Personally, I think clothes are just an expression: how you act is more important. I couldn't go out wearing any women's clothing while I look the way I do, would need loads of make up. However, I can move, sit, stand or lay like a woman just as well as any one else. Then again, there aren't really any rules as to how people should act or dress. At the end of the day, it's all about how society views different genders. Do what feels natural. Don't subscribe to societies "standards".