1 - 20 of 111 Works in Crime Boss Castiel (Supernatural)
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Through the last several years, Dean has done a lot of things he shouldn’t have.
Agreeing to have sex for money with a guy who has mafia affiliations is probably up there, though.
But Dean has a kid to care for and he can’t really afford to say no.
Especially not when saying yes feels like this.
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As the husband to the head of New York's Russian mafia, Dean Winchester was used to dealing with mob bosses. Giuseppe Moratoni, however, was another monster altogether. When a meeting with him goes south, Castiel and Dean end up all over each other in Cas' office.
At the same time, Dean remembers how they first met: at his garage in the Bronx, with a beautiful ’69 Ford Mustang Boss 429 between them.
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Castiel Novak has never loved anyone in his whole damn life.
So, when Dean is taken, he doesn't know how to deal with the gnawing, clawing, aching feeling in his chest. Doesn't know what to do besides tear Kansas apart looking for him, and shred anyone who stands in his way.
But he's the most infamous crime boss in Kansas City. Everyone should be afraid now, because no one takes what's his.
Series
- Part 2 of Deal With The Devil
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A twenty-one-year-old Dean Winchester balances work and unexpected challenges while caring for his seventeen-year-old brother. He navigates trust, loyalty, and personal growth, and through ordinary moments and intense situations, he learns to rely on others and discovers what truly matters to him.
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Disruption from the past by silver stake through the heart (Dusk_Sky)
Fandoms: Supernatural (TV 2005)
28 Mar 2026
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Dean loves living with Cas. Sure, his husband is technically a criminal, but they're happy together, committed in a perfect relationship, so who cares?
Until his mostly estranged brother shows up, dead set on dredging up their past—and judging Dean for his current life choices, while he's at it.
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A sequel/continuation to 'A Really Great Idea'
In a fantastic move, to top off an entire lifetime of them, Dean joins the Bratva, and he's totally not happy about that in the slightest. It's definitely all about keeping him and Sam safe after their fuck up. Nothing to do with the hot as fuck Avtor-something that keeps pushing him around. And he hates fighting and getting one over on cops and making bucketloads of cash. Really.
Series
- Part 2 of The Big Ideas
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Dean is horrible with money he ends up taking on loans from shady people that he can't pay back. In a desperate attempt to save himself Dean agrees to have his baby brother sold to be someone's sex slave to have his debt wiped clean. A local mob boss Castiel bids on Sam winning him in an auction. This is Sam's new life as a pet.
This story is loosely based on the manga Okane Ga Nai but I don't think you need to have read that to enjoy this story
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Dean Winchester is just trying to get by and thanks to opportunities being sparce for single Omegas in the early 1960s he finds himself in Sin City, Las Vegas, working as a waiter in a casino on The Strip. Unknown to him, said casino just happens to be owned by one of the most notorious mafia bosses in America, Castiel Novak, who just might have an appetite for pretty blonds with sassy attitudes.
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Internally groaning, Dean had to admit his brother was definitely improving his whole “lawyer interrogation shtik”, he better with all the money they put into Stanford already. Luckily Sam’s genetics had been kinder than Dean’s and there were a million scholarships just waiting for a genius dominant alpha with financial problems to waltz into the ivy leagues prepared to take the world by storm. In comparison to the shoddy existence of Dean’s recessive omega courtesy of his grandmother’s presentation, who he ironically carried the namesake of. No one would have thought at a first glance that taut muscles and blondish stubble hid an omega behind his masculine facade.
Truth is he hadn’t been raised in a traditional way with all the frills and submissiveness a normal omega would have been subjugated to. Partly because his beta mom had died when he was four, and mostly because his dad at the ripe age of twenty-one had no idea what to do with the kids he had directly out of high school. Not that you could expect him to-no matter what Sam said their Father did to Dean psychologically. It was fine. He was fine, and he certainly wasn’t anyone’s patsy.
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It seemed like it was going to be just another crappy night for Dean Winchester, stuck working the front desk at his father's garage thanks to antiquated ideas of Omegas lacking mechanic skills. That was until a gorgeous car driven by an even more gorgeous Alpha pulls up needing a new battery.
Before he knows it Dean's whole life starts to change and Castiel Novak (or at least that's the name he's given) is much more than meets the eye.
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If You're Gonna Ruin Me, Use Your Mouth by fallenoverbiblically
Fandoms: Supernatural (TV 2005)
03 Feb 2026
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Dean Winchester moved to North Jersey on a whim a few years ago.
