@liferadayjune day 20. Today I'm revealing my trans Jimmy head canon. I've read too much fanfiction of him being trans masc for me to not include it.
Please remember, this is about the character, not the actual Jimmy.

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@liferadayjune day 20. Today I'm revealing my trans Jimmy head canon. I've read too much fanfiction of him being trans masc for me to not include it.
Please remember, this is about the character, not the actual Jimmy.
the concept of lizzie helping her seabling try out fem clothes for the first time >>>>>>>>>
jack is an artist in training
inspired by this post
Everyone saying trans jimmy rights are actually the smartest people ON earth. Cas is trans and picks a trans vessel!!!! x
Hey I'm being mentally ill on main again but like I just really want some kind of reunion scene between Claire and Jimmy but Claire never knew Jimmy was trans and Claire was just starting to socially transition to being a girl when Cas took Jimmy the first time so they have like. These things that change each other's perception of the other but it only makes them closer.
oh your mind your mind, how i love you
Claire visits her dad in heaven
“Dad?” The word slips out of Claire’s mouth before she can think about it, the emotion of the moment overriding her common sense. It has to be Cas. She knows what Jack said, promised, but… it can’t be. Not really.
Jimmy turns around. “Claire-bear!”
He smiles wide and opens his arms, and Claire remembers this day. The waning afternoon sun, the barbeque seasoning covering his hands up to his wrists, the pork chops laying forgotten on the counter beside him in favor of greeting her. She takes halting steps to him, not trusting it completely. His grin is unwavering; he swipes a finger across her forehead and paints it orange with spice.
She had giggled, she remembers. That day, she had giggled and wrapped her arms around his middle and told him about her time at Sadie’s house. This time, she stands still and looks.
“Claire?”
Jimmy’s smile drops, just for a moment. “Hi, Dad.” She can see him realizing like he’s coming out of a dream, realizing that the girl standing in front of her is not his 8 year old. “Yeah, I’m… I’m not in your head.”
He looks around the kitchen, eyebrows furrowed. Claire looks around too, at the family home that seems like it’s from a lifetime ago, at the decorative plates that she sold on Ebay after her mom left, the favorite one she’d smashed to bits on a bad night. The pictures of the life that got ripped away from her. “Your mom’s making mac n cheese… with the pork chops,” he says quietly. “Sound good?”
Claire bites her lip. Jimmy keeps staring out the kitchen window. “Dad, look at me.” She reaches out and grabs his hand hard, crushing his knuckles under her grip. He looks at her.
“Claire, you’re-” He frowns, eyes flitting over her. She looks down self-consciously. Her ripped jeans and beaten up tank wouldn’t exactly have flown in her childhood home, let alone the tattoos climbing their way up her arm. Protective sigils and Kaia’s doodles, stick-and-pokes from Alex. And she does look a little… different from when he last saw her. Boobs, for one thing. A decade and HRT will do that for you.
“Yeah, I know. I grew up.” It comes out a little harsher than she’d intended. Jimmy flinches back out of her grasp, tearing up.
“You must hate me.”
She crosses her arms and swallows. “Yeah, I do.” She sighs. “You left me. When I was just a kid. When I had just told you-” that I was a girl. She clears her throat. “You walked out and demons waltzed right into our life. And mom- mom was just a shell. Her perfect husband? Gone. My perfect dad?” she wiped the seasoning off her forehead with a fist. “Gone. And I had to raise myself. I had to figure out how to survive… alone.” Jimmy hangs his head, tears slipping down his face. Claire steps closer and waits until he looks back up at her. “But you know what? I learned a lot. About me, about you…” She shakes her head. Cas had shown her the miniscule scars on his chest, barely visible after years of healing. Only visible because Cas let them be. “So yeah, I hate you. And I love you. And... I get it. I would’ve gone too far, too, to do the right thing.” She had a few times. “I would’ve sacrificed myself to save the people I love.” She had tried to, for months after Kaia…
Jimmy looks down at his feet.
“I forgive you. I forgive you for all of it. Everything.”
Her dad blinks. He looks at her. “Claire,” he pulls her close and hugs her and this time, she lets him. She lets herself sink into her dad’s arms and feel safe, because this time it isn’t a dream. This time his eyes won’t blink black and he won’t cough up blood and she won’t feel the burn of Castiel’s grace inside her. This time it’s actually her dad, even if she’s only visiting his slice of heaven, and he actually sees her. “My beautiful daughter. Claire, I’m so sorry.”
Claire pulls away sniffing. “Let’s skip over the mushy stuff while I’m here, ‘kay?” Jimmy nods gratefully. “Wanna play Uno?”
Jack had slipped her a pack of cards before she’d gone in, and she pulls them out now. Surprisingly, they’d been a good idea. Jimmy grins. “Yes. Yes, I do.”
