Though I have a different orientation than you, my experience was similar.  I wasn't aware at that age of being trans, but, in hindsight, it certainly affected my dating abilities and success (or lack thereof).  I didn't lose my virginity until I was 30.
I was only attracted to girls, but I simply couldn't figure out dating as a guy.  Everyone else seemed to know what to do; why didn't I?  I eventually got some support group therapy and figured it out enough to get married.  But I still felt like a stranger to the whole process.  I didn't have the brain wiring to be a guy, and I didn't have the socialization to be a girl.  
I can't imagine dating as trans.  It must be terribly difficult.  It probably will be better once you transition.