Rants, Feelings & Opinions

A Male Escort Recalls His Kinkiest John

September 17, 2017

If you’re a sex worker, being called upon to realize someone’s sexual fantasy is nothing new—at least, most of the time. Here, one male escort recalls a role play he will never forget.

S. Midtown
Atlanta

So, his story is easily the kinkiest experience I’ve had as a high-end male escort in Atlanta. I’d like to preface this story by saying that I love my job. There are some pitfalls, but the perks are amazing. Once I got over the stigma of my work, I couldn’t imagine doing anything else. I make thousands of dollars doing something people do for free. I look at sex work as a business, and that has helped me thrive.

My jobs are usually bears on business trips that want a nice piece of eye candy for the night—dinner, drinks, and some nice consensual sex at the end of the night. Often pretty hot, rarely anything that would shock even the minimally open-minded. But there was one “John” of mine, whom I will call Mr. X, that I will certainly never forget.

I met Mr. X at a hotel bar (his request) and I knew he was from money. He was wearing a four thousand dollar suit and a watch that would make an NFL player look twice. Mr. X was white, 6’4”, and in his mid-40’s. I’m no stranger to guys with money, but he had a way about him that made it obvious he was used to people waiting on him—mildly arrogant, a bit smug, but nothing I couldn’t handle.

Mr. X and I went on two dates that didn’t end in sex, but instead culminated in long conversations about my life and background. I thought it was weird that he hadn’t tried anything on me, but as long as the money was coming in, he could talk to me for as long as he liked. But after the second date thing started to escalate.

My liaison from the agency called and said that a package from Mr. X had showed up for me, containing something he wanted me to wear on our next date. I got the package and opened it to find a dress, high heels, lingerie, and a red velvet pouch of jewelry. I’m no stranger to gifts or a little cross dressing, but the fact that his fantasy involved me wearing no doubt twenty-five thousand dollars worth of clothing and jewelry was definitely, well, noteworthy.

On the night of our date I strapped on the black Agent Provocateur lingerie set, sequin Balmain dress, and platform Christian Louboutin heels and headed to the address he sent me. His home was a very beautiful stone manor in Buckhead with picturesque lighting. I knocked, and seconds later the door flung open. Mr. X was in dress pants and a blue button up (looking super J. Crew) and invited me in to the beautiful decorated home, which I later found out was left to him by his grandfather.

We ate dinner and talked a bit, and eventually Mr. X told me that he wanted to role-play. I said I was fine with it—I mean, it’s pretty common in this profession—but he suggested that this wasn’t the usual role-play. He lead me to the master bedroom where we started to kiss. Then he grabbed my almost shoulder length hair, and whispered in my ear, “I love my tranny son.” It took me a few seconds to really understand what he’d said, but I wasn’t sure how exactly to respond to that (this was outside the realm of my job experience, sorry). The talk continued: “My son the tranny slut, what if your mom knew you liked daddy’s cock in your boy pussy? Do you like wearing your mom’s panties?”

Usually, when I’m not into a John’s taste in fantasy, I will just make little noises and try to make the date go as quickly as possible (so like, the opposite of edging). But Mr. X was different—he was much more aggressive than the guys I’m used to. He stopped kissing me and demanded I take off the dress. I did it, because I just wanted to expedite the whole date process. He told me I looked “better in the dress than mom.”

As I started to ride him, the commentary continued: “I will buy you breasts if you want them; you do it so much better than mommy; I can’t wait until you have a pussy.” I rode him like a stallion—my trick for when I just want to get out of there. When he finally finished I laid there in the bed next to him for the customary five minutes, and then got up and grabbed my clothes off the floor and started to get ready to do a marathon sprint out the door.

He asked when he could see me again, and I told him to just make an appointment through the agency, trying my best not to make a scowl. But considering I’d just spent the last half hour being talked to as if I was his underage cross dressing son, I doubted I was coming back. I left the house, got in the car, and called my boss to say that I never wanted to see this guy again.

But… I did see him again. After a couple of months of Mr. X buying me clothes, shoes, and jewelry (all women’s by the way), I agreed to see him again for coffee for thirty minutes. We met up a few days later. Of course, being a sex worker myself, I am no stranger to judgement, and because of that I try not to judge other people. However, Mr. X’s fantasy was extremely off putting to me, personally, so I told him that we couldn’t meet again. I think he was expecting that.

About a year later one of my favorite clients, who I’ll call Teddy, took me to Los Angeles for an art gallery opening, where I ran into Mr. X and his wife. Mr. X never saw me, but I did have a very lovely conversation with Mrs. X about one of the pieces being sold that night.

Are you a sex worker who wants to share your story? Go on—we want to hear it! Please email submissions for Sex Work Diaries to karleyslutever@gmail.com. If your story is published, there is a small monetary compensation. 

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