For those of you who are working now, it doesn't matter. Just cross dress and show up for work
Crash's cross-dressing experience:
My dad teaches theatre at the university where I grew up, so he leads student summer tours of London, England. Sometimes the family gets to go. I was a freshman in college at the time, home for the summer, so I went along.
As part of the tour we stopped at the Theatre Museum (it's near Covent Garden) for a demonstration of period costuming. They asked for volunteers to put on a costume, and I volunteered.
I should have thought that something was funny when the other volunteers were all women and my parents were looking at me funny. By the time I realized that they were looking for volunteers to put a dress on, it was too late to back out.
Anyway, I did it. I immediately rationalized it by pointing out that a man dressed as a woman was totally authentic to the Shakespearian theatre.
The moral of this story, however, is that one's first cross-dressing experience should not happen in front of your parents.