First of all let me just say this is a FIERCE topic and one of the few on the Motherboards that left me so amazed I was stumped for an answer. Maybe that's why it's taken me so long to join it. I encourage everyone to be proud and be the best you can be in your chosen self-expression. OWN IT.
I guess all I can contribute is my own perspective and experience for what it's worth. As a gender bender/androgyne, I walk through a strange middle country somewhere between the gay archetypes of circuit boy and drag queen. This has had ramifications for me in both my professional life as a performer and my personal life.
On the professional side I've found resistance at times from the drag community as many people don't see what I do as "drag" – they just see a boy with make-up on. And it's true my image is much more boy than girl, more Duran Duran than RuPaul. And that's intentional. But as a result and despite the fact that I'm just as talented as most others on the club scene, I've often had to plead/beg/cajole/fight to get on stages where other full drag artists would get a booking on the spot simply by virtue of wearing wigs and gowns. Then once I'm on the stage – particularly in Chelsea venues -- I'm frequently greeted with blank stares of non-recognition because I'm not the typical Judy lip synching drag queen they're accustomed to. Not that I'm complaining: as a professional I've accepted these things as simply another due to pay and part of the business. As a performer androgyny is what I've chosen to give and it's what I want to express most on stage, and so I'm resigned to dealing with whatever comes along with that decision. I also take pride in being unusual and a gender rebel. There's a kind of "fuck you" punk sensibility about it that I enjoy on some level.
What's more difficult to figure out is the personal side – that is, when it comes time to get laid or meet boys. Many gay men instantly dismiss me as a potential romantic or sexual partner when they see me in make-up, rushing to call me "girl" and giving me the non-sexual air kiss (i.e. the brush-off) and saving their french kisses for some normal boy. (this in itself creates conflict within me ... part of me doesn't want my make-up messed up, the other part of me wants the tongue down my throat! Hence my preference of late for clear lip gloss) My look is drag queen-ish enough to turn off those men who want traditional masculinity in their partners and have no sexual interest in anything remotely tranny. I see boys in windbreakers and jeans cruising each other and I know I'm kind of outside of that. But at the same time, since I'm not doing full drag and therefore not presenting the illusion of womanhood, I don't get tranny chasers either. This leaves me in a weird pergatory path that is difficult to navigate at times. Of course there are exceptions and I do get laid and meet boys. So much of it is in your attitude and self-confidence and when I'm in make-up I feel like a star. It's also been my experience that when I do snag boys when I'm in make-up, said boys tend to have more open-minded/sophisticated tastes, and that gives me great satisfaction. Also as time goes on the younger generations have fewer and fewer hang-ups and less gender-specific preconceptions, and I've benefited from that and certainly exploited it. And the more I walk this strange gender blurred line the more comfortable I become ... so it only gets better. But it's a learning curve.