1 - 20 of 255 Works in Guilty Sam Winchester
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Sam is unraveling under the weight of guilt he can’t escape. Dean returns to find more than just bruises—he finds silence, distance, and something breaking between them.
In a motel room thick with memory and grief, old wounds resurface. Some things are too painful to say. Others... maybe don’t need words at all. -
the pain makes you feel like you earned it (and i probably deserved it) by loveinourowngrave
Fandoms: Supernatural (TV 2005)
24 Jul 2025
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“I’m sorry,” Sam says, limp on the bed, bracing himself.
Dean thrusts in like he’s saying: and I don’t forgive you.(Since coming back from hell—and since Sam let the devil out of his cage—Dean doesn’t fuck the same way.)
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A hunt gone sideways leaves Sam and Gabriel shaken in ways neither of them expected. Back at the Bunker, the silence between them speaks louder than words—until one late night changes everything. Some truths are only revealed when there’s nowhere left to hide.
Whumptober 2024 Alternate Prompt 01: BODY SWAP
Series
- Part 32 of Whumptober2024
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"Why? You gonna hate me any less? Am I gonna hate myself any less?"
"You'll never punish me as much as I'm punishing myself"Set after 5.04 The end.
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“Sam”
His brother’s voice put his brain’s self-pity party on hiatus.
“Yeah?”
Dean looked at him with a little concern and another expression he couldn’t quite place. “You okay, man?”
Again, Sam almost laughed. “Yeah, I’m fine”He's not. He's really not.
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A witch’s dying curse forces Sam and Dean to speak only the truth for 24 hours. What begins as harmless teasing spirals into an argument that unearths long-buried fears, guilt, and feelings neither of them dared to say aloud. In the end, the truth may hurt—but it also sets them free.
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After returning from Purgatory, Dean is cold and distant with Sam. Until he finds his journal — and discovers the painful truth about the months of absence.
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When thirteen-year-old Sammy takes a time journey, he is thrown into a future where the world is ending — and his big brother is colder, angrier, and more of a stranger than he’s ever known. Betrayed by the man little Sammy will become, Dean struggles to distinguish the boy in front of him from the brother who chose a demon over his own family. As the weight of the apocalypse bears down, Sam must face the guilt of the mistakes he will make in the future, and the sadness that his brother doesn’t believe in him anymore. Can they find their way back to each other before it’s too late?
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When Dean tells him to walk away, he does it. There's nowhere to go this time. Sam should know better.
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Sam and Dean are on a hunt for a malicious dryad—a type of forest creature. They knew how it killed, and how to kill it, but not how it lured its victims. Sam finds himself injured and exposed, forced to confront his deepest feelings he never meant to share.
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After Kevin's death, Dean Winchester drowns in guilt and self-loathing, isolating himself from Sam and Castiel in a desperate attempt to shield them from the "poison" he believes he’s become. Months pass with sporadic contact until a call comes from a South Carolina hospital: Dean has been found at the base of a waterfall, critically injured and barely alive.
As Sam and Castiel rush to his side, they grapple with the emotional wreckage left behind, Dean’s despair, Sam’s guilt, and the fragile hope of healing. With Dean’s life hanging in the balance, the brothers must confront the fractures in their bond and find a way back to each other. Can Dean find it in himself to fight for his recovery and trust Sam enough to help him, or will the silence and guilt between them prove insurmountable? -
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Embarrassing moments to waking up handcuffed to a bed with no memory. A collection of five standalone ficlets, each 500 words or less.
Chapter 1: Leather Coat (omegaverse)
Chapter 2: Half Eaten Pie (not omegaverse)
Chapter 3: "Praying" (Not omegaverse, Sabriel)
Chapter 4: Surprises at the Fair ( Omegaverse, Sam/Jess, background Destiel)
Chapter 5: Handcuffs (Not omegaverse) -
Sure by fictionallemons for burial_at__sea (bvrialatsea)
Fandoms: Supernatural (TV 2005)
05 May 2025
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Sam wakes up with a hangover and realizes he and Dean had sex last night while drunk. Guilty and panicky, he nurses his hangover at a nearby diner where he encounters a friendly local, Bethann, who’s more invested than she should be in his relationship problems. Bethann tries to talk Sam out of his shame spiral and make things work with Dean. But how can Sam be sure Dean wants this as much as he does?
An early-seasons getting together fic.
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In 1994 the world died. Now Sam and Dean are trying to survive.
Written for the SamWin JarPad Big Bang 2025.
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Seven Sam Winchester was left by his older brother and dad before a hunt. Spoiler alert: they never came back.
Ten years later, a strangely familiar car pulled up and an even more familiar man stepped out.
Sam is Seventeen
Dean is forty six
Fic title is from Demolition lovers by My chemical romance (chapter titles will probably also be MCR song lyrics)
WARNING: THE MAIN SHIP IN THIS FIC IS WINCEST. THERE IS DARK THEMES AND INCEST IS A GIVEN.
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Sam has been pining after his sister for years, even though he would never admit that to anyone. Especially not Dean.
Dean is nowhere near as oblivious as Sam is.
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I Tell You Everything (I Hope That You Won’t Tell On Me) by transgenderisms101
Fandoms: Supernatural
14 Apr 2025
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Sam hadn’t wanted to like the vampire. He’d made his animosity clear from day one. But Benny hadn’t cared, laidback and calm in the face of a brewing storm.
“Um…I was just wondering…what all that in the kitchen was about? What did it mean?”
Benny hums, thoughtful. “What did you want it to mean, bèbè?”
Or,
Sam hates Benny. Or does he?
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Dean didn't think Sam would take it seriously when he had said they should pick a hemisphere and stay away from each other. After nine months of searching he has finally found his brother, but he was just a shell of the man he once was, separating himself from the rest of the world in a self-made prison of solitude. Dean has no idea how to put him back together again.
Sam knew he was a disease that destroyed everything around him. He has spent a long time trying to convince himself otherwise, but now after the starting apocalypse and Dean kicking him out of his life, he has finally accepted who he was. He gets as far away from humanity as he possibly can with plans to live out the rest of his unworthy existence in isolation. The world would be better off without him.
Dean disagrees.
Dean POV. Canon divergence from when Sam calls Dean at the beginning of Episode S05E04 The end.
Series
- Part 1 of Better off without me
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Sam and his twin sister Olivia made a promise when they were 14 years old. A promise that they would get out of the life together. 4 years later, that promise was broken.
Sam goes to Stanford without her.
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A/U to season 8. Sam stumbles across a dirty and almost feral Cas while walking his dog. Clutched tightly against the rabid, snarling angel is his brother, unconscious and way too small to be real. De-aged!Dean with a sprinkling of protective!Cas and protective/guilty!Sam.
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Set sometime during the fourth season, after Heaven and Hell (4x10). "For years, Dean’s epilepsy had been nothing more than a distant memory—until Hell. Forty years without medication, without rest, without a human body to call his own. Now, back on Earth, something inside him feels fragile, cracked, unsteady. But will Sam realize in time that Dean may have never come back whole?" Oneshot.