I was in pretty similar situation - no friends or allies, no idea where to go and what to do. It helped to take small steps instead of plunging into it without any idea about consequences. So, I kept switching and adjusting various items of clothing till I reached very androgynous mode - where I did spend a lot of time actually. At some point of time, combined with effects from the HRT, it became obvious that next step should be taken, besides all those around have grown so much accustomed into my new, yet very gradual presentation that nobody said a thing when I showed up dressed in female outfit to my office. Granted, I never went full-time officially and I still dont wear makeup, but I can dress the way I like (well, if I dress like male, then I start getting stares...) and walk in the public with confidence.
Maybe this gradual approach would work for You too?