Well, that "first time" for me was when I first crossdressed back in 08/09. It was a mind altering experience for sure. Scary as hell too because I finally began to realize not only the 'problem' but the 'solution'. Man that resolution took a few years didn't it? LOL I came back here when I began my transition in 2010 and I have changed a lil bit since then. ;-)
The social aspect of the transition was emotionally difficult. I knew I was gonna be okay when I stopped making jokes about BEING a man and started making them about LOOKING like a man. I'm tall (5'11") I have big feet (11), a giant face and head, broad back etc. and I no longer try to minimize those characteristics. I just own them and make jokes. Me and the girls have so much fun laughing at each other and ourselves and it's extremely cathartic. As it turns out, women who have no idea about my history have the same issues with their body as I do. Four of us were nearly crying the other day when I made a comment about my hairy legs and how I had to prep for wearing sandals by shaving my toe knuckles. (toe fros, fro knuckles, etc.)
ALL women hate their bodies in some way or another, Tall women want to be shorter and short women want to be taller. Skinny girls want a bigger booty and curvy girls want to be skinnier. We are all striving for the kind of perfection that barely exists in our imaginations much less in reality. So you're tall. I have a penis. So what? ;-)