Personally I've never played a character of the opposite sex, for the simple reason that I wouldn't know how. I mean whenever I create a character I draw from my personal experiences and knowledge with that character's main characteristic. And having that in mind, I don't think a male would know how to play a female character accurately, because he doesn't know what it feels like to be a woman. A woman reacts differently to a situation than a man, and in one of his reactions to an IC situation he might be using his personal experiences, and that would be bad because his previous experiences are that of a man.
See what I'm trying to get at?
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