ Madeline sighed when Paris hung up on her.

“What did she want?” Louise asked from the next booth.

“She wanted me to send her my article for Franklin which is not due for another week.”

“Freak. And?”

“When I told her we were at the mall she flipped and hung up on me, also mentioning something about her being the only one who cared about the paper, and her Harvard future.”

“How often does she call you on a Sunday?” Rory asked.

“Too often for my liking.” Madeline said, her voice muffled by a shirt she was putting on.

“Oh good, I thought I was the only one she terrorized on the weekends.”

“Trust me, you’re not,” Louise chimed in. “One time she called me when I was getting hot and heavy with this guy I met at a party. He asked me who it was, and when I explained, he suggested we pranked her. So I answered the phone, and the guy leaned closer and started moaning my name out loud, like we were doing it,” Louise laughed. “She doesn’t call me as much anymore.”

“Wow… that’s… wow…” was all Rory could say.

“Paris is freaking out too much. There’s no chance she won’t get into Harvard, or any Ivy for that matter. With her grades and extracurricular it’s impossible not to get in. She needs to chill.” Madeline said.

“What she needs is to get laid.” Louise countered.

“Louise!” Rory exclaimed.

“What? It’s true, she’s way too uptight. And why? Because she’s not getting any. I’m telling you, a good fuck, and she’d be mellow as a jelly.” Louise finally stepped out from her booth fully dressed. “Of course, she would have to bribe someone to sleep with her first.”

“Why would you say that?” Rory asked her. Wasn’t it rude to talk about her friend like that behind her back.

“Because it’s true. Every guy in Chilton is afraid of her. She only goes to parties because her mom makes her. She doesn’t wanna hang out with anyone. Her only form of interaction with others are slights and insulting remarks. She’s always angry and aggressive. No guy would have a boner for that.” She looked at Rory pointedly. “Did you know a penis tends to shrink when the male is afraid?”

“I don’t think that’s true,” Rory frowned.

“True or not, no one wants to fuck her because they’re all scared shitless. I can’t imagine anyone being brave enough to even ask her out.” Rory decided not to mention Jamie that asked Paris out on their last day in D.C. As far as she knew, he didn’t call back and Paris was especially angry after that.

Finally, Madeline yanked the curtain aside and stepped out wearing a really tight pair of black leather pants, and a black lacy crop top.

“Halloween outfit. Thoughts?” she twirled around.

“Wow, Mads, you look hot. These pants really compliment your ass.” Louise nodded in approval.

“Yeah, you look very alluring,” Rory added.

“Awesome,” Madeline clapped her hands excitedly. “Hey, what did you decide about the jacket?”

“Oh, I won’t take it.”

“What, why??? Let us see!” The girls practically forced Rory back into the jacket, and she put it over her t-shirt, looking in the big mirror and falling in love with it again.

“Wow, Gilmore, I gotta admit, you can look hot too,” Louise said. “You have to take it.”

“Yeah, you look great! Jess would definitely love it on you. You have to take it,” Madeline nodded.

“I uh… Actually, I can’t afford it,” Rory blushed to the roots of her hair. Being from a low-income household was never this embarrassing. She never had to admit it out loud like that in front of someone who wasn’t from Stars Hollow. Everyone there was from middle class families, no one was filthy rich like the Chilton population. So she never had to voice her money status, as everyone in her home town already knew about it. But right now, being in this expensive store, saying it felt the most uncomfortable Rory ever felt about money.

“Oh,” Madeline faltered. The thought that she wasn’t as rich as them didn’t even cross her mind when she asked Rory to go shopping together. “What size are you?”

“Four. Why?”

“Me too. If you’re not gonna take it, I wanna try it on,” Madeline said.

“Oh, okay,” Rory gave her the jacket. Madeline quickly put it on, and it suited her just as well as it did Rory. “Oh, look, it fits me too. You know what, how about I’m gonna buy it for myself, and you can borrow it for the concert?” she looked at Rory with a hopeful smile. As much as Rory didn’t want to be anyone’s charity case, she recognized Madeline’s effort to smooth things over.

“That would be very kind, thank you, Madeline,” Rory smiled at the other girl.

“You’re welcome,” the brunette beamed and went to the booth to change back into her clothes.

“You know, I bought a few things when I was dating that punk guy to fit into his taste. I don’t wear those clothes anymore. So you can borrow something, if you want. All of it was properly washed, don’t worry.” Louise offered. Rory figured she wasn’t as sensitive as Madeline, so she probably didn’t feel bad about Rory not being able to afford the jacket. But the manner in which she addressed Rory didn’t seem demeaning, she looked sincere when she made her offer. So she found herself agreeing to go to Louise’s house sometime after to school to check her closet, and also get ready for the concert at her place on the day.

When they paid and exited the store Madeline turned to Rory and extended a hand with the bag to her.

“You better take it now and give it back to me after the show, otherwise I might forget.”

“Okay, thank you.”

Madeline gave her a warm smile. “What are friends for?”

~XXX~

It became a tradition of sorts for them for Jess to go to Rory’s place on Mondays. After they both finished with school, he would ditch the diner and go to spend some time with Rory before Lorelai came home from the Inn.

This Monday was no exception. Rory liked these visits, because it was a time when they could explore the physical aspect of their relationship. She was quickly becoming addicted to it, to his touch, to the feel of his skin under hear palms, to the sensations he awoke in her with his skillful tongue. She wouldn’t trade it for any movie or bookstore date. They found themselves in Rory’s room on her bed, making out passionately, his mouth driving her insane for him. She wanted to get closer to him, to feel him better, so she tugged on the hem of his shirt and he took it off immediately.

She took a moment to marvel at his torso. He was all firm and solid, sinewy muscles bulging under his olive skin. There was a smattering of brown freckles over his arms and front, and she wanted to kiss every single one of them, count them all, map them out so that she could conjure a picture before her mind's eye whenever she pleased. He was so handsome it made something inside her ache. His beauty was an art form in itself, and she was the sole admirer. She traced the freckles with her fingertips gently, following the path from his collarbone to his abs, and then noticed it. There was an ugly scar on his left side above the v-line of his hip, closer to the edge of the body. It was faded and uneven.

"What's that?" She asked him. He tensed visibly. Uh, here we go.

"Mugging gone wrong." She lifted a questioning eyebrow at him when he didn't elaborate any further.

"Are you gonna tell me about it?" she asked softly.

"There's not much to tell," he shrugged, even though it’s true, and she can see it. But he doesn't want to go back to that day. That particular memory is really something he could do without. She's too pure and innocent in his eyes, to taint her with that night.

"Please?" Her eyes pleading, and really, how can you resist those baby blues. He already told her about Danny, might as well share something else.

"I was going back home one night through a shortcut alley and there was this guy who tried to scare me into giving up my cash, but I didn't budge. So he pulled out a knife. His eyes were wild and his hands shook, that's probably the reason he didn't hurt me worse that he has. The knife basically just scraped my side, a couple inches to the right, and I might not have been that lucky. I think he was a junkie coming up from his high, in a desperate need for a fix, that's why he couldn't control his reflexes much. I didn't give him what he wanted, and he snapped." He cupped her cheek when he saw the horrified expression on her face.

"What happened next?"

“I had this friend, Bobby, his sister worked as a nurse in a hospital. He lived nearby and I went to his place, because I didn't have insurance. Thankfully Mandy, his sister, was home. So she stitched me up the best she could. It's uneven and crooked because she's not a doctor, and technically wasn't qualified for that. But it wasn't her first time patching me up either."

"What? Where else?" She croaked. He turned around and showed her a nasty scar on his left shoulder, right above the shoulder blade.

"How did you get that?"

"Liz."

"Liz? As in, your mom Liz?" Her eyes widened incredulously.

"Yup."

"How?"

"She was drunk one night, and was in one of her angry moods, and she didn't like something I said, so she threw a beer bottle at me. And apparently it was already broken, so when it hit my back, it cut me open. Mandy got a hard time with that one." His face remained impassive. The only way he could talk about it was trying not to relive all the emotions he felt that day.

"What about Liz? Did she even notice she hurt you?" Rory couldn't comprehend what he was saying. What kind of a world was that where a mother throws beer bottles at her son, her own flesh and blood? She never felt more appreciation for her mom than in that moment.

"She kept screaming. I just left. I was already on my way to the door anyway. Noticed the blood only when I got outside." He fell silent. He didn't want to let her in on that part of his life. She did not belong there. Her idealistic outlook on the world did not need an encounter with that side of life. Not yet anyway. His head was lowered, so he didn't see the tears rolling down her cheeks.

"Jess..." She trailed off, cupping his face. He leaned into her touch, afraid she might not want to have anything to do with him after this. “I’m so sorry it all happened to you,” she whispered.

“It’s fine-“

“No, it’s not fine! God, it’s so not fine!” Her fingers clenched into fists. “I swear to God, I hate your mom! I’ve never even met her, but I hate her with every cell in my body. I didn’t even know I was capable of hating someone this much!”

“I know the feeling,” he added darkly.

“I know you hate it here, in Stars Hollow I mean, but for what it’s worth, I’m happy you don’t have to live with her anymore.”

“Me too.”

“And there’s literally zero chance of mugging in this town,” she gave him a weak smile trying to lighten the mood a bit.

“Unless I am the one doing the mugging,” he chuckled bitterly.

“Hey, Jess… Don’t say that,” she put her hands on either of his shoulders making him look straight into her eyes.

“What? It’s what the entire town thinks of me anyway.”

“I don’t think that way. And Luke doesn’t.” he looked away at that, but she cupped his face again and turned it back to her. “I think you’re wonderful, and there’s nothing in this town or in this world that would make me change my mind, you hear that?” There’s such deep tenderness in her eyes when she says that, and he wants to believe her, desperately so, but doesn’t know if he can. There’s so many different ways he can screw everything up. He sometimes has nightmares about it, that keep him awake till dawn, hands never idle, playing with the edges of his comforter as a replacement of a cigarette. He quit smoking for her. The things he’d do for this girl. It feels like he’s a character in some romance novel, willing to go to the edge of the world and sail the seven seas for his fair lady. But he’s no knight, no noble gentleman. He’s just a punk from New York. Those big blue eyes can’t lie though. He’s pretty certain she believes in what she’s saying, she’s telling the truth. If only it was as easy for him to believe in himself, as it is for her to believe in him. He wants her trust and fears it at the same time. Fears not to live up to the expectations. The thought of bolting is somewhere in the back of his mind all the time, but he can’t help but coming back for more of her. Rory Gilmore is not someone you can give up that easily. Once you get a taste of her, you’re hooked.

When he didn’t answer, she pulled him into a hug and whispered in his ear “You are absolutely amazing.”

And then she kisses him. Her lips are on his, and her hands weave into his hair and it’s all sensual, and wet, and lots of tongue. He gets lost in sensation immediately. It’s always so easy to get lost in her. If only real world didn’t exist. He could spend his whole life hauled somewhere with her, with no glimpses of outside world, just the two of them, and her taste and her smell everywhere. His hands glide slowly down her back and under her shirt, and she moves to straddle him. He can feel the heat emanating from between her legs and it’s a direct punch to his crotch. His reflexes come into play, and everything else seems distant, muted. Her. Only her. The only thing that matters.

He grabs her ass and presses her onto his growing hard-on, and she moans into his mouth. What a sweet sound! He likes the fact she’s not a screamer, but her reactions are always so genuine, sweet, but lustful nonetheless. She rubs herself against his bulge and it’s his turn to moan. Oh what he wouldn’t give to be inside of her right now. He knows they can’t. They haven’t really talked about it just yet. Technically, it’s only the second time she sees him shirtless. There’s a whole other realm of conversations to be had about the intimacy, but he can’t for the life of him think about those right now. Right at this moment he’s just a teenage guy whose girlfriend is grinding against his cock, and he can’t help himself. He puts his hands fully under her shirt and cups her breasts over her bra. He has seen her topless before, so hopefully, she wouldn’t decline his advances. The bra she’s wearing is very thin to the touch, like it doesn’t have any wiring or padding, he can feel her nipples poking into his palms through the fabric. She digs her fingers into his shoulders and her grinding intensifies. He keeps rubbing her nipples while his mouth is traveling her face down to her neck. He puts open-mouthed kisses on her skin, and she whines softly. He goes to lift the hem of her shirt up and pulls away to look at her imploringly. She lifts her arms up instead of a verbal answer, and he takes her shirt off. The next thing he knows, she’s kissing him again, she’s hungry and forceful. He doesn’t complain. Her bra is a baby blue lacy garment that brings out her eyes beautifully. He can’t look away. She’s so gorgeous in her purity, he almost feels holy. His fingers outline the contours of her breasts over the lace and she flushes at the intensity of his gaze. He wants to tell her how beautiful she is, but it’s such a cliché word. And he wants to be anything but. Words lodge in his throat, he can’t find the right ones to describe her, but the hunger in his dark stare compensates for it plenty. Her gaze matches his and her eyes roam his torso. He looks just like she imagined during those restless nights in D.C., even better maybe. Better because he’s real, and he’s right in front of her. She doesn’t need to imagine how his biceps, or abs, or pecs would look like under his clothes, now she knows that for a fact. And she loves it. She never had a sexual crush on any celebrity before, like many girls her age, who claim a certain actor or a singer to be their sexual awakening. For her, it’s Jess, he’s her awakening. And unlike any celebrity, he’s real, and he’s right in front of her, and she can feel him, and taste him, and do whatever she pleases with him, because he’s her boyfriend. The giddiness overwhelms her and she giggles. It earns a confused glance from Jess, who doesn’t understand what’s so funny about being on top of him. He bumps his nose against her and asks her what it is. But she giggles some more.

