Today's question is:
Do you feel comfortable answering questions about being trans if say your teacher/friend/stranger asked you?
I would be really offended if a rando on the street asked me a question about me being trans. Typically there's no risk of that, though, because of years of hormones. The reality is that being read as trans makes many of us feel really bad. So if you do figure it out by seeing some of the markers of trans-ness on my body--my hand size and feet size for instance--you should really just shut up about it. That's not to say that incidentally reading somebody as trans is inherently bad. I'm actually really "good" at reading other trans men (which is one of the world's most useless skills by the way). But many of us are really self-conscious about people finding out, and finding that somebody noticed can be very scary.
If somebody knows through some sort of interaction... say they recognize me from high school or some other pre-transition life period, or I've come out, or something like that, then I'm fine with answering most questions that aren't horribly invasive, the latter being gauged by how close I am. A close friend could ask me damn near anything. Hell, for really close friends I'm not even bothered by genital questions if there's a reason for them. I can't think of any good reasons right now, but they might exist.
If somebody who knows is asking a question about sensitivity, then I encourage that rather than deplore it. It gets annoying after a while if it's excessive to the point where it's disruptive, but otherwise it's fine.
I despise when people ask questions like "Is this offensive?" when their motivation is to try justifying why they can like it. Like, I'm getting a lot of "America's Got Talent" traffic to this blog asking of Ray Jessel is offensive, and I can just tell from the wording that they're looking for that one trans voice that's going to tell them it's totally cool and hilarious and they're still good people. That's gross.
That's not the same for everyone, of course. Some trans people don't want you to acknowledge their transness in any way, and that's their prerogative. I, though, am typically fine with it.