So I'm having a bit of a problem. 60-70% of me wants to transition ASAP, the other 30-40% of me says not now. As far as I can tell one of the main things that is holding me back is a disconnect in my self image. When I try to picture my ideal self alone, (e.g. sitting and watching TV) I see a woman. But when I think of myself doing romantic things, dating, courtship, spending time with a girlfriend I see myself as a man. Here's the kicker, while I think of myself as a man during romance, when I think about sex I see myself as a woman.
Because of this there's a little voice in the back of my head saying "Now that you know what's going on in your head you can find a good relationship and make it work as a male. However I think this is just a return of the whole "I need to try harder" mentality. On the one hand, I will most likely not start hormones until the fall, and I would like to have a relationship, but I wonder if it's a good idea to try before transitioning. Finding a woman who is OK with me transitioning and actually meaning it may be difficult. Furthermore since I'd feel obligated to tell her if things got serious, she might react badly and start outing me before I'm ready.
On the other hand I don't want to have any regrets, and having at least one good relationship would be nice before I change sides. I've spent most of my life looking for someone who could "fix" me, and because of this things tended to get weird. I've accepted that I don't get to have a normal life, so it would be nice to at least have an eventful one.
But on the gripping hand I'm not getting any younger. If I were 23 instead of 33 I would be willing to take the slow approach, but I'm worried about my age. I want biological children of my own one day, and assuming I stay attracted to women it is still possible if I don't wait too long.
Another quasi-related problem is that I'm a 33 year old successful professional who has mind melded with an 18 year old girl. I feel like I want to have my 20s back so I can go through them as the proper gender, however I worry that if I spend my 30s reliving my 20s I'll hit my 40s and find that life has passed me by, that I'm too old to have the adulthood that I want and I will have squandered my life. In other words I'm worried that it may take so long for my internal maturity to catch up to my physical maturity that I've spent my whole life just getting back to zero.
Has anyone been able to thread this needle? I can't just ignore the part of me that wants to wait anymore than I can ignore the part of me that wants to go forwards. Has anybody figured this sort of thing out?