“Hey, what is it, Gilmore? Are you mocking me or something?” he’s confused, but he’s smiling nonetheless.

“No, I’m not mocking you. I was just thinking how happy I am to be your girlfriend.” He clearly doesn’t believe her, if the arch of his brow is any indication. ‘I’m serious! I’m so glad we’re together. I can kiss you whenever I want,” she beams at him, and it kind of makes sense. Only Rory would be giggly about something like that. “And I can also hug you whenever I want, and I can hold your hand for everyone to see, and I can talk about anything and everything with you. You make me really happy, Jess.” Her eyes are sincere. And maybe it’s a detour from their previous lustful moments, but he likes it, appreciates it. No one ever said that about him before. Truth be told, he wasn’t much of a boyfriend material, especially not in New York, so maybe there weren’t really any chances for him to be told such things, because he wasn’t really anyone’s boyfriend before. But he’s glad he is one now. Because, really, how can you be Rory Gilmore’s boyfriend and not be happy about it?

Chapter Text

Later on, Jess and Rory were almost caught by Lorelai, who came back from the Inn just ten minutes after Jess left, but not before Rory convinced him to go to Louise’s Halloween party.

They were lying on her bed, both topless, Rory half on top of him placing soft kisses along his collar bones.

“You know, I’ve been meaning to ask you something…”

“Shoot.”

“Well, my classmate, Louise is throwing a Halloween party this weekend at her house.”

“The one who’d sleep with anyone with a penis and a pulse?” Rory giggled in response.

“Yeah, that’s the one. Anyway, she invited me to come, and she also invited you, after she saw you in the Chilton parking lot the other day. I’ve been to Madeline’s party once, and her house was huge, and they had a DJ and everything. It’s not really my scene, but Louise said we can ‘fool around in any room’,” Rory looked at him imploringly trying to gauge his reaction. “I normally wouldn’t have gone, but the idea of being alone with you away from the townies is kinda appealing. I was thinking I could borrow Lane’s cheerleading uniform. But you don’t have to dress up,” she hastily added.  “If anything, we can always say you’re dressed as Rocky Balboa’s son.” Seeing the skeptical look on his face, she added, “Well, if they were making a sequel where Rocky had a teenage son, I think you definitely could’ve been cast as one. Sooo…. What do you say?”

“Rory,” he leaned up to press a kiss on her lips, “You had me at ‘fool around’’.

“Really?” She beamed at him. “Thank you!!”

~XXX~

On Tuesday Jess was running a little late for his first class. Kirk had some kind of accident with his cat, which made him stutter terribly, meaning his usual order bit he did with Luke took two times longer to complete, then Luke dropped the coffee pot on the floor, the brown liquid splattered everywhere, Kirk stepped on a shard of glass, slipped and fell. It was a total disaster. Jess had to go upstairs and change his shirt twice before he escaped the war zone.

The school halls were almost empty, safe for a few late students. Jess was about to enter a science lab when he saw a guy picking on another guy in the distance. Their voices sounded familiar. Jess stepped closer and recognized the bully as non-other than Chuck Presby and his victim was Scotty McNally. Presby was cornering Scotty, making a faux jump, Scotty dropped the thing he was holding in his left hand, and it clattered away. Finally, Jess decided to intervene.

“Hey, is there a problem?” he said coming closer.

“What is it to you, Mariano?” Chuck challenged.

“Oh, so you remember my name, great. Then you might also remember that time when I kicked your ass. Want some more?”

“Fuck off,” Chuck spit venomously.

“Or what?” Jess raised an eyebrow calmly. “Leave him alone, Presby.” Chuck knew the odds were not in his favor. Jess fought like a rabid dog, like someone who had nothing to lose, he didn’t shy away from any dirty street moves, and the black eye he gave him didn’t fade away for a lot longer than Chuck expected. It made him hate Jess, but it also made him afraid of him. He knew he doesn’t stand a chance with Jess one-on-one.

“It’s not over,” Presby muttered to Scotty, and walked away. Jess was watching him until he disappeared around the corner. He then leaned down and picked the object Scotty dropped. It was an inhaler.

“Is it yours?”

“Yeah, thank you,” Scotty took the inhaler and pressed the button to use it. “I have asthma.”

“I figured. Does it happen often?”

“What? Chuck Presby acting like a Neanderthal? Quite often.” Scotty shrugged. “It’s no big deal, I’m used to it.” He tried to play it cool, even though his entire being was flooded with relief. Jess was the first and only person in this school who stood up for him, who saved him from Presby’s incessant bullying. To Scotty Jess was basically Superman at this moment.

Jess eyed the skinny guy for a second accessing the situation. He remembered how Rory told him about McNally being bullied by Chuck Presby and his friends. Despite his better judgment and general philosophy to stay out of people’s way he decided to keep an eye on Scotty. He liked working with him on the AP project. The guy was really smart, too shy and hesitant to voice his opinions at times, but now Jess knew why, at least partially. Jess wasn’t really bullied much in his previous schools. He changed them too often for the bullies to even register he was there. And then he learnt how to fight, and after that nobody picked on him. But Scotty was going to the same school his whole life, and every day probably felt like an episode of Survivor for him.

“What’s your next class?”

“Uh, science,” Scotty pointed at the lab door in the other end of the hall awkwardly. He had absolutely no grace in his movements, it seemed like he was too much for his small frame, like his limbs didn’t belong to him, and he was surprised at their length every time he had to use them.

“Let’s go then, it’s my first class too,” Jess motioned with his head for Scotty to follow. Without even knowing Jess got himself a new friend.

~XXX~

During lunch Jess usually sat at the corner table reading. Now that he started attending school more often it was a regular occurrence. He usually sat alone. In the beginning of the school year when he was still with Shane, she sat with him sometimes, but he didn’t stop reading, which made her bored, so often times she left him for her friends. After all, there was too much new gossip to discuss. After the break up Jess’s table was a fortress of solitude once again. Except today. The tray clanked against the table’s surface and someone plopped on the bench opposite Jess. He raised his eyes from the book and saw non-other than Scotty McNally. He was smiling hopefully at Jess, and he just didn’t have it in him to shoo him away.

“Do you mind if I sit here?”

“It’s a free country,” Jess shrugged. Scotty took that as a yes and started sorting through his food.

“You know, I wanted to uhh.. I wanted to thank you, for what you did this morning,” Scotty’s head was lowered, he didn’t dare to look at Jess. “I really appreciate it.”

“Okay,” Jess paused. “You know you don’t have to keep me company just because of what happened this morning.” Scotty looked up at that, and Jess saw his hurt expression. It was like kicking a dog, jeez.

“Oh, uh, okay, then I can sit somewhere else, it’s no problem,” he deflated. Jess rolled his eyes.

“What I meant to say is you’re welcome to sit here if you want, but you don’t have to. You don’t owe me anything or whatever.”

“Oh, uh, yeah, uh, sure. I’d love to sit here though. It would be nice to sit with someone. Are you sure you don’t mind?”

“I don’t mind.”

Scotty was obviously relieved. A realization dawned on Jess that maybe he wasn’t the only person in this school who ate his lunch alone. And while it didn’t bother Jess much, it must have been a very depressing experience for Scotty.

“So, do you think we did okay on our project?” Scotty asked. He was clearly making an attempt at conversation, and Jess didn’t feel like rejecting the guy.

“Yeah, I think we did alright.”

“I really wanna get good grades in this class,” Scotty said unwrapping his turkey sandwich. “It’ll help me raise my GPA. I wanna be a doctor. I’m applying to John Hopkins University, and I need all the GPA points that I can get. Even though English is not exactly the main subject for medicine major, Stars Hollow High doesn’t offer many AP classes, so I’ll take anything that I can get,” Scotty kept rambling, while Jess kept eyeing him in amusement. This kid got bullied every single day of his school career and he still wanted to be a doctor? Help people? It didn’t harden him, it didn’t make him want to show up at school with a gun one day and avenge, but the exact opposite of that. It only solidified Jess’s decision to keep an eye on this guy.

When the lunch was over, Scotty rushed to his biology class leaving Jess alone. Then he noticed Shane walking to his table. When he was about to take his book out and start reading again, she came closer and said, “Hi, Jess.” He didn’t respond. She walked by. Then he noticed Lane who was sitting with cheerleaders on the other end of the cafeteria staring right at him. Great.

~XXX~

Rory didn’t have the chance to hang out with Lane lately, so it was nice to finally catch up with her while Mrs. Kim was busy with a very promising customer. The girls were sitting in the gazebo, a bag of chips between them which Lane kept discreetly stealing from. They were chatting and laughing for about fifteen minutes, a true luxury in Lane’s world, when she finally worked up the courage to ask Rory about Jess.

“So, you and Jess, how is that coming along?”

“It’s going really well actually. He’s great,” Rory smiled with a dreamy expression on her face. It made Lane feel even worse because of what she was about to reveal to her best friend.

“Oh? Well, uh, that’s great,” she kept shifting in her seat and Rory caught on that something was off. When she asked Lane about it, she blurted everything out.

“Okay, don’t freak out, but I have to tell you something. About Jess. Kind of.”

“What is it?”

“Well… you know, Jess goes to Stars Hollow High, and so does Shane, his ex,” she paused collecting her thoughts. “So, a few days ago I was about to leave the locker room when I heard Shane talking to her friend about Jess and you.”

“Oh… What did she say?” Rory’s eyebrows furrowed.

“First of all, she said that Dean slept with Sydney Waller, who’s on the cheerleading squad, and when he uhh… finished, he called her by your name.”

“Wow…”

“Yeah, it’s all over school, but repeated in hushed tones, so everyone knows, but doesn’t mention it in front of Dean.”

“That’s... actually pretty gross,” Rory scrunched her nose.

“Yeah, they also said that Dean told one of his friends about the reason you guys broke up. That you, you know, didn’t wanna sleep with him.”

“Oh my God, so everyone knows?? But that’s so private. I can’t believe it!” Rory cried in indignation.

“Yeah, unfortunately. But again, no one is talking about it out loud, it’s kind of a hush-hush thing, because Dean has gotten kinda popular, with his success on the hockey team and all,” Lane shrugged.

“Wait, you also mentioned Jess.”

“Oh, yeah,” Lane looked down at her knees, fiddling with the hem of her sleeve. “She also said that Jess likes it rough, and he also prefers… uhhh… “ she blushed hardcore. “Well, that he likes… you know… when a girl is …. Uhh… when she gets his thing into her mouth...” growing up in a religious home, made Lane unable to work sex-related terms into her daily vernacular, so the whole thing was making her really uncomfortable.

“Oh… Was there anything else?”

“Yeah… she also said that as soon as Jess realizes you’re not gonna sleep with him, just like you haven’t with Dean, he’s gonna break up with you and go back to her.”

“Wow…” Rory sat back dumbfounded.

“I’m sorry, but I thought you should know,” Lane looked at her apologetically.

“It’s okay, thank you for telling me. But honestly, I don’t think Shane will be a problem.”

“Really? Why?” Lane turned to Rory all alert and curious.

“Uhh… Lane… I’m gonna tell you something, but you have to promise me you won’t tell anyone.”

“When have I ever told anyone any of your secrets?” Lane gave her a pointed look.

“You can’t even tell my mom.”

“Oh,” Lane was taken aback. Never ever in her life she heard of Rory keeping secrets from Lorelai. “I promise, not a peep from me.” She faked a zipping motion with her fingers across her mouth.

“Soooo…. Jess is definitely gonna be my first.” Rory writhed her fingers. “And it’s gonna happen soon. Well, not like soon soon, but not at the end of the year at prom or something. I’ve been thinking about it a lot, and I want to do it with him.”

