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I did 3 days out and about in Taos New Mexico a few years
ago with no problems . I am pretty comfortable in any place
With lots of tourists. I really dont get hasseled much and if
I do have problems just figure that is the price I pay for being out !
Key West gets my vote! As Jimmy Buffett once said in an interview, "Nobody here cares what you do". Did I mention it is always warm, with balmy ocean breezes long after dark. Think sandals, skimpy dresses and thongs, and tropical breezes all over! And the tourists and locals expect to see crossdressers. Nobody cares! And if you catch Fantasy Fest, BONUS! :battingeyelashes:
https://www.youtube.com/watch?v=wTn6iIdX8B8
Yes, Portland Oregon...very accepting and open culture.
Don't come to Texas...
San Francisco was my test run in October 2015. I wasn't fully 24/7, but I did have two days out and about dressed, and didn't have any issues.
In April I took the train from St. Louis to Chicago. This time was 23/7 (I went to the exercise room in my guy workout clothes for about an hour a couple of times) from Sunday to Wednesday. Otherwise I was a girl from door to door, home to Chicago to home.