Dude, Haruna Ai rocks so hard. She's so awesome.
Okay, gushing aside... I apologize that I can't give you specific advice about MTFs, or transgender or anything like that. I do wanna say, though, I wouldn't rush him with questions. I think this holds true for just about anything exotic, especially something as personal as this, but the general tendency is that people usually aren't that fond of answering millions of questions about something that sets them apart, except, maybe, an area of study or expertise. It seems like you're really curious as a result of this being new to you. It's understandable, but at the same time, at this point, I think it's more important to consider his feelings, as he's the more vulnerable one in this situation, so it seems. If you have some things you really want to ask, I would space them out a lot. Maybe once every few times you meet, without making a really big deal about it. Also, I would try and be vague about it. I've found that people will tell you as much as they want to tell you, if you ask. When you push, or ask specific questions, and things like that, some people can find it invasive, or rude, as holds true with any subject. And, I mean, this is just a generalized stance, that can be applied to any situation, but I feel it works particularly well for sensitive subjects.
Additionally, I'm not trying to criticize you, or anything like that, but I think you might be thinking too far ahead. I understand the point of view of not bothering to date if there's no possibility of marriage, and things like that, but I wouldn't think too much about it. Whatever happens happens, and you'll cross those bridges when you come to them. For now, just have fun. Don't worry so much. Enjoy yourselves.
And, I'm sorry, I have to ask, is this an AMWF relationship? If so, I seriously commend you, and wish you well!! XD We need more representation!! XD
