1 - 20 of 204 Works in Prostitute Dean Winchester
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Dean hunched his shoulders against the November cold on his way down the alley that led to their camp.
- Language:
- English
- Words:
- 909
- Chapters:
- 1/1
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- 30
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Dr. Castiel Novak is a cardiothoracic surgeon with steady hands and a hollow chest. His nights are filled with blood, silence, and the hum of machines. When a referral leads him to The Eros Protocol, an elite and anonymous escort service, he expects something transactional. Clean. Forgettable.
What he gets is Dean. Sharp, obedient, and shamelessly skilled, Dean fits the need perfectly. Their arrangement is simple. No feelings. No names. No questions. Just heat, precision, and silence after.
But routine becomes ritual. And ritual becomes dangerous. The lines begin to blur. The contract ends. Something else begins.
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For sex worker, Dean, sex is exactly that: work. Something to endure, not enjoy.
Enter Castiel, a new client who seems determined to show Dean that there is more to sex, than just a paycheck.
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”Dean, what was that?”
”What, that?”
Cas approached him and reached under to grab the box that was literally peaking out, cas tried to open it but dean stopped him. “Dont.” He said snatching the box away.
”Why? Dean what are you hiding.” He tried to grab the box again but dean pushed his hands away. “If you dont want to say it, ill use my-“
”Fine! Its my savings, okay?” He lied, half lied actually, it was his savings, but the half of it.. well it Had 900 dollars inside, and cas would maybe go like “how did you get that money?” Then they would know how fucked up he is, because he is.
Cas squints his eyes for a moment, suspicious. “Savings.. are you sure?” Dean nods in response. “Okay, i believe you.” PHEW, that was close.
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Dean has dug quite a hole for himself, or maybe he is the hole being dug into.
Posting that video of a fantastic gloryhole session was a mistake, garnering the attention of not only hundreds of thousands of views but also of the dangerous man who dicked him so good. He easily hunts down Dean, trapping him in one hell of a predicament as he finds himself at the whim of Castiel's will.
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Castiel deals in control—drugs, power, desire. He doesn’t do softness.
Then Dean Winchester shows up with green eyes full of shadows and a mouth built for sin. He doesn’t talk much, but he doesn’t have to. Castiel sees it right away: this boy wants to be ruined.
**
He circled him slowly, letting his fingertips trail along Dean’s back, down the ridge of his spine, until he stood behind him, body radiating heat like an open flame. His mouth hovered just behind Dean’s ear.
“I’ll pay you,” Castiel murmured. “But not for the blowjob.”
Dean inhaled sharply, and Castiel felt it—the stutter of surprise, the tick of anticipation under the skin.
“I’ll pay you to kneel when I say. To take what I give you. To shut that smart fucking mouth unless I want it open.”
Dean swallowed. He didn’t speak.
So Castiel added, softer, darker:
“Say yes.”
**
Now Castiel’s hooked. Not on the cash. Not the thrill. On Dean—quiet, dangerous Dean, who’s running from something and asking for all the wrong kinds of hurt. Castiel’s more than willing to give it to him. And in the meantime? He’ll make sure Dean never forgets who he belongs to.
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Dean Winchester is an omega who was abandoned by his mother at a young age, being left behind with his bitter and abusive father. He’s alone, scared, and developmentally behind, childlike and not even able to read when he’s thrown out on his ass as a teenager. By the time he’s 27 he’s no better off and more damaged than ever, homeless and working on the street. He tries to be happy, childlike mind clinging to hope, but he’s tired. He waits for an angel.
Castiel is an alpha who’s recently experienced a fall from grace after falling into a psychotic episode at work and attacking a man while on duty. He’s lost his job and now works nights at a run down gas station, living paycheck to paycheck and preparing to go before the board to plea his case for why his credentials shouldn’t be taken away. He’s going to get his life back together, there’s only one problem. Castiel believes he’s God-like, a twisted angel of justice, and takes that belief to violent extremes.
*watch me write about Cas’s decent into madness and violence/Dean’s tragedy of a life but make it a love story.*
*All the warnings, this one gets dark friends (but I promise a happy ending).*Series
- Part 1 of Till The End Of The Line
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Castiel is forced to attend his little sister's wedding. And Castiel is forced to turn to a professional to pretend to be his fiancé.
