TRANS GENDER!!!!  
 
anyways. I have hcd fluttershy as trans for a while now and have accumulated some headcannons about her and what she was like as a teen so here they are : ) if youre transfem and any of this is Bad please tell me.  
 
as a high schooler fluttershy was pretty heavily bullied, but not for being trans. trans ponies are pretty accepted in equestria and her parents supported her from the start. she was unable to go on HRT due to her family’s financials so she transitioned socially first and didnt get any hrt or affirming care until she met twilight. ANYWAYS, she was bullied for being clearly autistic, unathletic, and relatively poor compared to her peers. rainbow dash was pretty much her only friend for most of her youth, and they had one of those very intense homoerotic girl friendships. them getting together was clearly endgame to everypony but them. i put her in an oversized graphic tee and skirt because i can imagine her being interested in dressing feminine, but not having the confidence to go any further than this. i also made her hair hang limp in front of her face since i can see her not having the skills or means to take care of her long hair when she first grew it out.  
 
respectable young adult!!! here is a more put together and happy fluttershy. After meeting twilight she came into a bit of money and was able to get started on hrt, and also buy cuter clothes that she liked. With rarity’s help and guidance, eventually fluttershy learns how to take care of her hair and it is much healthier and more full now. by the end of the show, fluttershy is also regularly hanging out with tree hugger and smoking weed. it helps her a lot with her anxiety which was hard for her to admit.  
 
and at last we reach proper adulthood. without all of the problems she dealt with as a younger pony (low income, bullying, getting hrt), her anxiety eased up significantly. she still is a nervous and kinda frail person, but the really bad days are less frequent and less severe. a benefit of her lessened anxiety was lessened dysphoria, since she was less worried about being judged, she was able to explore her sense of style and has nestled comfortably into her more outdoorsy and comfortable wardrobe. the ultimate benefit of her lessened anxiety and stress was weight gain. with access to all the affirming care she needed in her transition, namely hormones, she was able to fill out quite nicely into a more curvaceous figure, something she always wanted. fluttershy is happier now than she has ever been before! : )