So I've been dressing on and off for the past few years and have never been out in public. A few people know that I dress and two of which have suggested I go out on the town en femme. The idea is intriguing but I'm apprehensive to agree for a few reasons. First being the fear of being recognized and social stigmas, the second being I don't really fit into the lgbta community as I consider myself a heterosexual male.
I suppose what I'm really asking is if it's better to dive head first into the scene with support or to do something on the down-low on my own? What all have you done for your first time out?