1 - 20 of 43 Works in Dean Winchester Wears Makeup
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Short, sweet and bitter.
Dean gets pregnant with Cas.
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Still beautiful, still Dean Winchester by Werewolf_Origins
Fandoms: Supernatural (TV 2005)
31 Aug 2024
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“I am Dean Winchester. Daughter of Mary and John Winchester. I am Sammy's older sister. I am….a woman.”
Her tired reflection gazed back at her in awe.
She did it.
She actually did it.
Or: snapshots of Dean's journey through life as a trans woman, and how she comes to accept herself.
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Slutty black eyeliner and skinny jeans by princeofsnowfield
Fandoms: Supernatural (TV 2005)
25 Jul 2024
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"Dean. I'm pretty sure the goth club won't let you in if you don't make an effort with your outfit.”
Where Sam and Dean do some shopping and a make-up session so they can blend in at the Black Rose. -
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Sent into the future by Zachariah, Dean finds himself handcuffed, alone, and with no easy way to escape. As he works to free himself, his mind wanders to that long ago night, and just how much he'd liked those pink panties.
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he lives for me, says he lives for me by according2thelore
Fandoms: Supernatural (TV 2005)
21 Oct 2023
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And it’s that weakness for agreeing to Dean’s stupid plans that has Sam in too-big shoulder pads and a too-big jersey with Richards emblazoned on the back in the middle of a Halloween house party full of people he doesn’t know.
Dean had insisted on keeping his costume a surprise, and Sam definitely had not prepared to be dressed up.
Someone squeals as the song changes again, some electro beat that Sam has no hope of recognizing. He stares down at the contents in his cup. Fuck it.
Or: In a world where monsters don't exist, and Sam and Dean are raised normally by two parents, things between them come to a head at a Halloween party. Some things are inevitable like that.
Written for WincestWednesday's October 2023 Event, Week 4 Prompt: "Is that your costume?"
Series
- Part 4 of WincestWednesdays October 2023 Event
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With the debts of his father and the obligation to help his brother fulfill his dreams weighing him down Dean has resigned himself to his fate of being a destitute lounge singer. Working a job with borderline unfair working conditions with a boss that does not respect him leaves him exhausted in numerous ways. To put it short, Dean was going through the motions day by day as he just tries to survive. And with barely any free time he certainly didn’t hold out any hope of forming any other kind of relationships besides friendships.
So imagine Dean’s surprise when his world gets turned upside down by a handsome Melittologist who just walks into his life one night.
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John doesn’t say that he loves you, but that’s fine, the lingering touches and the hot breath on your neck communicate what words can’t begin to describe.
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let me get what i want (lord knows it would be the first time) by izharptitsa
Fandoms: Supernatural (TV 2005)
22 Aug 2023
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When Sam leaves for Stanford, Dean realizes something. He is nothing without Sammy.
Unfinished one-shot that was collecting dust.
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Missionary Man by AmberXBoone, corrupt_touch (AmberXBoone), tallula03
Fandoms: Supernatural (TV 2005)
06 May 2023
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Castiel Novak, Esq. is a struggling Manhattan attorney who has made one too many mistakes at work. In order to make up for it, partners Chuck Shurley and Zachariah Adler task him with killing the star witness in the firm’s biggest trial, a fraud case against Niveus Pharmaceuticals. That witness is disgraced whistleblower neuroscientist Dean Winchester, who has been playing rock star since being fired from his job. But after stalking Dean in the bars and clubs where his band plays, Castiel winds up in Dean’s bed instead, and the two decide to take out the people after them to save themselves.
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Dean has done the work to be comfortable with who himself but some reassurance from his boyfriend Castiel goes a long way as they head to a concert. Dean never dreamed he would be so lucky to find someone who could love him for all of him, panties and all.
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"Don't say something you might regret."
Castiel Novak is a single father with two children struggling to make ends meet after his ex-wife takes off and refuses to pay Child Support.
After being losing his job and being evicted from his home, Cas's older brother Gabriel offers to let them live with him. There, Cas meets Gabriels' infamous coffee wizard (and part-time drunk), Dean Winchester.
His world gets turned upside-down in a swirl of hazelnut lattes, sickly-sweet lollipops and maybe-kind-of-dates.
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Cas is human now, and doing his best to hunt the things that go bump in the night. When he finds out a siren is targeting a gay bar in New Orleans he heads there to deal with it alone. He can't risk having Dean around in case the siren manages to enthrall him. But Dean shows up at the leather bar where Cas is drinking with the siren, and throws a wrench in his plans.
An unbelievable, incredibly distracting wrench, at that.
Series
- Part 1 of Year of the OTP 2023 prompt list
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Dean is in his last year of college and struggling to write his thesis paper. None of his professors have available office hours, so he's forced to either do it himself or accept help from an uptight English professor with impossibly blue eyes and a non-existent sense of humor.
Cas hates giving up his office hours to people who aren't his students. He also hates people who can't show up on time. So when Dean Winchester shows up to their meeting ten minutes late with a cup of coffee and a cocky attitude, Cas isn't pleased. But the topic of Dean's thesis paper is interesting enough that Cas is willing to put up with his harmless flirting.
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We Didn't Break, We Didn't Burn (We're Still Looking Up) by lefurlong
Fandoms: Supernatural
24 Nov 2021
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When Castiel returns from the Empty, Dean realizes just how much there is to learn about him. He never wants to stop.
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Newly titled Lord of Winchester, young Dean must host a ball for all the nobility. A masquerade seems like the best way to go about getting to know them all. Besides, it's Castiel's idea, so it must be a good one, right?
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- Part 31 of Suptober 2021
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When Rowena bets the Winchesters they can't go a single month as women, Dean thought it'd be the easiest favor they ever won, Sam's just reluctantly along for the ride, and with the Book of the Damned at stake, there's no backing out.
31 days in a girl body? What could possibly go wrong?
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Sam and Dean Smash the Patriarchy
Series
- Part 13 of Suptober 2020
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It was bought on a whim. He might as well carry on with it – on a whim.
So he does, and Dean dresses up – for himself, at first. But then Cas helps, and maybe it doesn’t have to be just for himself? -
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Dean Winchester is secretly getting ready to go to a club when his best friend Castiel bumps into him.
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Basically, Dean tries out eyeliner; angst ensues.
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On Christmas Eve, freshly-uncloseted Dean is dumped before his first-ever date with another dude. There to lift his spirits is Castiel, a talented mall-kiosk makeup artist with blue hair and a shy smile. But Cas is all that and more: he also happens to do seasonal work for actual, literal Santa.
Contrary to all plans ever made, Dean is swept away for one spectacular night with Cas and his sleigh-pulling moose, chasing storms, delivering gifts, and talking about Dean’s ideal first time with a guy.
Okay, cool.
New plan?
Date Cas.