1 - 20 of 28 Works in Sam Winchester Can't Catch a Break
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Summary
Leviathan Dean is not a fan of self-restraint. Other restraints, now, they can be useful.
Series
- Part 21 of kinktober 2025
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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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a look at the loves of sam winchester.
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Since I've seen my face in your eyes by Delphistrawberryfarms
Fandoms: Supernatural (TV 2005)
13 Aug 2025
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Sam Winchester has fifteen voicemails he hasn't listened to yet. Two are from unknown numbers, one concerning his financial aid, three are from his annoying friends, eight are from Dean, the oldest being five months old and the newest is from yesterday.
These are all normal, and none are the reason he's nervous.
His advisor is very hands on, it's strange.
Sam's friends call him during the worst times for the silliest reasons, if it was something urgent they'd come find him.
And Dean, he always calls when John leaves. And when he's lonely, or drunk. Which means Dean calls a lot, and Sam would listen. But if he does he'll call. And if he calls he knows he'll go back to hunting.
So he doesn't listen.
But the voicemail from eighteen minutes ago is making him nervous. Because this one is from someone he hasn't heard from in four years. And even before that this person never called him.
The fifteenth call is from John, which makes him extremely nervous. -
Six Blade Knife, After Dark by cosmictardigrade
Fandoms: Supernatural (TV 2005), From Dusk Till Dawn (Movies)
04 Jul 2025
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Two pairs of brothers. One twisted night in Mexico, when they walk into a bar. What happens next, one might ask?
Bloodshed.
[Sam and Dean Winchester head south to lie low after a case goes sideways, only to wind up at a seedy desert bar on the edge of Mexico called The Titty Twister. Across the room, Seth and Richie Gecko are trying to celebrate making it across the border without getting shot—again. When the show begins and blood hits the floor, the Winchesters and the Geckos find themselves back-to-back, surrounded by creatures that shouldn't exist.]
Series
- Part 4 of Cosmictardigrade's Supernatural Fics
- Language:
- English
- Words:
- 2,214
- Chapters:
- 1/?
- Kudos:
- 3
- Hits:
- 41
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Sam Winchester had been doing a pretty good job recently at avoiding his hellish thoughts. However, that all comes to a dramatic halt after what he thought was a ‘close call’ on a hunt takes a turn for the worse. The same ‘close call’ that he may or may not have forgotten to mention to Dean.
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Room 03 by SpookySwordUser
Fandoms: Supernatural (TV 2005), Deadpool (Movieverse), Wolverine (Movies)
01 May 2025
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Logan has some fun outside of Dean's motel room.
- Language:
- English
- Words:
- 358
- Chapters:
- 1/1
- Kudos:
- 4
- Hits:
- 211
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The arguement that made Sam remember everything..
- Language:
- English
- Words:
- 484
- Chapters:
- 1/?
- Hits:
- 2
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It’s one thing to have a crush on an angel, it’s another to have that angel know you have a crush on them. That you’re, god forbid, lusting after them.
Sam Winchester’s life absolutely sucks. And the world won’t let him forget it. -
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Summary
Based on 4x16
Sam and Castiel have a conversation after the events of Sam killing Alistair and Castiel killing Uriel.Series
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On December 21st, 2001, Sam Winchester is dropped off at a hunter’s cabin with: a broken leg, two cases of Spaghettios, half a chocolate bar, his duffel bag, a box full of MRE’s and ammunition, one sawed-off, two hunting knives, a single VHS copy of Joseph and the Amazing Technicolor Dreamcoat (starring Donny Osmond), and a burning hatred for everything his dad stands for.
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Drinking in the Multiverse by jublke
Fandoms: Supernatural (TV 2005), Big Sky (US TV), Walker (TV 2021)
17 Jul 2022
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A deeply grieving Sam Winchester misses Dean so much he’s willing to try anything to see him again. Beau Arlen and Cordell Walker get tangled up in his attempt. (Crossover between Supernatural, Big Sky & Walker. Set after the ending of Supernatural and after the end of season 2 for both Walker & Big Sky. Potential spoilers for all episodes, but especially Supernatural 15.20, Walker 2.20, and Big Sky 2.18.)
Mild trigger warning for a very depressed Sam.
Series
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Migraines sure are a pain in the ass, huh? by orphan_account
Fandoms: Supernatural (TV 2005)
12 Mar 2022
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Sam was definitely not unfamiliar with migraines- and neither was Dean. As much as the younger Winchester hated to admit it, sometimes the best cure is a bit of TLC from your brother.
“... Can I ask you one more favor..?”
“Anything.”
“Stay with me for a while, please?”
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When Sam Winchester painfully awakens the morning after his bachelor party, the major highlight of his day is finding an injured angel face down in his backyard. Now Sam has to heal the angel, explain to his fiancé, Ruby, what really happened, then keep his friends from plastering footage of the angel all over the internet. Oh yeah, and maybe keep his future father- in- law from killing him. Is it any wonder he has a migraine?
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The brothers go to the grocery store after realizing that food supply is low. Sam gets mixed up in a personal vendetta against two hunters.
Protective!Big Brother!Dean is bound to happen.
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The ghost gives a final shriek, moves towards them.
Sam swings, a powerful, swift motion. The bar goes through the figure, it flickers out with another scream and then dissipates.
Sarah looks up at Sam from the ground, all six feet of him, and tries to breath.
“I said,” Sam pants out, sweat drenched hair clinging to his forehead. “I need some goddamn salt.”
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Of course Sam Winchester would end up in haunted psychiatric hospital. -
Fight Club, But Sam is So Done by Quinny_555
Fandoms: Supernatural, Prodigal Son (TV 2019)
11 Nov 2020
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Sam was just going for a walk; they weren't even on a case, for Christ's sake. Yet somehow, he still managed to get himself kidnapped.
or
In which Sam just can't catch a break.Series
- Part 10 of Carry On My Prodigal Son
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“You’re a real Cass-anova, aren’t you?” He hears Dean mumble, but his mind sounds far away. “Man, your penmanship is crappy. You got a pen?” Dean asks.
“A-at the bunker.”
Sam is straining to see what’s written on the paper but it’s too crumpled and too far away. He knew he should have brought along his binoculars.
“We have to leave then.” Dean says gruffly
...
When Sam enters the bunker he’s drenched in complete silence. He had expected to walk in in the middle of their blow out.
But silence.
Sam’s eyes dart around looking for anything out of place. It takes him a minute but he finds a crumpled piece of paper on the map table.
Jolting forward he unwraps the note with trembling fingers.
(2) Country Holmes Apple Pie………$23.00
Lover’s Double Smoothie……………$5.00
He casts the paper aside in frustration before he can make it to the taxes. He runs a hand through his hair and he lets the paper drop.
That’s when he sees it: blue ink on the reverse side of the bill.
It’s Cass illegibly scribble alright.
Do you want to be my boyfriend?
Yes
No
Maybe
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Summary
It seemed that trouble followed Sam even off-duty.
The all-too familiar crack of a gunshot suddenly filled the air, followed by another. And another. Someone crumpled to the ground. Panic erupted as people screamed and ducked for cover.
Series
- Part 4 of Whumptober 2019
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Summary
"He didn’t feel anything. No pain, no happiness, no sadness. How could he?
None of this was real, just a shattered dream."
aka:
The one in which Sam goes a little too far to get Lucifer out of his head.