I think the passive / submissive crossdresser being "forced" into femininity is sort of a very male thing, it only works if you find femininity demeaning rather than glorious. I hope I haven't offended anyone with that statement, but it's where I've gotten to in transition.
but if it floats your boat make sure you find a cute little sailor outfit to wear http://www.pinuppassion.com/images/pinupg8.jpg