Recently I saw a post which asked which song the readers liked better, specifically Lola by the Kinks or Take a Walk on the Wild Side by Lou Reed. Those for the most part were main stream tunes and of course there were others. Such as in 2006 when Jayne Country sang Man Enough to be a Woman. I don't know if my
wife's musical tastes went farther than I thought but she told me nearly the same thing one day when we were having a huge fight caused by my cross dressing when I was rapidly thinking of if I could make it as a full time transgender woman. She (my wife) accepted me as a cross dresser but never accepted any thoughts of being a transgender woman.
Before I ended up in the commercial food service business, I was a disk jockey in college and in the Army. I also pursued it for awhile following my stint in the military until my daughter came along and I ended up buying my own pub/pizza parlor with a friend. Lola was actually released in 1970, two years before I was drafted. During the one radio show I was running at night while I was still in college, I had a guy who positively loved the Kinks.
One night he called me up in a panic and asked if Lola was really about what he had heard and thought it was. In other words was Lola really a man. I couldn't hold back and told him yes, in reality Lola was really a man. He hung up in a panic and I never heard back if his beloved Kinks maintained their spot as his number one group.
Take a Walk on the Wild Side was released by Lou Reed in 1972. as a tribute to Andy Warhol's glamorous transgender ladies from his famous Factory days. In those days, I was taking my own walk on the wild side by taking on Army basic training.
As I said, due primarily financial reasons, I left the radio business and stayed in the food service business after my pub closed. Perhaps I am missing other strong transgender and/or cross dressing music but the next I remember was Dude Looks Like a Lady which was released in 1987. Ironically the song was about Vince Neil of Motley Crue when it was released by Aerosmith. It turned out the song wasn't meant to describe actual cross dressers or transgender women at all. Even though, it was the music which caused me the most amount of pain.
The more I began to sneak out in my medium sized town as a novice transgender woman, the more I would encounter the occasional person who would recognize me. I will never forget the night my wife and I attended a party of my store employee's and as soon as I got there the DJ played "Dude Looks Like a Lady." I just ignored it and my wife didn't seem to notice it, so all turned out without a problem.
The problems with the Aerosmith music came a couple years later when I was out trying to live my new life in a feminine world. As I was sitting at the bar enjoying a drink with a transgender woman friend of mine, these guys decided it was cute to play the "Dude" song five times in a row. It got so bad we were asked to leave by a spineless manager.
It all turned out in my favor nearly a month later when the manager was fired and the crew found me in a close neighboring venue where I was welcome. They invited me back, which I took advantage of.
I'm sure you all my be aware of other cross dressing or transgender music I possibly missed. If so, please let me know.