Harlotry: The Sad Story Of The Crossdresser Who Paid Me To Teach Him How To Be A Woman

“I do drugs!” said Buddy proudly.

“Do you?” I asked, sure that I didn’t want to know where this was going, but a slave to coutesy until the end.

“Oh yes! Let me tell you about this one time when I was living in Arizona!”

It seems that during the 1980s, Buddy lived happily in Arizona. He frolicked in the sun, he hugged cacti, and he smoked a shitload of crack. He cooked his crack himself, which made me wonder why he didn’t just skip the cooking step and do coke, but I made noises of approval at his enterprising nature. To hear Buddy tell it, Arizona in the 1980s was a paradise. All Buddy did was smoke and cook all day. Hilariously, he often smoked while he cooked! Such fun! One day, Buddy was cooking his daily crack, but he was so high that when he went to pull the tray of freshly baked crack out of the oven… he forgot oven mitts! Since he was incredibly high, he didn’t even realize he had flash-baked his hands until he set the tray down and looked at them! So funny!

It wasn’t funny at all. While the story itself was only mildly disturbing, the fact that this man was relating it as the comic high point of his life was terrifying. I suddenly didn’t care that he had drunk a pint of schnapps and all but one can from a case of beer, Buddy had to go. I pulled out the one bulletproof excuse I had, “Um, I have a doctor’s appointment in like, an hour.”

That excuse seemed to speak to Buddy. He paid me the fifty dollars we agreed on and I was too exhausted and unsettled to ask for more. Before he walked out the door, he cracked the last beer “One for the road!” he grinned cheerfully and swayed down the stairs.

Buddy texted me a few days later to tell me he had a wonderful time and we should do it again sometime. It took me a while to figure out what he really wanted–obviously not a sex worker or someone to teach him the finer points of traditional femininity. He just wanted a drinking buddy to regale with stories of his crack-smoking glory days, but that was not something I could be. His texts came fewer and farther between, and soon I stopped hearing from him altogether.

Cathryn Berarovich is something of a renaissance sex worker; she’s currently employed as a stripper (and writer) but has held numerous interesting jobs in the industry. Each week, she shares her stories in Harlotry.

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    • Jen


    • Breezy

      I must be way too suspicious of all people everywhere. I was convinced that story was going to end “and then he stabbed me to death with a stiletto.”

    • Rye/Alyssa

      As an open and happy crossdresser with no history of crack cooking or hand burning, and a penchant for being sober behind the wheel, I also found this story very sad, yet also amusing. If he ever texts you again just tell him there’s youtube videos for all that training.

    • blhblhblh

      I know it’s been a while since this was posted, but what disturbed me the most about this story was that you didn’t get the $50 up front. Come on, Cathryn… that’s sex worker 101!