My little bean, Harlee.
It sounds like this person thinks your gender is your entire personality, and that by transitioning gender you are becoming an entirely new person. I think it’s normal that they turn to stereotypes and binaries to try and understand something they are unfamiliar with though. The “will we ever hook up” would absolutely throw me off if a friend I trusted said that, and that’s a whole thing to digest alone.
I’ll refrain from giving advice because it wasn’t asked for, but unfortunately yes. Lots of cis people need the boxes and stereotypes in order to interact with others in the “socially correct” way rather than making those determinations on a person by person basis. I think it’s part of the cisheteronorm standard that is still said quietly rather than out loud.
I think the whole “should I think about fucking you” part is pretty toxic if it’s coming from the mouth of a person you thought was your friend. Yeah, OP makes a generalization about cis people that doesn’t hold water but ultimately all the questions posed leave zero room for any ambiguity that the friend in question needs them to be either a “man” or “woman” in gender which frankly is a poor view on gender. What if they transitioned to non-binary? The friend in question is treating OP like a whole new entity that needs to be reassigned rather than a human who is making subtle adjustments to their social role.