1 - 20 of 387 Works in Taking Care of Sam Winchester
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“Is this the end?”
If this was the end, it was better than he’d dared hope.
“Sam,” a gentle voice said.
Sam was out of the Cage - or so said the stranger with blue eyes. He talked about soup, about healing, about someone called Celine Dion. But Sam knew exactly how far Lucifer would go to fake tenderness.
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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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35-year-old Dean Winchester is a veteran of the adult film industry seen every side of the adult film industry who thinks he's seen it all when newcomer Sam Campbell walks onto the set.
Sam is beautiful, cocky, and way too young, though he swears up and down he's 18. Dean quickly realizes he's hiding far more than just his age.
Dean Wants to help, Sam doesn't want to be helped, and neither is prepared for the violent collision that will force them together.
Note: Sam is 16 (the age of consent in NV where the story takes place)
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Little Dean wakes up and tries to make breakfast for himself and Sammy. Daddy reminds him that he doesn’t need to try to be a big boy and take care of Sammy all alone; he can rely on him for help.
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The First Morning of the Rest of Their Lives by shadowhuntingdauntlessdemigod
Fandoms: Supernatural (TV 2005)
19 Nov 2025
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After the world-shattering revelation that their lives are finally their own for the first time since before they were even born, Sam does something he never does: he sleeps in. Naturally, Dean is concerned in a way that only a big brother could be.
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Sam doesn't go to Stanford. Sam POV
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“You know, your mother died trying to save you. She’s dead because of you! The least you could do is stop being an ungrateful piece of shit and avenge her.”
Sam froze in his spot. His duffel bag slipped out of his grip and landed on the dirty motel carpet with a soft thud.
John won the big fight. But at what cost?
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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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scared of what's above (oh what will I become?) by need_more_meta
Fandoms: Supernatural (TV 2005)
08 Nov 2025
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California nights are warm and lonely, even with your hot girlfriend right next to you in your bed.
Sam, however, doesn’t want a girlfriend who is right there.
He wants his brother who is God knows where, but at least he has bars on his phone.
Series
- Part 43 of Meta's Wincest Fics
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During a long trip in the Impala with Dean, Sam ends up needing to use the bathroom. But Dean refuses to stop with the excuse that it'll slow them down and that he'd rather reach their destination before nightfall. And either way he forced Sam to put on a diaper before he left so if it's that much of a problem he can just use it.
Unfortunately Sam is quite stubborn, wearing a diaper is embarrassing enough so he refuses to use it. But he can only hold it for so long, and his big brother can be oh so convincing.
Series
- Part 6 of Omovember 2k25
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A series of one-shots with my favorite Ghostbusters, Sam and Dean Winchester, following Sam Whump.
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I thought you were dead by HadrianPeverellBlack
Fandoms: Supernatural (TV 2005), Harry Potter - J. K. Rowling
13 Oct 2025
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Dean wasn't happy at all.
Sam had faced two demons on his own, and then arrived calmly, looking perhaps even a little annoyed when Dean tried to hug him.
Series
- Part 18 of Cultober 2025
- Part 34 of Jerk, Bitch & Brat series
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Big Brother, Little Brother by castiels_golden_chariot (cleverunseenviper)
Fandoms: Supernatural (TV 2005)
13 Oct 2025
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In which Dean is doing his very damnedest to be a good older brother and take care of Sammy.
Series
- Part 11 of Suptober 2025
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you're your mother's only son, and you're a desperate one by strongestriddles
Fandoms: Supernatural (TV 2005)
30 Sep 2025
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Dean’s thread of life has a knot in the shape of Mary’s body burning on the ceiling. He still sees mama Mary in everything.
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EXPLICIT ART for J2 Wincest Kinktober Fling Exchange! Sex In The Impala by xpurdyglambertxART for Fatima_O
Fandoms: Supernatural (TV 2005)
23 Sep 2025
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Filling the prompt of "Dean Winchester and Sam Winchester having sex in the back seat of the Impala after a hunt."
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Lucifer vs That Damn Coconut Shampoo by areallygoodsheep
Fandoms: Supernatural (TV 2005)
14 Sep 2025
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Summary
Sam wacht im Panikraum auf, schleppt sich bis zu der verlassenen Klinik, bricht dort zusammen. Dean kümmert sich um Sam, kämpft zwischen Reparaturen und Verzweiflung. Sams Zustand bleibt trostlos. Dean ist mit den Nerven am Ende.
⛦
Series
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Lucifer vs That Damn Coconut Shampoo by areallygoodsheep
Fandoms: Supernatural (TV 2005)
14 Sep 2025
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Sam wakes up in the panic room, drags himself to the abandoned clinic, and collapses there. Dean takes care of Sam, struggling between repairs and despair. Sam's condition remains bleak. Dean is at the end of his rope.
This fic describes what Sam and Dean might have experienced between the end of the episode “The Man Who Knew Too Much” and the beginning of “Meet the New Boss” until Sam wakes up again.⛦
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Dean’s found Heaven to be the bare minimum of what it was chalked up to be. Paradise? Sure. Immortalized and doomed to his own thoughts for the rest of eternity? Sure. Death wasn’t all that permanent for the Winchester, and he wasn’t about to let being ashes and dust stop him from attending Sam’s wedding.
And if some other feelings arise from the ceremony—well, Dean’s track record for prophecy’s wasn’t all that good to begin with.
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Or;Castiel & Dean attend Sam’s wedding. Overfeeding the fandom’s Destiel fans (I included), and finally making something for us Eileen & Sam believers.
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“Dean?” he asked, voice small.
“Hm?” Dean hummed, still not looking at him.
“Can you pull over?”
“We’re on the highway, man, no I can’t pull over. Why?” He finally turned his head, an annoyed expression on his face that melted away the second he saw Sam, pale and shaky, raising one hand to cover his mouth and swallowing thickly again.
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Or, Sam gets sick on the road and Dean shows off his rusty big brother skills.
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What if I'm far from home? Oh, brother, I will hear you call. by MoNsTeRsAmOnGMeN
Fandoms: Supernatural (TV 2005)
08 Sep 2025
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Summary
Then he was somewhere else.
The room was dim, orange light flickering against floral wallpaper. The air smelled of old smoke and spilled beer.
Sam staggered, bracing himself against the wall. His boots made no sound on the carpet. He looked around, trying to orient himself—and froze.
There was a crib in the corner.
He knew that crib.A misery spell sends Sam and Cas back in time to follow Dean, to walk his childhood with him
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Dean is almost 20 years old and attending college out of state. He lives off campus with his roommate—Castiel, who he definitely isn’t falling in love with.
Sam, 15, lives at home with their dad. Nobody knows what goes on behind closed doors.
That is, until Dean finds out. Suddenly, his will-we-won’t-we with his roommate doesn’t seem so important.