“Oh wow… Oh my God… Wow!” Lane blinked owlishly a few times without saying anything.

“My relationship with him is different, and so much better than with Dean. I didn’t wanna go all the way with Dean, but I want to with Jess,” now that she’s started talking, there’s no stopping her ramble. “And the reason I know it is because we’ve been doing… stuff.”

“Stuff? What kind of stuff?”

“Well…. We’ve seen each other topless and he uh, kissed my breasts,” Rory blushed at this revelation. “And also, he touched me… down there…” she whispered the last part looking around not wanting to be overheard.

“Wow… Oh my God, wow…” this seems to be Lane’s only reaction, she couldn’t string together a coherent sentence if she tried. Sex was always such a faraway concept for her, so to imagine her best friend she’d known since childhood doing something remotely intimate seemed unfathomable.

“And, he also… went down on me after my birthday party,” Rory said hushed.

“Went down, as in…?” Lane was not sure what that means.

“As in, putting his mouth on me down there, licking. I had an orgasm and everything.” Rory admitted.

“Wow… that’s… huge! And Lorelai doesn’t know about it? I thought you tell each other everything.” Lane frowned in confusion.

“Normally we do, but I don’t feel like sharing this with her. Remember what an enormous deal she made out of that one time when Dean and I accidentally fell asleep at Miss Patty’s after the dance? And we literally just slept, nothing happened, yet she yelled at me, we haven’t spoken for a week. Imagine what happens if I tell her about Jess. You know how much she hates him, so if I told her we were… exploring… she would totally freak out. So I’m not gonna tell her until I actually wanna go all the way. Then I would need her to set up a doctor’s appointment for birth control.”

Lane hugged her sympathetically. After a minute of silence, she asked. “Sooo… how was it?” Rory giggled in response.

“Oh Lane, he’s so wonderful! He makes me feel so… sooo… I don’t know, like I’m floating on air, and like I’m on fire, and like I’m freefalling from the sky all at once. I’ve never felt this way before. It’s like I’ve woken up from a deep sleep, and now all of my feelings are alive.” She gushed.

“So you were a Sleeping Beauty and he awakened you with the kiss of true love?” Lane teased.

“Kinda yeah, but in a more… carnal way,” Rory averted her eyes, blushing even deeper.

“That’s great. You look happy,” she noted.

“I am happy,” Rory gave her a broad smile. “I like him so much.”

“I’m really happy for you,” she squeezed Rory in a tight hug, but then she saw the man leaving Kim’s Antiques, and jumped from the seat.

“Shoot, I gotta go. Bye!”

“Bye, Lane.”

Having told Lane made Rory feel a little lighter, knowing she’s not carrying this huge secret about her personal life alone.

~XXX~

Lorelai was surprised to learn Rory was going to Louise’s Halloween party on Saturday. When Rory first transferred to Chilton Lorelai tried to help her daughter to befriend the girls, because obviously every new kid needs friends. And Rory was getting along with Madeline and Louise just fine, but Lorelai never suspected she would be getting closer to them in her Senior year. They didn’t seem to have much in common, yet Rory purposely chose to spend time with them the second weekend in row.

Rory was getting ready for the party when Lorelai leaned onto the doorframe of her bedroom. Rory was wearing Lane’s cheerleading skirt and long sleeved top, but without the outer jacket with a furry hood. The outfit was completed with white tights and sneakers. She tied her hair in a ponytail and curled the end for good measure. She was currently standing in front of the mirror putting make up on, dabbing her lips with a fruity lip gloss.

“Wow, you’re really taking this party seriously. If I didn’t know any better, I’d say you were primping for a guy,” Lorelai commented. It took every shred of will power for Rory not to blush. She was really looking forward to this party, especially for the fooling around part, and the very thought of it made her feel girly, like she wanted to look her best for a guy she really liked.

“Just wanna look in character,” she shrugged.

“Yeah, cheerleaders totally primp for guys,” Lorelai nodded. “Soo…. Jess is still gonna drive you there?”

“Yeah, he’s gonna be here soon.”

“Be careful, okay?”

“Mom,” Rory sighed, a hint of exasperation on her tone. “Are you gonna say this every time I get in a car with Jess? I told you a million times, it was an accident. How does his desire to protect the furry thing make him an antichrist?”

“That’s not what I’m worried about,” her mom started. “Well, the driving-with-Jess part too, but getting-sloshed-at-the-house-party-and-being-alone-with-Jess-in-a-free-bedroom part worry is prevailing right now.”

“I’m not gonna get sloshed, you know full well I don’t drink,” Rory conveniently left out the last part. How do you tell your mom you’re actually counting on being alone with your boyfriend in a free bedroom for that exact reason, it being free? Free from authority figures, free from Taylor, free from Luke and other townies, and more importantly free from your mom.

“Yeah, that’s also not my main issue.”

“Mom… Look, what happened with Dean is not gonna happen with Jess, okay? He’s not pressuring me into anything, I promise. You have nothing to worry about.” It’s not exactly a lie. He really doesn’t pressure her into anything. She just wants to do it all on her own without any external pressure at all. But Lorelai doesn’t have to know that.

“I’m just saying, guys like Jess, experienced guys are used to doing more, and they try to get it sooner or later. So I can’t help but worry. It can’t be helped, okay, I’m your mother, and I love you and I don’t want you to get hurt.”

“I know, and I get it. I love you too, and I promise you, Jess is not like that. I know him better than you do. You have to trust me on this, please?” Rory tried to placate her mother. She figured it’s not the time to blow up on her, no matter how frustrated her mom’s assumptions about Jess made her. She’s going to need her mom on her side, so Rory felt like she had to start preparing her mom for the thought Jess is actually a good guy, and she’s safe with him, and she will also be safe when it’s time to go all the way.

She noticed Jess’s car in the driveway through the window. “He’s here, I gotta go.” Rory grabbed her purse and a jacket and went out of her room.

“Have fun!” Lorelai yelled. “Don’t get sloshed! At least not until midnight! Only lame-os do that!”

“I won’t.” Rory yelled back closing the front door.

~XXX~

Jess kept sneaking glances her way while they were in the car. Her skirt was really short and albeit covered in white tights her thighs were still on display.

“I gotta say, I’ve never really had a thing for cheerleaders, but you wearing this outfit is kinda doing it for me,” he cleared his throat.

“Eyes on the road, Mariano,” Rory said biting on her lower lip to not let the smile escape. His compliments always made her feel giddy and excited.

Finally, they pulled over to a huge mansion, the whole driveway was packed with expensive cars, so Jess parked outside the gate.

“This is….” He started.

“Yeah,” she nodded.

“Soooo, what happens now, do we go straight for the room or...?” she socked him on the shoulder, he just laughed in response.

“Let’s go inside and try to find Louise, at least let her know we’re here. Just using her house like that would be rude.”

~XXX~

They were wandering around the house for a bit. It was similar to Madeline’s in terms of a party set up. Louise had a DJ stand placed in the foyer, people were already dancing holding solo cups in their hands. The walls were lined up with tables where bowls of punch, chips and other snacks were located. The huge beer kegs were situated on either side of the room so not to create a line. Some dudes were already chanting ‘chug’ to some other guys who were apparently in some kind of drinking competition. The whole thing looked like a standard party, but everything was a thousand times more expensive, than what Jess used to see at the parties he attended in New York.

All of the people were dressed up, girls were wearing mostly slutty outfits, basically a set of lingerie with a pair of animal ears on top of their heads. Guys were even less elaborate, a lot of them wore various sports uniforms. So Jess wearing a white t-shirt, dark jeans and a leather jacket didn’t stand out like an underdressed at all.

Finally, Madeline and Louise popped out from the center of the crowd, and Madeline shouted “Rory!” She was obviously excited to see her. Her hips swaying a little due to the alcohol she’s already consumed. She was wearing the outfit they bought together last weekend, her hair was pulled back and held with a pair of kitty ears, she looked really cute.

“Hey,” Rory smiled at the brunette, and pulled Jess closer. “Madeline, this is my boyfriend – Jess. Jess, this is my friend from Chilton – Madeline. And this is Louise.” She addressed the other girl who came closer after untangling herself from a tall blonde guy in a basketball jersey.

“My, my, my, you’re even better up close,” Louise purred at Jess. “Nice one, Rory. I’m glad you made it. Enjoy the party. The third floor is a lot quieter than here, if you catch my drift,” she said with a wink. Rory blushed.

“Oh, and I think the punch is spiked,” Madeline added. “But it’s really good nonetheless. I’m gonna go find Jake,” she giggled tipsily. “He’s such a great kisser, you would not believe. Okay, bye!” She waved at them and disappeared in the crowd.

“The cat ears worked, apparently.” Louise rolled her eyes fondly. “Anyway, feel yourself at home. I’m gonna go find my date as well. Ta-ta!”

“Sooo… that was Louise,” Jess stated.

“Yep,” Rory nodded. “So, do you wanna find something to drink that is not spiked, or maybe you wanna dance, or… God, I’m kinda nervous. Can you tell I’m nervous? I mean, these parties are totally not my scene, and I don’t really know how to act, and how do you even dance to a music like this? The bass is pumping so hard, I think my eardrums are gonna burst in three more beats-“ he stopped her rambling by pulling her closer and covering her mouth with a kiss. It started light and chaste, but when he pulled back, she followed him and kissed him again, this time their mouths opening and tongues finding each other. When they stopped he pressed his forehead to hers, their nose touching, eyes closed.

“We can do whatever you want,” he said. “I’d prefer something less loud though.”

“Yeah, let’s go upstairs and explore the house. I’m actually kinda curious about what other rooms they have.” She took his hand, and he followed her as she navigated them through the masses of dancing people.

They found a broad stairwell and walked up to the second floor. As tempting as Louise’s hint about the third floor was, Rory thought that going straight for it would be moving too fast somehow.

They turned to the right and wandered down a broad corridor. All the walls were adorned with paintings and small tables with statutes and vases and other pieces of art, which made it look more like a museum than a house real people lived in. Rory always thought that her grandparents’ house wasn’t really cozy and often times it didn’t feel like a home, but Louise’s mansion was beyond that. She definitely would not want to live in a place like this.

“Hey, do you think they have a library here somewhere?” Jess asked.

“They might, actually. Do you want to look for it?”

“Might as well try.”

They wandered some more until they found a set of double doors with intricate golden handles. Jess pushed one of them and the door opened with a squeak. They peaked inside and saw rows upon rows of bookcases with all sorts of volumes.

“Bingo,” Jess smirked.

“Wow,” Rory exhaled when they entered, she’s never seen this many books in one place before. It surpassed anything her grandpa had by miles.

“Hey, if I take something, do you think anyone would notice?”

“Jess! You can’t steal books from here,” she admonished.

“Why not? Look at the dust layer on them, you said they bought this house not that long ago, but the books obviously haven’t been used since they were unpacked. I’m gonna go look for something.”

“Jess, wait!” She hurried after him. “You can’t just... Jess!”

“Look, the first edition of Gatsby. I actually need it for my AP class.” He fished out a book from the bottom shelf.

“Jess, you can’t just take it, it’s first edition, it’s probably super expensive, and it’s just rude to steal from a house you were invited to, not to mentioned illegal.” She huffed.

“When you throw a house party you get what you get. I bet you a fifty, no one would notice it’s gone.”

“What? No, Jess put it back.”

“Fine,” he rolled his eyes. “You’re no fun.”

“Just let’s get out of here. I don’t wanna stave you off of stealing every other book from here.” She dragged him by the sleeve.

“You just want to get me alone and naked,” he gave her a cocky smirk, and she blushed in response, because that was exactly what she wanted, why she agreed to go here in the first place.

They exited the library and continued their journey around the house stumbling on a few couple looking for a place to hook up.

When they reached the third floor, it was significantly quieter, but they could also hear faint sounds of people who successfully found a place to copulate. They walked down the corridor listening closely, trying to identify the unoccupied room.

Finally, they seemed to find one. Jess pushed the door carefully and peered inside. It was empty, so he ushered Rory in, and closed the door turning the lock to avoid intruders.

It was a guest bedroom. The bed was made, and the dresser and vanity lacked any personal items that could belong to an occupant of the room. At least they weren’t trespassing on anyone’s personal space.

Rory suddenly felt awkward, which was stupid, she knew that, they’ve already seen each other shirtless, they’ve done some stuff too, it shouldn’t be this awkward, but she couldn’t help it. She was standing there in the middle of the room not knowing what to do with her hands. Jess turned to her and slowly stepped closer.

“Hi,” he whispered nuzzling her nose.

