For goodness sake! Stop trying to figure this out. You can't. Trying to figure out the "why" of something is a typical guy thing. That's why guys are so good at fixing things. Figure it out. Then fix it. But crossdressing doesn't have to be "figured out". In fact, I think that's a distraction.
Crossdressing just has to be enjoyed. Add a little femininity to the mix. Smile. Laugh. Come on, it's fun, isn't it? If it isn't fun, then why bother? And why worry at all about the whys?
Stephie
