1 - 20 of 1,338 Works in Sam Winchester Has Issues
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Sam wakes up to you getting busy between his legs. It should be everything he could wish for - but his body, once again, is his worst enemy.
Series
- Part 9 of Sorry's Smutober Spectacular 2025
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When Sam Winchester got admitted, he was expecting rest and medicine. Since being transferred, things have been a little awkward since one of the apparent resident patients can't stay in the same room as him for even a few seconds.
An alternate universe where Sam Winchester stayed in the mental ward for longer/ was transferred to a mental hospital.
Series
- Part 1 of Blythe
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i cut the fuck out of myself (and soaked the bed sheets with blood again) by coquetteackles
Fandoms: Supernatural (TV 2005)
15 Oct 2025
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Drowning for years on end in an ocean of sorrow and depression, Sam Winchester cannot find a single buoy.
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Sam survived eleven years of hell. Now he has to learn how to live.
At twenty-two, Sam Winchester is attempting his first real relationship—with Jess, a woman who doesn't know what he's survived. She expects him to be "normal". The PTSD makes it hard. The years of sexual trauma and learned behavior make it damn near impossible. But Sam is *trying*.
Dean, twenty-seven, finally has his baby brother back. But watching Sam struggle—watching him self-destruct in slow motion—is killing him. Especially when Dean finds himself unexpectedly drawn to Benny Lafitte, and has to figure out his own shit while keeping Sam alive.
The Winchester brothers learn what healthy love looks like. It's far messier than either of them expected.
Note: this was originally titled Sex and the Single Winchester. I had intended it to be sort of a rom-com-dramedy but the subject matter is way too dark. So the new title reflects that.
This is Part 2 of the
Brothers, Man Series
It can be read standalone, but context from this first part, will deepen the experience.Series
- Part 2 of Brothers, Man - Series
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Here is a riddle to guess if you can, sing the bells of Notre Dame - what makes a monster and what makes a man?
A rewrite of Hunchback of Notre Dame with Sam as Quasimodo, Dean as Phoebus, and Azazel as Frollo.
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delirium of disorder by sam1nterrupted
Fandoms: Supernatural (TV 2005), House of Wax (2005), Gilmore Girls (TV 2000), Walker (TV 2021), Friday the 13th Series (Movies), Fire Country (TV 2022), Cry_Wolf (2005), Young MacGyver (2003)
12 Oct 2025
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Ever wonder what happens when you put Satan's ideal vessel, a candle, a cheater, a cowboy, a Pinterest board, a firefighter, a stuck-up Senator's boy, and MacGyver's teenage nephew in a room together?
Same, dude. Same.
that isn't a normal thought process . get help.
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Sam has enough and demands they talk, only for Dean to say something unexpected.
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- Part 9 of multi-fandom whumptober2025
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Sometimes, Sam needs to prove he's good. Dean is more than happy to make him.
Series
- Part 2 of swjp kinktober 2025
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All I Want is to Have My Peace of Mind by Golden_cosmic_laurel
Fandoms: Supernatural (TV 2005), The Librarians (TV 2014)
10 Oct 2025
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Sam's psychic powers are back, and Eve Baird is the only one who knows. Sam is spiraling when she forces her way onto a case with him, Dean, and Cas to keep an eye on the freaking-out younger Winchester. But the case ends up being a lot more dangerous than it would've first appeared, and reveals a lot more about Sam than Eve expected.
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Sam is still seeing Lucifer. Dean has a traumatic brain injury. Cas is ready to break.
(Must read past two stories to understand what is happening in this one)
Series
- Part 3 of One year gone
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The spell was only in case everything went wrong.
Everything went wrong.
But maybe everything had always been wrong.
And Sam only had one chance left to fix everything- and save Dean.