“Hi,” she whispered back and closed her eyes instinctively. A second later his lips were on hers, and all the thoughts about awkwardness evaporated from her brain, being replaced by the white noise and the overwhelming sense of him, his taste, his smell, the feel of his curls so soft between her fingers. She moaned lightly into the kiss and pulled him closer. His mouth opened wider and he devoured her with a passionate kiss. His arms found its way around her, pressing her whole body to him, no inch of space between them. She leaned up standing on her tip toes and relished in the feeling of her chest brushing against his solid torso. He lifted her up easily and took her to the bed. She lied down and he moved to lie on top of her. She kept kissing him, trying to tug his jacket down his shoulders at the same time. He helped her by lifting his one arm up and holding his weight on the other, and then repeating the motion until he was left in just his white t-shirt. It was one of his tighter ones. Liz insisted on doing laundry one day, and he couldn’t save this one in time. It shrunk during the washing because Liz set the temperature regime for a different kind of fabric. So now it was hugging him tightly, outlining his biceps, which made Rory salivate. The whiteness of the shirt complimented his olive complexion, his dark curls and hazel eyes stood out more.

Rory pulled back from the kiss to get a closer look, her eyes turning dazed, a clear hunger in them.

“Like what you see?” Jess couldn’t help the smug feeling her staring gave hm.

“Oh yeah, so much,” she replied honestly, and traced his features with the tip of her finger. She squeezed his biceps and went lower to toy with the hem of the shirt. “Take it off,” her tone a breathless whisper.

“As you wish,” he said back, and leaned back on his haunches to shrug the shirt off in one smooth movement. Her breathing hitched. Fuck. He was so hot. And hers. All hers for the taking.

She beckoned him closer with her arms and he situated himself on top of her, resuming their heated make out session. Her hands couldn’t stop moving for a second, covering every inch of his hot skin, her delicate palms squeezing and pressing everywhere, at his sides, at his strong back, at his flat stomach, his abs contracted when she dragged her short nails over them, to the delicious V of his lower belly. His back muscles flexing under her fingers, his mouth trailing down her neck to set fire in every spot he touched. Wet mouthed kisses, gasps, moans, hungry hands, soft locks at the nape of his neck, the desire was consuming her. She already forgot there was a party downstairs, that they didn’t mingle even for a minimum of socially acceptable time, that maybe it was rude to go search for a room right away. Right now Jess was everywhere, all of her senses were filled with him and she wouldn’t want it any other way.

His hands trailed down her body and sneaked under her shirt. The top she was wearing was long sleeved, and rather long, it didn’t reveal any skin at all, which was designed to fit a cheer practice in the cold of New England, so finally touching her bare skin sent an electric current through Jess’s body. Rory gasped and lifted herself up a little instinctively, helping him to take the garment off.

He pulled on the hem, and she set up readily to get rid of the offending fabric. She was wearing a white lacy bra underneath, which complimented her creamy skin, and made Jess’s mouth water.

“Fuck,” he whispered under his breath and pushed her gently to lie back down. She wrapped her arms around his neck and pulled him with her. They resumed their kissing, and his mouth wandered down her neck again. He licked her protruding collar bones, the hollows of them and went down, nuzzling her chest. Her upper breasts that weren’t covered with a bra felt so soft and supple to his touch. The left one was trembling with each beat of her heart, that hammered like crazy in her chest. He placed an open-mouthed kiss there, his tongue hot against her skin in the cool air. He traced the rim of her lingerie by his tongue and her lower belly filled with a hot burning sensation. The arousal made her push her pelvis upwards and her center brushed against his hips that were slotted between her legs. He hissed as she brushed his erection and pressed his forehead to her skin, inhaling sharply. She did it again, and he had to stop her, holding her hip firmly. “Rory…”

“It feels so good,” she whispered, lost in sensation, wanting more of it.

“I know, it really does,” he mumbled into her chest, breathing rapidly. Just being on top of her like this filled his brain with flashes of images of her naked under him, of him thrusting into her, a kaleidoscope of all of his fantasies swirling in front of his mind’s eye.

He reached behind her and unclasped her bra, letting it loose around her chest. She eagerly pulled it off and tossed it the side. His hungry stare sparkling something deep in her core. She pulled his head to her chest again, showing him what she wanted, no, craved for since the first time he’s done it. He obliged and twirled his tongue around her nipple, making it instantly hard and she couldn’t help but moan at the feeling. Her head fell back on the pillow, but then she lifted it again, wanting to see him kissing her like that, imprinting the image of his handsome face pressed against her breasts like a photograph, committing it to memory. His hands were holding her ribs, his fingers long and beautiful, trailing upwards until they curled around her other breast, just the perfect fit for his palm. Her nipple was poking from between his fingers and he closed them together, putting pressure on her sensitive bud, making her hips jerk upwards, where his hips were. 

“Jess-“ she whimpered. His amazing, talented mouth was doing these wonderful things to her, nipping and licking at the underside of her breast, teasing her with the tip of his tongue drawing something across her soft mounds. She read somewhere that some women are able to have orgasm from only a nipple stimulation. She didn’t know if she was one of them, but this thorough attention he was giving to her breasts made her arousal reach new heights. Her brain turned to mush, she couldn’t think straight, she just wanted him to continue. Her fingers were pulling gently on his hair, guiding him to the spots he missed and she wanted him to touch. Her legs wrapped around his waist on their own, and she pulled him closer to her core. He moaned into her skin when his hard-on hit her opening.

“Let me touch you there,” he asked hoarsely, looking up at her flushed face. His eyes were completely dark, pupils blown wide, only the tiniest strip of hazel visible. He looked criminally handsome. She could only say “Okay” to that wild plea.

His hands went underneath her skirt and tugged on the elastic of her tights. She lifted her hips to help him, and he pulled them off completely, tossing her sneakers along with them. That left her legs completely bare. He hasn’t seen her like this before, and the new image adding fuel to his arousal. He traced his palms upwards, from her ankles to her thighs, trailing her smooth skin, leaving goosebumps in his wake. She was watching him with bated breath, as they were crossing some new line in their physical relationship they haven’t crossed before. Finally, when he reached her upper thighs, his fingers lightly glided to her inner thighs, her skin so sensitive there it made her inhale sharply.

He put his fingertips on the band of her panties and tugged on them softly. “May I?” He would stop if she said no, but it would definitely kill him, if she did.

She gulped nervously, but nodded nonetheless. After all, he already went down on her, he’s seen her down there before. He slowly took her panties off, carefully untangling them from her toes. She pressed her legs together shyly, and he gave her a reassuring smile. Then he moved to lie back on top of her again, and kissed her softly. She hugged him closer, their naked torsos pressing together, her nipples brushing against his hot skin making them both moan. His hand cupped her face, then her neck, tracing nonsensical patterns on her, down her chest and stomach, and then finally between her thighs.

He nudged her legs apart and pressed his hip to her inner thigh, balancing his weight on his right forearm, while his left hand landed on her center. Finally. He covered her with his entire palm, pressing the heel of it to her clit. She couldn’t help the needy moan. She clutched at his bicep firmly, urging him to continue.

He started stroking her slit with his fingers, marveling at how wet and hot she was. Her reactions to his ministrations made his throat dry, his dick straining in his pants. He carefully pushed his middle finger inside, just the tip, and she mewled in pleasure. He then proceeded to push it further, slowly sliding his digit all the way in until it couldn’t go any further. They haven’t done it before, not as deep. He only ever teased her entrance, but this was different, new, exciting, exhilarating. The heel of his palm kept pressing on her clit and she wiggled trying to get more friction. The sensation overwhelming her, flooding her every sense.

Jess started slowly pushing his finger in an out matching it with the pressing to her clit, and she couldn’t hold back her moans. He was slowly speeding up and her hips were jerking trying to match his rhythm. He started to push his own hips into her inner thigh, mimicking his finger motion, creating an illusion of sex. His erection pressing against get just went harder if it was even possible. He was fucking her with his finger, while his hips were rutting into her thigh, and she closed her eyes shut at the onslaught of the sensation. She imagined him actually fucking her like this, with his cock inside her, with the hot skin of his chest rubbing against her nipples, his weight on top of her, their combined heavy breathing, and the pressure inside her core was building up, and she felt it, this amazing feeling of an upcoming orgasm.

She clutched at him harder, whining his name in the crook of his neck. She was so close, so close, her hips started moving more erratically, chasing the high his hand promised, she was groaning non-stop, until finally she reached her peak, the white and yellow spots exploded behind her eyelids, she rubbed herself onto him messily, as she was chasing her orgasm, whimpering and whining in his shoulder, babbling something incoherent, mixed with his name. The sight of her like this almost finished him, it took all of his willpower not to bust the nut into his pants. Walking down the party with a wet spot on his crotch was the last thing he wanted.

Finally, when she came down from her high, she slumped back on the pillow. Her eyes glassy and unseeing.

‘Wow,” was all she could say. He chuckled lightly, rolling off of her and lying next to her, facing her.

“I… wow…” her brain functions obviously needed some time to restart. He didn’t push her. Just went to trace patterns up and down her arm with a finger that was just inside her. The smell of her arousal hitting his nostrils, sending a jolt down his body. Fuck.

A few minutes later, when her systems finally kicked back into motion, she turned on her side to face him, and her hand accidentally brushed his crotch. He winced and pulled back.

“What’s wrong?” she asked looking down. “Oh…”

“It’s fine, it’ll go away if you don’t touch it.”

“What if… what if I want to?” she bit her lower lip timidly.

“Want to what?” he looked at her, confused.

“Touch it,” she gulped nervously. She really wanted to see his cock, today was as good day for it as any.

“Are you sure? You don’t have to do this, if you’re not ready.”

“Yes, I’m sure. I wanna see it,” she looked back at him, her eyes round and wide, and so impossibly blue. “I mean, you just did something really nice to me, it felt, God, it felt incredible, Jess!” she closed her eyes for a moment, the blush creeping back on her face. “And I wanna make you feel good too.”

“It’s not a give and take kind of thing, Rory. I don’t want you to think you’re obligated to do something like this back, just because I did.”

“I know, and it’s not my motivation, trust me. I really wanna make you feel good, not just because of what you did, but whenever. So, can you please teach me how to touch you?”

“Okay,” he nodded. He was about to unzip his jeans, when she softly nudged his hand away, and repeated his earlier question. “May I?” He leaned back on his elbow leaving his crotch at her mercy. She carefully unbuttoned his jeans, and slowly pulled the zipper all the way down, until the flaps of his pants fell open, revealing black fabric of his boxer-briefs. She gulped nervously, and tugged on his jeans, urging him to lift his hips up to assist her. When his baggy jeans were half way down his legs, she stopped and looked back at his erection. His underwear hugged him like a second skin and didn’t leave any doubts about the state of his arousal. The bulge under the cotton seemed massive, and Rory couldn’t help but remembered what she heard Shane saying on the phone ‘big dick too, well he is Italian”. The realization that she was just about to see his cock for the very first time hit her, making her throat go dry, and heart beat faster.

She carefully placed her hand on his bulge, and he hissed. She stroked it over the fabric experimentally, outlining the contours of his dick. The more she did that, the more defined it got. She was fascinated with the lines and dips it made. Finally, she hooked her fingers under the rim of his boxers and tugged carefully, her hand trembling slightly, in anticipation and nerves. He helped her by lifting himself up again. And there it was. Jess’s penis in all its glory, hard and throbbing, a thick vein lining its entire length from the underside of the head to his heavy balls. Rory gasped barely audible.

She was right, it was beautiful, just like the rest of him. The head was proportional to his length and thickness, the drop of precum that leaked from the top mesmerizing her. She reached her fingers unconsciously and traced her fingertip along the slit, collecting the moisture with it. Jess groaned and threw his head back. This whole scene was killing him. Her just staring at his cock like that, all flushed and awed, it was too much. He desperately wanted her to do something, but he didn’t want to rush her at the same time. After all, it was the very first time she was seeing this part of male anatomy. God only knew how much time she needed to get acquainted with it properly.

Rory looked at his face, and then back at his cock, and wrapped her fingers around his length. He hissed in pleasure, his breathing turning labored. She struggled to remember what she read about the male stimulation in those books on D.C. She recalled, it needed some lubricant for it to be pleasant, so she licked her palm and went back to hold him. Then, she stroked him slowly, carefully, trying to get used to the feeling of his girth and weight in her hand. It felt heavy, solid, and so impossibly hard. Touching him like this made something inside her throb again. He looked so fucking hot, lying like this, his abs flexing, his gorgeous v-lines on full display, and his beautiful, beautiful cock hard and pulsing in her hand.

