In another game I played a girl character, Sibila Wuchenco. By Playing i mean, i used "I" not "She" and it was not awkward or creepy. I'm pretty happy about the response, because as a GM I would have to "impersonate" a female NPC and have to RP her well (entertaining and consistent).
Its not that hard to gender bend without being creepy, simply because there is a huge list of things NOT-TO-DO when playing a female character discussed all around the interwebs. All you need to do is listen, and it makes sense why those NOs are creepy.
- avoiding needless detail - be discreet
- of course understand the subject matter - hopefully your common sense and experience that tell you how the world is to women. I guess if its coming from somewhere it has to come from your wife, sister, daughter, friend, mother, or >insert healthy female relationship<.
- know your audience - the other players and the GM, obviously knowing their tolerances helps RP a character that hits entertaining without being creepy.
- an honest motive - why you are playing that character*
*Honest portrayal is basically having no hidden motives, despite the most "cunning" of intentions hidden motives can quickly be exposed on the table because you have to "feed that beast". GMs are usually too busy to have any hidden motives when gender-bending, so following through the core-character motives is easy. In my case, I was playing about 6x that week and I wanted something different, very different and something I can flex my empathy muscle since these are old friends.
The woman I played is a mish mash of many women I know, there is a certain patterns that can explained by "personality physics" of a character. One particular woman I am "impersonating" is this very skilled broker who uses active listening and industry expertise to make clients comfortable. there is nothing untoward about interaction with her, everything is very professional and courteous. What I find amazing is that gender does not become an issue, a tool, a weakness, or a factor when I deal with her.
A motive I can dig up, is that i wish life was not as messy and complicated when it comes to gender in real life. I guess an appreciation of how complicated it is, might be tempering the way I play.
I don't think i'll playing a female character in the future, its good to play with old friends I don't think its good to play with new people. Its going to be creepy regardless of how skilled you are, and the first impression you make is going to WEIRD.