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it won't hurt this was forever (it ain't worth the over time) by sunshineriptiee
Fandoms: Supernatural (TV 2005)
09 Oct 2025
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“Shit, Sam,” Gabriel says, kneeling by his side. Sam has pushed himself up to his elbows, looking down at the hole in his tigh like it had offended him. These Winchesters were made by very contradictory stuff. They’d survived more than any other human basically ever, but were still just that, human. Easy to break, quick to bleed out. So Gabe, being the kind and considerate archangel he was, reached out to heal Sam, because he could at least do that. He’d expected at least a thank you, maybe even get the tough guy to crack a smile, but before he could even reach him Sam had jerked his head back.
For a moment, Gabriel’s hand simply hung in the air between them, unsure what to do next as Sam eyes him warily.
“Um,” Gabe said, intelligently, before letting his hand drop in between them. He noted the way Sam relaxed just slightly, shoulders dropping a little bit from his ears, and Gabriel leaned back, giving him his space. “I guess that’s a no?”----
or, sam doesn't like to be healed. gabriel deals with it, and falls in love at the same time
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The Alpha, The Vampire and the Perfect Animal by Katnissonfire1
Fandoms: Supernatural (TV 2005)
09 Oct 2025
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After Dean and company rescue Sam from Crowley's clutches, Crowley is pissed. With Rowena still on the loose, and his only sure-fire weapon to take her out stolen from his grasp, Crowley is determined to take Sam back and use him to end her once and for all. But with Dean Winchester officially back from Purgatory and resuming his role of protecting Sam, Crowley knows no demon is going to get near Sam Winchester now. Instead Crowley enlists a fellow monster who has already had his eyes on the Winchesters to get the youngest Winchester back. But Crowley isn't the only one with an agenda, and rumors of his interest in Sam have spread. Specifically in the power laying dormant in the young man's blood. And the desire to control blood that special, that potent, is spreading, leading the young hunter to be put in an unwanted spotlight, and leaving it up to his big brother and their ragtag collection of friends to try and keep him safe when the scent of blood in the water has the sharks, or rather monsters, circling. With a new, but equally dangerous enemy in play, the boys lean on a new friend for his experience in the arena they suddenly find themselves playing in.
Series
- Part 2 of Blood Bound
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Not enough to save you by HadrianPeverellBlack
Fandoms: Supernatural (TV 2005), Harry Potter - J. K. Rowling
09 Oct 2025
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Summary
Harry from the Jerk, Bitch, and Brat world has ended up in Winchester canon (where Gabriel and Jack are alive in the Bunker together). How are his brothers coping?
Series
- Part 10 of Cultober 2025
- Part 26 of Jerk, Bitch & Brat series
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Castiel Novak-Shurley is a 25 year old emergency room nurse from Little Rock, Arkansas, having moved to Sioux Falls, South Dakota after his best friend Kelly Kline died and left him with her three year old son Jack.
Dean Winchester is a 20 year old mechanic who's been raising his now 16 year old brother Sam his entire life.
The two meet when Jack does a week long soccer camp as part of a 'sports trial' with his preschool.
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Please Be Rude by Ashpishposh0990, peachesandcream (peachesand_cream)
Fandoms: Supernatural (TV 2005)
09 Oct 2025
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When Sam leaves for college, Morrigan is only ten years old. Now, she's fourteen and knocking on what Dean said was his front door, trying to recruit him to help her and Dean find their dad, John Winchester. She felt guilty for disrupting Sam's new life, but Dean told her that they needed him, and she always listens to Dean. Sam agrees, but only for a few days, until he has to go back to college and do an interview. But, then Jess, Sam's girlfriend dies, and he decides to come with them indefinitely. Morrigan is unsure how hunting with both Sam and Dean will be, but she supposes she'll figure it out.
Series
- Part 1 of peachesandcream's supernatural ocs <3
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Something happened to his Gabriel in Apocalypse World. Sam just can't prove it yet.
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No summary!
- Language:
- English
- Words:
- 3,729
- Chapters:
- 1/1
- Hits:
- 8
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Summary
Gabriel and Castiel decide to show Sam one hell of a good time.
Series
- Part 8 of SPN Kinktober 2025