His groans didn’t stop while she kept stroking him, so she felt more confident to experiment with pressure and firmness of her grip. Then suddenly he covered her hand with his and showed her how to touch him, what kind of grip was the best for him, and she memorized it like a dutiful student that she was. He showed her how to twist her wrist around the head, and she obliged. Then she remembered reading about some men liking their slit being touch. So she swiped her thumb over it, pressing a bit harder into the slit. He hissed at that, and said “No, don’t do that.”

‘Sorry,” she mumbled, and continued to stroke his head like he showed. His moans were back and he opened his eyes, to look at his cock disappearing inside her grip. He was getting close, the view of her naked form in front him, of her dusty pink nipples being perked up in the cool air didn’t help matters. He couldn’t hold back any longer.

“Rory, I’m about to cum,” he rasped.

“Oh... Uh, what do you want me to do?” She looked at him, the question in her eyes.

“Just keep going, and direct the tip to my stomach,” he heaved. She nodded and continued with her movements, until she felt his length straining in her grip, muscles contracting, and he spilled a white load on his toned abs. She kept stroking, and he had to put his hand on hers to make her stop. “Now it’s really sensitive, so it’s best not to touch it after I’m done.” He guided her gently.

“Oh, okay,” she blushed. “I’m gonna go find something to clean up with.” She stood up and went to the en-suite bathroom. She went up to the sink and looked at her reflection. She was flushed, her pony tail ruffled, her lips swollen and bright. She saw Jess’s cock for the first time. It actually happened. The lazy smile that graced her face at the thought did not look innocent in the slightest. Rory Gilmore just gave her first hand job. She bit her lip to hold back the elated giggle. Then she looked around, and noticed a box of paper napkins on the far end of the enormous marble sink. Perfect.

She went back to Jess and handed the box to him, pulling her panties back on while he cleaned himself off. Then she climbed back on the bed with him and he pulled her in a tender embrace, pressing his body to hers.

Rory realized that she felt completely comfortable walking around almost completely naked, while he could see her, while he watched her. It felt right. They were lying there, softly drawing patterns on each other’s skin.

~XXX~

After a while, Rory’s rational part of the brain kicked in as she was coming off of her endorphins high, and she couldn’t stop her thoughts from wandering. She burrowed her head into his neck to avoid looking at him directly and asked.

“Jess… do you prefer it rough?” She was clearly nervous and Jess couldn’t understand how did they go from a heavy petting session to this.

“What?” he asked, confusion written all over his face.

“Well… Uh…”

“Where is this coming from?”

“Well… Lane overheard Shane talking to her friend in the locker room, and she said you liked it rough… and…” she fidgeted.

“And?” he prodded.

“And that you like oral to be performed on you…” Rory trailed off not knowing if she should continue with the rest.

“Is there anything else?” Jess inquired.

“Well… there is actually… she also said that you’re gonna get tired of me soon and get back to her.” She lowered her head in anxiety and embarrassment. Jess sighed and leaned back on the headboard.

“Please tell me you don’t believe in that crap?” that made Rory look at him. She couldn’t quite decipher his expression, again, his face became hard to read.

“I… I don’t know… I mean, she’s experienced, and I’m not… And I am one hundred percent sure I want you to be my first, but we agreed to go slow, and what if this slow is too slow for you, and you get tired and bored of me, and just…” her throat closed in and she couldn’t continue, as the very thought of losing him made her heart constrict. Even though she felt confident telling Lane about Shane not being a problem, somehow being with Jess, and knowing he had so much experience brought her insecurities back.

“Rory…” he leaned forward and pulled her in a hug. “Look, the only reason I started hooking up with Shane is because I wanted to get over you. I was so angry with you for not calling me after that kiss, that I needed a distraction.” He was rubbing her back soothingly. “But now that I got you there is no reason for me to go back to Shane, I don’t need her anymore. It wasn’t even dating for God’s sake. It was just sex.”

“That doesn’t really make me feel any better at all,” she managed to say.

“Rory, I promise you, your slow is not too slow for me. I wanna be with you no matter what pace we’re moving. I’m sure she only said that because she was bitter or something. I wasn’t exactly the nicest person to her.” Rory looked up at him.

“So you’re not bored?”

“How can I be bored with someone who read Rand at the age of ten?” he smirked. That brought a shy smile to her face.

“But do you prefer it rough?” he sighed again realizing he wouldn’t get out of this conversation.

“Sometimes. But again, I was angry and frustrated with you, and I let it out on her, which just so happened to be a rough sex. That doesn’t defy my preferences in general.” He squeezed her shoulders. “Are we done with this thing?”

“One more thing,” she blushed at what she was about to ask.

“What is it?”

“Do you like oral performed on you?” her blush intensified. He smirked.

“I’m pretty sure Shane would never use a word ‘perform’ to describe a blow job.”

“Well no, she used more crude words which Lane refused to repeat, so I’m using substitutes. That doesn’t answer my question though.” She looked at him still feeling shy.

“Every guy likes blowjobs.” He looked pointedly at her.

“Oh,” she wilted. Even though she’s been fantasizing about it in D.C., actually doing it seemed like a pretty big step, considering she only saw his penis for the first time about twenty minutes ago. Insecurities took over her mind. Shane was so experienced, she probably gave really good blowjobs, while Rory has never done that before. What if Jess doesn’t like it? Is he going to compare her to Shane? Or others? Her mind was quickly going into overdrive and she didn’t know how to stop it.

“Rory?”

“Yeah?”

“Are you okay?” he moved to face her.

“I… uh…”

“Rory, c’mon, look at me,” he lifted her chin with his fingers to look her in the eyes. “You’re gonna stop doing that. Overthinking everything. What happened to the girl who wrote the letters?”

“I never thought you’d read them. You were never supposed to read them.” She whispered.

“Do you regret it?” he asked grimly. That made her look at him in alarm.

“What?”

“Do you regret that I found them? Would you rather I didn’t?” His jaw clenched.

“No! I don’t regret it!” she hastened to placate him. “It’s just… When I was writing them I didn’t think I’d ever get a chance to try out all of those fantasies with you and act on my feelings. But now that we’re together, and it’s not just fantasies anymore, now that it’s a reality, it’s a little scary. Also, when I was writing them I didn’t even know Shane was in the picture. Also, you never told me anything about your love life from back in the day, so the very idea of you having one was vague. Like, I obviously know it existed, with how you look and the way you kiss and everything, but since I didn’t know any details about it, it was easy to ignore. But with Shane existing in my very home town, it kinda became real, and I can’t ignore it anymore. So I have to take that into account, and also the fact that you go to the same school as her, and I don’t go there, and it’s just… God, I don’t even know what I’m saying anymore.” She stopped rambling to take a breath.

“Rory,” he asked with a cheeky grin. “Are you jealous?”

“What? No!... well… yes, maybe a little,” she groaned. “God, I’m a terrible person.”

“You’re not a terrible person,” he chuckled. “Just trust me when I say you have nothing to worry about regarding Shane, or any other girl for that matter. We’re gonna explore your fantasies as fast or as slow as you want. Deal?”

“Deal,” she gave him a genuine smile and leaned forward to kiss him.

“You know, it just so happens, that I not only like the oral to be performed on me, I also like to perform it myself. And I remember something about having permission to fool around in this room for as long as we want, so…” he pushed her to lie back on the bed and slid down her body, his face nearing her crotch. She blushed bright red at the implication, and lifted her hips happily, helping him remove her panties from under her skirt. A minute later the room was filled with her soft moans and labored breathing, which was successfully muffled by the music the DJ put on.

Chapter Text

Mrs. Gabrielle Norris worked as a guidance counselor in Stars Hollow High for over twenty years, and she prided herself on doing a good job. She thought she knew everything there is to know about teenagers, so when Jess Mariano transferred to their small-town school from New York she pegged him for a trouble-maker, a possible drop-out, and a future career criminal. That is why she decided not to waste her time on him, not that he showed up in her office anyway. Imagine her shock of surprise when she received this year seniors’ SATs scores. She could not believe her eyes when she saw Mariano’s score. Her heart beat sped up. It was nearly impossible to cheat on SAT test, everybody knew that. Then how on Earth did he manage to get such high scores on both sections? The committee couldn’t be mistaken, could they? She did not want to be blamed for a badly organized test which allowed students to cheat.

She remembered how in the beginning of the semester, the new English teacher asked her about him. Mrs. Norris looked at Jess’s file, and found out he was attending AP English literature and Composition class this new teacher, Mrs. Wilson, taught. Her eyes widened when she saw the grades he was receiving. She also noticed his overall grades started looking up, especially compared to the last year. Could she have terribly misjudged him?

Later that day in the break room she approached Mrs. Wilson and informed her about Jess’s results. She also voiced her concerns about the possible cheating, but Mrs. Wilson said that Jess Mariano was perfectly capable of achieving those grades fair and square, completely on his own. That elevated Mrs. Norris’s fears a little, and she decided to let it go. Mrs. Wilson was in a great mood all day.

~XXX~

On Tuesday after school Rory managed to successfully avoid Luke noticing her when she entered the diner, so she headed immediately upstairs, hoping to get some alone time with Jess before his uncle realized they were left unattended. She could really use some uninterrupted time with her boyfriend, without Luke barging in every ten minutes under the false pretense of forgetting a ladle, or a wallet or something else.

When she entered the apartment, Jess was nowhere to be seen, but she could hear the water splashing in the sink in the bathroom. Waiting for him to come out, she took a few wandering steps and found herself standing next to Jess’s desk. She liked how Luke changed his space to accommodate Jess, and that he now had his own desk to study and a bookshelf, and a dresser and everything. A slip of paper on top of his notepads pile caught her attention. She picked it up and saw that it was his SATs results. Her curiosity immediately peaked. They never really talked much about school and his grades, because that topic seemed to set him on edge. So, this was probably the only chance for her to know how he was doing at school these days. She scanned the page to see his final scores, and could not believe her eyes. Pride swelled in her chest, making her smile. Jess got 780 in English and 760 in Math, making it 1540 points in total. Rory hasn’t received her SATs results yet, but Jess’s score was even better than her PSATs she took last year.

“Hey,” his greeting made her turn around swiftly, she blushed being caught red-handed snooping in his things.

“Hi.”

“Whatcha doing?” he then noticed the paper in her hand, and the look of annoyance flashed across his face. “Are you going through my stuff now?” she couldn’t decipher his tone.

“I was just waiting for you, and it was lying right on top, so it’s not like I was going through your stuff exactly. Jess, this is amazing! You’ve got such a high score! Any college would kill to have a student with such a score.” She beamed at him, but he did not reciprocate.

“Well, since I’m not going, they wouldn’t have to kill anyone. Bloodshed avoided.” He stepped closer and snatched the paper from her hand pushing it inside the top drawer of his desk. Her brows furrowed in confusion.

“Are you not happy about this? You’ve got over 1500 points, that’s a big deal.”

“Not to me, it isn’t.”

“Jess, this is a good thing. Why are you acting like this? You could apply to any college with these results-“

“But I’m not applying to any college, so it doesn’t matter. Can you drop it?” He’s had enough of a pep talk for one day. First, Mrs. Wilson, now Rory. The teachers were not even supposed to know the results, yet, she caught him in the school hall this morning and congratulated him, saying how proud she was of him, and how any school would want him. Never mind that his GPA was crap, and his attendance was barely there, and he had no extracurricular activities. He wasn’t stupid. He knew what was required to get into college. Ever since he started having lunch with Scotty, he regaled him with his apprehensions about not doing well enough to get into John Hopkins. Jess has learnt all the acceptance rates in all the other schools with medical programs in about ten minutes completely against his will. Also, everyone in his AP class seemed to be determined to go college. That was all they could talk about before class, since October was the application season. He seemed to be the only one who wasn’t fretting over writing the perfect paragraphs in his essay to impress the board. Frankly, it was getting on his nerves. Because for the first time in his life he was surrounded by people who actually had academic goals, who weren’t just sitting in class waiting for the day to end. After Scotty, Jess and Andy received an A for their AP project, it became even more apparent, that Mrs. Wilson had some unfounded faith in him, she was always encouraging him. She gave him positive feedback on every assignment he turned in for her Creating Writing class. He felt this weird tugging in his chest, like a longing for something he didn’t know existed, a desire for something he never knew he wanted, that he could want something like this, the praise, the recognition. Comparing himself to all the other students in his class only made the differences between him and them more obvious. He did not have what it took to get into college, any college. His entire school career up until this point proved he would not be worth the time of a college board to even consider his application. Even if he did apply, no school would accept him, he just wouldn’t have enough in his resume to offer. So, all that encouraging seemed like pouring salt into an opened wound, only proving how incapable he was. But if he didn’t care back in the day, now he had a taste of what he might have, and it made the realization he wouldn’t get it even more painful. The restlessness he always got when something even remotely good happened took control over his body again, this instinct, a reflex, to run, to get away before it turned out to be a trick, an illusion, revealing that nothing good was actually happening, that it was all a ruse, another proof of the fact he should never get his hopes up. He was on edge ever since the moment he got his results, his fingers twitched wishing for a cigarette, his leg couldn’t stop shaking under the table, he couldn’t sit still for five minutes. It was all driving him crazy.

