For me there have been a few incidents that have been embarrassing while out in public.
Back in the mid 90’s I worked as a manager of a group of aircraft mechanics, so had to keep up appearances and therefore couldn’t grow my hair long. At the time, I was also sidelining with someone that owned his own business working with dry cleaners, basically doing pipe fitting. This friend I had met through a a Crossdressing group in South Florida. At the time, I was rather shy but passed pretty easily. At least every week or week and a half he would convince me to go out as girlfriends to many different events. So one night he planned to go roller skating at an indoor rink. I was quite rusty and spent a good amount of time squarely on my butt. One of those times my wig went flying. I overheard as I was scampering to get my hair “OMG, she lost her wig.” From a girl going by. She got to the wig before I could retrieve it then assisted me on the floor and in the ladies with straightening myself out. It was good, but was embarrassing. Another time after I’d left aviation, I’d been growing my hair out, but was marked by a clerk at a department store. She had evidently had a bad experience sometime in the past and completely broke down while trying to check out with a couple of blouses and a skirt. The manager had to finish the transaction, I really felt badly for her, and myself too as all the other shoppers figured it out about the same time. Yet another time, I was out with a coworker (don’t remember how she figured out that I was a CD) but she wanted to see Jessica and we did a day of thrift shopping together. While I was in the changing room trying on some things, someone stole the wallet out of her purse. The cops were called, and although they were really quite respectful, they knew after looking at my drivers license.