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Time To Address The Cross-Dressing Thing

, , , , , , | Related | July 14, 2022

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!

Timothy Might Be Having A Chat With Mommy Soon

, , , , | Right Romantic | July 7, 2022

A father and his maybe four- or five-year-old son are perusing used cars in the lot.

Me: “Can I help you with anything, sir?”

I realize the father is reading something on his phone as I have approached and is distracted. His son, however, is VERY chatty.

Customer’s Son: “Daddy needs a second car so Mommy doesn’t see Daddy’s special friend!”

The man grabs his son, almost dropping his phone.

Customer: “What did we say about telling that story, Timothy?!”

As For Breaking The Law OUTSIDE Of Work…

, , , , | Right | June 29, 2022

I work as a janitor in a shopping mall. It’s a decent enough job, and every now and again, people passing by really make my day — though most often it tends to be kids. One of my favourite moments was when I was using a floor scrubber machine, one of those big ones you sit on. A kid, probably five or so, walked up to me with a deadly serious expression on their face and proceeded to drop the best icebreaker ever.

Kid: *Pointing at the floor scrubber* “Could you get away from the cops with that?”

Me: *Stifling laughter* “No, not quite. It doesn’t move very fast.”

Kid: *Nodding, still looking very serious* “Uh-huh. So, don’t get caught if you do something bad, then.”

Me: “I’ll just try to not break the law at work.”

Kid: *Flashing me a smile* “Good. Okay, bye now!”

And off they went, running to their mom. Made my day.

Optional Behavior

, , , , , | Right | June 2, 2022

I am checking out a mother with her young daughter, aged maybe three or four. She keeps grabbing candy and placing it on the conveyer, giggling adorably.

Mother: “[Daughter], stop it. You have candy at home. I thought we agreed you’d behave.”

Daughter: “I tried to behave, Mommy, but there are just so many other options!”

I had to stifle a giggle as I finished checking them out.

Calling It As She Sees It

, , , , , | Related | May 28, 2022

On the New Year, we were having a family dinner party at my granduncle’s place, as usual. After some drinking, Dad got suckered by his cousins into promising to show up at the next family event while crossdressing. And unfortunately, there was video evidence, so he couldn’t get out of it.

Now, Dad’s essentially the stereotypical East Asian pretty boy. You know the K-pop boy bands? Dad’s as pretty as those guys, so there was quite a bit of enthusiasm over how Dad would look in a dress.

A few weeks later, during Chinese New Year, my granduncle throws another family party.

I’m waiting downstairs with Mom while Grandma helps Dad get ready. And finally, Dad comes down the stairs wearing a wig, makeup, and a really nice dress.

I am a tiny six-year-old girl at the time, so I essentially have no filter. My reaction to seeing Dad?

Me: *Starry-eyed awe* “Daddy! You’re prettier than Mommy!”

Mom never forgave me for that. It was true, of course, but that was still the last day I was my mother’s favourite child.