And now there was Rory. Rory who strived for Harvard, for an Ivy league. Rory, who was a class vice-president, who was on her school paper, who was attending a stupidly expensive private school. Rory who had her rich grandparents to cover any fees should she need it. How can she possibly understand that in his world high SATs scores don’t mean jack shit. Even if he got 1600 points out of 1600, he would still be Jess Mariano from a shitty neighborhood with almost zero attendance and zero ambitions, not to mention zero budget.

“But why wouldn’t you even try? I’m sure you could get in, if your application essay was good, everything else wouldn’t really matter-“ but he interrupted her mid-sentence.

“Why are you pressing this so hard? Can’t stand the idea of having a loser boyfriend? Can’t date a failure who’s not gonna go to an Ivy league school? Well, that is exactly who I am!”

“Jess, that’s not-“

“Isn’t it? Why are you pushing me so hard to be someone I’m not? Or what, are you regretting getting with me in the first place?” that was his biggest insecurity, his biggest fear, that one day Rory Gilmore wakes up and realizes she made a really dumb decision of dating him, and she would just stroll in the diner, tell him it’s over, because he’s not good enough for her, and go back to her perfect life of college applications and Ivy dreams.

“That’s not true, Jess,” the look of hurt crossed her angelic features. “What’s wrong with you? Why are you acting like this?”

“Like what? Sick and tired of everybody getting their nose in my business? I’m not going to college, so stop pushing your ideals onto me.”

“I’m not-“

“Save it, I’m out.” With that he grabbed his coat from the rack by the door and stormed off, leaving Rory standing in the middle of the apartment hurt and confused. So much for the alone time.

~XXX~

The next day Luke was sorting the mail, when he came across an envelope addressed to his name sent from Stars Hollow High. He frowned. Jess couldn’t be in trouble this early on in the school year, could he? Luke opened the envelope to find a letter to him as Jess’s guardian to inform him of his SATs results. Reading the paper Luke whistled in surprise. He wasn’t an expert in education, but even he could understand that receiving 1540 points out of 1600 was an excellent result. A proud smile tugged at his lips. He knew his nephew got it in him to do better. Maybe some of Rory’s aspirations finally rubbed off on him, maybe not, but this was definitely a reason for celebration. He walked across the apartment, and put the paper on the fridge, sticking it with magnets.

Just as he’s done that, Jess entered the apartment, pulling his jacket off. He nodded to Luke, and paused for a second seeing his uncle’s shit eating grin. That look did not belong on Luke’s face. Something was seriously wrong. A second later Jess understood what. He came up to the fridge and pointed at the paper.

“What’s that?”

“Your SATs results I received in the mail today.” Luke kept smiling, and it annoyed Jess to no end. “I’m no genius, but I’m pretty sure you can go to some decent school with these.”

“Not you too,” Jess rolled his eyes. “I am not going to college. Geez, how many times do we have to have this conversation?” Jess was annoyed, exasperated, and defensive. Why can’t Luke just leave him alone? Why can’t everyone just leave him alone?

“As many times as it takes for you to consider it!” Luke snapped; his patience was wearing thin. They’ve been over this before.

“And why would I do that?” Jess’s tone was mocking, fake-attentive, egging Luke on.

“First of all, I told you when you decided to come back, that you can live here if you get back to school! And second, don’t you want a better future for yourself? You’re smart, Jess! Don’t you wanna go to college? Study something you really like?”

Truth be told, all that praise he was getting from Mrs. Wilson, the good grades in her AP class, the positive comments he was getting on his essays in Creative Writing, and Rory telling him he could do more kind of got him thinking about the prospect of college, education, but the harsh reality was not only his school portfolio was lacking in pretty much all the aspects except SATs, also, he couldn’t afford it, so what’s the point in considering it knowing it could never happen.

“Even if I wanted to go to college, which I don’t, who’s gonna pay for it, huh? I sure as hell can’t!” Jess raised his voice.

“I will pay for it!” Luke yelled back. Then a silent pause fell upon them. They were staring at each other with wild eyes, both shocked, neither of them expecting such an outcome of their argument. But seeing the bewildered expression with just a hint of hope on Jess’s face told Luke everything he needed to know. It was apparent to both of them Jess has never even considered the possibility of Luke paying for his tuition. The longer they looked at each other, the more right it felt for Luke. He wasn’t actually mulling over this thought for long, it just sort of popped into his head as a counter argument to win the screaming match, to make Jess see reason, at least just this once, but something in his nephew’s face told Luke it was the right decision, and even just voicing it out loud irreversibly changed something in this boy’s soul. For someone who was always on his own, haven’t been properly taken care of his whole life, the very fact that someone was willing to pay a huge chunk of money to secure his future was cathartic. Luke could literally see Jess’s carefully constructed walls crumbling in front of his eyes. Liz’s son was looking at him with such a vulnerable expression, it made his heart squeeze. He had to say something, before it became too much.

“Just, think about it, okay?”

“Okay,” Jess exhaled softly.

~XXX~

It’s been twenty-four hours since Rory had a fight with Jess. Well, maybe not exactly a fight, they didn’t yell at each other, he wasn’t mad like Dean usually got when he screamed at her. It was more of a weird argument where he looked annoyed and talked back at her. But there was no contact from him ever since. She didn’t follow him after he stormed off. She just stood there confused for a moment, and then just went downstairs and out the diner without even having lunch. The next day she had her coffee at home, and headed straight to the bus stop avoiding the diner all together. She couldn’t understand what she did wrong. She just found out her boyfriend did amazingly on the most important test in their entire high school career, but instead of being excited about it, he blew her off, accusing her of regretting ever getting together with him. What he said made Rory wonder, how important it was for her to have a boyfriend in college really. She liked Jess a lot, so she wouldn’t mind him not going to school, because his school aspirations were not why she liked him. But at the same time, it bothered her that he wasn’t willing to put his brilliant brain to good use. He was so smart, and his margin notes were always so insightful. It was like he could see into the very nature of things, getting the hidden meanings in the most intricate paragraphs. His opinions were always unique and thought-provoking. She could listen to him talk all day. She was convinced his mind needed more stimulation than Stars Hollow High could provide, and he could thrive in college, electing the most challenging and interesting classes, he would write the best papers in every subject. She was so sure of it. Why wouldn’t he consider the idea of going to college even for a minute? It didn’t have to be an Ivy League school. God knows how expensive those were. She secretly dreaded the fact she might get in but without a scholarship. How on Earth was she supposed to afford that? But there were plenty of really great school that didn’t cost as much, that provided scholarships for brilliant students. She was sure Jess can get a scholarship if he tried. He still got a full year to turn his life around, to improve his grades.

When Wednesday turned into Thursday with still no contact from Jess, she started to worry. Did he break up her? Did he not want to be with her because she wanted to go to college while he didn’t? She never thought it would be like that with Jess. She remembered her conversation with Dean they once had. When he asked her what would happen when she gets into Harvard, would they break up or what. She never thought Jess would be concerned with something like this. They still had their entire Senior Year to figure things out.

Also, it was currently Thursday, October 31^st. The Distillers concert was in two days on November 2^nd. And Jess and her were not talking to each other. Does that mean they weren’t going? Rory was getting more nervous by the minute. Add the anxiety of waiting for her own SATs results on top of that, and you get a very agitated Rory.

Later that day she checked her mailbox and pulled out an envelope with her SATs results. Her heart was pumping in her chest twice as fast as normal, and the driveway never seemed longer than when she ran from the mailbox to her house. She dropped her backpack in the hall, and froze for a second, not daring to open the envelope. She paced in the living room for a bit before promptly plopping on the couch, and swiftly opening the flap, fast and steady like ripping a band aid.

She got 750 points in English and 760 points in math, 1510 points total. Which was better than her PSATs, and still surprising for her that she did better in math than in English. But then the realization dawned on her. Jess did better that her, and he didn’t even go to Chilton.

She was still recovering from that revelation when her phone rang. She picked it up before it went to voicemail, and heard the frantic Paris on the other end.

“Did you get your results yet?” Paris started with no preamble.

“Hello to you too, Paris.”

“Don’t patronize me, Gilmore. Did you get your results yet?”

“I did. Did you?” Rory asked.

“Yes. What did you get? I got 730 English and 750 math. It’s the exact same numbers I got last year in PSATs. It’s 1480 in total, which is supposed to be fine, but I’ve read that Harvard only accept students with over 1500 SATs this year! I am freaking out! What did you get?” There was an edge in Paris’s voice which told Rory her friend was barely holding it together.

“I got 750 English and 760 Math.” She really didn’t want to tell Paris her results after she realized hers were better than Paris’s. She managed to avoid revealing her PSATs scores to her last year, but they weren’t exactly friends at the time, and she could blow her off. Now, after rooming with her in DC and helping her with her date with Jamie, Rory felt like they were growing closer, and there was no way to avoid telling her the scores.

“Oh my God! It’s 1510 in total! You’re totally getting into Harvard! It’s thirty points better than me! How in the hell did you get a better score than me? I study my ass off, I started practicing my SATs test when I was in middle school! While you were galivanting through your stupid hick town doing tree planting or some bs no doubt! How in the world did you get a better score than me? How did you do it when instead of studying you were sucking face with that dim wit farmer John? And now with that beatnik wannabe? That’s so not fair! I’m definitely going to schedule a retake in November! You have to study with me, review my notes, see what I did wrong-“

“Bye, Paris.” Rory pressed the off button stopping Paris mid-rant. That was Paris in all her glory. Revealing her insecurities, insulting her town and romantic life, and asking for her help in one go. What she said though got her thinking. Paris was right. She studied her ass off. She worked harder than anyone Rory knew. She killed herself for assignments and school projects, being the last one to exit a library on a school day. She had no life beside her studies, she never enjoyed parties, never had a boyfriend, she studied all the time, and yet, she still didn’t get the perfect score. But Jess did. Jess who had a part-time job, Jess who didn’t spend in school more time than was strictly necessary to scrape the minimal attendance, Jess who didn’t spend any extra hour pouring over textbooks. He aced the most important test like it was no big deal. And he didn’t even appreciate it. Paris was about to have a mental breakdown because of some extra points she didn’t get, while Jess just received the higher mark than both Chilton students, and didn’t even give a damn about it at all. The thought made Rory angry. She stood up from the couch abruptly and went to the diner on an autopilot thinking about the wasted potential. When she was tugging her coat on her phone rang again, and she heard Paris once again ranting in her voicemail, but she didn’t pick up. She closed the door and went to seek Jess.

Luke said he wasn’t in the apartment, and it wasn’t his shift. So, she went to the second place he could be at– the bridge.

She saw him sitting there, looking at the water with a faraway look on his face, his fingers curled around a cigarette, twirling it absentmindedly. The closer she got, the more riled up she was getting. The short walk from the diner did not alleviate her frustration and anger.

He heard her steps but didn’t look up.

“Hey,” she snapped. Her tone got his attention, and he finally lifted his head. The look of fury was so unusual on her face, he was taken aback, and stood up slowly. For some reason he felt like he should not be sitting down for what was about to go down.

“You know what I got today? My SATs scores. And you know what else I got? A phone call from Paris telling me about her scores. And you know what I’ve learnt? That both my scores and hers are lower than yours!” she was fuming, her cerulean eyes bright with agitation.

“Rory-“

“No, I talk, you listen!” she pointed a finger at him. “Do you know how much time Paris spends on studying each day? Her entire life is studying non-stop, and all of that since pre-school was for one goal, to get a perfect SATs score to get into Harvard. And you know how many points she got? 1480. Which apparently is not enough for Harvard this year, because they only consider candidates with 1500 points and above. She went to the most prestigious private schools money can buy, she’s killing herself over school, she has literally no life outside of school, and she’s the smartest person I know. Yet, she still gets lower than 1500 bar. And you got 1540 without even trying! Do you know what it means? Your score is good enough for Harvard! More than good enough actually. And you don’t appreciate it at all! You take it for granted, like it’s nothing! You don’t appreciate how smart you are, the potential you have! And why? Over some misplaced belief you’re some loser who’s not going to an Ivy League? That is so ridiculous, and I don’t even wanna hear it. You are smart, and talented, and you have an official paper to prove it. It’s not just me saying this because I’m your girlfriend. It’s official, with a stamp and everything! How can you be so dismissive of your achievements? You know what Paris would say if she found out about your results? That not doing anything about it would be a terrible waste of talent and potential! That smart people like you not going for higher education is the reason why our country’s economy is declining or something to that extent. My point is, you are good enough for Harvard! You are better than Paris Geller, and that is saying something, believe me. And I am not going to sit around and let you waste the gift you have! And I’m gonna be sleeping on your doorstep if I have to, until you write an application letter to at least one school and send it!” She finally exhaled after her long rant.

