As many of you know, I dress virtually full time. The reason I say "virtually" is, when I started dressing full time, I told my wife that I would dress male anytime she wanted or needed it. All she had to do was ask. That arrangement has worked well for 5 years. The times when she wants me male are generally...
1. When we're going to be with family
2. When we're going somewhere romantic, where kissing and hand-holding in public would be fun
3. When she's really upset
It's usually not hard to tell the reason she wants me male.
And I'm usually happy to oblige. Sometimes not so happy when it comes to family. We have a rocky relationship with her family. At one point, she told her sister about my CDing and sis has been trying to use it against me periodically since. It doesn't do her much good, but all the family knows about it now. Her father doesn't like it, but as long as I don't dress around him, he knows there is nothing he can do. What he doesn't know is that my wife's eldest brother also crossdresses! Brother surprised us with that one day--that was a complete surprise to both of us.