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Showing posts from March, 2025

Gigolo Part III

 I knocked first and joked, “Housekeeping,” even though I had a key card. In my line of work, people rarely use their real names. Their profiles should be accurate, but they often leave critical information out that others might be able to trace. This particular client was new and was referred by a mutual friend and client. She asked that we skip the formalities and get straight to business. She informed me that she reserved a suite at a fancy hotel and that a key would be waiting for me at the counter. I entered without waiting and heard “back here,” as I said, “Hello.” It didn’t register right away, but as I entered the master bedroom suite, I came face to face with a longtime, close friend. She gave me a thousand-watt smile as if to say surprise before I picked her up and swung her in circles like long-lost friends would, but she wasn’t long-lost. She is in my current friend group, and I often play ball with her husband. I’ve never been a fan of his, and he has always simply bee...

Gigolo Part II

 “Cum on my feet,” and without hesitation, I withdraw my cock from her flexing hole to finish on the bottom of her feet. I’m easy and don’t judge; I mean, I’m cumming, and where is only a preference, and it might as well be hers. She does have great feet, and even though I’m a novice when it comes to footplay, I still know what I like. Her feet are always perfectly manicured and clean, so soft and aesthetically pleasing as far as feet go. I was amazed by how tight and accommodating she was able to present her feet and I have no shame saying that I fucked the hell out of her feet. On the contrary, she likes my feet all-natural, fresh out of the shoe, and even a little funky. Ultimately, I am still just a man, and I’m honestly happy, making my partner happy, and getting to get off at the same time is just icing on the cake. I knew her well-documented proclivities from reading her profile before she hired me. Like I stated, I’m game for anything, well, until I find out otherwise. Funn...

Gigolo VI

 There are few things more beautiful to me than a pregnant woman. My newest client came to me because she wasn’t feeling beautiful and expressed that her husband was treating her like a leper. I’m no therapist, and I wouldn’t attempt to justify his behavior, but I did try to put myself in his position. Once I did and discussed with her his possible perspective and how he might have reservations because of the baby, she shut that down real quick and was adamant that it was way more than that, and she knew how she allowed herself to be marginalized way before this and made it clear she knew and didn’t want to discuss it. I took my queue and returned to what I do best and simply listened.  On our first date, we went to this local and exclusive private place I know that is renowned for being just that. We created a back story that I was one of the OBGYNs in her group in case she ran into anyone, and we ate like two pregnant women without the guilt or shame she was apparently accus...

Gigolo V

“James, I want you to fuck my Rose,” “Whew,” I responded. “When you asked for the meeting and requested that I keep it between us, I was concerned.” He followed, “The only caveat being, I want to watch.” Relieved and realizing the cat was out of the bag, I chuckled, “Okay, but standard rates apply,” and I made sure he understood that he was strictly a cuckold in this scenario, but I’d give him the family discount.  This job is a bit different than business as usual. This request was made by one of my closest friend’s father. I’ve been friends with the family for over two decades, and his son obviously let my second job be known to his father, not thinking about the possible repercussions. He asked that I bartend his house party for her birthday the following weekend as a front and stick around after “To clean up.” I let it be known that I hadn’t made drinks in a decade, and he cut me short to let me know that there would be a real bartender and that I was more of a party favor. “N...

Gigolo Part I

I love my job. I feel I was built for what I do. Last night, like so many others, I had the absolute pleasure of spending the evening with a beautiful woman nearly twice my age. We enjoyed a fine dinner followed by drinks before we retired to her place. She is one of my regulars, and we’ve been intimate before, but last night, she preempted that she just wanted to fall asleep in my arms, with the caveat being that I spent the night. Sleepovers aren’t normally on the menu, but there are some regulars that I’m tickled to make the exception for. She requested a bath when we arrived at her place, and so I ran the water to a perfect 102 degrees. She has a classic Roman tub with a reading chair next to it so that I can read to her, which she often enjoys, or like tonight, I use the chair to bathe her and brush out her long silver-gray hair. I had already showered while running her bath before I put on the staple of my work clothes, medical scrub pants. Tonight, we’re happy in the silence, an...