Well, I've been dressing and going out, for over a year now, and I really have not been bothered about the way I look. Do I think I'm passable? NO!
But I enjoy my life and people who knew me as a guy, show genuine respect and acceptence of my fem persona.
Is it fun? YES! But it's really more about me being comfy with myself.
Naughty? Hmm, if I were in my twenties, maybe, but for now, I enjoy dressing in a manor that is acceptable for the general public.