Charlie, his high-school bestie, scored him a paramedic job in one of the most violent areas in the country. Dean didn’t even blink. He’s wanted to be a medic ever since he spent his childhood patching up his dad’s various open wounds. He could tell you it’s because he’s noble, but nope — Dean just likes digging around in the squishy parts.Also, Dean’s an idiot.
His adrenaline addiction sends him straight into a dark alley one night, where he ends up on his knees in front of an ocean-eyed mafia god who looks far too eager to let (force) Dean explore the insides a bit more. -
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Beta John Winchester has been on the road with his omega sons, Sam and Dean, since his mate Mary was killed by a demon,not just hunting, but staying off the radar due to restrictive policies around omegas that could cost him custody of his sons. He takes a job for mob boss Kate Milligan, completes it, and hooks up with her before leaving, unaware of her pregnancy.
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Dean woke up that morning with one single mission in his head: pancakes.
Golden, fluffy, dripping with syrup, stacked high enough to count as an architectural achievement. He stumbled into the kitchen, rubbing the sleep from his eyes, and reached for his trusty frying pan.
Which immediately broke off in his hand.
If only he could have predicted that the innocent idea of frying pancakes would entail with a person hogtied in the trunk of his car.
But why? Why him of all people?
Worst morning ever. Worst morning ever and right on his day off. Life was a bitch.
Based on the reverse trope where the MC kidnaps the mafia boss. But make it an accident.
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Gone either way (and kicked on the way down) by skrongly_Bastard
Fandoms: Supernatural (TV 2005)
16 Jan 2026
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Dean has gotten used to being the pathetic omega John thinks he is, but when he's had enough what will he do? With his father out of the way, his only worry is who Alistair is-and John sold Dean to the guy.
So how does this beautiful, blue eyes alpha come into play?
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After an unfortunate run in with the mafia John's in debt to Dean is forced to work with the apposing mafia that's been trying to take over Hell's Torturers territory for years. The fight becomes personal when Castiel catches feelings on Dean who is always in danger due to his idiotic fathers debts.
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Supernatural mafia AU bc freewill is freewill -
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in a quiet pool, devils dwell.
Dean Winchester is twenty-four, living alone in New York while Sam is across the country getting his law degree. He’s working guard shifts at a supermax prison, protecting him from the monsters he’ll prosecute one day. He may teeter on the edge of poverty, but he’s doing everything he’s supposed to. Good, honest work that would make John proud from wherever he fucked off to, pay his bills almost always on time, roof over his head, dinner most nights of the week.
He’s content.
He’s miserable.
He’s bored.
Then he’s put on Krushnic cell watch.
The corruption begins at the mouth, the tongue, the wanting. The first poem in the world is I want to eat.
Update 1-12-26: Not abandoned, life is just kicking author’s ass rn! Update expected late January/early February ;)
Update two 1-30-26: My unstable home situation has gotten worse and I’m prioritizing my family and safety. I will do my best to update before the end of February. -
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Dean Winchester has only been back in Kansas for a couple of months when an undercover gig comes up. Infiltrate the Kansas City mob and discover the identity of the infamous 'boss' that has alluded arrest for decades.
It's risky, and Dean has more to lose than he thinks, but what's life without a bit of risk? Besides, he loves a challenge.
Series
- Part 1 of Deal With The Devil
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Based on the reverse romance trope 'accidentally kidnapping a mafia boss.'
Sam's got debts, and because Dean's been taking care of the overgrown dumbass his whole life, what that really means is that Dean has debts. But Sam's had an idea to clear them, get them both off the hook. A foolproof idea, really, one they're both able and willing to pull off.
Just an eensy little kidnapping and ransom, easy breezy.
Series
- Part 1 of The Big Ideas
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Dean has never been great at feeling his feelings. Doesn’t particularly want to, thank you very much. That’s where the coke comes in handy. And Cas. Cas has the drugs, Dean has the money (most of the time. Or, well… some of the time at least). One thing about Cas, though? He’s willing to barter.
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In the Year 2029 Dean is an undercover ‘hunter’ who last touch with his commanding officer John and his brother Sam. It has been 6 years since he last heard from them. He abandoned hunting gangsters and petty criminals to look for his family but gave up when he heard in the rumor mill that John had been killed by the Russian Mafia.
He now works in the redlight district of a random bar under the rule of a Gabirel – no last name. And then a man called Castiel enters. And Dean's world turns upside down. In this epic tale of love, loss, betrayal, criminals and technology is there a space for an epic love story?