May I suggest that before going out completely en femme, try a trial run. As Jennifer suggested, what is in your head is important. If you are stressed about what will people think, take some baby steps. This weekend I went shoe shopping at various stores in the mall, wearing a light lip gloss. I took time to handle the shoes and tried to see if anyone was paying attention. They weren't. My confidence went up several notches. Now thinking about a professional transformation. If you are inexperienced in makeup as I am, I think professionals can teach you a lot about how to adjust your look to be less noticable as a man wearing women's clothes in public.
Just a couple thoughts from someone wanting to come out more.
Hugs all - good thread.