I've never had a problem with crossgender roleplaying, either as GM or player.
I know a lot of people who are pretty bad at playing the opposite gender, but I know many more who can do at least an acceptable job. Then again, I've known people who have every character sound and act exactly the same, and that as GM! Those are very confusing games unless we have "Okay, Galthron says..." asides all the time. As a GM it is pretty much necessary to be able to do both, unless you are going to be playing an a highly restricted world.
Then again, crossgender roleplaying seems to be a major "comfort zone" issue for a lot of folks on the various boards. I've read a lot of threads about "No one should be allowed to play a man if they are a woman and vice-versa"; I find that odd given that authors have been writing believable crossgender characters for hundreds of years -- witness William Shakespeare's Lady MacBeth if nothing else.
I always bring out one of my odder stories about crossgendering. I joined a game once and decided to play a female character. Everyone at the table looked very uncomfortable. Then I noticed that the two female players in the group were both playing male characters. When I pointed this out, everyone got a little sheepish, then relented, and thus one of my all-time favourite characters, Julia Peregrina fillia Cerebus Facto, was born. By the second session no one had any problems with me, a man, playing a woman, Julia.
The point in portraying any character is to make them what they are supposed to be. Some characters are going to be two dimensional cardboard cutouts. As such, you don't need to put too much thought into them beyond what they are needed for in the game. The long term characters are the one's you want to think about. If you are going to have a major NPC who is the opposite of your gender (either way), think about how you are going to have the character talk and act. There isn't one right way to play a female character -- if you need proof of this watch the new version of
Battlestar Galactica. Don't make the character a bad parody (unless that is their specific role); choose different vocabulary, think about body language a bit, pay attention to how loudly or softly you are speaking, how quickly or how slowly. Small changes can make all the difference.
Yeah, for me rpgs are a good way to get out my frustrated acting talents, and I am quite good with that. That and storytelling
