Hello1234 Hello, I think this could depend on person to person basis. Like depending on the awareness and nature of the individual you run across doing the verification.
I've had okay/good experience at some places. And at others there was a lot of .. sigh unnecessary checking/ grins etc. Some people are nice, some people can be extra nice and end up making more of a mess.
For example say I am being clocked as F by someone, and they use Ma'am to refer to me, then other person checks ID or notices something else and they try to correct this person that _ is _ title, not _ title. And hilarity and confusion ensues as they start arguing about how to refer to me or start staring/rechecking etc. Ultimately putting me in an awkward place ofcourse. (Someone should make a skit on that lol).
So yeah, I think your personal experience will depend on who you run across and their perception/knowledge etc.
If you're decided on some particular airport or rail route I think it'd be more useful to ask about experience at that route or airports. As experience may vary.
Legally (regarding breasts)
Legally, there shouldn't be a problem. A lot many guys are affected by gynomasticia, so although you may have some deep glaces / suspicious stares you could still kinda sorta "boy mode" if you really wish to. For international crossings, you can simply tell them you had surgery to be transparent in name of security. For other domestic travel etc, I think you may not have to really explain yourself. Just keep composure and act in a matter of fact way.