1 - 20 of 25 Works in Sam Winchester Wears Makeup
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Sam Winchester wears makeup,
..And, he kind of likes it.
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After saving a woman’s life, Sam becomes the object of affection by the serial killer Lucifer.
This story is dark, like really dark. Please be aware of the tags.
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Sam Winchester and growing up trans while hunting.
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Several moments in Sam's life where he's not the boy he's supposed to be, but rather who they want to be.
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Sam's on a date.
It ends the same way they all do.
With his brother’s load in his ass and a body to dispose of.
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Suck It Up, Buttercup (Your Brother's Got Your Back) by candy_cigarettes
Fandoms: Supernatural (TV 2005)
12 Mar 2025
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“I don’t really know what I’m doing here,” Dean admits with a dry laugh, picking up a mascara tube and turning it over like he’ll find instructions carved into the side. “But if this is something you wanna do… someone you wanna be…” He looks up and offers up the most genuine smile in his arsenal. The one specially saved for his kid. “I’m here to help, Sammy.”
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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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Sam chews on his nails a lot. Too much. You come up with a plan to break the habit.
Please note: this fic contains mentions of Sam wanting to explore his gender : ) not much, just mentions of him enjoying feeling feminine
Series
- Part 75 of Tumblr Request One Shots (Multiple-Fandoms)
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Sam loses a bet, but gains a kink.
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Rowena laid a perfectly manicured hand on Sam’s jaw, cupping the slightly damp skin. “Speak, pet.”
Beneath the silk blindfold, Sam’s eyes rolled back, and he moaned. “Mommy, please…”
Sam and Rowena have some playtime.
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Dean goes through Sam’s bag and finds a little black pencil.
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- Part 2 of SPN Drabbles
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Sam Wesson and Dean Smith have an office "romance" that doesn't include much romance. Zachariah is a dick. (From Tumblr)
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* please check authors note before reading
Sammy gets some makeup for the first time, how will Dean and John react?
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He feels good. Like something in between them unknotted, putting themselves and the car back together under Pacific Northwest cedars.
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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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They’re in Jess’s room, studying for that week’s biology exam, when she finally asks Sam one of the questions they’ve been dreading.
Jess is sprawled on her stomach on the floor, poring over her battered textbook. She keeps chewing on the end of her pen, and Sam thinks it’s adorable.
Sam is sitting up, leaning back against the leg of Jess’s bed. They’re flipping through their notebook, foot tapping mindlessly.
And then Jess speaks, and Sam’s heart rabbits right up into their throat.
“Have you ever thought about wearing makeup, Sam?” -
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John gets back from a hunt & his boys wake him up with an early surprise for his birthday.
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kinktober day 11 - Object Insertion | Sounding | Cross-dressing | Tribadism/Scissoring
Dean gets absolutely hammered on cheep whiskey, and can't believe his luck when a gorgeous,tall girl in a pretty dress steps into his dark broody room and asks him for a kiss. Alcohol and hormones make it all go down heavy, but Dean is in denial about who he's with.
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- Part 11 of kinktober 2018
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Sometimes, Sam likes to feel pretty.
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- Part 9 of Write Me
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A bit of backstory and bit of kink.
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- Part 8 of And That's How It Works
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Maybe Dean will look at him and tell him he's beautiful. Maybe he'll sweep him off his feet and fuck him into the mattress, holding his small and delicate wrists in his bigger, firmer ones. Maybe Dean will notice him this time, tell him he loves him and actually mean it.