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.

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.

When Buddy finally appeared into view, my eyes nearly popped out of my head: Buddy’s idea of “a little something” was a pint of peppermint schnapps and a case of beer. My bemusement turned suddenly to concern as Buddy stashed the case of beer in the trunk, got back behind the wheel of his car, opened the peppermint schnapps, and took a spirited swig. If my apartment hadn’t been just a block away, I would have bolted out of the car faster than you could say, “don’t drink and drive,” but I figured one block and one swig wasn’t so bad.

Once we got upstairs, I was relieved that Buddy didn’t seem to notice the mess. I had done my best to clean before he arrived, but the squalor of every room in the house (besides my bedroom!) was difficult to control. Seemingly oblivious to his new and squalid surroundings, Buddy just plopped down on the sagging couch and opened the case of beer he had laboriously hauled up the stairs.

I decided that doing makeup first was the way to respond to this situation. Perhaps if I got his makeup finished, I could convince Buddy that we had done enough for one day and he needed to go home. Such an easy way out was not to be, however. Although I painted his face very simply, the process took about 45 minutes because he kept requiring breaks to gulp down a beer and regale me with a story.

At first the stories were very innocuous and boring: he talked about events in his daily life and bragged to me about how he had one line in the press conference scene of The Dark Knight (he claims to be the man who yells “Things are worse than EVER!”) and despite the fact that he didn’t actually appear onscreen, it was the proudest moment of his life. Gradually, though, he became drunker and his anecdotes became more distressing.

In the hopes that he would be forced to concentrate and refrain from sharing any more stories, I suggested to Buddy that he put on his high heels and we could practice walking. I wasn’t sure how worthwhile this attempt would be; in the forty five minutes that I’d been doing his makeup and listening to stories, Buddy managed to finish off all the Schnapps and more than half of the beer. Here I was, stuck with a very large, very intoxicated man in very glamorous makeup, slurring about runway walks. I had no idea what to do, I couldn’t expect him to drive home in such a state–he lived in the suburbs–and cab fare was likely to be too expensive. …But he absolutely could not stay here.

Buddy seemed to have completely lost his motivation for the afternoon and besides that, there were three beers left and he was beginning to sway. I didn’t think it was a very good idea to continue lessons in walking and I didn’t want to just sit there listening to him, but I felt I had no choice. If I were to send him home now and he got into some kind of drunken accident, that would be on my head. Buddy cracked another beer and asked if I did any drugs. At this point I was legitimately worried that he might produce a baggie of meth in order to sober up for his drive home, so I told him I was straight edge. I doubt the Jack Daniels bottles lined up on top of my television helped my case, but I hoped Buddy was too drunk to connect the dots.

“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.