1 - 20 of 502 Works in Trans Sam Winchester
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Sam’s dealing with cramps and just for the love of the game Castiel gives them to Dean instead.
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On March 4, 1997, a hunt doesn’t go the way it should, and Sam Winchester pays the price.
It’s been eight years, three months, and seven days since Sam was stolen away from his family by a demon. After years of torment as Lucifer’s prisoner, with the help of an angel of the Lord, he’s finally free. With his son, Jack, in tow, he reunites with his brother and father. But adjusting to this new life is anything but simple.
In which Sam suffers, John hates his grandson, Dean gets to be an uncle, and Jack tries to be a normal kid.
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When Sam was eight, he had his first period.
He couldn't understand why it was happening, why it happened so soon. He talked to other girls at the schools he hopped between, and some of them didn't even know what he was talking about. John had sat him down and told him he was a woman now, even though at this point, John was treating him like his son. It through Sam through a loop, and from that point on, it only seemed to get worse.
He got questions more often. Asking him who he was, what he was, and he still doesn't know. He tried looking it up in college, Jess helped him get diagnosed with PCOS, but there was still something different.It wasn't until years later, after... After a lot of things happening, that he found out more.
~~~
Or, Sam really needs Dean to fuck him, and he finds out something new about himself that gives him a grand old time.
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WE'RE SO BACK BABYYYY
(DAYS 2-7 ISH WILL BE POSTED LATE AS I AM AWAY FROM MY COMPUTER)
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in a gasoline burn our bodies will churn by ace_does_words
Fandoms: Supernatural (TV 2005)
01 Oct 2025
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Sam Winchester is tangible.
Jo Harvelle never will be.
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Because that's what dad taught him to do.
Dad taught him to make it seem like he never even existed.
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Ultimate by Lukesfrag
Fandoms: Supernatural (TV 2005), Spawn (Comics), Legion (TV), Ghost Rider (Comics), Hellblazer
29 Sep 2025
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In the aftermath of a major global pandemic, a transformative shift occurs in society, giving rise to a futuristic world where individuals develop extraordinary powers. This paradigm shift not only alters the fabric of everyday life but also extends beyond the mere acquisition of superhuman abilities.
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he's so good to me and to nobody else (so you can fuck yourself) by Anonymous
Fandoms: Supernatural (TV 2005)
19 Sep 2025
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After a case, Sam thinks he can finally blow off some steam and jerk off. Bad news: Dean interrupts him. Good news: Dean's got girthy fingers and a good cock.
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Dean Winchester shows up to Stanford to get his brother's help finding their father, only to immediately find out he no longer has a brother.
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What leads a righteous man down to hell?
Dean Winchester has just about run out of people to loose. First his Mom gets killed by an unidentifiable shadow-creature. Then Dad and Bobby have a fight so bad that Dean isn't allowed to visit anymore. Then Dad and Sam have a fight so bad that Sam leaves. And now? Now Dads phone has been disconnected.
Dean can face ghosts. Dean can face demons. Dean can face almost anything that the world throws at him. He can even face loneliness. But he'd like to have one family member in his life, so he can at least pretend that he isn't completely alone in this world.Or: The Secret Good Supernatural TM, as pieced together from rewatching the show to figure out what makes my brain tingle, reading a ton of character-analysis-posts and picking out my favourite, and filling up the rest with what ever works well in this format. Sometimes the actual plot happens.
Series
- Part 1 of I Can't Belive It's Not Natural!
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Sam hasn’t been the same since his soul has left the cage. He’s exhausted, hallucinating, and in dire need of some peace and quiet.
Lucifer may have a bargain for him tonight.
Sam may be desperate enough to take him up on it.
Whumptember 2025 Day 4: “Keep your eyes open” | car ride to the hospital
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- Part 4 of Jasper’s SPN Whumptember 2025
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Live through this, and you won't look back by DrowningInRedInk
Fandoms: Supernatural (TV 2005)
30 Aug 2025
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Sam didn't have to feel so gangly and hulking and awkward, buried in his own broad shoulders. It was possible to slip out of his masculine costume and feel smooth, lithe and beautiful. He didn’t do it often, and he certainly never transformed completely—it was impossible to notice that a bra stuffed with gym socks didn't sit on his chest the same way as actual breasts—but for a few stolen hours at a time, Sam had felt whole.
But Sam didn’t own a bra anymore. It burned in the fire.
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Sam becomes caught in a type of longing his companions can’t fulfill. He visits Lyle to fill the gap.
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Jess wondered if her desire was as obvious as his – if he could see the sudden urge she had to push him against the nearest flat surface and mount him. For the first time in her life Jess lamented being born a woman, if only because it meant she wasn’t able to accurately imagine how it would feel to bend Sam over the bar and sink into him the way she craved.
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“And this girl just totally ditched me because I pressured her into seeing his little middle school production of Romeo and Juliet and she was so over it. But you were the best part of the whole play,” Dean giggled. He had taken to retelling stories of the girls he had dated for Sam’s entertainment.
“You know I’m kind of sad I never got to put on Shelly’s pretty dress.”
“Well me too. I bet you would’ve looked damn good in that dress, better than she did for sure.”
“Thanks, Dean.”
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5 things that are different now that Sammy is trans (+ one thing that is not)
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- Part 3 of Sammy the Telekinetic Trans Girl
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It’s Sam’s birthday and she is sparkling (literally)
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- Part 2 of Sammy the Telekinetic Trans Girl
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Maybe it was his hair, he’d been letting it grow subconsciously. He looked at the long strands of hair and felt something like awe. Maybe it was his clothes, thinking about it made him feel weird, “his clothes”, for the first time he was wearing something that hadn’t been passed down to him through his older brother.
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Sam discovers himself after going to college -
Through the Sleepless Night by SiriuslyThatBitch for whoremoantreatments
Fandoms: Supernatural (TV 2005)
13 Aug 2025
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When kisses turn to touches.
Series
- Part 2 of I Can't Decide If It's A Choice
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Nothing Safe is Worth the Drive by SiriuslyThatBitch for whoremoantreatments
Fandoms: Supernatural (TV 2005)
13 Aug 2025
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The only thing better than bonding with you brother, is bonding with daddy too.
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- Part 3 of I Can't Decide If It's A Choice