hi 88,

i tried to post something yesterday, but then i thought i don't really know much about this issue anyway, and hoped someone else would come along with their insight instead. but i do want you to feel like someone has read your post at least, so i'm going to try and reply, but forgive me if i'm completely off the mark, ok?

it sounds like there are a few issues at play:
1) you have issues with your own gender. it's ok, sometime i fall into this too. but i think there are many aspects of being a female which are great also, which men don't get. i guess being a mother is meant to be one of them (i'm not a mum, and i'm kind of scared to be one, but i've heard lots of women say that this is the best aspect of their womanhood). but there are other things that i appreciate. i find a lot of guys are more willing to look out for me than they are to look out for their chums. i kind of feel protected that way. i like how i'm allowed to be interested in fashion, and also how i'm allowed to be emotionally expressive, when guys are typically expected to bottle it up. i'm not saying all aspects are great (and yes, i do think there is a fair amount of discrimination out there still), but it sounds to me a bit like your issues go a bit deeper than that? forgive me if i'm wrong. but if you agree, then maybe it's something you could talk over with someone you trust (your boyfriend, a parent, a therapist, whomever).
2) it sounds like you have expectations on what being a girl means, and you are projecting this onto your boyfriend. i was in a same-sex relationship for 5 years, and believe me, not every girl on the scene is "girly", and no - not every girl there wanted to be a guy. so if your boyfriend did go ahead with this transition, he would definitely find a group of girls he would fit in well with.
3) i can't really tell from your post if this transitioning is something your boyfriend really wants to do, or if right now he's just expressing his desire to be a woman. some people are that uncomfortable in their own bodies that they want to change genders, whereas some ppl are sad they are not the opposite gender but eventually grieve it and learn to accept the body/gender they were born with. because i was on the queer scene for a while, i met a lot of guys who dressed in drag and adored that opportunity to buy into the female splendour. hell, the inspired me to pick up my act!! and i'm a very very girly girl. but it was something they could radiate and bask in, if only for the night/weekend, and it was enough for them, and they could do it in a safe space where everyone was accepting. i guess that is something your boyfriend could try if he wanted?

i dont know if any of this is 'advice' as such... i'm sorry if it's not what you are looking for... i guess it's very hard for me to tell, because i dont know what your boyfriend wants, and also (importantly) what this would mean for you. i hppe you are able to find what you want somehow, though. good luck!