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

After greeting me, the first words out of his mouth were, “Do we need to buy any makeup?”

Buddy seemed to have decided that I was not only going to teach him to walk in high heels, but that I would also be giving him a lesson in the rudiments of cosmetics. If there was going to be a makeup tutorial, we certainly did need to buy some: Buddy was a somewhat swarthy man, made swarthier by the garden of whiskey roses blooming abundantly over his cheeks and nose. Even if I could have been persuaded to part with a few dabs of my precious Chanel foundation, it would have made him look a Kabuki performer.

“Yes,” I said, “If I’m going to teach you about makeup, we’re going to need to buy some. There’s a Walgreens right around the corner, I can help you pick stuff out.”

The Walgreens was about four blocks away, but Buddy insisted we drive. He claimed that, due to his recent knee surgery, he would be unable to walk long distances. I found this somewhat confusing as he expected to practice walking in high heels, but hey, fifty bucks was fifty bucks. And, if I could while away the time with makeup purchasing, I figured it would be a win for both Proctor and Gamble and me. At Walgreens, I helped Buddy select foundation to match his skin tone, a tube of mascara, and an eyeliner pencil. He seemed pleased with these purchases, but when we got to the register, things began to go downhill.

“You’re paying for this, right?” Buddy asked.

No, I was absolutely not paying for it. When I explained that he could either buy his own supplies or go makeup-free, Buddy grudgingly paid.

I thought that would be the end of my problems, but I would soon see how very, very wrong I was.

Things started to get really out of hand when Buddy noticed the liquor store down the block from my apartment building. He decided he would stop in for “a little something”. I was somewhat puzzled at his desire to consume alcohol at the relatively early hour of one in the afternoon but I wasn’t too worried. What was the worst he could do? Pick up a 40 and maybe get buzzed? Buddy was a big man and he looked old enough to know his limits. I gazed idly out the car window as I waited for Buddy to return from his liquor store jaunt.

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    • Jen

      Yi-i-i-i-i-ikes.

    • 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!