I didn't want to hijack Fastchanger's thread, but this is along the same lines.
Going out to gay bars is a recurrent theme on here. It seems that many girls who won't go anywhere else are ok with going to a gay bar. Even many who are comfortable out at mainstream places seem to default to gay bars when in unfamiliar territory.
I, on the other hand, am more likely to be found at places your dowdy neighbor lady would go than anywhere else. Part of it is I've never been a bar person in the first place. I've been to more (straight) bars since I started dating my current gf than I have in my entire life previous. No way I would go (dressed) to a bar by myself! And a gay bar, double no way! I'll except hotel bars (where I'm staying), but that's a little different.
I've been to only one gay bar, and that was for a support group meeting. One of only two meetings I've ever been to. Actually, on that particular night, even aside from the meeting, it would have been ok. We were about the only ones there. There was gay porn on the big screen and a couple of young guys making out in a booth. Not something I'm used to, prude that I am, but not scary. Still, if I'd been alone sitting at the bar I think I would have looked like I wanted to be picked up. Same with a straight bar, for that matter. But gay bars have that added "zing" of being defined by sex (OK, sexual orientation, but you get the point).
I think for a woman to sit alone at a straight bar makes it appear likely that she's open to the possibility of being picked up. I think that for a male dressed as a female (that's already upped the sexual ante) to go into a gay bar alone is multiplying that appearance.
There's hardly a shopping center, hair salon, nail salon, or restaurant that I'd hesitate about going in to. Yet I see on here all the time, girls who are relutant to go to those places who are quite comfortable in a gay bar. I can see it being a really good place to go as a group, but alone, no way! Probably just my overall prudish nature (at least on the outside ), but it would scare the crap out of me! I'll be at Red Lobster, thank you!