Agender Cas (and their SO Dean) headcanons
they’ve been going to the same school since Kindergarten but were never really that close. Sure they’ve been to each other’s birthday parties but they weren’t best friends material. Then in the 7th grade Cas comes to school in a skirt and well that’s the biggest event that happens all year. They try to tell people that they’re agender and they’re not a boy or a girl but well 12 year old can be assholes. Dean doesn’t like how the kids are treating Cas though. By the time he gets home he’s pretty upset about the whole thing and after a long talk with his mom they make a trip to Target and Dean’s got a game plan and some new clothes. The next day at school Cas is looking miserable and is back to wearing “boy” clothes but Dean... Dean has a sparkly pink and grey flannel on over his Hello Kitty shirt. People try to give him shit but they’re not going to start anything since Dean is one of the biggest kids in the class and he punched out Alistair in the 4th grade because he was picking on Jo. Dean tells the other kids that “clothes are just clothes. Nobody should tease Cas for what they want to wear it is their choice and they look really cute in that skirt!”
in college Dean makes an ignorant comment about pink being a girly colour and this does not go over well with Cas (Yes Dean realises he was being a dick and apologises profusely but Cas is still ticked because Dean definitely knew better). So when Dean asks them to pick him up a new toothbrush the following day Cas buys Dean a pink one. And Cas continues to buy Dean nothing but pink toothbrushes (and razors) out of spite for the next 3 years. They eventually feel Dean has learned his lesson and buy Dean a really nice green one. The next morning Dean wakes them up because he can’t find a pink toothbrush and he is late for work and he just can’t go to work without brushing his teeth! When Cas tells him that he has a green toothbrush this time he looks so crestfallen that Cas has to go out and buy him a new pink one later in the day.
Their most serious fight is Dean’s fault. They’re out drinking and Dean blurts out that he thinks Cas’ outfits are terrible. He tries to take ti back immediately but the damage is done; Cas is upset and Dean winds up sleeping on Benny’s couch since he’s too ashamed to go home. When he does come home the two of them sit down and Dean explains that he loves Cas’ clothes and their eclectic tastes and how they will wear anything (though he really hates that fuzzy yellow cat sweater but they’ll talk about that later). And what he meant was that Cas can’t match for shit. The colours clash and oh my god they can’t mix patterns like that. With a sigh Cas admits that they are a little overwhelmed by trying to match so they just kind of wear the first two things they grab more often than not. So they compromise. Cas will pick out a skirt or top they want to wear and Dean will help them build an outfit around it. Dean won’t ever admit it aloud but he almost has more fun dressing Cas up than he does undressing them.
For their trip to Hawaii Cas wants to bring a bikini. There are an endless number of cute tops and Dean has to limit Cas to like 3 (”jeeze we’re only going to be there like a week, how many swimsuits do you need? Aren’t you bringing like 3 pairs of trunks too?”). But the bottoms pose a problem. A lot of the fun ones pose a problem for tucking and its really bumming Cas out. They really wanted the cute blue ones with the pink flowers. But it seems they’re doomed to choose between black, black, black, navy blue, black, or (surprise) black. Dean of course spends a lot of late nights trying to find a solution and he does in the form of a sarong. The one that dean surprises Cas with is a royal blue with yellow/gold dragons on it and Cas is THRILLED. And since Dean is such a big sap he totally lets Cas buy like 6 more of the damn things because the way their face lights up just makes Dean’s heart melt.
When Dean and Cas go to see their first metal show it’s in an intense heat wave. There’s no way it should be this hot in May but it is. And being in the crowded venue with 100s of other metalheads moshing out to Amon Amarth is going to be hell. So Cas decides they’re going to wear their cute skull skirt. Dean’s honestly kind of jealous because the thought of wearing jeans is already making him want to die. They get a few odd looks when they are standing outside the venue waiting to get in (to be fair most people in line are getting weird looks from passers by) but thank god nobody decides to be a dick. That is until they’re standing in line to get water after the opener has finished playing. Some huge burly guy (like seriously he might be taller than Sam even) with a huge beard and sleeves on both arms comes up and says “Uhh hey, I don’t mean for this to come out rude or anything but.... wheredidyougethatskirtitisreallycute...” It takes them a moment to process what the guy said but then Cas smiles and explains how their sister in law is a seamstress and gives the guy her card. He thanks Cas profusely and disappears into the crowd. They think that’s the last of mystery guy but two weeks later Sam phones to say that some huge hairy dude came in to his wife’s shop and special ordered a dress for himself and left a silver pendant of Mjolnir for Cas.
(feel free to add your own cute agender!Cas/Dean headcanons!)
