1 - 20 of 113 Works in Twenty-Something Dean Winchester
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Sam and Dean are separated when they are young due to a dark presence surrounding Dean. John, sensing something malevolent in his son, fears for Sam's safety and decides to split them up. He entrusts Sam to Bobby, who raises him as his own, keeping the truth about Dean and John a secret. Sam grows up believing Bobby is his father and has no knowledge of his brother or John. Meanwhile, Dean, harboring deep resentment towards John, embarks on a relentless quest to find his Sammy.
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Name’s Dean Winchester.
I died. Got my peace. Heaven, pie, the whole shebang.
Didn’t last.Next thing I know, I’m back on Earth—and not just back, way back. Time travel crap. Again. But hey, I’ve broken space-time before breakfast, so what’s one more cosmic headache?
Rules? Screw ‘em. I’ve got work to do.
There’s a whole mess of things that went sideways in this timeline, and I’m gonna fix it. Alone, if I have to. Always have, always will—Winchester tradition. Only problem? Seems I’m not as solo as I thought.
Turns out, some people still give a damn. They're alive, kicking, and dead-set on not letting me play the martyr—whether I like it or not. And they’re sneaky. Real sneaky.Oh—and Cas? Yeah, feathery bastard time-traveled too. Says it’s fate, destiny, whatever. I call it Tuesday.
And me? I’m older. Wiser. Grumpier. Fully upgraded into Dad Mode. These kids running around thinking they can fight the dark? Not on my watch. I'm gonna train 'em, protect 'em, and if that means grounding a few hunters or scolding an angel, so be it.
This isn’t just about saving the world anymore.
It’s about saving my people.And Chuck help anything that gets in my way.
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"I've been hiding in my skin
And learning how to live in my head
Come cut out my heart
We'll go driving in the dark
And start fighting in the car again"
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Everything was as good as it could be.Until Sam turned eighteen and wanted to go to college.
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In Heaven, Dean Winchester and Castiel were supposed to finally find peace — but something unsettles them. There is silence where there should be relief, and Jack realizes: not everyone rests as they should. In an attempt to fix it, he tries to bring them back to Earth, to 2025. But something goes wrong. The spell shatters, and the two wake up in 2002.
There, Dean is twenty-three and drifting aimlessly through Palo Alto, watching his brother from a distance. As he observes Sam’s freedom, he feels the urge to try something like it — even if just for one night. He ends up getting sucked off by some guy in the Impala. He just didn’t expect to be seen.
Castiel, a socially awkward barista with scared blue eyes, witnesses the moment. Worse: he’s the acquaintance Dean had promised to rent a spare room in his apartment to. Now, the two are stuck living together, carrying secrets they don’t even know they have — while Jack, somewhere between Heaven and Earth, tries to find a way to fix everything.
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It had been a long day, and Sam was tired of it all. He was sick of all the conditions he had to endure as a result of the clustered mess that was his family. Raveled inside a history that defined them all. He could berate John and Dean after they’d had the chance to settle, after all, they’d be immobile for a week. He could settle in his fathers silence and accept that he would have to trust that he knew what he was doing.
But, within him was a fire that burned. One he could not snuff out, even when faced with the somber lines that traced his fathers face. It would go against everything that he was, everything that made up who he was. Hunting monsters, fighting with his father, that was hard enough. Having to fight against himself in the midst of all that seemed impossible.
…A hunt gone wrong leaves Dean, John, and Sam on the road. With Sam left in the dark, his frustration boils over when the three stop at a motel, where tensions grow between them.
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When all is said and done, this is the end of their night, and it is just this night, it is a version of Sam and Dean that can exist outside of everything else. And if it is just a fantasy, then anything can happen from here. Their contract is up, their fate has been written.
So pour one out, whoever you are. These are their final whispers now.
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If Claire didn’t know better she’d think an angel had brought Dean Winchester to her. But she’s known for a long time that angels don’t care about helping her.
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Sam and Dean spend Sam's seventeenth birthday in an abandoned building while John is out on a hunt and Sam has had enough, he can't take it anymore, he doesn't want this life, he doesn't want this suffering. He wants to go to college, he wants to have friends and most of all he wants to have stability, a home to come back to and a life outside of his father's control and neglect.
But he can't give up hunting and he can't do it without Dean, he doesn't want people to die because of his selfishness and he's never lived without Dean, he doesn't think he can start now.Or: Sam wants to go to college and he wants Dean to come with him, he even made sure they could keep on hunting so everyone wins.
