Relationships: Sam Winchester/Ruby (romantic), Sam Winchester/Jessica Moore (romantic)
Characters: Sam Winchester
Tags: Queer Themes, Genderqueer Character, Trans Character, Character Study (of a sort), Identity, Canon-Compliant
Summary: Sometimes she feels like she’s in drag, an elaborate performance, layers and layers. A girl dolled up as a boy dressed up as a girl disguised as a boy, and on and on.
Originally posted on the Archive of Our Own on February 5th, 2021. Complete.
“You’re so pretty, Sam,” Jess muses, running her fingers through Sam’s hair. “You’re not like any of the other boys I’ve dated. It’s funny, y’know—sometimes I forget you’re a boy.”
“Mm?” Sam mumbles, half asleep.
“Yeah,” Jess continues. “‘S’like having a girl best friend, but you can kiss and stuff.”
“And stuff. Gee, thanks.”
“Shh. Go to sleep.”
A few minutes later, as Sam’s nodding off, Jess starts laughing to herself. “I’m a LUG, except I have a boyfriend,” she says. She laughs like it’s the funniest thing in the world.
Sam is eleven years old when Dad drives to Nevada for a case. A drag queen was murdered in her locked dressing room, after everyone had left the club for the night. No suspects, no one shows up on the video footage. Dad and Dean think it’s probably a ghost.
In the motel, Sam plods through his math workbook, lying on one of the twin beds, and Dean scribbles in a sketchbook on the couch across the room.
“Dean?” Sam asks. He twiddles his pencil.
Dean grunts in response.
“What’s a drag queen?”
Dean flips over on the couch so he’s lying on his back and sighs. “Guy who dresses up like a lady.”
Sam squints at him. “Why would someone do that?”
“I dunno, man. Gets off on it, or somethin’.”
Sam considers this. He flips to the next page in his workbook. When Dad comes home from the hunt, he’s tired and bruised, and he spits blood into the motel sink and says, “All that, and for what? Those kind of folk are more trouble avenging than they’re worth.”
Sam joins a mythology role-playing server when he’s in highschool. It’s relatively anonymous, and under a screen name he gains minor popularity. He’s good with the legends.
The June after Sam’s sophomore year, Dad finds a case that ends up lasting the whole summer, and Sam’s stuck at the library for hours each day, doing research and calling back and forth with Dean to relay the details. He doesn’t have any time to log into the forums. The case finally is wrapped up by September, and Sam’s left at home while Dad stays with Dean at the hospital, who’s laid up with a broken ankle after being tossed around by the vengeful spirit. Sam pulls out John’s clunky laptop and scrubs at his eyes, logs into the site and scrolls idly through the forum threads.
He stumbles upon a thread, only a page long, listing available characters for this September’s rounds of role-playing. Tiresias, one of the lines reads. Seer, blinded for offending the goddess Minerva . Had his sex changed as a punishment from Hera  and became a woman for seven years. OPEN for claim.
Sam swallows. He glances, reflexively, at the motel room door. Hesitates.
He opens a new tab and types “Tiresias” into the browser.
A few hours later, John and Dean return, the latter doped up on painkillers. “What’ve you been doing on that computer this whole time, watching porn?” John says with a chuckle, and swats Sam lightly on the head.
Sam shoves the laptop into his backpack. He cleared the search history.
This is what is in Sam’s journal:
The Dewey Decimal classification for Delaney’s Dictionary of Saints, so he can find it in the library in whatever town they’re staying in, without having to ask the librarian every time.
A taped-in postcard of Joan of Arc he got from a museum, corners smoothed down.
A photograph of the mother he doesn’t remember.
“Joan… oh, fuck,” Ruby whispers into Sam’s ear as they press down into each other. The first time she said it during sex, he pushed her away, startled, and asked, “What the hell?”
“Oh, you know,” Ruby had said, smile widening. “I think you like it, don’t you.”
Sam’s used to it now, used to the feeling of his heart clenching when she murmurs the name. It’s terrifying, exhilarating, like getting too close to lightning when it strikes and smelling ozone.
That’s just what life is like with Ruby, though. Teetering on the edge.
Ruby plays with his hair as they lie on the bed, after, sweaty and breathless. “I like you, Joan,” she says, head against Sam’s chest.
“Don’t call me that,” Sam says. It’s different when they’re not in the heat of the moment. When she does it like this, for a second, he can almost believe she means it.
“Oh, cut the bullshit,” Ruby snaps, and Sam feels the mood change like a finger snap. “I know everything about you, Sam Winchester. I can recite your secrets the same as you can chant your exorcisms.”
“C’mon, Ruby,” Sam says, placatingly, but only because he needs her around.
“Playing nice, I see,” Ruby says, and smirks. They lock eyes. Sam’s anxiety rises.
“Don’t tell Dean,” he breathes, chest tightening. She feels heavy, leaning against him. He resists the urge to push her away.
Ruby grins. “Don’t tell Dean what?”
There’s something funny about the fact that the only people who have ever called Sam “she,” are the same ones who tell her that her destiny is to become the Girl Queen of Hell. Demons. Not people.
Dean and Sam hunt demons who press Sam up against walls and bite on her neck, shove their tongues down her throat.
There's a joke in there, somewhere, Sam's sure of it.
“Samuel,” the angel says, contemplative. “It means Name of God. In Enochian, that would be G-DO IAD.”
“Don’t call me that,” Sam snaps.
“Samuel, Samantha,” Lucifer crows inside Sam’s head. Sam left the cage, spent a year out of it, but it’s like he hasn’t been gone a day. “Like Victor, Victoria. I like you better, though, then that pretty Julie Andrews. You’re more fun.”
Sam can’t answer. He’s frozen, locked inside his own mind. All he can do is stare at his bare wrists under the fluorescent light of the hospital room.
“Would you like me to call you Samantha, Sam?” the Prince of Hell asks sweetly.
“These trials, they’re purifying me,” Sam pleads. He has major burns and corrosive damage covering several internal organs, but he doesn’t know that.
Anyway, it’s not important. It’s trials are like drinking bleach. He’s never felt cleaner.
He’s lying in bed on his back, tossing a tennis ball up at the ceiling and catching it right before it hits his face. Thunk. Thunk.
“Did you mean it, what you said?” he calls to Jess, who’s brushing out her hair in the bathroom.
“Hm?” she hums. “Did I mean what?”
Sam, mortifyingly, feels himself start to blush. “Coupla days ago. When you said I was like a girl. And it made you a lesbian.”
She turns to face him, illuminated from behind in the doorway. He can’t see her face, but her hair shines white where the light hits it.
“Sure I meant it. Wasn’t drunk, was I?”
“No,” Sam says, tossing the ball again, “but you were tired, so.”
“Did I hurt your feelings?” she asks, with genuine concern, and goes to sit next to him on the bed.
He laughs, absurdly. “No. No, of course not. Just… seemed like a weird thing to say, is all.”
“Good weird, or bad weird?” She looks at him, contemplative.
Sam is caught. He hasn’t thought about this in what feels like a long, long time. But this is Jess.
“Good weird,” he hears himself say, “I think.”
She smiles. “Good weird, that works. And anyway, whoever says boys can’t be lesbians? I think the concept’s outdated, if you ask me.” She tucks her chin and lies down beside him on the bed, curling up under his arm.
He squeezes her shoulder and laughs. “You’ve got a very interesting view of these things.”
Jess gets up to turn off the light, tiptoes back to bed. They lie together in the dark.
“What do you think about lipstick?” she asks, and Sam pulls her closer, not answering, just listening. “I could give you a makeover. Huh? Thoughts?”
It’s exactly one week before the fire.