1 - 20 of 274 Works in Sam Winchester is Not Okay
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Heaven's Second Chance by ClairAragon
Fandoms: Supernatural (TV 2005), Charmed (TV 1998)
30 Oct 2025
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“Goddammit, Gabe,” Sam gritted through his teeth. The mirror stared back with a face fifteen years younger—wide-eyed, unscarred, and unhinged. He grabbed his jaw, ran a hand through his hair, and started laughing. Sharp at first, then manic, until the tears came.
After watching Dean die on that spike, Sam’s thrown back into the past—to Mystery Spot. Same motel. Same Tuesday. Different hell.
He’s convinced Gabriel’s behind it, but the trickster swears it isn’t his doing. So who—or what—sent him? And how is Sam supposed to carry the weight of the world on his shoulders again, knowing exactly how much it cost the first time?
This story twists canon into something new: a Sam-centric journey through grief, guilt, and second chances. There’s still Destiel, still heartbreak, still laughter through the tears. The Charmed crossover adds new allies, new chaos, and just enough magic to make it hurt a little less—
—or maybe a little more.Each reset brings new cracks—between brothers, between lovers, between what was and what could be. Sam’s trying to fix the past, but the more he fights it, the clearer it becomes: some loops aren’t meant to be broken.
Some are meant to break you open.
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Sebastian has always been there for Sam.
Sebastian understood everything Sam wanted to get across without saying anything. Sebastian cared deeply for Sam, and comforted him in his time of need.
The townsfolk watch this blossoming relationship unfold.
Yet there's one glaring issue making itself known.
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I thought the plot of Sam getting his soul back and hallucinating from the cage felt rushed so I wanted to make my own kinda way of how he felt. (Unfinished)
- Language:
- English
- Words:
- 264
- Chapters:
- 1/1
- Kudos:
- 2
- Hits:
- 34
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Summary
Apocalypse Michael has a different approach after beating Lucifer
Series
- Part 24 of kinktober 2025
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A retelling of Rapunzel but in the lens of Mary's deal with Yellow Eyes. Demon deals always cost more than one can afford.
Series
- Part 23 of Hollandween's Return
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Leave Me With A Good Memory Before You Go by Tomhollandsfandom
Fandoms: Supernatural (TV 2005)
22 Oct 2025
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As much as it hurts to physically touch Castiel, it hurts so much more being apart from him. He is all he has left and they both see the ticking time bomb. Sam only requests for one thing, a night to remember. He doesn't need anything more than that.
Series
- Part 22 of Hollandween's Return
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The only resignation the Hunt accepts is Death by frenchfries21
Fandoms: Supernatural (TV 2005)
20 Oct 2025
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Whumptober Day 20: Resignation
„The Hunt takes everything — and when there’s nothing left to take, it takes you too.“
Series
- Part 17 of Whumptober 2025
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Dean's latest ill-advised bar hookup turns him into a werewolf. Contrite and resigned, he goes to Sam and begs him to kill him. No way is he becoming the very thing he hunts. But Sam refuses. Instead, Sam helps Dean through his cycles, and helps him stay off of human flesh. The problem is that his new wolf instincts are driving him towards an even more profound bond than he already has with his brother.
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11.11.2011
America, for the first time in its tumultuous history, is united in morbid curiosity when bodies begin to wash up on its shores. The same body. Over and over. A young man, as handsome as he is strange, sporting a dirty brown trenchcoat, and more than a few delusions of grandeur.
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The first part of my long series rewrite, starting with season seven!! Godstiel plays the part of Big Bad, splitting into his various elements and terrorising the nation in the form of a new urban legend: The Trenchcoat Man. Homosexuality ensues. Also Sam is going clinically insane.
Series
- Part 1 of Dead Girls & Gods
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After leaving the BAU, Spencer Reid rebuilds a quiet life teaching philosophy in a suburban high school : a life measured in lesson plans, flickering classrooms, and shared coffees with his favorite colleague, Charlie Bradbury, the computer science teacher.
When Sam Winchester joins the staff at the start of another school year, Spencer doesn't expect much more than polite conversation in the teachers' lounge. But the new quiet teacher carries shadows in his eyes and nowhere to go when the day ends.
