All the time. I honestly can't remember precisely when I dressed as a guy (sometime around Jr. High, I think.) I went to High School, college, and grad school as Kara. When I was job hunting it was as Kara. My neighbors know me as Kara (who can't cook to save her life). They know me as a girl that's got a bit more than average up top, as something of a geek, the one that will come over and change light bulbs and fix their TV's. (I tell them I'm like Peggy Bundy - I flunked Home Economics!)
The things I'd do (if I won the Lottery) would be to go under the knife for some facial surgery and to get rid of that last little bit of **** meat down there! (Of course, with my luck, I'd never get the three weeks off to go to Boston (or Bangkok, or Havana) and do it. I'd get called back for some 'emergency' that wasn't.)