I did, a few months ago, go out "on the town" with two other people. One was a transwoman (not on HRT at the time), the other CIS female, and I was in male mode. We went to a restaurant to eat, and then to a trans-friendly nightclub here. Unfortunately, the transwoman had been drinking earlier and was literally outing herself as we ate at the bar in the restaurant. In that semi-drunk loud voice she kept asking us other two "do I look like a woman? and proclaiming "I have it down..I look like a woman! etc. It drew some looks at the bar. But not a big scene. I guess I was more annoyed that she was drunk and acting obnoxious than anything else (I'm a non-drinker) That was the only part that bothered me really. It didn't occur to me there, but I wondered later, if the event didn't errantly get me clocked as a transmale. But that didn't bother me either.
Of course the club was fine, and I just kicked back with my diet coke, but at one point she did ...now being even more drunk.. make a sexual advance to me, which I had to pleasantly decline. That bothered me mostly because I was afraid I had hurt her feelings. (but I bet she didn't even remember it the next day) It's not a trans-phobia thing tho. I just don't feel anything more than friendship with this particular individual.
I guess the point I'm making with this post, is that for me it seems that how a person acts matters more than what they look like. Next bold step for me is to go out as Marly, but hopefully not with someone who has been drinking all afternoon before.