Sooo...I have read tons of these topics, and often I see different answers to similar stories, even different answers for one story!
Up front: I am a genetic man who is only interested in woman. I am bipolar 2 with general anxiety and a touch of agoraphobia... I am on some medication for that which has sapped away any creativity, I feel, but keeps the mood swings a little better than without. Lots of this must have been inherited from my mother, who has been agoraphobic since I was 3 (I'm 40-ish). Also I have not been formally diagnosed with OCD, though I do have a sort of germophobia in some circumstances (touching things like doorknobs). It's bothersome yet also contrary, I will handle money and then eat with the same hand I handled it with, and money is like the dirtiest thing you can touch! But the germophobia might be important.
I do not believe I had any transgender signs as a child. However, around college age I did become interested in trying on women's clothes, and would sneak wear some of my mother's things in my bedroom when at home on break. Several times, not just once. I did not do this for sexual gratification, I don't think, though there was surely a little turn on at first, I also would admire myself in a mirror. Once I wore my normal jeans and shirt over the bra, panties, etc and sat in the living room with my mother watching TV, to see if i could pull that off at least. But that all sounds like a fetish.
Sidebar: I have an interest in BDSM/fetishy things, and might be stuck in a situation where I need facets of that in any "funtime" for it to be satisfying. But, since I've become a bit of a hermit, that's been a nonissue in real life (more on that soon).
So thoughts of wanting to cross-dress would come and go, but life did not let me try to indulge. The details are honestly not important, just suffice to say that it had been hard logistically so I would push it to the side of my mind. And those desires are not quite an obsession, unless you'd call a slow burn one. I also might finally be able to try it out due to some changes.
One time I did get very irritable at a store, looking at the women's clothing section, wishing I could shop there, but not being able to. Almost a manic episode of agitation. I do steal glances at those sections all the time in any store, but I haven't gotten so irritable again. There were also some other circumstances at the time, a weird online thing with a difficult person, so who knows if that added to it.
Sidebar 2: I play on Second Life. Probably most of you know about it, it's a virtual world, with avatars. I originally played as a guy, had that relationship with someone who was toxic, etc., not important. I would try to introduce BDSM things there with limited success, but that didn't matter too much. I would also cross-dress my character sometimes. I also had to make an "alt" (a second character) for privacy at times and that was a girl avatar. Just seemed like something I wanted. Anyhow, after that relationship stopped, I went scorched earth and restarted, and picked an ambiguous name, unsure what I'd be. I quickly chose to be female, and have presented as such for years now. Some know that I'm not that in RL, and I know of some. The joke is that a majority of female avatars are guys, but also that's often due to them being horndogs wanting sex with a female avatar who is probably also a guy behind the screen. That wasn't my motivation at all. However, I do partake in non-sexual BDSM role play on there. It's a different thing than just going online for hawt seX0rs, we talk about this a lot at hangouts. And I'm on a tangent. Anyhow, I have never regretted being a gal on there, and when I use my old, first avatar for whatever reason, I feel very "meh" about it and would rather be my current one. I feel like that's an idealized me.
Anyhow, things have been in the back of my mind for decades. This isn't an overnight thing. Any time there has been something on television about ->-bleeped-<- (I hope that's an ok word, if not I apologize!) I make an effort to watch, secretly if so. However, the Caitlyn Jenner thing did get to the point of annoying me, maybe because "oh now that a CELEBRITY is doing something, everyone cares!", sort of like how bipolar was thought of as devil juju until Catherine Zeta-Jones said she had it. Just stinks of bread and circuses. Tangent. Point is I've always paid attention, for ages.
So the other night I got into a "deep conversation" on Second Life with a TG friend, and really mulled over things. I have an urge to come out as a male typist to people on there for whatever reason, which also led to me talking about real life things, and she even thinks I might be a "lesbian trans-girl", but that's a guess by one person, of course, and trying to label something for someone who is a bit frazzled at the moment. Then I go read up a lot and watch tons of videos online, and some will be like, "if you're watching this, you are transgender", and other things are "you probably have OCD if you didn't feel this way since you were 3."
Sidebar 3: I tried making a list of every possible sign throughout the years. I know that's confirmation bias so it's useless, but I did remember some things, like, when shaving a patch on my leg for whatever patch you use for low testosterone (important?), I shaved almost my whole thigh to see what it'd feel like. Or doing a quick "tuck" (as in just squeeze that stuff out of sight with your legs, ouch!) after a shower to look in the mirror.
So now I'm confused more than I was 3 days ago. This isn't some sudden obsession since I've felt feelings for over 20 years, but this time seems a little obsessive since I've done so much research in a short time. I'm doing it all in free time I'd otherwise be using to play Angry Birds or something. But I'm not anxious about it, just very interested, and now am upset at the idea that it was an OCD thing I've never had before, since it's yet another thing to add to my "crazy list". I think I would be relieved to be transgender (which is NOT crazy)! All of this seems sudden but it also could just be the straw that broke the camel's back. Every other time it comes up, I push it away, and now I'm sick of that since I now know SO many people of various sexualities and gender states on there (the SL BDSM people are usually very open about things and accepting, so in private you find out a lot of things about others).
Sidebar 4: I am sexually awkward, and I honestly don't know how I got that way out of college. Also the nearest thing to body problems I have is, sometimes I get really angry from nocturnal emissions...I'm inconvenienced, embarrassed, and mad that that stupid thing is causing me annoyance. I have cursed at it. I don't really have any overriding desire right now to physically transition (though I'd be open to the possibility, with fears I'd be ugly, though), but I DO "hate" that darn thing sometimes. I cannot even really pleasure myself, I don't have any desire to so I don't bother trying. I might actually be borderline asexual, but that's another issue that I don't care about right now and doesn't have any bearing on this I hope.
When sometimes daydreaming, I think, if there's a heaven, I will appear, and my grandparents and whoever else I care about who is dead will greet me, along with my pets, etc., and I will not be this average guy I am now, but a nice women, looking roughly like my avatar in Second Life, in a nice spring dress, and I will be greeted as "me" - same soul, just in this other form. That might be something to help guide me to figuring out things, or just cross-dressing urges with spirituality thrown in.
Anyhow I might be rambling now, I could go on forever with 50 more stories/theories. This evening I have my regular psychologist appointment, and will try my darnedest to talk about it...I've wanted to many, many times and have chickened out. I'm afraid he's going to say "aha! undiagnosed OCD!" or "quit Second Life, it's twisted your mind finally!" (he knows about it and that I play a female). I will be angry if either of those things happen. I am prepared though a little scared, I think fairly, to make an appointment with a gender therapist if I am not satisfied with the answers I get later.
Anyway, any ideas? I don't expect anyone to diagnose me, but, anyone else feel these ways? Any input would be helpful, thank you!