This is my first post, so I guess I should lay it all out.
I've been dealing with transgendered feelings since around the age of 9. I remember, back when I was innocent and ignorant, wishing to God I'd just wake up as a girl. A few years later I learned a little more about the possibility of transitioning, but I could never build up the courage to come out to my family. I still regret that. I don't always get on well with them, but I think they'd have been understanding.
Instead, when my half-sister moved in with us, I'd borrow her clothes and at least pretend for a while. She eventually went back to stay with her mother and step-father, and that ended that. I've tried to dress up a few times since then but it isn't particularly easy to pretend anymore after what puberty did to me... Over the years I kept telling myself I'd do something to set myself in the right direction, but I was always too afraid of what could happen. What would people think? My gossip of a mother would tell every relative and anyone else she possibly could over the phone.
I'm almost 25 now, and I still live in fear. I never told anyone my secret up until late last year. I'm not sure what brought it up, but I eventually told my girlfriend of 3 years how I feel. We talked about it off and on over several weeks, but eventually there wasn't anything left to say and the subject didn't come up again for months. She was really understanding and it was relieving to finally not feel completely alone in this.
I plan to start seeing a therapist in the next couple of weeks, but I don't really know where that'll take me. Transitioning is something I still consider from time to time, but that could go wrong in so many ways. What will it do to my relationship and my sex life? Will my girlfriend (soon to be fiancee, hopefully) leave me? If not, what will her family think? Will my extremely masculine build/facial structure/voice make passing impossible? Probably. Will I be able to stick with my career plans?
I don't see this ending well for me no matter what I do.