Connie sent in this comment which jogged my ancient memory about one of my cross dressing experiences:
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Many years ago, in another life, I had a very well paying restaurant job. In fact, my monthly bonus check were enough for me to buy a brand new Porsche Boxster. Even though I knew I would be playing with fire driving it around in my favorite blond wig, I kept thinking you only live once.
One night, I took it to a little lesbian bar when I was cross dressed in my tight jeans and top. I had just settled into my first beer when another female patron walked in and loudly exclaimed "Who is driving that car?" I politely explained I was and of course she then asked for a ride. It was at this point the whole idea became a little dicey. Very simply put, my wig wasn't attached very tight to my head and I was driving with the top down. I had a very real nightmarish idea my wig could come of in front of a stranger and fly into the night.
To make a long story short, my wig stayed where it should have been and the ride was very successful. I was just fortunate no one else asked for a ride.
Sadly, several years later when I lost almost everything else in my life, I lost the car too.