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

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.

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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!