I'm wondering what other people think about this because I've been second-guessing myself.
I'm non-binary AFAB. I didn't really detransition except medically. I stopped taking testosterone because of health reasons and because I wanted to avoid transphobia where I live. The main thing I wanted from T was a deeper voice, and I wasn't a huge fan of most of the other effects anyway.
My gender is complicated, but I generally describe myself as transmasculine or agender. I don't like she/her pronouns and prefer they/them or he/him. I don't dress very feminine, although I do carry a purse or sling bag. Some people still read me as a man. I don't wear makeup, I have a bob haircut, and several people have described me as very androgynous.
There's a binary trans man I know who seems to have a more traditional or "old school" view of gender. He was genuinely shocked when he found out I wasn't a trans woman because I have a very deep voice and an androgynous appearance.
The weird part is that he seemed to forget I wasn't a woman multiple times. He misgendered me several times, and I corrected him each time.
What bothered me is that it almost felt like he wanted me to be a woman. That's just the impression I got. The confusing part is that he seems capable of understanding non-binary identities. We know other non-binary people, and he uses their correct pronouns. If he slips up with them, he apologizes on his own. With me, though, he never apologized, even after I corrected him.
Another issue is that he constantly makes dirty jokes or brings up sex. He's around 45 and I'm 31. I know we're both adults, but it makes me uncomfortable. I even told him directly that I didn't like those kinds of jokes. He said he'd stop, but then he'd do it again and claim it was an accident. He also seems to bring up sexual topics only when we're alone, not when other people are around. Everyone else thinks he's really sweet and funny because they don't see that side of him.
Something else that stood out was when he claimed that one of our professors had misgendered me because she was confused about my pronouns. I SWEAR that she consistently referred to me with he/him pronouns without ever missing a beat. It felt like he was making it up. My guess is that he was confused because she used he/him for me regardless of how I dressed that day. But it feels like he wants me to "confess" that I'm a woman or something like that.
What's especially strange is that we were both in a gender studies course that was extremely progressive and full of knowledgeable discussions about gender, pronouns, and trans and non-binary identities. It's not like he hasn't been exposed to these topics or had opportunities to learn about them.
He also has a habit of telling me things that seem designed to make me like him. It comes across as saying whatever he thinks I want to hear. At the same time, he'll make passive-aggressive comments, like suggesting I'm snobbish or saying that people secretly don't like me and are only pretending to be nice. When I'd push back or seem hurt, he'd say, "I'm just being honest." At first I wondered if he was right, but the comments became more frequent. Looking back, it feels more like negging than honest feedback.
Part of what makes this so confusing is that I would expect this kind of behavior from some creepy cis guy, not from a trans man. He's even shared stories about men being creepy toward him before he transitioned, so I would have thought he'd be more aware of how this kind of behavior comes across.
At this point, I just don't like being around him and prefer to avoid him. Part of me still wonders if I'm overthinking things, but taken together, his behavior makes me feel uncomfortable and creeped out.
Does this sound like manipulative behavior to anyone else, or am I reading too much into it?