Although I've known about Monica Greene, owner of Monica's aca y alla in Dallas being a transperson, I've never really heard her story. I found a link to an article in the Dallas Observer from 2003, ten years after her surgery.
It's a very good piece, but it also points out how accepted Monica is. She was a successful restaurant owner who had serious doubts about staying in Dallas and transitioning, yet managed to do so and making her business successful. She did not hide her transsexuality; at times she used it in her advertising to make a point about change.
It also says something about Dallas. I'd never have thought when I moved here that you could be openly trans and successful. But Dallas does seem to have its surprises...
Today, Monica's is still a very successful restaurant, and she even placed second in 2005's city council race. And still happy with her choices.