The old advice applies here...when in Rome, do as the Romans do. When out as a woman, dress as women your age do. Go to places where women your age go. Avoid places that women avoid. That goes double when alone. Behave as women your age behave. Not sure? Go in drab to places you want to go later en femme and do your homework. En femme, you become your twin sister for all practical purposes. Dress and act like it. Rare indeed will be your troubles if you use your head.
My worst occasion was riding the T from Cambridge through downtown Boston to North Station, mid afternoon on a Saturday forty years ago. It was my first year crossdressing regularly in public. A smart woman would observed her surroundings to see nearly everyone exiting at Government Center. She would have chosen to walk with the stream of people those last two blocks to North Station. An irony of crossdressing is that we are safer in a crowd than being alone when out and about. I stayed on the streetcar, alone but for three punks in the back of the car. They gave me an obscene catcall as I exited. Scary but I survived. And that is my worst experience. It was a wake up call to not only make the extra effort to look like a woman but more importantly, to make the extra effort to think like a woman.