Jess was already shocked and softened by Luke’s offer to pay for his education. He’s been thinking about it since Tuesday. They never got back to that conversation, but the small glimmer of hope that was planted in his heart was slowly blooming, expanding in his chest, giving way to fantasies, dangerous fantasies of a future better than his childhood, better than minimum wage jobs, better than small rat-infested New York apartments that smelt like piss. He could see himself wearing a messenger bag across his chest with the paper on modern literature inside, rushing to his next class, after perusing the vast college library for too long, getting lost between the shelves of all the books he’s never even heard of. It was dangerous because it felt so real, he could almost taste the hotdog he would grab for lunch at the street vendor on campus between classes. It was dangerous because he could see himself studying with Rory, or calling her on the phone lying in his college dorm to go over the notes for his class with her. It was dangerous because it became more available to him with Luke’s money.

So, when she stopped her rant to take a breath, the croaked “You’re right.”

“What?” She faltered. She didn’t expect him to surrender so soon. Frankly, she expected some more yelling, but she didn’t care, she was even willing to endure him breaking up with if she was able to get her point across and push him in the right direction for a better life. His wellbeing meant that much for her. So, him agreeing with her right off the bat threw her off a little.

“You’re right,” he mumbled. “I’ll think about applying.”

He looked so vulnerable in that moment, so young and lost, her heart squeezed in her chest from the desire to make it better, to help him, to protect him, to love him, to make him believe in himself.

“I wouldn’t know where to start though.” He added.

“Oh… well, how about you go to a college fair in Hartford with me? It’s this Sunday. We could look for potential schools, and majors and get the brochures and everything.” She added excitedly. “Oh, and we can talk to the representatives in the booths too, they could give us some valuable insight.”

“Don’t push it.” He smirked. “I don’t want it to be about me.”

“Well, I also wanted to check the backup options with the journalism programs. So, it wouldn’t be just about you.”

“Good to know.” He nodded.

“So…..” she stepped closer to him, tentatively, trying to gauge his mood. “Are we good?”

“Yeah.”

“Oh, thank God! I hated this so much! Hey, it was our first fight, and we survived.” She smiled softly at him, wrapping her arms around his neck.

“That we did.” He hugged her waist right back.

“It was awful. Let’s not do it again.” He nudged her nose with his in a tender gesture she grew to like so much.

“Okay.” And then he kissed her. Of course, they probably needed to talk more about this whole situation, but they could do it later. Because they haven’t kissed for two straight days, and it was too much for them to handle. For a blissful minute they could pretend that everything was right with the world.

Chapter Text

Rory has been thinking about what to wear to the Distillers show ever since Louise suggested her to raid her closet for it. Sure, Louise's wardrobe most likely had everything she could possibly need, but at the same time, Rory couldn't shake the feeling of playing a character in that case. Like that one time she dressed as Donna Reed to put on a show of a good little housewife for Dean. While being an interesting experience, she did not want a repeat of that. One of the huge aspects of her affection and appreciation for Jess was the fact she could be herself with him. He liked her exactly the way she was, and didn't want her to be or play anyone else for his sake. He just wanted her. Dressing up in Louise's clothes for the concert felt like stepping away and losing herself. On the other hand, if there was one lesson Emily Gilmore was adamant on teaching her granddaughter, it was that a woman should always be dressed accordingly to an event's dress code. And in case if there weren't any specific dress code, she should still dress appropriately for the type of the event. There was no worse faux pas than choosing a wrong outfit and be the talk of DAR meeting the next day in Emily's book. Even though a punk rock concert was not exactly a black-tie event, it still had a certain style that was expected from the audience. The style that Rory's wardrobe did not possess. Hence, the trick was to dress appropriately, but still look and feel like herself. How in the world would she be able to pull that off?

Rory's been sorting through her clothes for days now. The first thing she realized when she opened the doors to her closet was that she didn't wear her Doc Martens in a long time, probably since she started Chilton. Those stupid saddle shoes were the only ones she was allowed to wear, and going to school five days a week didn't leave her many opportunities to wear anything else. She used to love her Doc Martens, she wore them all the time, even when it was too cold outside to wear them. But now they were collecting dust for almost two years, safely buried under boxes of kitten heels and dressy shoes she wore for Friday night dinners. Next thing she dug up was her black skirt she often paired with the boots. She could still fit in it, even though it was a little shorter now, that Rory got an inch taller since her freshman year. Come to think about it, this skirt and these boots would do just fine, especially if she paired them up with black tights with runs in them. Now she had to find a top, and pairing that up with Madeline's jacket she would look punk enough to fit in, but herself enough to feel comfortable in her own skin. Maybe Louise could help her with the top.

The girls agreed to meet at Louise's house after lunch time to get ready. Madeline and Louise were going to a party that day, so they would have to dress up and do their hair and makeup also. Rory would go there by bus, wearing her normal clothes, and she would change into her punk outfit there. Jess would pick Rory up from Louise's place and they’ll go to the venue in his car.

If Rory was being completely honest with herself, she was looking forward to this part of getting ready with the girls just as much as she was looking for the concert itself. She never had many friends her age, there was only Lane really. Hanging out with Madeline and Louise was exciting and new, so different from what she was used to with Lane, or even Paris and her mom. Of course, she still loved them dearly, but couldn't help but want these new experiences as well.

When she rang the doorbell to Louise's mansion, a maid opened the door to great her. She was then instructed to where Louise's bedroom was, and went upstairs to the third floor. She heard music and laughter from behind one of the doors, fortunately not the one she fooled around with Jess at the party. She knocked softly, but when no one answered she just pushed the door to reveal Madeline and Louise sitting on the floor Indian style in their underwear, going through each other's makeup kits exchanging products.

"Hi." Rory stepped in awkwardly. She definitely did not expect to see the girls in this state of undress.

"Rory!" Madeline said happily, a big grin lighting up her face. "Come sit with us, we are deciding on the makeup we wanna wear. Louise just bought this new Givenchy mascara, and I'm just dying to try it out! The ad says it makes your lashes look almost fake."

There were fashion magazines strewn across the floor where they sat, Louise going through the pages looking for a particular image. "Yeah, I really hope it's true, because it looks really good in the pictures." Louise added. "Do you want anything to drink? Soda or beer or anything? I can ask Rosa to bring you something."

"I'm fine, thank you." Rory sat down next to them. "So what look are you guys going for?"

“It’s not a themed party, so we are not limited by anything.” Madeline said.

“Thank God.” Louise rolled her eyes. “As much as I love Halloween, I have too many cute outfits to let them just hang in the closet.”

“I brought three dresses to choose from, because I couldn’t decide which one I like best. I want your opinion on this.” Madeline jumped up and gestured to the outfits lying on the bed. Rory stepped closer to look at them.

“I like the black dress.” She pointed to a skin tight black velvet dress with spaghetti straps.

“I think the red one is better, but I’m not sure if I wanna wear red tonight also. So we have to decide if we wanna match or not.” Louise piped in. “So, Rory, did you figure out what you wanna wear? My punk phase clothes are in that closet.”

“Oh, actually yeah, I settled on a skirt and shoes, but I’d love your help with the top that would go nicely with Madeline’s jacket.” Rory took her items out of the bag. The girls looked at them critically.

“Well, no offence, but these are kinda old.” Louise commented. “But then again, maybe it’s for the best. Have you ever been to one of those shows? It’s a mayhem, pure chaos. So you don’t wanna wear anything nice, unless you wanna ruin it.”

“Uhh, I haven’t actually, but thanks for the advice.” Rory chose to ignore the part about her clothes being old.

Louise had a walk-in closet; the kind Rory only saw in movies. Going to Chilton with all the rich kids, of course, made Rory aware of the state of their parents’ bank accounts, but everyone wearing a uniform in school still blurred the lines a little bit. It did not put that much weight on Rory’s shoulders knowing she wasn’t as wealthy as them. Seeing a walk-in closet in her classmate’s bedroom was still a shocking experience. Louise led her to the farthest wall on the left.

“Here, these are the tops, and here are the bottoms.” Louise pointed to a whole rack filled with shirts and skirts. Beneath them was a pull-out drawer with a glass top with lots of studded belts and chains. For someone who claimed a punk style to be just a short phase, Louise definitely had too much items in her closet. “Choose whatever you want.”

“Wow, thanks.” Rory smiled.

“Sure. Did you decide on the make-up and hair yet?”

“Uhh, I don’t know, I thought maybe it would come to me once the outfit is complete.”

“Okay. I’d recommend smokey eyes regardless of the outfit. Anyway, take you time.” With that Louise closed the slider door and left Rory to her own devices.

The closet also had a full-length mirror, and its own lighting, and a pouf in the center of the space. If Rory didn’t know any better, she would’ve easily confused it with an actual boutique. She started to go through tops one by one. There were all kinds of shirts. Half of them were way too revealing for Rory’s liking. Some of them were actually pretty cool. It made Rory think of Lane, how she would’ve done anything to wear something like this in public. Finally, her eyes settled on a white button-down with a three-quarter sleeves and mild cleavage. It didn’t have any décor at all, just a simple shirt that revealed the forearms. Rory already noticed some leather bracelets she would like to wear that reminded her of Jess, and this shirt was perfect for that. She also picked a studded belt from the drawer that had two rows of square studs. She put all the clothes on, and adorned her wrists with the bracelets. She was thinking about some jewelry for the neck, but decided the leather chokers with rings in them reminded her too much of dog collars, and she wouldn’t be caught dead in something like this.

She looked at herself in the mirror and was momentarily struck in awe. She looked… well, cool, sexy, punk. She grinned giddily and twirled. Yeah, she definitely looked cool.

Rory stepped out of the closet to see Madeline with her one eye done and Lousie hovering over her with a shadow palette. The girls both looked her way when they heard the door sliding open.

“Wow… Rory, you look amazing!” Madeline said.

“Yeah, I gotta admit, you clean up nice, or should I say dirty up?” Louise smirked. “The hottie will definitely lose his mind when he sees you like this.”

“Oh Louise, you need to do Rory’s make up! Remember that smokey eye look you did for me for Spencer’s party? I hooked up with Mason there, so the shadows totally worked. It would look so good on Rory.” Madeline turned to Rory. “Also, the jacket looks gorgeous on you.”

“Thanks guys. Thank you, Madeline, for letting me borrow it.” Rory blushed under their praise.

“You’re welcome. Now come here, we’re gonna do something with your face.” Madeline clapped excitedly.

And so, it began. The girls were fooling around, making faces into Louise’s polaroid camera, trying on different hair accessories, singing along to Madonna that came on the radio, made fun of the boys in Chilton. Rory never had a get together like this before.

~XXX~

When it was Rory’s time to leave, she stepped outside the house to see Jess’s car parked at the front door. The look on Jess’s face was so worth it. He looked as hot as always, leaning on the door of his beat-up car, wearing his usual wool-lined denim jacket, his hands in his pockets. His facial expression didn’t change dramatically like in cartoons, where the guy has heart eyes falling out of his eye sockets seeing the hot girl, but Rory has learnt the subtle ways his eyes darkened when Jess was turned on. He definitely appreciated the outfit. His gaze lingered on her legs, that looked so much longer in the short skirt. Rory turned around towards the house to see Madeline and Louise through the window giving her thumbs up. She waved at them and turned back to Jess, still feeling the girls’ eyes on her.

“Hi.” She greeted Jess when she stepped closer to him.

“Hey.” He said nonchalantly. The only thing betraying his appreciation was his eyes, they were almost black.

“Shall we?” She gestured to the car door.

Wordlessly he opened the passenger door behind him for her to climb in. He took her bag and tossed it in the trunk, while she fastened her seatbelt.

They were out of Louise’s driveway when he spoke again.

“You look hot,” he said looking straight ahead. She smiled.

“Thank you. You too.” She saw him smirking at that.

“Ready to rock’n’roll?”

“I think so.”

“Good.”

They didn’t talk for the rest of the drive. He was subtly stealing glances at her the whole way there.

