1 - 20 of 104 Works in First Time Bottom Dean Winchester
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after sam’s death in 2060, dean and castiel disappear from the world.
what follows is decades of silence and drifting—two immortals moving through a world that has begun to forget them. dean, a vampire, struggles with the slow crawl of time and the crushing weight of outliving everyone he’s ever loved.
eventually, they stop running. a cabin. a quiet life. a stillness brings both peace and dissonance—until the past begins to echo forward again.
when family comes looking for them, bringing warnings of supernatural unrest and signs that jack’s heaven is slipping out of reach, dean is faced with the hardest question of all: what does it mean to keep living, when everyone else is gone?
PLEASE NOTE:
1) sexual content is indicated with a !, so feel free to just skip if desired
2) although all chapters will include trigger warnings where appropriate, any particularly difficult chapters will include a # as well
3) any chapters in need of some serious tlc that I haven't gotten around to yet will be indicated with a @
4) consequently, any new alterations will be indicated with a *Series
- Part 2 of night shift
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In March 1999, John and Dean Winchester arrived in Arrowsmith, Illinois, regarding a string of disappearances dating back twenty years. John is thirsty for blood from anything that goes bump in the night after losing Mary to the Yellow-Eyed Demon. Meanwhile, with Sam having ditched them for Stanford, Dean is desperately trying to make up for a recent string of failures he's committed as a newbie hunter.
So, when John reluctantly agrees to let Dean take on their latest hunt by himself, Dean knows he can't do anything that could jeopardize his golden opportunity to prove himself. Provided he follows the two simple rules he laid out for himself after their first 24 hours on the job.
Don't screw it up, and by all goddamn means...don't fall in love with the mysterious smooth talker at the local dive bar.Flash forward to 2015, and leave it to Sammy to find the two of them a new case in the only small town Dean was hoping to leave in the rearview mirror of Baby forever.
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Another moan, louder this time, gets out, and Castiel’s palm shoots up to cover his mouth.
“Shut the fuck up,” he hisses, teeth sinking into the tender skin of his neck.
The stranger moans against his hand at it, clutching at Castiel’s shoulders, hips twitching. Castiel’s grip never falters, his mind stripped clean of thought, existing only in the act of finishing what this man had started. -
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It’s Sam’s birthday, so Dean lets him be in charge for the day. He’ll do anything Sam tells him to, and he promises to bottom for him at the end of the night.
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Dean didn’t mean to open Castiel’s package. He really didn’t. But he did. And even after returning it, he can’t stop thinking about its contents.
Finding the website of the store definitely doesn’t help. And what he discovers about his neighbor?
Let’s just say it kicks the air out of his lungs… and sends all the blood rushing down. -
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Dean Winchester and Castiel Novak are the agency’s best field team—until the worst-kept secret becomes the worst-timed scandal: they’re together. As their relationship comes under fire, a string of high-risk missions forces them to prove their value under scrutiny while navigating the fragile, intimate bond growing between them. Bullets, bureaucracy, coffee, and quiet mornings. They didn’t plan to fall for each other, but in the line of fire, some lines are worth crossing.
Series
- Part 1 of Undercover Hearts
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Dean Winchester never thought he'd find himself in a bar in L.A. flirting with a firefighter named Buck — let alone wanting more than just a one-time hookup. But when Dean asks for round two, rougher and more intense than ever before, Buck’s more than willing to give him exactly what he needs. First times aren’t always gentle... but sometimes, that’s what makes them unforgettable.
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After tracking down and bringing demon!Dean back to the bunker they tied him up and locked inside the devil trap with the intention to cure him. The thing is Dean as a demon has no filter and flirts with Cas admitting his true desire for him, how will Cas react? Well, for sure not how Dean was expecting. Second chapter is mostly pure smut!!
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He really didn’t think this would- or could- ever happen. Melodramatic mental breakdowns were for suicidal teens and sad poets. Not a hunter. Not the hunter, Dean Winchester. One of the best, fate’s least favorite, died more times than he can count. The luckiest, unluckiest sonofabitch kicking on this globe, and one of the few things stopping it from kamikaze-ing itself every week. Dean Winchester, who had done more, felt more, seen more than billions will ever see, hated himself.
