Background: I was born female and I am hetero-romantic, but I'm starting to think that I might be both asexual and agender. I have always been uncomfortable with the idea that I am "supposed" to look, act, and feel certain ways because I am female, but I don't want to be male, either. Overall, "gender" just doesn't make sense to me. I also find the thought of reproduction absolutely repulsive. I dislike listing myself as something other than straight, and it's a really new idea for me to do that, but using the term seems to help other people understand my position on the whole ...situation.
Situation: Now, I have this straight male friend whom I've known for over 12 years now. I have had a crush on him for at least the last four years, and I am fairly sure he likes me as well. He asked me out once, but I never actually answered him, and we've continued being "just friends" since then. We have started seeing more of each other lately, and I'm starting to get the idea that he wants to move things forward romantically.
The problem is, we talk to each other about all kinds of things, and one time our conversation turned to LGBTQ issues and gender dysphoria. He explained that he didn't really "get" the whole concept and found it really weird and unsettling. If I had to choose one word to describe him, it would be "gentleman". He holds the door open for women, took cotillion classes as a kid, and hopes to someday have a wife and kids. Although I have mentioned that I dislike being called a "woman" and the idea of physically having kids, it was always in a semi-joking way, and I don't think he is aware that I was serious.
I really like this guy and I enjoy having someone to talk to with virtually no subjects off-limits. But I'm stuck between a rock and a hard place: either keep a really massive secret from him or risk alienating him. In addition, if he does ever ask me out, should I even pursue a relationship knowing that he will always want someone without reservations about sex or her role as a wife. That is all pretty far away, but it just seems cruel to enter a relationship thinking there is a 100% possibility of both parties being hurt and no chance of achieving the ultimate "goal".
Question(s): Do I tell my friend I think I am not straight? Do I pursue a romantic relationship with him with or without sharing that secret? Should I risk losing him as a friend by possibly breaking up with him later because we are just too different?