Spencer knows what it means to fall apart, to miss the sunrise after too many dark nights. So when Sam's world starts to dim, he can't look away. But as secrets unravel and old wounds resurface, Spencer learns that saving someone isn't as simple as offering help.
Sometimes, it's about keeping a faint candle burning when the darkness comes back.
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The Mark of Cain wanted Sam dead. Dean? He has...other uses for him.
Series
- Part 18 of kinktober 2025
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Dean Winchester has all the perks of a classic rock star life; fame, money and a tragic lost love story he draws on for his lyrics. Until the day his past and present collide in a way he never saw coming.
A life-changing act brings him face-to-face with a person he thought he'd never see again and it leads him on a road to redemption. -
New rule. Whatever the Dursleys said, you ignore it. by HadrianPeverellBlack
Fandoms: Harry Potter - J. K. Rowling, Supernatural (TV 2005)
15 Oct 2025
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“Harry,” Sam swallowed, kneeling in front of Harry, placing his hands on his younger brother’s shoulders. “New rule. Whatever the Dursleys said, you ignore it.”
“But…” Harry began, interrupted by Sam.
Series
- Part 38 of Jerk, Bitch & Brat series
- Part 22 of Cultober 2025
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Screw Heaven and Hell, the only important thing is that you're safe by frenchfries21
Fandoms: Supernatural (TV 2005)
12 Oct 2025
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Whumptober Day 12: Sacred Place & Angstober Day 12: Hollow
"Hopefully, I am not too late...
Dean sprinted the small distance that separated him from the rotten front door of the church, immediately stepping inside with one thing on his mind: I have to stop him."
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Dean discovered that they had been lied to regarding the Trials of God. Is he fast enough save Sam in time?
Series
- Part 11 of Whumptober 2025
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"I wanna be your dog" - Kinktober Day 10 (Punishment + Oral) by cosmic_caden
Fandoms: Supernatural (TV 2005)
11 Oct 2025
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A typical day where Lucifer plays with Sammy in the cage. Afterall, pain and guilt are the two most delicious things for the devil.
Series
- Part 12 of Kinktober 2025
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Trapped by Sandy aka Yokoth the Lovecraftian horror, Dean has a brilliant idea...not. Two married monsters will gobble up the world, and if that wasn't bad enough, Sam's fate is worse than being devoured.
Series
- Part 9 of kinktober 2025
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Wound Debridement and Its Side Effects (Except It's On A Soul, So There Will Be Complications) by sofacat16
Fandoms: Supernatural (TV 2005)
02 Oct 2025
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Castiel isn't able to fully heal Sam's mind from the effects of the wall breaking, but he tries to take on some of the burden. And now, the aftermath.
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"Mom, I'm tired/Can I sleep in your house tonight?"- Kinktober Day 2 (Age Play) by cosmic_caden
Fandoms: Supernatural (TV 2005)
02 Oct 2025
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Summary
Dean is not okay and neither is Sam. They can't talk about their feelings like normal people, but perhaps they can get it all out another way?
Or: What happens when Dean lets himself cry for the first time since he was a childTakes place during season 4 after Dean gets out of hell!
Series
- Part 3 of Kinktober 2025
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When the Levee Breaks, It's All My Fault by green_tea_bag
Fandoms: Supernatural (TV 2005)
02 Oct 2025
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Summary
Dean comes home with Sam in tow and throws him into the panic room in Bobby's basement. Their little sister is scared, confused, and angry. She doesn't know what's going on, she doesn't know what to do. And her brother is screaming for her to let her out.
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Sam and Dean's little sister let's Sam out of the panic room and it all goes sideways.
Series
- Part 27 of Celeste Winchester
- Language:
- English
- Words:
- 1,948
- Chapters:
- 1/1
- Kudos:
- 8
- Hits:
- 195
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'When we all fall asleep where do we go?' - Kinktober Day 1 (Incest +Masturbation) by cosmic_caden
Fandoms: Supernatural (TV 2005)
01 Oct 2025
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Summary
Dean is exhausted from a hunt and just wants to sleep, however Sam and Cas have other plans. When Dean agrees to let Cas use his sleeping body however he pleases he certainly doesn't expect this.
Or alternatively: Sam lets his desires win, Cas agrees to help, everyone wins.Series
- Part 1 of Kinktober 2025