I think your perspective is just one end of the spectrum. For me, it isn't just about wearing clothes. When I am in "Jen" mode, I want to project the entire female persona. I don't want stares and I don't want to put other out as a result of my decision. I have no gender issues at all. I am male. I like being male. When I am dressed I do not think of myself as a woman. I am a man who happens to enjoy looking like a woman from time to time.