Aka: Cas and Dean are both suicidal, but Castiel decides to confess instead of apologize again. Sex ensues, and the morning after, Dean does what he does best to the people he loves
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Dean’s just trying to survive a brutal afternoon of taxes, sweat, and the relentless chaos of the Pride parade outside his window. He’s hot, pissed, and one noise away from losing it. When he finally storms out to yell at the world, he doesn’t expect to crash into a rainbow-flagged stranger - especially not one who’ll flip his whole day on its head. Turns out, Pride might have brought more than just glitter and traffic.
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(like they do on) The Discovery Channel by BlueDaysDreaming
Fandoms: Supernatural (TV 2005)
03 Jun 2025
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Dean is happy topping every time they have sex - Sam is his baby brother and that's the way he likes it. But when he reluctantly agrees to try bottoming he's more than a little caught off guard by how Sam acts when he tops.
Featuring a very Toppy Sam.
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if Jesus was a teenage girl by objectlesson for Wonderfulwaytooweird
Fandoms: Supernatural (TV 2005)
06 Apr 2025
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She’s never even thought much about the why before–it’s just the way she is. She doesn’t need it, it feels like too much effort, too much work to peel back the layers and share her body and wonder if it’s good enough or coach some one night stand through the process of bringing her off when she’s perfectly happy just eating pussy. But the way Sam’s looking at her–
“Why not?!” she asks, baffled.
Dean shrugs. “I dunno. I don’t like it.”
“How do you know if you like it if you’ve never done it?”
“Well I’m about to do it,” she says, shoving Sam lightly, playfully, cheeks already hot with something that’s not quite shame. “With you. If you want to.”
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What if things went a little differently...? From Dean's deal to his death. What if he never gets saved? What if he doesnt want to be saved? Maybe that'll change too whe his savior is a lowkey cute asf angel with bright blue eyes and hot messy hair. Or maybe that angel only exists in his brother's visions.
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Dean is supposed to get married in two months. Too bad he's in love with the priest...
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Castiel Novak is the owner of a bakery on the brink of bankruptcy. In a bid to save his business and keep his employees from losing their jobs, he decides to sell his late grandmother's house. This leaves him in need of a new place to live, and he soon finds one.
However, his new roommate is none other than Dean Winchester, his homophobic pastry chef. While they maintain an ideal professional relationship at work, their home life is a different story. Dean reveals himself to be a bossy, neat freak roommate, making their living arrangement far from harmonious.
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kinktober day 29: teacher/student pt3
Castiel thinks his student has grown bored of him, but what he finds in the boys locker room proves otherwise.
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- Part 29 of Kinktober 2024
- Part 3 of think of all the education i've missed
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DISCLAIMER: THIS IS THE DARK VAMPIRE ROMANCE VERSION OF BEAUTY AND THE BEAST THAT NOBODY ASKED FOR BUT ARE RECEIVING ANYWAYS. YOU HAVE BEEN WARNED.
A devastating tragedy that upends Dean Winchester's life leads him into the clutches of one Castiel James Novak: a mysterious man who owns a decrepit victorian/gothic-style mansion deep in the Virginia countryside. Why is he so pale? Why does he only go outside at night? Why can't he leave his property? Why is it always raining on his property? Where did the two puncture wounds on Dean's neck come from? And why won't he let Dean leave?
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kinktober day 17: jealousy / oral fixation
Dean has been hopelessly in love with his roommate for years now. He never imagined that jello shots would be the thing to make them cross the line into lovers.
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- Part 17 of Kinktober 2024
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“Hullo?”
A crackle down the line, a static hiss. Sam almost expected the caller to hang-up. Then, a familiar voice; pitched low, gravel and grit down the phone line.
“Sammy? It’s Dean.”
As if he needed to tell Sam that. As if Sam’s entire body hadn’t tightened up, a visceral reaction to his brother’s voice, a taut line down his spine.
Or;
Serial Killer Winchesters with a hefty dose of rampant co-dependency and sexual tension.
ON HIATUS! -
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Dean and Cas' dynamic doesn't change much, Dean stays in control and Cas obeys. But, Cas wonders whether Dean is tired of telling everyone what to do all the time and taking the lead... So, when Cas attempts to flip the switch and allow his dominant lover to bend over for him this one time, how will he take it (literally)?