“Cool. Then you can tell me why you never told your trans daughter that you were the one who gave birth to me.”
Jimmy’s laugh comes out tinged with tears, but they’re the giddy kind, the kind that can’t believe this is happening. They sit at the table and Claire deals. “Your mom didn’t want-”
Claire waves him off. “Yeah, yeah, fine. Amelia.” she snorts and looks up, and Jimmy’s wearing the same bittersweet expression. “You start.”
Jimmy takes a moment to look at his cards, but Claire knows he’s thinking of what to say. “You look good.” he finally decides. He lays a card down. “I never got to tell you after- when I came back…” Claire presses her lips together and stares at her own hand. “The long hair suits you.”
Claire runs a hand through her hair, swearing to herself she isn’t blushing. “Yeah, my girlfriend thinks so too.” she ventures, laying down a +4 card like a challenge. “Green.”
Jimmy’s expression is an indescribable mix of happy and proud. Claire has only seen it on his face a few times, ironically mostly with Cas’s subdued version. He takes four cards like it’s nothing. “Well, she has good taste.”
Claire’s mouth twists into a grin. “Yeah. I’m lucky to have her. Lucky to have everybody I’ve got.”
“I’m… I’m so glad, Claire.”
His voice has turned strained. She squints at him. “That includes you, dumba-” He raises an eyebrow and she stops. “Dad.”
Jimmy reaches across and grabs her hand. “Claire-”
“I’ve kinda got an in with God now, so, you’re probably gonna be playing Uno a lot more,” she says casually, taking her hand away so she can keep playing. She doesn’t look up at him.
“I like Uno.”
“Good.” She lays down another +4. “Yellow.”
Super cute transnatural fic for y’all!
Shelter by howevernot
Cas wonders, Is he a man? He's never really considered his gender before. He's been comfortable in this vessel, comfortable with the way humans respond to him while in this vessel. Mostly. The way the men in the shower responded to him, the new awareness of his own otherness, even now away from them, settles in his stomach like lead. What is he? He’s human now, but he lacks the context to understand what that means. He is in a man’s body, a body that Jimmy worked hard to make comfortable, but does that mean he too is a man?
"I-- Yes, I am a man."
OR
After being turned out by Dean, Cas goes to Rexford and finds friends in the local trans community.
Wait wait shit can’t believe in all my thoughts about how transable Jimmy‘s gender is I didn’t think of connecting it to his everything around romance!
Transfeminine Jimmy whose reactions to Thomas, Ivy, Thomas, and Anstruther are ALL tied up in this Thing she doesn‘t consciously understand or even consciously process most of the time around her body and role. She liked Thomas looking at her in the livery closet because it was like a man looking at woman but she doesn’t know that. She oscillates between spite and hey-look-at-me-give-me-your-attention with Ivy and Daisy (Ivy more because Ivy gives her more attention which is wonderful and awful), she’s going to beat Alfred at being a man and finally get rid of this screaming thing in her chest that must be hatred of the feeling of Failing At Manhood (and oh how she does hate Failing At Manhood but even when she ought to be experiencing success the thing just screams in a slightly different pitch), she’s so damn scared after the kiss when everyone is going to think things about her (they’re going to See things they’re going to Know things even though there’s nothing to see or know - unless maybe there is there’s the sickening way it felt good for a heartbeat before it was awful - but she’d never ever show it or act on it she doesn’t - it‘s safe it’s fine it doesn’t even count that’s how secret it is - but they’re just going to Know - something. they’re going to Know), the bubbly pleasure at sending Lady Anstruther valentines from a distance and the dull nauseous horror that starts quietly in her chest when she suggests they meet up and then takes over her whole body when she shows up in person, the frustrated anger with Ivy when Ivy gets angry with her for doing what a man does what a man’s supposed to do, the way she feels in this moment:
there’s a lot here, is what I’m saying
Been thinking about the hc of jimmy being a trans girl, and i think that when she comes out as jenny (i think maybe in freshman year) all the cul de sac kids support her, and whenever someone doesnt respect her they all gang up to kick their asses. Sarah obvs charges on first
Also, as jenny starts her transition, edd starts getting interested in lgbt+ matters, and thats when he starts to question his gender, probably in later years of highschool. He wants to experiment with his presentation and pronouns, but gets super nervous about looking ridiculous, and is still self conscious about the time the kids laughed at him for having a girly middle name. Jenny then realizes edd is going through a tough time and talks to him, which helps him a lot to ease his anxiety and also find out he is nonbinary.
Idk, i just like the idea of jenny supporting edd in gender stuff bc its complicated and jenny wishes to be there for edd bc she knows how hard it is to be so confused without someone to help you ;v;;;;;;;