dove the idiot

Dean has a complicated relationship with femininity since she never got to do traditionally girly things as a kid; overall, she tends to be pretty masculine or androgynous. She never got to play with Barbies or dress up or put on make up — her “toy” was a rifle, her outfit only ever consisted of the same dirty boots and tattered flannels, and she never learned how to doll herself up. Sometimes she picks up those magazines with the pretty models on the cover and tries to imagine her face on their body; she mostly just ends up feeling weird and guilty over it, like even imagining something like that for herself is wrong. 

Dean’s only real agency is over her hair. John never knew what to do with it — it was always so long and silky, even when the Winchesters spent days on the road without a proper wash. Dean had to take it upon herself to learn how to braid her own hair, how to keep it out of the way on hunts; her hair is her pride and joy. (It also makes her look so much like Mary that John can’t stomach it sometimes.) She probably has to cut it at some point when it gets caught or grabbed on a mission; she cries about it alone in a corner somewhere after John chops it off. 

Dean doesn’t get to play around with traditional femininity until she’s an adult. John starts sending her out for hunts on her own, and she soars with that little bit of freedom; she buys a dress and goes out to a bar alone (with a fake ID, of course), and her first time putting on make up is when one of the drunk girls in the bathroom says she would look so pretty with a little mascara and some lipstick. Ironically, this is also the first time she comes to terms with the fact that she is most definitely not straight — she loves the attention too much to be heterosexual. 

She never officially comes out to her father. John is at the halfway point between knowing his daughter is different and being willfully ignorant of the truth — so long as she stays loyal to her family and does her job like a good little soldier, John doesn’t dare to question it, and Dean never brings it up. 

She meets you on a hunt — you’re being tormented by a particularly nasty spirit, and it’s up to Dean and her father to save you. John is none the wiser when he sees his daughter hanging out with you. It makes sense, really — you’re about the same age, and Dean is a social butterfly. She gets you out of your head, reassuring you that everything will be alright, to stick beside her in case anything goes wrong. Who are you to deny a strong, beautiful woman with arms like that? 

By this point, Dean has been with a handful of people — men, women, and everything in between — but you’re of the odd few that she hated to part with. Cassie was Dean’s first love (and her first real girlfriend), but where Cassie couldn’t bear to lead a life with a hunter, you’re more than eager to ditch everything should Dean say the word. It scares her, your loyalty. She gently turns you down — as gently as she can, anyway. Leaving you breaks her heart and yours. 

You meet again years later when Dean returns with Sam to your town. Another spirit, another case to solve — and you just so happen to be right in the middle of things again. This time, you’re hunting, too — after Dean left, you picked it up in hopes of finding her. You never did get to see her again, but you found out you weren’t half bad at hunting given all the ghostly shit you went through in the past. Dean is impressed, and a little shy to admit that she missed you. 

When Sam heads to the library to do some research, it leaves you alone with Dean. She’s antsy without her sister to act as a buffer between you two, and you notice; you tease her for it. She laughs a bit. Unfortunately, you never quite got over her, but soon enough, she makes it clear that she didn’t get over you either. 

Dean takes you to bed, and after more pillow talk than she usually offers her bedmates, she asks you to stick around for a while. “Just until we find out what’s wrong with Sammy,” she insists, even though it’s more than that. As if you’d ever let her slip away from you again. 

SAM WINCHESTER:

Sam has always looked up to her big sister. She stuck by Dean since birth, always clinging to her more than their father. Sam just thinks she’s so cool and pretty in a way that Sam could never be. She’s especially jealous of her sister’s hair, which leads to Sam always growing it out. The most she can manage is getting it down to her shoulders before John winds up making a comment about how “His hair is getting too long” and “He’s starting to look like a girl.” Sam doesn’t mind looking like a girl, though — but of course, she doesn’t realize what that means until much later in life. Instead, she sniffles when her dad chops her hair away while Dean tries to reassure her little brother that it’ll grow back soon enough. 

Sam loves the toy section at the store. Even though John only ever takes his kids out to the store strictly for essentials, Sam always manages to convince her big sister to let her look around. Dean groans, but she caves easily — she makes up some excuse to their dad about getting herself some tampons only to drag her little sibling to the toys. Sam doesn’t care for the monster trucks and nerf guns, though — she gravitates to the pretty Barbie dolls and the ponies. Since Dean never got to indulge in many toys as a kid, she makes a point to buy something for Sam — when Sam wants a Barbie, Dean doesn’t bat an eye. 

Even though Dean is far from girly herself, Sam likes to borrow her clothes. She’s always delighted to get her hand-me-downs. She likes to play with her sister’s hair, too, practicing how to braid — which becomes a necessity after a mission in which Dean breaks her arm. Sam is all too happy to step up for her sister; and when Sam grows her hair out, she begs Dean to braid hers in return. 

Sam doesn’t like how much she starts to look like her father as she gets older. It isn’t until she’s in college that she starts to realize why she’s so different. When she first starts dating Jess, Sam is still guy-Sam, still waiting to hatch out of her shell. Jess is the one to point out that Sam is different from other guys she’s dated — Sam’s just not manly in a traditional sense. Sam gets along better with other women, fits into their circles and conversations and understands them in a way that a typical guy wouldn’t get. It takes a few conversations about this before Jess finally asks: “Do you think you might be a girl?”

Jess is cool about it — she doesn’t leave Sam, doesn’t treat her any different than she ever has. Jess is his first love, the first person to see her for who she really is and not be afraid of it or avoid the topic like the plague. Sam starts to transition, but of course, she doesn’t tell Dean or John about it — partly because she doesn’t want anything to do with being a hunter, but also because she’s not sure how they’d react. 

When Dean eventually reappears in Sam’s life, they don’t mention the obvious right off the bat. It isn’t until an anxious car ride later that Sam finally asks why Dean hasn’t said anything at all about her appearance — years of estrogen shaping her to look so much like their mother — and Dean just sighs: “We’ve always kept an eye on you, Sammy.” 

You’re a hunter. When Sam and Dean need some extra help on a case, they call on you (courtesy of their father’s contacts via his journal) to help them. Dean notices right away that you and Sam get along well — a little too well. Dean teases her sister every time they’re alone, wearing that stupid smug grin and elbowing her every time your eyes linger for a second too long. Sam is hesitant to start anything; she’s still mourning Jess, still haunted by nightmares of her when she tries to sleep at night. The visions aren’t helping, either — how could she possibly be with someone when she’s halfway to getting locked up in a psych ward forever? 

Despite all her insecurities, you’re patient. You wind up sticking with Sam and Dean for longer than anticipated; you round out the sisters, temper them when emotions get too high, butt in when they fight over something stupid. And, of course, you’re always there to offer Sam a shoulder to cry on when she’s suffering from her powers or the weight of the world. 

When Sam finally manages to make a move on you, she’s a bundle of nerves, hands shaking as she cups your face to kiss you goodnight after a diner date. For once, she has a good night’s sleep knowing you’ll still be there in the morning.