Sweetie the first thing I'll say is that it's very likely a gender therapist could help you. Even if just to talk everything through with and get a fresh perspective on. I think it would be worth trying to get in touch with one and telling them how you feel.
Something kinda leaps out at me from your post. This person you're attracted to. It strikes me that he embodies everything you wanted to be, at one time in your life. See the thing about feeling things is that we never forget we felt them. Even if, later on down the road, we don't follow those feelings anymore. For that time in your life, they were there. They were real. And the memory of that never really goes away.
It's not my place to tell you if you're trans or not, Ron. That's not really something I, or anyone else here can do. That's something that has to come from you and you alone. But from what you have said in your posts, this guy is taking you back to a place where you felt that way. Whether you still do or not. Just by virtue of who he is, it's making you remember, and it's making you think about it. With memory comes emotion associated with that memory. It's not enough to just remember something, we have to feel how we felt then too, because that's how the mind locks our experiences in place.
It's like... hmm... have you ever smelled a smell that reminded you of something? Like... for me the smell of floor cleaner always makes me think of school. First thing in the morning after the cleaners had left, and the corridors smelled like that. Every time I smell that I'm taken straight back there, with a lot of the emotions that went with that time in my life. Memory is more than just an image. It's a plethora of sensations all locked up with a lot of triggers, to help us remember. Maybe this is what's happening in your case.
It's possible that in this guy, you see one way your life could have gone. One person you could have been. And how he interacts with the world. Like if your life branched off in two paths based on one decision, and he is the other path. And it's making you remember, you know? Making you wonder what if you'd stayed with it. Like seeing the person you thought, at one time, you were. And because of that, it's making you feel the same way again. Making you question if you did the right thing.
Again, I'm not going to say that you're trans, Ron. And I'm not going to say that you're not. Because it's really not my place. It's also possible that these feelings that are being thrown up are the result of you repressing how you felt because it felt too bad to carry on with them, and in this guy a dam has burst and you feel like you really do want to be someone like that. That's something that the individual can only really figure our for themselves. I do think we see in others, parts of ourselves. Whether this part is in the past or in the present... sweetie, that's really your call.
It does seem that this guy has taken you back to that place though, because of who and how he is. And it's made you think about it. Go see a gender therapist, okay? If you can. Tell them what you've told us. They have way more training and experience with these issues than most here. And can help you work through it face to face. Which is definitely a benefit.
*big hugs*