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Everyone, and I think probably especially intellectual people, questions their sexuality (am I attracted to the opposite gender in some way?) and at least their gender expression (am I masculine / feminine enough?) to some extent. It's no different for a lot of people I think than imposter syndrome and can be tied to a lack of self confidence.
Everyone is also capable of fantasizing about, basically, whatever, and enjoying it, without the fantasy or enjoyment having to mean anything about how they feel about themselves or how others will feel about them.
Also, sexual preference, as kinks and fetishes, develop and change in men at least until some surprising age, like, into your 50s. Like you could live your entire life identifying and living as a one thing and by fifty-five be identifying as something else. I think, and I'm not sure yet, be that's just life. Most people who don't live in a safe space bubble and don't leave their home town or school aged friend group have to reinvent themselves multiple times in life.
Also also, sexual pleasure and gratification is a full body and mind experience and it's possible that different partners stimulate and gratify different parts of that experience, even different encounters with the same partners. And none of that has to be carried around with you as if it changes anything about who you are or how you should be treated.
And lastly, it's fine to treat this person and anyone else in a positive and fun way for both of you. It could be that this person expresses themselves femininely and so your instinct is to be a little different, whether that's with more compassion and tenderness and even flirty, and I would say confusion is probably a very healthy and intelligent, internal reflex to something like this that is new to you.
And finally, anyone that says the Roman Empire collapsed because of all the fucking without making babies is a right cunt. If society collapses because of who any of us are fucking then... it was coming either way.
Edit to make sure someone catches that joke, which may be one of the best I've written.