An interesting question, and one that I've been reconsidering recently. In my current home situation, I'm pretty cautious for various reasons. I don't want to deal with the unknown reactions of neighbors and coworkers in an area with predominantly very conservative (and judgmental) attitudes. I don't want my son to have to deal with this at his age since he has plenty of issues to address anyway, and any public knowledge could easily widen the circle to include him.
But we're now seriously considering a move to a new job in a new state, one with much more liberal attitudes, hundreds of miles from my son. Perhaps in such an environment I could be more open about my crossdressing. Perhaps. Definitely need to explore this possibility with my wife. Thanks for the food for thought.
Miriam