I noticed that I gave some (hopefully) encouraging responses, but haven’t replied to the question as posted:
My biggest fear, going out en femme, is that no-one will talk to me and I will spend my entire outing alone.
I love talking with people, which is the polar opposite of my male side, who lacks self confidence in a very big way – although much less so, having had multiple opportunities to express the feminine side.
CDing “in public” has been a total revelation to me – like looking at my self in a mirror, and finding that, although there are dark, horrible bits, there’s a lot of light too – and, while en femme, I am at total liberty to express and be that lighter side, even if only for a day or 2.
It is quite literally liberating – a kind of unshackling.
But it does take some validation from others – and I find it hard to shake off the almost uncertainty that no-one wants to even look at a 6′ 4″ guy in a dress.
Luckily, every outing has provided dozens of people who want to congratulate me and make me feel good about myself.
I just love people!!!