I mentioned on Twitter today that when I first started playing, I almost went with a male character instead of a female one. Someone replied that he knows a woman who refuses to play anything but a male character. This preference confuses him a bit and he asked the reasons why I had the same initial preference. 140 characters are a bit too few to explain my reasons completely (particularly when I'm in the middle of a game) so I wanted to explain a bit more here. I want to warn my readers in advance though, this isn't a pleasant topic and I'm going to show a bit of my soul here. I can't tell you that any other woman has these same reasons; I can only attempt to explain myself.
My parents raised my brother and I in about as gender neutral of an environment as one can get. I got matchbox cars as well as dolls as presents and the only reason they were concerned about me playing sports was due to my heart condition. My brother and I had the same chores and I often was my dad's helper on construction projects.
Most of my town, however, didn't show the same outlook. I was told my love of sports was a phase that I would soon outgrow. When I wanted to play basketball against the wishes of the boys in my class, I was offered the position of cheerleader. When I brought out the classroom ball, the boys attempted to take it away from me and dragged me across the playground. I was told that as a girl I should have known better and just let them have it.
All of this resulted in me hiding my gender for much of my youth. Since only boys were allowed to do the things I loved, I took on the look of a boy. I had my mother cut my hair as short as she could bear it and wore boys clothes. Of course, this confused many adults and some of my classmates, but to me it made perfect sense. Of course, this was in elementary and middle school. By the time I hit high school, I had convinced enough people through sheer force of will that I didn't have to do this anymore and could just be myself.
Beyond this highly-personal learned behavior, when I play, I don't want to feel like the girl of the group. I don't want the male players or characters to feel like they need to heal the girl over anyone else or to protect her from the evils of the world. Many guys are more than willing to treat me as an equal, but when I'm in a group of people I don't know, I like the neutrality of playing a male character.
No easy way exists to discuss this topic. For a subset of players, and I think it's actually a really small minority, playing a fantasy game like D&D brings out their dark side. I'm well acquainted with how dark things can get, although I haven't had it happen to me at the table.
When I was in middle school, honors students were given passes that allowed them to go outside early during lunch and study hall, without adult supervision. I loved this as it gave me an opportunity to play sports. However, boys that age aren't always nice, and for months I had to undergo a number of tortures, everything from pretty detailed descriptions of what some of the boys wanted to do to my mother to threats, by some of them, that they were going to rape me in the woods by the school.
One day they finally broke down my will and my cousin could see I was upset during class. After I told him what was going on, he convinced me to tell the principal. So here I am, in 7th or 8th grade explaining to my male principal the bullying I was undergoing. After he heard my story, he told me that the only way he could do anything was if I repeated my allegations in front of my tormentor. Except it wasn't really in front, he sat the boy next to me. The end result was the boy got two days of in-school suspension and, while the overt sexual tone decreased, the bullying got worse.
Now, I know there are many wonderful men who would never do anything like this. And I have enough wisdom now to know that this was more about power than sex. But I always have that fear when I meet a new group of guys. So, at least in my mind, playing a male character is a protection mechanism against this darker part of society. It may not be fair and it might not even work, but it is what it is.
So those are the two main reasons why I might prefer playing male characters to female ones and, to a large degree, why gender issues are so important to me.