When i was younger, and ostensibly male but not acting very male, I got asked fairly often if I was gay. I didn't like it, because the subtext was, "you show your emotions, you don't act like an ass with women, you're weird, what gives?"
I don't get asked if I'm a lesbian, now, unless I mention a girlfriend or something. Then I sometimes get a surprised, 'oh, you're into women!" I don't mind that, it's just conversation, and i brought it up. If i don't want it brought up, I keep that stuff out of the conversation.
I've never been asked by anyone except a medical professional whether I was trans, but I am sure I would dislike it if i were. I HAVE been asked, by people who know my history, whether I've had SRS or not, and my answer is always, "none of your goddam business."
One last thought: I've been taken to task at least once by a female friend who was somehow offended that I call myself a lesbian. To her, I can't be. As far as she's concerned, my "Y" chromosome makes me a MAN, no matter what. Needless to say, we are not friends anymore. But while the man bit was nonsense, there are a fair number of lesbians who don't consider a transwoman to be a lesbian. And if I'm seen as an outsider, then I'm not going to find community there, and that makes me want to not call myself a lesbian, even though I am a woman who loves women. Aughh, I think I just gave myself a headache.