So there was this daddy — for the sake of this story, let’s call him V. We connected online and from the get go, I got weird (but not too weird) vibes. By this point, I had been sugaring for a while, so I was savvy enough to run for the hills when too many red flags popped up too early on — being overly sexual in the first few text exchanges, living far away and expecting me to commute, owning up to the fact that he’s not made of money and can only pay something ludicrously low like $300 per meet.
Though none of these applied to V, he made it clear that he was not interested in a pay-per-meet situation. While it was sketchy that he was so against the whole cash allowance thing — especially because he kept making references to his high roller life working in mergers and acquisitions — it wasn’t a total deal breaker. I had other streams of income and was not as financially desperate as I had once been.
I had also spent enough time around high net worth men to know what makes them tick. Oftentimes, their obsession with money stems from the power it wields when it comes to snagging premium pussy. This power allows them to surround themselves with pretty, little “things,” who signify their clout, in a way that is much more impactful than driving around in a fancy car or sporting an expensive watch. Anyone can buy a car. Not everyone has the magnetism to keep beautiful, interesting women in their orbit.
It’s not always about the actual act of sex. I worked for a wealthy entrepreneur like this. He was this larger-than-life, Andy Warholesque character who only hired super leggy, stylish youngsters to be part of his team — let’s call him Gerard. Gerard was always going on about costly signaling and the damage that could result from having an employee show up to a business meeting looking like a slob. He had billionaire friends in his circle and was constantly dangling all these lucrative opportunities in front of us, seemingly genuine in his mission to elevate the lives of those around him.
Gerard got us to work for him for free under the guise that we were putting in sweat equity and would eventually get ownership in his latest company. But he had so many different projects and moving pieces within each project that the timeline kept getting pushed and I eventually left, disappointed I wouldn’t be walking away with a big payout but more business-minded and self-assured in my ability to become an entrepreneur in my own right than when I had started.
Perhaps most importantly was the vast network of high net worth individuals Gerard had introduced me to, who — so long as I continue to avoid burning bridges — I can still tap into for work and seed money opportunities if I so choose. It was this experience — which some of my peers viewed as purely exploitative, but which I chose to view as more of a learning experience that opened doors — that made me willing to take a chance with V.
To me, V’s biggest green flag was his openness. He told me he was married and that he had multiple sugar babies. He also told me that he was not the kind of guy who expected or even wanted to have sex on a first date. Our texts left me intrigued and I figured he was worth making the trek to midtown for — which is saying a lot for a Brooklyn hipster who avoids this tourist-ridden hellhole like the plague.
I met him in his hotel suite and we hit it off right away. He was super personable and handsome — a swarthy brown man in his early 50s with a great physique. I told him about my goals and he explained how his arrangements were mentorship oriented. He had (allegedly) secured his babies internships and jobs at prestigious financial institutions, claiming to have remained close friends with all of them. In my case, as someone uninterested in working in finance, he proposed potentially becoming an investor in my startup.
We talked sex stuff. He evidently had a thing for incest. He showed me pictures of his college-aged daughter and said he would love to watch me fuck her – red flag number one. I indulged him, interested to see how candid the conversation would get. While he remained firm that the daughter thing was purely a fantasy, he proceeded to open up to me about his actual experiences with incest. V had grown up in what he called a “very sexually repressed country,” where, at the age of 14, he had lost his virginity to his 16 year old sister. He had continued to have sex with her well into his thirties, until she had decided to call things quit. He had another sister who he said he still fucked every once in a while.
If it’s consensual and everyone is having fun, who am I to judge? But the fact that he was so into taboo sex definitely made me weary of the fact that his sexual demands would be high. When our time was nearly up (he had told me he had a business meeting), he came clean: “I’m enjoying you so much that I don’t want you to leave. This business meeting is actually just another meetup with a potential baby. Can you just wait in the other room while I talk to her? I’d also love for you to join me for dinner. I’m celebrating the birthday of one of my babies with some friends.”
Per my say-yes-to-adventures-cause-they-make-for-great-content-for-the-memoir approach to life, I obliged. About 15 minutes later, he entered the room I was in with a friend — a super fat guy also in his 50s. V explained to us that the woman he had interviewed had been a total catfish, but that not to worry; there were two other women he had interviewed a couple hours before who had passed the test and would be joining us shortly. Sure enough, two cuties in their mid-twenties showed up to the hotel pre-game. One was in grad school and the other was also trying to start a business and looking for investors. V and his friend disappeared for a few minutes, at which point the three of us got to talking and realized that we were all new to the fold.
