Quote Originally Posted by RachelB. View Post
I have done the Halloween dress up. My lovely wife and I came up with the story that she did my make up, clothes were rented and she made me practice in the heels for the last couple of weeks. You could also say the clothes and heels came from goodwill, even the wig. Your SO or a female friend did your make up. Be sure to complain about the heels and exclaim that you don't know why women wear them.
You can't say anything to anyone who doesn't ask. Most people will just make a mental observation of how well you pull off the "woman" thing and decide that this is not your first time dressing as a woman.

I have been on the other side of this as the observer.