Interesting, largely because I find myself usually playing games as female characters. But… this isn't a "I am playing as myself" mentality. My elderscrolls characters are just a typecast character I can assist with exploring the world. It's not perfect, as I rarely role play outside of my own moral set - I usually don't play a thief or 'evil' character even if I try to set out with that as an idea. So there is obviously an inextricable aspect of myself - but I guess it boils down to I'd prefer having the female body as company. Perhaps it's closer to a desire to be accompanied by such a woman on an adventure and I am merely there in spirit or something.
As for my first online experiences - there was an amusing bit where one of my closest friends, I thought was a male and she thought I was a female. I never really enjoyed playing with people's emotions on the net - other than correcting people who were wrong on my internet.
I do agree that there is not enough in terms of mentorship toward an acceptance of self as-is. I also wonder how much of this is rooted in early development. I won't say my upbringing was strict - but it was just obvious to me that I would one day grow up and become a father, raise a family, etc. It's not a question of whether or not I am a man - if I am to raise a family, the question is what woman can I form a healthy relationship with to do that. I wouldn't say there was a time where I said I "identified with women" - although perhaps this is just because I did not view my antics to mimic my mom (who I spent much of my time with) as such, and there was absolutely no way my parents would interpret my prancing around in my mom's high heels as anything other than me being an 8 year old jackass. One day, when I was extremely young, mom was painting her nails and I wanted to paint mine, too. So, she let me. A discussion was had and it was allowed for me to use the clear fortifier/base coat in immitating Mom.
Even if, for some reason, I were to have come to the conclusion that I felt more like I wanted to be like a girl - I already wanted the role of a father/husband, and I see clothing as more a tool of communication - so even if I did find it hilarious or "pretty" to dress up in a feminine fashion - it's not getting me what I want/need out of society to complete the role I want - so, meh. There's no real need or desire to dress up as a girl or anything.
Although that utilitarian view of my body does come in handy for practical jokes and the like. When the equation shifts, I have a greatly diminished sense of shame. Well, at least when it comes to the superficial.