In this day and age, it is becoming more acceptable for men to express the feminine side of themselves – I want to to.
I have dresses as a woman in public a few times, and in private several times.
How I did it: I started wearing women's undergarments, so as not to be noticed. As I got bolder, I wore more complete outfits to places I wouldn't normally go (a different mall, for example). Hanging around places that are more acceptable to gays, lesbians, cross-dressers is a help - I'd fit right in.
In this day and age, it is becoming more acceptable for men to express the feminine side of themselves – I want to to.
I have dresses as a woman in public a few times, and in private several times.