[TLDR on most of the thread]

I think that desire to be "like a woman" in a lot of CDers is a desire to pass as a woman. If you can create an image that says "WOMAN" or at least "woman" rather than "woman? man?" or "MAN" then you have a good chance of blending in. Most CDers know that going out in skirts and dark hose and done up to the nines to do grocery shopping does not = blending, but most CDers have to deal with having limited time to present this side of themselves.