At the Risk of Losing a John

I’ve received requests to discuss my experience in the sex industry during my time as a Rentboy. While I enjoy documenting the various events and shows I attend, it’s a bit more difficult to do that with the guys who have and may continue to hire me. I value discretion when working with clients. Hiding the identity of clients can be done through pseudonyms and omissions of key identifiers so, at the risk of losing this John, I’d like to share the time I was fucked by your coach.

After Manhattan recovered from the effects of Hurricane Sandy, Rentboy recovered their systems and had the website back up and running which opened the floodgates to a gaggle of horny men messaging me. After making the rounds one evening, I made my way to the Financial District for my last client of the night. I was surprised to discover that this John was one of the guys with whom I had been talking online earlier in the week. We weren’t able to meet then because I, like many other New Yorkers in unaffected areas, was hosting refugays at my apartment. While I was more than appreciative of the money, and definitely needed it at the time, I would have gladly given myself freely. When I asked why he didn’t ask me while we messaged he replied, “I took your reluctance to meet as a sign that you weren’t interested. So I decided to cut to the chase and hire you for the night.” I was immediately hard.

Upon arriving to his hotel room, he opened the door and wasted no time stripping me down and throwing me onto the bed. His arms, covered in tattoos, held my legs apart as he plunged his tongue inside my hole, lubing it up for his pleasure. He started to reach for the condom next to me when I took him by surprise and pushed him onto his back so that I could climb on top and straddle his cock. Slipping the condom over his thick meat, I slowly sat on it and took every inch until he was deep inside me.

I rode him for a few minutes, taking pleasure in watching his eyes roll to the back of his head as he groaned in ecstasy. Holding me to his chest, he lifted me up and positioned me on my back where he took advantage of our significant size difference by pinning down my squirming body. I playfully struggled to regain dominance, but he easily wrestled me into submission, putting one hand on the curve of my back and the other to hold my hands above my head. He looked down at me and smiled as he drove his cock deeper into my tight hole, knocking the breath out of me.

After we both came he held me against his furry chest and tried to explain the rules of American football. As cute as that was, I pulled him into a kiss to quiet him so as not to ruin the moment. Laughing, he stroked my hair, pulled out another condom, and asked, “Are you ready for the second quarter?”

Photographer: Patryk Chaou

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