Teddy had been doing trade for about six months. In the sort-of relationship he was in at the time, his sort-of boyfriend had done erotic massage for clients and suggested that Teddy do the same; his hard rubdown is top notch, I can confirm from personal experience. Teddy was considering the proposition more and more, until finally, he recruited the wisdom from some friends in the sex work industry and signed up for a Rentboy account.
We were hanging out a lot when he first got his account, and I was keenly interested in the requests coming in from various johns. I was both jealous and turned on when the first guy wanted to pay him $200 to jerk off while he licked Teddy’s feet, but that didn’t end up going anywhere. (Hint: don’t send the guy pics of your feet, he’s just trying to get off for free.) Then there was the guy who wanted to know if Teddy had a cold because he was really interested in having him collect his dirty tissues and eventually come over to sneeze on him. No shame man, do your thing, but Teddy just isn’t the guy for that kind of gig.
He didn’t really do it much but he did pile on a handful of regulars, all in the mostly vanilla area of satisfaction. It all seemed pretty casual and playful, and certainly financially lucrative.
A mutual friend of ours, a female bodied beauty who goes by the name Lolita, has been doing sex work on and off since adulthood, catering to the imagination and fantasies of her clientele, orchestrating beautiful and erotic scenes that most people only dream about. Her focus is on ass play and providing space for straight-identified men who don’t typically have many options for that kind of eroticism. She also caters to a high-end clientele, meaning she comes at a premium price tag. Lolita had an out-of-town client who was interested in an encounter with her and another man, so Lolita asked Teddy if he was interested. He happily accepted, thinking, “There’s a first time for everything!”
The two of them embarked to Birmingham where the john—we’ll call him John—had arranged a stunning multi-room suite for their sexcapade. Teddy describes the guy as a “cute, bearded, mid 30s, submissive entrepreneur . . . just my type.” Being so new to this type of scene, Teddy was mostly shy as they went into the suite and exchanged drinks and small talk. John complimented Lolita and Teddy on their chemistry, which served as the perfect segue to get things going as Lolita leaned in and starting making out with John on the couch they all shared.
Teddy started to rub John’s back, and John acknowledged by rubbing his inner thigh. Both boys immediately got hard and the three bodies intertwined in shared kisses as clothes started to quickly peel away. Most of the session was about focusing on John, and Teddy was the featured guest as Lolita led the way; this was her gig, she was the domme, and she ran the show. Having been primarily focused on the client, Teddy caught a moment to admire the beauty of Lolita’s body and presence. Seeing the two of them together was a huge turn on, and he was enjoying the view. Voyeurism is participation after all.
Throughout the eight-hour scene, there was an array of dick sucking, ass eating, and fucking, but John really loved having his ass played with. For a long time Lolita used several toys on him, “dildos of every shape and size!” John hadn’t seemed the least bit interested in Teddy’s cock during their encounter up to this point, but never underestimate the lure of butt sex! John practically begged Teddy to fuck him.
“Have you ever been fucked by a guy before?”
“No. There’s a first time for everything!”
Teddy put on a condom and slowly penetrated John while looking in his eyes and kissing him. He fucked him slow, then fast, until they both came while Lolita sat on John’s face and jerked his cock to completion.
It was amazing and wild and fun! After a while the three temporary lovers took a break and ordered delivery for dinner, but once they had rested a little and their time started to dwindle down, things heated up for a final round. John and Lolita fucked for a bit and then he looked at Teddy and said, “Your turn to fuck her.”
Teddy and Lolita exchanged glances and with little hesitation, being the true professionals they are, embraced as friends and lovers and colleagues, experiencing one another’s flesh in penetration. Their sex was passionate and effortless, the demands of the scene outpouring in beautiful ecstasy. John stroked himself as he watched the two of them together, eventually joining back in for a final explosion to bring the scene to a climatic end.
The thing that Teddy didn’t tell anyone was that he had never had sex with a girl before. There’s a first time for everything.
They each made $2,500 for the encounter, and John’s feedback made it sound like he was very satisfied with how he spent his tax refund this year. Teddy and Lolita had a brief moment of concern about how the other was feeling after the encounter, which only required a single conversation to realize they were both feeling great with how everything went down. So good, in fact, they’re planning on teaming up again for the right client. There’s a second time for everything!
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