Series
- Part 1 of Monsters and education, a tricky balance
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Sam is hit with what is commonly known as the ‘first touch curse’. Without the cure, the condition is fatal. Fortunately, the cure is very simple. Having sex with the first person to touch you after being attacked will reverse the otherwise lethal outcome. Unfortunately, the first person to touch Sam is his own brother, Dean Winchester.
“You idjit!” Bobby cried in frustration. “How am I gonna explain this to John?”
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Dean Winchester is famous, in his own right, as masked country music singer Wesson Colt. But when country legend and Dean’s idol, Castiel Novak, reaches out to collaborate, Dean obviously can’t say no. It’s the opportunity of a lifetime, and a life’s dream come true.
What he doesn’t expect is the immediate chemistry between them, despite the significant gap in their age, and where it takes them as they work on a duet cover of one of Castiel’s iconic songs, “Cowboys Are Frequently, Secretly Fond of Each Other.”
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i'm not about to compromise, give you up, or say goodbye by CassandraCainBB
Fandoms: Supernatural (TV 2005)
31 Mar 2024
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“Did you find it, yet?” His dad asked, his face swimming in Dean’s vision.
“Find...Find what?” Dean asked, his own voice sounding muffled to himself. The tilting of the world got more violent. Dean staggered to the side, catching himself on the wall by his shoulder. Something was wrong. Something was really wrong.
“Dean? Dean!” His dad was shouting. He saw his dad’s flashlight disappear and a hand was waving in front of Dean’s face. “What’s going on here?”
“I don’t—” Something was dripping from his nose. “I don’t know. My head—”
Dean gritted his teeth and bowed over, squeezing his eyes shut as he tried to alleviate the pain. God, it felt like his brain was inflating until it was too big for his head. He lifted his gun hand to his nose, wiping, and pulled back to see a dark stain on his hand.
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Or, Dean's on a hunt with his dad when his brain gets scrambled by whatever they were after. When his dad begins to insist that the only way to kill the monster is for Dean to die, Dean doesn't even think to question it. But Dean puts off the inevitable to do one last thing—say goodbye to Sammy. Sam, as it turns out, does have questions.
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Sam and Dean are on a hunt that’s taking a long time where Dean finds a girl that he starts dating. Sam gets jealous and wants Dean for himself, he has always been in love with Dean and Dean should be his and his alone. One day Sam gets drunk and confesses to Dean and a rollercoaster of an affair starts.
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The Slutty Winchester Brothers by LarryTomlinsonStyles_28
Fandoms: Supernatural (TV 2005)
17 Feb 2024
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They are taking a break in for hunting after Sam got a spell casted on him to have a vagina and boobs. Sam is attending university and Dean lives with Sam in his dormitory. They are two big sluts who have a lot of fun and kinky stuff up their sleeves. Sam is a complete slut for his older brother and boyfriend.
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Who knew Sammy had a daddy kink? Not that Dean is complaining.
Series
- Part 3 of What Happened When Bobby Wasn't Watching
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Bonus Materials for There Is No Point In Staying Anywhere by MissMisdemeanor
Fandoms: Supernatural (TV 2005)
26 Sep 2023
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A loose collection of additional media for anyone interested. It contains a list of settings with some author's notes, some visual aid for the vehicle in part three, two companion poems, and a drabble about an adult Dean's life and emotions after the events of No Point.
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He has nothing now. His friends, the people he was close with, the everyday of getting up and going to his classes, and living a quiet existence are now long gone. He has nothing. As he begins to sink into the murky depths, a strong hand pulls him back to the surface.
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Dean is grieving John's death. Sammy comes to terms with what a Dad really is.
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Another addition to my verse. Dean is twenty-six. Sam is four. You get the gist.
Series
- Part 3 of Safe
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Becky believes that her brother is being framed for his girlfriend's murder because really, how is it possible that he was in two places at once? Impala67, a user she met on a chat forum, thinks he knows what happened.
A Skin rewrite but Sam is four and Dean is twenty-six. Part of an AU I'm working on.
Series
- Part 2 of Safe
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Sam is four and Dean is twenty-six during the pilot episode. Everything else remains the same….for the most part.
An AU verse in the making.
Series
- Part 1 of Safe
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Dean Winchester is a 20-year-old omega pregnant after a one-night stand with Lisa. He avoids his dad finding out by fleeing to Bobby's house with his kid brother. His job at the convenience store introduces him to an alpha whose family doesn't accept anything about him. They try to alter both his autism and queerness.
Things are different at Bobby's house.