So I ended the conversation. While also feeling a little insecure about my looks. Looking in the mirror why he asked me such a question.
Most Helpful Guys
In the last few years this has become somewhat of a problem especially in online communication. There are plenty of trolls that try to trip you with some "hot" trans chick pic. It happens quite often in the "How do i look" section. It is therefore to be expected for guys to become a bit suspicious of even slightly masculine features on attractive women. All women have some features that can be a bit masculine so I wouldn't be to concerned about that question. The guy was probaly just overly cautious and lacked tact.
Guys have to ask nowadays because there's so many men pretending to be women on dating apps trying to trick straight men in dating them. It's fucked up, so don't take it personally
Most Helpful Girls
If you are really gorgeous a guy will ask you that.
Ex. If you wear heavy makeup, have any work done.
I've been asked too. And was explained i looked to perfect, and that was an aspect of trans guys sometimes trying to cover up.
So dont take it as a bad thing, clearly you're gorgeous.
But then there's always a case you are really tall and a tomboy... that may be telling you something