I travel for work and the first was a walk in the hotel parking lot, late at night. Then, a drive somewhere and a walk close to the car. Then I went to a transgender bar in San Francisco. Then gay clubs. The breakout day for me was when I went shopping in broad daylight. Now I am pretty comfortable and will go out most everywhere; although I still will not go out to a place like a sports bar. The first steps were quite scary, although nothing bad happened. I think I pass at a distance or in the dark, but up close you can tell what I am. I have had a few incidents while dressed, locked keys inside and had to deal with tow truck guy, pulled over by cop, guy hitting on me at bar, lady talking to me at MAC counter (I think she thought I was real). But, each incident really made me stronger and braver, and gave me the feeling afterwards that it is all ok. Good luck.