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

Chevalier d'Eon by Thomas Stewart

During my mission to find sex work that didn’t actually involve any sex I picked up a number of highly unusual jobs. My mission wasn’t limited to my attempts to become a fetish porn star, and even the creepiness I experienced there had nothing on the absolute tragedy of my dealings with Buddy.

Buddy was a crossdresser, which is not to be confused with a transgendered woman. Crossdressers identify as the gender they were assigned at birth but enjoy wearing the clothing of the opposite sex. They are very common and they are–in my experience at least–mostly men. I found Buddy during one of my daily Craigslist perusals; while he didn’t want any kind of sexual services, he did want a woman to teach him how to properly walk in heels. He promised fifty dollars for what he claimed would be no more than an hour and a half of work. Although fifty dollars wasn’t a lot of money, I figured none of my clothes were coming off so it was a fair enough price. Besides, at the very least I could get an amusing story out of it.

During the email stage, everything seemed to be going well. Buddy agreed to venture out of the suburbs where he lived with his mother to come see me in the city, and we agreed on a time and day. It wasn’t until two days before our appointment that things started to go downhill. Apparently the fact that he had knee surgery scheduled for the day before our appointment had somehow slipped his mind and Buddy would be unable to meet with me for at least another month. This did not bode well. I was pretty sure the appointment would never happen, but I was interested enough in the experience that I gave him another chance.

After much rescheduling, the day of the appointment finally rolled around. Buddy was over an hour late and did not answer his phone when I called at the half hour mark. I had resigned myself to the fact that our meeting wouldn’t happened when he called to inform me he was downstairs. I had never hosted a client at my house before, partly because I was uncomfortable with the intersection of my personal life and my professional life, and partly because my roommate at the time was a slob of epic proportions. While I had cleaned the apartment to the best of my ability, I was still very concerned about whether its cleanliness would pass muster.

When I got downstairs to let Buddy in, I quickly realized that the cleanliness of my apartment was the least of my worries.

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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!