Time To Address The Cross-Dressing Thing

This took place around 1997 or 1998 when I was around seven or eight old in West Virginia. West Virginia is a conservative, Republican state. Luckily (or unluckily, depending on how you look at it) I was raised by very liberal parents. It probably helped that my dad was from Detroit and my mom lived outside West Virginia for a while before she came back. They had raised me to always look for the good in people and not to go by race, sex, religion, etc.

My dad’s best friend and coworker at the time was a lesbian and I was raised to call her and her partner my aunts, so I knew about gay people and was fine with it. However, I had never known about cross-dressing. We were in a home improvement store and I happened to see a very tall, pretty lady. She was wearing a short blue dress suit with high heels. That’s what made me notice her. Why would you be dressed like that walking in a home improvement store? Then, I noticed something else.

Me: “Mom! Daddy! See over there? That’s a man wearing a dress and high heels! He’s also got a blonde wig on! Why is he dressed like a lady?!”

My dad just looked at me, choking on his laughter.

Dad: “[Mom], you explain to her.”

Then, he walked off.

Mom: “That’s a man who sometimes likes to dress as a woman. There are men that do that; some women like to dress like men, too. Now, [My Name], I think you’ve embarrassed him. The whole store heard you yelling about he was dressed. Next time be quiet! There are people that don’t like people like that man.”

Of course, after she told me that, I felt terrible. I didn’t mean to embarrass him or make him feel like it wasn’t okay to dress that way. So, when I saw him again in another aisle, I did the only logical thing. 

Me: *Very loudly* “Look at how nice he looks! That’s a pretty dress and his hair is pretty! Look how pretty his legs are in those pantyhose!” 

To be fair, he did have pretty legs for a man.

Years later, I asked my parents about that incident. They told me he was a prominent lawyer in that city, was happily married with kids, and liked to do his home improvement shopping while dressed as a woman. To that man, I’m sorry little kid me possibly embarrassed you. But you did look very nice!