@Makaila, sounds like you're either a former gang member, or an operator. If it's the later, thank you for your service.
@lorileah, I understand the reason to go all Stonewall, but like others have said, you have to respect others' situations and circumstances.
I think that there's the assumption that we are all crazed CDers who constantly "go out" or are scheming on how to "go out." I can't speak for anybody else, but I don't really care much about "going out."
I usually wear girl panties under the guy clothes, and dress up fully maybe a dozen days a year, maybe. Seven of them will come starting this week. I'll take a few vacation days, hit the salon, play dress up around the house, get my jollies (alone and with my wife), and will find I'll get bored with it after five or six days. It's a good thing my desire to dress is fairly low, as it gels with my wife's wishes regarding "going out" (she's generally opposed to it). But, for Halloween this year, she's kind of pushing me to go all out en femme. I might, but there's a cool guy costume I'd be happy to wear as well.
So, to answer the original question, Why Not? Maybe because I don't really care all that much to.