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Dean nods. "Yeah! I hope they believe me that i have been working in a convience story for 5 years but the manager fired me for such reasons, and i finished college but i didnt have a dream job so here i am."
Sam chuckles. "Your a great liar, dean.”
Dean smirks, crossing his arms confidentaly. “Thanks, y’know they call me the king of lying.”
”Your a king?” Cas asks, confused by his joke.
Dean sighs deeply, uncrossing his arms. “It was a joke, cas.”
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I guess it's a good thing, I'm not a good thing... right? by BlueDaysDreaming
Fandoms: Supernatural (TV 2005)
03 Jun 2025
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It started with Dean beating up Sam's bullies and became something else entirely.
A serial killer fic.
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A Supernatural story following the Pretty Woman plot until it goes completely off course. Dean is working the streets and happens to be the one around to give Castiel directions. Lust turns into unexpected love. Castiel teaches Dean how to cherish his body, Dean teaches Castiel to enjoy life.
Tags will be updated regularly.
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Sam is away at Stanford and John is going on hunts without Dean more and more often, so Dean finds new ways to make ends meet. While stuck in a motel room with a recent client during a torrential downpour, Dean has a chance to see himself in a different light.
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Cowboys from all over the American West travel to Abilene, Texas, just to get a taste of Dean Winchester, one of the only—and best—male prostitutes out there, and he makes good money from them, too. Unfortunately, most of that money goes toward his family, who he’s not even allowed to see on account of his no-good piece of shit daddy who kicked him out.
When tenderfoot cowboy Castiel rides into town, Dean starts to crave something he hasn’t had in a long while— a real home.
Together, Dean and Castiel have to navigate the inhospitable world of the American West, and discover for themselves what family means, when family pushes you away.
**Previously titled "A Boy Whore From Abilene"**
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The man he’s riding with is a nice guy, Dean thinks. Cas, is his name. About 30 years old.
Dean had thought he was nice from the first time the guy fucked him. He wasn’t too rough about it, even though he paid enough that he could be. He touched Dean’s hair when Dean blew him, which made Dean embarrassingly hard.
He doesn’t get a lot of affection, out here on the road, living truckstop to truckstop. It’s why even the hint of it had had Dean gambling, offering his ass up for the next few weeks if the guy agreed to take him along for the ride.
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Dean is a truckstop hooker. Cas is a trucker. He hitches a ride with Cas, planning to head out towards California and his brother. What he finds along the way, though, might make it hard to get out.
Series
- Part 1 of Ramble On
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At sixteen Dean discovers he can turn tricks to make ends meet. At 25 he was a professional. Maybe this is all he will get. Maybe his father was right he will end up in a ditch somewhere or on the side of the road with no one caring what happens to him while his body rot away.
But what is it about the specific blue eyed client who swears his name is Jimmy giving him that damn hope again.
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What's the Difference Between a Prostitute and a Lawyer? by Go_get_Jakes_gun
Fandoms: Supernatural (TV 2005)
16 Sep 2024
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Sam never enjoyed going home for the holidays. It was the most depressing-fucking thing ever- no wonder Jess'd found a way out of it. Oh well, there was always Dean to make fun of. That never got old.
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Dean is a foster kid who at nineteen is now out of the system. He has a day job, but a lot of his nights are occupied too.
A casual meeting one rainy night brings another person into his life.
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Who knew having one of the world's stronget hunters become a demon would be such a hassle for Crowley
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Dean likes his job just fine for the most part. Sure, there are days, clients, that suck more than others (no pun intended), but overall, he makes a decent living out of it and experiences things most people couldn’t even dream of.
Recently, there’s been a new client, though, and Dean wouldn’t trade him with any of his fellow whores for the world. Castiel Novak, or Cas, for short, is a walking conundrum. It starts with his name, really – I mean, who gives his real name to an escort?
That’s not all, though. See, Cas had a very specific kink, the one thing that would get his rocks off like nothing else (or “help him achieve preeminent pleasure”, as he phrased it). To put it short, Cas had the hots for fucking people while they were sleeping,
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It's been hours and Sam is waiting for Dean to return from his late-night excursion. But it becomes clear that something has gone terribly wrong. Sam goes out looking for Dean and is stricken by what he finds. He faces challenges that he is determined to overcome to get Dean to safety, and then he returns, to extract revenge against the human monster that hurt his brother. Just hoping that he makes it out in one piece.