1 - 20 of 131 Works in Dean Winchester Character Study
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Though you've set aside the world of hunting after your father's death, an unexpected visit from John Winchester's sons pulls you back.
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Kevin spoke, his words shaky. “I don’t know what I want. I don’t know what’s too far for me, or too painful. All I know is that I just want to be–” he bit his lip, hesitating, then– “a prophet.”
“A prophet,” Dean repeated, slowly. “Which means?”
“Useful.”
Or, Kevin Tran was chosen to serve a higher purpose. He just never learned how to stop. Dean might be the one to teach him how.
- Language:
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Please Don't Ask Me (How I've Been Getting Off) by ZOMBIFICATION
Fandoms: Supernatural (TV 2005)
22 Jan 2026
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dean can't handle thinking about having sex with men normally so he fantasizes about them forcing themselves onto him instead like a fucking weirdooo.
not canon-compliant. set at a completely random point around s4-5, and don't pay any attention to the bullshit cases they're working i just cbf. mostly pwp/dean study. cas has wings and all that good stuff. -
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when dean was 4, he lost his mother.
and when he was 41, he lost cas, again.here are some of the things that happened in between
and some of the things that happened afterSeries
- Part 1 of Blueberries
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Dean's ruminations upon coming back from Purgatory.
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You can't always get what you want (but if you try sometime, you’ll find you get what you need) by Miasalice
Fandoms: Supernatural (TV 2005)
03 Dec 2025
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“Where’s the line between wanting and needing?
When does a pull at the heart becomes your very heart and opens your chest cavity from within?”Or:
A short study on Dean's relationship with wanting and needing and where Cas fits in the picture through a The Rolling Stones song.
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“Castiel’s deal required him to be happy.” Jack continues, encouraged by Dean’s forced calm, “What made him happy? What could have, in that situation?”
Dean can’t understand why he’s asking. Sam has the same question, it’s so clear in his eyes every time the subject has come up, but he’s at least accepted that it’s just a detail. That he doesn’t need to know. That Cas was his friend too, but that moment belongs only to Dean.
But Cas, more than Dean, more than Sam, Cas was Jacks dad. So Dean reframes the question, turns it over in his mind until the edges are less sharp and the shape looks much more like himself, fours years old, asking why his mum hadn’t survived that fire.------
Or: the world is saved, but Cas is still dead. Dean struggles, Sam rebuilds, and Jack has plans for a better world.
And somewhere far beyond their reach, Castiel wakes up.
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Dean Winchester doesn’t bind himself with biblical tales — especially ones that concern angels. So, when he and Sam accidentally convoke one via ouija, his views imminently, and prominently, change.
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Sam knows what the angels think about his use of demon blood. He's decided that he doesn't care.
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A Curse of Obedience is cast on Dean. Dean finds himself forced to obey every “order” given to him (very literally). Worse, the witch made sure that he can’t even tip off Sam or Cas with what’s going on. Will either of them figure it out? Or will Dean be stuck doing what they say (even if it isn’t what they mean)?
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Dean Winchester grew up learning all about all the monsters that lurk in the dark, and more about the ones that can hide plain in sight. Witches, demons, shifters, changelings, even creatures nobody’s ever heard of. Dean gave his entire life to hunting them, with a few simple comforts to ease the way. The Impala. Music. Whiskey. Women. Not wine, but beer’s good. A sliver of freedom. He also took comfort in knowing that, of all the horrors of the world, vampires aren’t real. Of all the things Dean had to be grateful for, that those suckers were just a myth, definitely makes the top 10. Alone and injured after a hunt gone wrong, Dean is already at rock bottom when his father calls in distress—only for it to drop as suddenly as it began.
A dead-end case. An eerie town. An impossible monster. A missing father. And one ragged Dean, struggling to string it all together.
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After Chuck’s fall, the world has finally gone quiet.
Too quiet.
Dean prays — at first every day, then less and less.
And always with the same question: “Can you hear me?”Series
- Part 8 of Suptober 2025
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"Though, he guesses that's what faith is anyways, asking for something not knowing if anyone is on the other line."
Dean doesn’t know how to do easy. But for one morning, he tries. -
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Dean has spent years flinching at pet names that cut sharper than they comfort. Now, the world’s saved, the road is quiet, and he’s still learning how to live without fighting.
And when Cas calls him things like honey, the words that once stung start to mean home instead of hurt.*Inspired by ‘Honey’ by Taylor Swift.
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The first petal fell on a hunt in Ohio.
Every petal that Dean coughed up after felt like salvation. He didn’t have to hide anymore, or even do the work of admitting the truth to himself. The flowers did that for him.
And they’d do it ‘til they killed him.
Or: Dean gets Hanahaki Disease after Cas' confession in "Despair."
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Rising from Hell came as a shock to Dean Winchester. Castiel now stands before him in a human vessel, the shadow of his wings plastered against the wall of the barn. He preaches endlessly to Dean about being the future savior of the world. No matter how hard Dean tries, he just can't seem to escape him. The fate of the universe lies in his frail human hands. The angel still trusts him despite all odds. When problems arise with Sam, Dean and his angel discover a new bond emerging from the shadows. With the seals being broken, Lilith rising, and Sam being right in the middle of it all, Dean must find a new way to fight.
Or: The one where Dean Winchester fights the memory of his father to taste safety in his angel.
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In the midst of a hunt with his father, Dean Winchester finds himself stuck on the same drive, night after night, pursued by an entity he can't quite manage to catch or identify. Between that and the strange phone calls he begins receiving from a deep-voiced yet gentle man, Dean isn’t quite sure if the world he’s found himself in is his own; or if he can ever manage to get back where he came from.
All he knows is nothing good comes from being alone.
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casefic exploring a very repressed dean winchester in the middle of 2003
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Supposedly, not too far from the Bunker, there lay a field of daisies, left, it seemed, entirely undisturbed. A sea of white petals that stretched as far as the eye could see.
While Dean felt far too familiar with daisies to be impressed by the description, the little flowers sprouting just about wherever they pleased, something about the way Castiel had said it made him keep his thoughts to himself. His fingers twitched as he spoke, eyes far away, locked solely onto the image in his mind, as though possessed. It must have been something to behold with the way it left the angel at the edge of his breath.
So he agreed to be taken there.
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good luck, babe! (you’d have to stop the world just to stop the feeling) by orphan_account
Fandoms: Supernatural (TV 2005)
25 Aug 2025
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title from (you guessed it): good luck, babe! by chappell roan
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Realizing his feelings for Cas after a spontaneous kiss, Dean drives to the closest bar and finds the nearest attractive woman to hook up with.
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please leave feedback/comments, i love reading them :))
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“Once there was a tree… and she loved a little boy,” John read from the shiny green book Dean had brought him.
He didn’t know yet it would be the last bedtime story he read to Dean. Didn’t notice the furrow in Dean’s brow or how much attention he was paying to the story.
Didn’t know that soon, a demon—one who had long ago twisted itself around the roots of their family tree and spread like rot—would kill his wife, upend their life, and leave him to raise two boys alone.
Didn’t know that the second he’d place baby Sam in Dean’s arms and say, “Take your brother outside as fast as you can and don’t look back,” that it would change their dynamics forever.
As he watches Dean grow up, growing around him and Sam, so eager to help, he starts to have terrible dreams of his oldest son ripping out clumps of his own hair, ripping off his skin, cracking open his rib cage, and handing it all to them, just to keep them safe and warm.
It was wrong.
But it was something he could use. And any ‘wrong’ he could use was an excusable wrong.
Or, 5 times someone notices how much of himself Dean gives for his family, and one time that it doesn’t matter anymore.