~XXX~

After they left their jackets at the checking room, Jess took Rory's hand and led her to the concert area. The room was slowly filling up with the Distillers fans. Rory could feel the soles of her Doc Martens adhering to the sticky floor covered with unwashed traces of beer and other liquids spilt by the generations of concert goers, every step ripping off the rubber with a crunch. The club wasn't big, but was famous for hosting all rock shows in Hartford over the years that were worth seeing. Jess asked Rory if she wanted anything to drink, she shook her head no. Some punk music was playing though the speakers hyping the audience for the main act. Rory looked around her taking in the scene. All the people in the audience were roughly their age, give or take a few years. All sorts of crazy hair styles were on display. Heavy make-up, ripped shirts and checkered pants along with chains of all shapes and sizes were all around them. Rory had a strange mix of feeling insecure and out of place, even though visibly she looked the part. Her black tights were ripped in several places, having runs down her legs, courtesy of Louise. Her black skirt was adorned with a studded belt just like every other person’s, the top buttons on her white shirt were undone, sleeves rolled almost to the elbows, wrists wrapped in leather bracelets. Louise’s punk guy phase was definitely long enough to buy all sorts of appropriate paraphernalia to fit the image. Rory was sporting a heavy smokey eyes make-up, and her hair was swept to one side with lots of mini braids that turned into one big braid on her left side. "Never wear your hair loose to a punk concert unless you wish to leave the club without it," Louise advised. Jess's grip on her hand was firm when he led them closer to the stage, expertly maneuvering among people. The stage wasn't big, and there were no metal bars meant to serve as a safety measure. Rory had an inkling she would be able to feel Brody's sweat sprinkling on her face when the show started.

Rory's nerves created this weird mix of emotions, feeling out of place, feeling like a fraud among these true punk people, but feeling excited at the same time. Jess seemed like he belonged there. He wasn't dressed like a punk, his hair was in his regular updo, but his confident stance made him look like he belonged there, in his simple black Metallica shirt, loose fitting jeans that always had a book in its back pocket. His leather bracelet on one wrist and huge watch with a leather band on the other made him look very edgy, hot, which Rory could clearly see other girls in the crowd noticed. She fidgeted uncomfortably. Jess pulled her to the stage and stood behind her encircling her in his arms, leaning forward to kiss her neck. She unconsciously leaned back into him comforted by his presence and firm chest. 

The amount of people in the hall got bigger and bigger, and soon they were pressed to the stage by the crowd behind them. Finally, they saw the Distillers bassist came onto stage, he took the last drag from his cigarette before dropping it to the floor and stepping on it. He grabbed his guitar from the stand and pulled at the strings. In the next moment Brody Dalle ran to the stage, her guitar at the ready, and the crowd went wild. The drummer smashed the plates, and mayhem ensued.

Rory has never felt like this before, pure excitement, exhilaration, the unity with the crowd. She was screaming the words along to the songs to the best of her ability. She heard Jess do the same, although their voices mixed and got lost in the crowd who were doing the same. The flashing lights created an atmosphere like she was transported in a movie or something, equally as unrealistic. At some point some guy from the crowd decided to do a stage dive. He jumped right in front of Brody, and the next second fell off the stage to the awaiting audience, who grabbed him and carried him on top of the sea of heads. Jess tugged Rory to the side after the guy’s boot flew in a very close proximity to their faces. Jess dragged Rory more to the side as some other punks decided to follow the first one’s example. The show was getting out of control. Rory followed Jess obediently. He pressed her to the side wall away from the mass of sweaty bodies.

He leaned closer, raising his voice. “Are you having fun?”

“Yes! Are you?” he nodded.

The boot incident aside she still felt that buzz under her skin, that electric energy that made her feel lightheaded and reckless. She pulled him closer by is neck and pressed her lips to his. He responded immediately, devouring her in a passionate kiss. He was pressing her against the wall, his leg went in between her thighs and she arched her back in response. Nobody cared about them here. Nobody judged them for acting inappropriately. She followed her instincts and ground on his thigh. His arms around her tightened. They continued to make out like this oblivious to the noise and people around them for maybe quarter of an hour, until someone bumped into them, raising their hands in apology. Jess pulled away. Both of them were flushed, their breathing heavy, they looked at each other with darkened eyes. No matter how good it felt, it was still not the time or place to get closer. So, Jess pulled her by the hand to the merch stand nobody was paying attention to while the band was on stage.

He picked up shirts for them with the Distillers logo on it and CDs.

The rest of the show came in a blur, they were jumping and singing along with the rest of the crowd somewhere closer to the side avoiding the mosh pit. Even though in his New York days Jess wasn’t a stranger to a mosh pit, and eagerly slammed with the others getting rid of his angry energy that always lingered after an encounter with Liz, today was not a good time to do that. He was here with Rory, and frankly, he didn’t even feel like slamming. For the first time in ages, he felt at peace almost. The happy and bright look on her face was enough to ground him, to settle his nerves into place.

After the show ended, they waited in the endless line to get their coats back. Some people started chanting some words from the songs, and they sang along. Rory was giggling all through the song, and he just held her tighter to his chest.

When they finally exited the venue, the cool November air did nothing to cool them down.

Adrenaline and endorphins were mixing in Rory’s blood creating a crazy cocktail that made her drunk on happiness, on this feeling of being totally free, on Jess.

She threw her head back and laughed out of sheer exultation. Jess enclosed her in his arms and lifted her up, spinning around. She laughed harder and hid her face in his neck, where the lingering smell of the concert engulfed her. In that moment in time, she was absolutely, blissfully, unguardedly happy, and Jess gave her this feeling. She thinks she loves him, and the warmth envelops her heart at the thought. She kept it to herself, this precious feeling she wanted to revel in for a while, by herself, hers, no one else's.

When he put her down, she looked up at him with the widest grin tugging at her lips. 

"I don't wanna go home just yet. Let's go for a ride," her heart was thumping in her chest in anticipation of something, anything.

"As you wish." She kissed the small smile off his lips and hoped it's not just a phrase but a reference to The Princess Bride movie, subtly telling her he might feel the same way about her as she does him.

When they got in his car, he took three CDs out of the back pocket of his jeans, and gave her two to put away in the glove compartment. He opened the third one and put it in his stereo system.

"Why did you buy three CDs?"

"One for you, one for me and one for Lane." He answered.

"You bought a CD for Lane?" She asked incredulously.

"Yep. Thought she might want one since she couldn't go to the actual show," he shrugged. His answer made her heart swell, the affection bloomed in her chest sudden and strong. He bought a CD for her best friend, not because she asked him or because they were also friends, but because Lane was important for Rory. She couldn’t breathe for a second, choked up on her emotions. Then she launched herself at him and caught him in a surprise kiss, it's bruising and hard, and he's taken aback for a moment, but quickly recovers and kisses her right back. He's been reveling in the fact he can just make out with her in public whenever he wanted without having to second guess who's watching. He welcomed this new passionate side of Rory with opened arms. When she pulled back her eyes were sparkling with an unspoken promise that made his breath catch for a second.

"Start the car. Let's go somewhere." He didn't need to be told twice.

Her hearing wasn't quite back to normal yet after the sound level at the venue, so the loud volume Jess dialed in the car didn't bother her. They were singing along with the songs to the best of their abilities, neither of them being on pitch. They were driving around the outskirts of Hartford for a while until they found a secluded spot in the tree line on the edge of the city. Jess killed the engine, the car turned silent. 

They didn't know who was the first to initiate it, but one second they were looking at each other with unspoken questions, and the next they were making out fiercely in the backseat of the car. Rory’s sitting on Jess’s lap, eagerly straddling him.

She took his face into her palms and whispered “Thank you for giving me the tickets, I had an amazing time.”

Her eyes glint in the pale light of the full moon. She smiled right before she kissed him on the lips. His mouth opened automatically to accommodate her, and they made out with a growing passion. The adrenaline is still coursing through their veins, and they’re so high on this happiness, on the great feeling of experiencing something so exhilarating together, on liking each other, on wanting each other. Their kiss becomes more frantic by the second, their hands wandering, the windows of his car getting foggy. Jess pulled off her jacket over her shoulders and down her arms. She helped him, carelessly throwing the jacket on the seat next to him. Then did the same to his jean jacket leaving him in only his black t-shirt. His gorgeous arms are on display, and she can’t help but slide her hands up and down his biceps, admiring his physique openly. He leaned forward to kiss her neck, right at that sensitive spot that always makes her tremble. She moaned his name. His hands went to her neck to trace her throat down to where her shirt buttons begin. He flicked his fingers carefully, getting the top button undone, then the second one, and the third one, following his fingers with his lips. Rory didn’t protest, she missed his touch and his lips, so she welcomed the caress. He worked on the buttons until all of them were undone, and opened her shirt to reveal a white lacy bra. It was a push-up one, so his throat dried as he saw her breasts form an especially enticing cleavage. He leaned forward to trace the outline of the lace with his tongue, and she moaned again. He tugged on the cup to reveal her perked up nipple and took it into his hot mouth. She couldn’t help the throaty moan that escaped her, and ground onto him, making his breath hitch. He went to repeat the action with the other breast, and she entwined her fingers into his hair pulling his head closer. He reached behind her back to unclasp the bra for an easier access, and kept on showering her chest with kisses, until she’s whimpering his name repeatedly.

“Jess… Jess, I... I want…” He looked up at her to see her eyes closed, lips parted, the pulse point on her neck was trembling like crazy.

“What do you want?” he asked hoarsely.

“I… I want… I want you to touch me… down there, please.” She’s grinding on top of him full force, and there’s going to be a mess in his pants soon if she doesn’t stop. He squeezed her thighs and glided his hands up until he reached the elastic of her tights. He pulled it down, and she lifted her hips to help him move it as low as they can go down her legs in this position. He pressed his fingers right at her panties, and felt how wet she already was through the fabric. She let out another moan, as he rubbed her clit. Jess pulled her panties down as well, and then finally, his hot palm covered her core, and he slipped his middle finger inside her soaking heat. She arched her back in pleasure and gripped his shoulders for support, while he was thrusting his finger in and out. Then her natural instincts took over and she started riding his finger at her own speed.

The heal of his palm was pressing into her clit every time she went down, and she wanted him so bad she was shaking. She felt like one finger just doesn't cut it anymore, so she whimpered 'more' into his ear, and he hesitantly slipped a second finger inside. It was a little uncomfortable at first, but she adjusted quickly and kept going, feeling the arousal reaching new heights. Her desire took her by surprise, she didn't realize she could want him this bad. She realized she wants him, and soon. It's clear as day they're gonna do it soon. She's so sure. She's shocked to recognize she still wants more. The pressure to her clit is just right, and he feels great inside, but there's just something missing. She squeezed his shoulder whispering another 'more'. He carefully added a third finger and she lost it, exploding in an orgasm so intense, she couldn’t really control her reflexes anymore, trembling and twitching on top him. The long moan she let out sounded nothing like her. She slumped into his chest, breathless and powerless. Her face was tucked into his neck, breathing heavily, breathing in his scent she loves so much. It's the absolute best place in the whole world to be. She only stirred when he moved lightly, adjusting his pants. She pulled back and looked down. His erection was straining his jeans and he looked a bit uncomfortable. 

She went to kiss him deeply, trying to convey what just transpired in her mind, the revelation she had, while her hands slide down his chest to grip him through the fabric. He moaned into her mouth, and she pulled away to unbuckle his belt. He helped her lifting up his hips, to free himself from the confinement of his boxers. When she took him, his cock was heavy and hard in her hand. She got distracted for a second, transfixed, his beauty is still new to her, and she felt her cheeks heat up. When she stroked him she was thinking about him being inside her. Would it feel better than his fingers? If it's just as great, she doesn't know if she'd be able to behave around him any longer. He moaned as she touched him the way he likes, and it's the best sound, to get him like this, to see him, to hear him being so vulnerable and opened in front of her. She relished in the moment, cherished the closeness. He moaned her name when he came, and she shuddered at that. It’s her favorite sound in the whole world maybe. He looked at her with a reverent expression, lifting his tired hand to tuck a strand of hair behind her ear. He thinks he loves her, but he keeps it to himself, it’s too early to say something like this out loud, and it’s a lot to unpack. He's not sure what it’s like to love someone really, never experienced that first hand. So, this new revelation, this conclusion needs to stay hidden for a while, until he figures it out. That’s what he thinks.

~XXX~

When Rory got home, she pinned the ticket stub from the concert and polaroids she took with the girls to her Harvard bulletin board. She idly thought she also needs one with Jess. Maybe she would be able to convince him to go to some photobooth in the mall or something, to take some pictures with him. She would love to have a picture of him on her mirror, to look at his handsome face every morning when she gets ready. She smiled to herself at the thought. But now it was time to get ready for bed. Big day tomorrow and all.