1 - 20 of 207 Works in Dean Winchester Has Internalized Homophobia
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What Color is Outer Space? by castiels_golden_chariot (cleverunseenviper)
Fandoms: Supernatural (TV 2005)
15 Oct 2025
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The scene is set, sitting on a bench in the highest place to be found, they sit to watch the sunset and the reveal of the stars above.
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- Part 12 of Suptober 2025
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Kinktober, day 15. Prompt was object insertion.
Dean was cursed by a witch and the only way to break the spell is to hunt her down and kill her. Pretty easy for an hunter like him, no? But... this is no ordinary spell, it's making him feel all hot and bothered, and the worst thing? Looks like he's not just horny in general, his lust is specifically aimed at his best friend Cas.
But that's not gay... right? It's just a spell, right? -
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Still rolling through Massachusetts, the Winchester brothers find themselves tangled up in yet another case: A string of grisly murders in Salem, disturbing the peace following the end of the Halloween season. All signs seem to point to the vengeful spirits of Witch Trial victims, but perhaps something more wicked this way comes...
Set during season 3, following the events of "Red Sky at Morning"
- Language:
- English
- Words:
- 617
- Chapters:
- 1/?
- Kudos:
- 1
- Hits:
- 11
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Sam and Bobby have finally convinced Dean to go to therapy (only after Sam pre-paid for a months worth) and he finds himself learning a lot more about himself than he thought.
OR
Dean gets thrown into therapy and finds out his therapist doesn’t have to be a woman to be hot too.
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It means nothing by HadrianPeverellBlack
Fandoms: Supernatural (TV 2005), Harry Potter - J. K. Rowling
11 Oct 2025
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In chapter 34: My brother’s past is embarrassing, we talk about Richie and Dean.
Yes, it happened. Yes, this is the aftermath.
Yes, Dean didn’t deal with his bisexuality.Series
- Part 13 of Cultober 2025
- Part 29 of Jerk, Bitch & Brat series
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night shift is a series of one-shots set in an au where dean never gets cured after being turned into a vampire. Instead of going back to his old life, he’s stuck living in the dark, trying to find some kind of new normal. each chapter is a snapshot of his life, set at varying points between season 6 and season 15, as he navigates the aftermath of his transformation, the toll it takes on his relationships with those he loves, and the hunger he can’t shake.
PLEASE NOTE:
1) i have tried to list the setting for most of them. that being said, some chapters will be more obvious when they are set than others2) sexual content is indicated with a !, so feel free to just skip if desired!
hope you enjoy!
Series
- Part 1 of night shift
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"I tell myself
there’s not a world
without my brother in it.
I tell myself
I’d follow him anywhere
to keep the world
from ending."(The World at Its Beginning - Dustin Pearson)
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The story of the Winchester brothers is already written, it's a Gospel they can't escape; yet, two variables, two unforeseen elements, can upend everything.
The stage is set, tragedy is inevitable, and the script must be respected.
But perhaps its Narrator is losing control of his creation.or
A rewrite of Supernatural
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25 year-old Dean meets the man he’ll become: worn, broken, and haunted by love and loss. Time bends, walls crumble, and choices past and future collide. Can he face the truth about himself before it’s too late?
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What if Season 1 Dean met Dean after Cas goes to the empty and had the chance to fix everything?
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Sooo, first of October, that means kinktober time.
Day one, masturbation.
Cas is experiencing hormonal problems like a little bird due to increasing temperatures on Earth (basically global warming is making the angels go into heat) and Dean has to teach him how to touch himself, Cas' not a very good student though... -
So You Remember How It All Went Wrong by swishydetective
Fandoms: Supernatural (TV 2005)
30 Sep 2025
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The year is 2014, Castiel and Dean are living in Camp Chitaqua and the world is infected with the Croatoan virus. The Apocalypse is here. Castiel, barely an angel, barely human, is reading his journal entries from when it all started to go wrong five years prior and reminiscing on the key moments of his and Dean's relationship.
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Strikes, Spares, and Accidentally Feeling Things by kurokencanon
Fandoms: Supernatural (TV 2005)
30 Sep 2025
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Dean and Castiel go bowling. It’s supposed to be casual. It’s not. There’s laughter, longing, and a biblical verse that hits harder than any prayer. Dean starts to realize what he’s been feeling all along
or Strikes, spares, and the worst kind of heart attack: feelings.
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Dean writes letters to Cas he never intends to send. After Cas’s confession in the Empty, the words Dean never said weigh heavier than ever. When Cas finds the box of unsent letters, the truth Dean’s been hiding finally comes to light.
(Or a love story in unsent confessions, discovered truths, and finally saying the words aloud.)
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A search that turned out to have dire consequences. by Pon_228_5
Fandoms: Supernatural (TV 2005), The Boys (TV 2019)
21 Sep 2025
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Sam and Hughie were looking for Dean, not knowing it would end with dire consequences.
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Based off of this prompt from Pinterest:
“cas brings dean a 4am cup of coffee while they're still researching in the bunker library; another all nighter to save the innocent. cas puts the steaming mug down in front of dean, and dean snags cas' sleeve, yanking him down and kissing him on the cheek as a thank you; just barely catching the side of cas' mouth. it isnt until dean has pulled away and taken a large sip of coffee he realizes with startling clarity that he just kissed cas for the very first time.”
Credit for prompt: Nyx
****complete****
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In the heavy Southern heat, faith tastes like ash and desire feels like sin. Dean Winchester carries his father’s sermons in his bones, Castiel carries his silence like penance, and Sam has grown tired of watching them break. Between hymnals and cicadas, shame and longing, something has to give.
A story of damnation, desire, and the small mercies that might still be called love.
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Adele sang that regrets and mistakes are memories made. What she failed to mention in dulcet tones and a smooth British accent is that they're not always bittersweet, sometimes, they're just bitter.
Dean's only just getting his life back together after his mistakes cost him his husband, his son, and damn near his liver. There's a long road ahead, filled with pain and heartbreak, the difficult navigating of two parents trying to make divorce work for the sake of their son. Of course, Dean's being morose because it's not all bad, he has his sobriety, he has his brother, he has friends and a job he loves...
And maybe - just maybe - one day he'll have Cas back too.
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Our poor, sheltered boy gets on 5th Base after Alice explains to him what it is, and he may need to rethink his whole life afterwards. A good pegging will do that to a guy.
- Alice has AFAB bits, but otherwise you get to decide what she looks like.
- Can be read by itself
Series
- Part 3 of Dorks Do Debauchery
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When Dean goes to buy beer and finds that he has bet all his money away, the cashier lets him have the case, but when Dean returns the next day to pay, he gets more than just a case of beer.
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Dean is a lonely hunter on the road with nothing but his guns, the clothes on his back, and Baby, his horse. He visits a town once he here's word of a potential infestation of werewolves. While investigating he runs into the town priest. He finds he’s not as alone as he thought and doesn’t want to be, anymore.
(Posting every Wednesday)