1 - 20 of 391 Works in John Winchester Tries
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Dean thought he knew what home was... until he didn't. After everything he's lost, he finds himself in a place beyond life, where choices, reflections, and quiet moments force him to confront what truly matters. But even here, the heart wants more-and some endings aren't as simple as they seem.
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John Winchester parenting advice on how to handle childhood trauma by ilovetvshows
Fandoms: Supernatural (TV 2005)
06 Mar 2026
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In 1987 Chicago, six-year-old Dean Winchester witnesses his father, John, committing a brutal basement torture, only for John to convince him the trauma was a hallucination caused by a 104-degree fever. Twenty years later, now elite mob enforcers, Dean and a baffled Sam finally confront John during a nearly identical hit, shattering the "illness" lies of their childhood. John darkly jokes that he only used the fever trick to protect his image until they were old enough to pull the trigger themselves, leading the trio to embrace their roles as the true predators of the Chicago underworld.
- Language:
- English
- Words:
- 3,085
- Chapters:
- 1/1
- Kudos:
- 1
- Hits:
- 10
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Seeking a witch to decode a spell for him, John Winchester becomes painfully aware of the life he's made for his sons and makes the decision to do it all again. The right way.
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theres a starman waiting in the sky by huachengssilverbutterflies
Fandoms: Supernatural (TV 2005)
02 Mar 2026
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Castiel has always been watching over Dean and wishes Dean would see himself the way Cas sees him.
or
cas comforts dean with his regrets
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John finally decides that Dean is ready for his first hunt. This leaves Sam to be shipped off to Bobby's house for the week.
Sam has always been the little brother needing to be protected. But for one night, Sam knows he can be brave too.
Series
- Part 8 of The Winchester family being a disaster
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"Fathers weren't kind or nurturing. They were protectors, doing what needed to be done, even if there were consequences."
(This is short and for a good reason, please read author’s notes)
- Language:
- English
- Words:
- 657
- Chapters:
- 1/1
- Kudos:
- 5
- Hits:
- 55
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Summary
At Hexford High, your future is decided by a card.
Kings rule. Queens pull strings. Jacks break bones. Everyone else learns how to bleed quietly.The Shurley family transfers in with too much history and not enough restraint. Secrets surface. Lines blur. Then someone draws a card that shouldn’t exist.
A Joker.
The hierarchy starts to rot. Authority panics. Rules become optional. And in a system built on control, the most dangerous thing you can be is impossible to label.
Multiple POVs. High school AU.
Slow-burn, forbidden Castiel/Dean—charged glances, bad decisions, and the kind of love that ruins people beautifully. -
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Dean is four years old when his mom burns up on the ceiling of his little brother’s nursery.
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Dean is twenty six years old when he starts the drive to Stanford University.
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Dean Winchester grows up a lot of things. Happy isn’t one of them.
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The sickfic aftermath of 'Tired'
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Dean's fever doesn't get better, neither do the nightmares.
Series
- Part 9 of Mysterious and Convenient Entity AU
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You and John were happily married with your two boys, Sam and Dean, but when the yellow-eyed demon showed up; he took you with him. For centuries, you were stuck in hell forgetting who you are. Not knowing you had a life on earth.
When the gates of hell open and sucked a bunch of demons out, you were sent back to your previous body without any memories of who you were. Will john and the boys ever find you ?
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Welcome to another AU, Wincest story. This resulted out of a single scene my beta came up with and whoosh developed to an outgrown story about two brothers, raised apart of whom one knew about the other and one didn’t.
I hope you’re in for the long haul, because – even though I just ended plotting and started actually writing – it appears as if this is going to get damn fucking LOOOONG, stuffed full with Hurt/Comfort, Angels, a dash of demons and well … explicit content in later chapters.It’s practically a love-story with a slow start, considering – to set the scene – it’s mostly John Winchester’s POV we’re going to start off with.
That’s gonna change, though. -
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After an accident during a hunt that kills Dean, he is buried by his family and friends.
He goes to heaven as expected, though somethings not quite right.Or
Dean dies and becomes an angel.
Series
- Part 1 of The One Where Dean Becomes An Angel
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Deanna didn’t understand a lot of things. She was only four, and the things the adults said didn’t really matter to her. She didn’t understand why mommy got mad when daddy called her Dean.
She doesn’t have to worry about that anymore after the fire, but as she grows up, the things the adults say do start to matter.
(trans!Dean fic)
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ideas/headcanons that I have but can’t manage to develop beyond a few hundred words. Free to take inspiration from any of these (please tell me if you write any of them! I want to read.)
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When John Winchester reveals the truth Sam was never supposed to know the fragile Winchester family fractures beyond repair. Caught in the middle, Dean must choose between his loyalty to his father and his need to protect his brother from a truth that might destroy him. But some truths can't be hidden forever, and some wounds run too deep to heal
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Mary cursed her husband and son when she left. (Dean is 17 when they finally have sex.)
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Love is a Vow Best Taken Kneeling by postmortem_analysis
Fandoms: Supernatural (TV 2005)
25 Jan 2026
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Dean Winchesters discovers he wants to fuck the priest officiating his father's wedding.
Castiel Novak is not a man to fuck with.
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(A SUPERNATURAL FLEABAG AU)
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After Mary’s death John can’t handle being a father of two while also hunting the thing that killed his wife. So in an act of desperation to not go over the deep end, he gives up his youngest to the authorities. Hoping for a better life for Sam, John continues hunting with Dean by his side.
Years later, Sam Campbell is haunted by nightmares of a man he doesn’t know. After one vivid night that leads to the man’s death, he catches sight of him on his campus asking about two recent suicides. Deciding against his better judgment, Sam follows Dean Winchester into the life of saving people, hunting things and finding a family he never knew he had along the way.
Or: Sam grows up in the foster system, gains a scholarship at one of the best law schools in the country and promply throws it all away after his life comes crashing down around him with the arrival of a man named Dean Winchester.
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“Most people would freak out after finding out monsters exist.” Dean says, eyeing him from the couch.
Sam shrugs as he opens his laptop. Most people don’t have dreams that come true, he wants to say. He doesn’t, keeping that little fact to himself. Instead Sam states, “I’m not like most people.”
Series
- Part 5 of 🎓2025♟️
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Dean was four when the werewolves took him. At seventeen, he returns to Lawrence, Kansas, following instincts he does not fully understand.
What he finds there is a vampire nest, a child in danger, and a hunter who looks at him like something that needs killing.
John Winchester spent thirteen years believing his eldest son was dead. When a young werewolf-like creature starts hunting vampires in his territory, John does what hunters do. He treats it as a monster.
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"Yeah, sure. You go right ahead. I'll stay here with your fucking son" Bobby ridiculed, raising his voice in frustration at the Winchester.
"He's fine, Bobby. He's got a stomach ache" John turned and braced to continue the hike.
"Dad" Dean croaked, hands shaking as he held his light facing the sick on the green ground. He looked up when he didn't hear John stop. "Dad" he choked out a little louder.
"What!?" John snapped, turning back around.
"It...it's blood" Dean choked.
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Dean seemingly has a stomach ache while on a hunt. John gets frustrated with him until he finds out his son is much worse than he thought.
Featuring both John and Mary and Bobby and John bickering, potentially some Sam and John bickering as well
Series
- Part 4 of Mysterious and Convenient Entity AU