Welcome to Susan's, Blaine.

Actually, a lot of your story sounds like mine. I wore a beard most of my adult life because I knew I would never make a passable woman and so why not? I didn't want to transition because I was afraid I would be seen as a freak. I felt like I didn't fit in - somehow accepted but always on the fringe of the groups.
Finally I didn't care any more. I shaved off my beard, came out to my friends, and began living as a woman. Remarkably, now just about everyone sees me as a woman - including the friends who knew me before. Oh yeah, I also learned a lot of courage in the process.
I'm not saying this is how it will work for you. I'm only saying I was where you were and now am an empowered and unbelievably happy woman.
I never took Zoloft, but I was on Lexapro for about a year. I couldn't wait for my life to stabilize enough to get off it.
Good luck to you. And again, welcome to Susan's. There are a lot of nice people here and there's plenty of good information (plus a little bad

). Pull up a keyboard and explore.
- Kate