It struck us as a bit odd that he had decided to play this whole smoke-and-mirrors game (red flag number two) — lining up back-to-back-interviews and inviting us to a dinner that had been planned, but which we had had no idea about until just then. “We’re going to look out for each other, ya?” asked one of them. “Yes, let’s start a group chat,” I responded. Once V and his friend returned, the group made its way to Tao — a nice (but in my opinion cheesy) nightclub. Three of his regular babies were already there, along with another portly male friend of V’s.
His regular babies were all college girls — 19, 20, and 22 — who were clearly in a different place in their lives than the “new” babies, myself included. They were dressed up like dolls in over-the-top dresses and stilettos with full glam and an earnest desire to prove themselves. There is no amount of money in the world that could convince me to go back to that time in my life. Sure, you have that youthful glow. But you’re so lost in life, not to mention wildly insecure and desperate for external validation.
I was seated at the end of the table next to the other aspiring entrepreneur. We became fast friends, talking about all things holistic health while psychoanalysing everyone else at the table. “The 19 year old literally looks like that American girl doll, Kit Kittredge…what the hell is she even doing here?” she whispered into my ear, causing me to burst out laughing. The wine flowed freely and by the end of the dinner, everyone was loosened up and ready to continue the party — back in the hotel room. What came next was a full-on orgy.
Having gone into this whole situation blind, I was less than prepared. I hadn’t showered since the morning, was rocking granny panties, and was less than enthused to participate in group sex. I was down to make out with the girls, all of whom were super hot. But when I locked lips with the younger ones, I could sense their discomfort, which leads me to red flag number three. It felt as if they were going through the motions as part of a performance, rather than genuinely enjoying the experience.
It was all so sleazy. When I was 20, I was in a sugar relationship and having orgies with old people. At the time, it had felt exciting and edgy. But now, in my mid-twenties, I was able to see the borderline-predatory nature of it all and felt weird even pecking these naive, young women on the lips. Meanwhile, V was directing them to take turns sucking his dick, as well as his friends’. They happily complied, but as I caught their eyes, I recognized the disassociation that had overcome them and that I had subjected myself to in my younger days. “They are so going to be unpacking this in therapy someday,” I remember thinking to myself.
Red flags number four and five were the ugly friends who V was trying to get me to fuck (for free mind you) and the total lack of regard for STDs. I had never met any of these people before tonight. They had never met me. And yet there wasn’t so much as: “Hey you’re clean, right?” before clothes were taken off and genitalia was licked. Ultimately, that was what made me to decide to get the fuck out of dodge. Luckily, I had anticipated not wanting to go all in and had let everyone know I had somewhere to be at 11:30 beforehand. I left, as did my new holistic health buddy. “That was straight out of a movie,” she said, as I nodded in agreement.
We had similar conclusions, namely that V was a total creep who didn’t deserve any more of our time or energy. While everyone was of age, there was undoubtedly a Jeffery Epstein vibe to the whole thing. From orchestrating the evening under false pretenses to pimping out innocent, young women to his friends, it was pretty damn cringe. V wasn’t fake rich, like many of the creeps on sugar daddy websites are, but he was certainly well versed in manipulating women eager to get ahead into giving and giving without providing anything tangible in return.
Maybe he really has secured high paying jobs for his babies. Maybe he is a good guy who just likes to have fun. Maybe he would have been the angel investor willing and able to change my life. But having gotten myself into too many exploitative situations with high powered men before, I decided to cut my losses and walk away for good. I’ve ignored his texts inviting me to come to more of his dinners, which he hosts a couple times a month, and plan on staying as far away as I can from him and his harem of sugar babies.
As far as I’m concerned, I’m the winner of all this. I got an entertaining story, made a new friend, and managed to escape this bizarre sex ring STD free.
Jules
Based in Brooklyn, Jules has dedicated her twenties towards harnessing her pussy power, exploring the muse, whore, and wild woman archetypes along the way. When not blogging, you can find her sweating the toxins out in a hot yoga class or sipping a matcha latte at a pretentious coffee shop, whilst she scribbles away in her journal.
