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Another had a fetish for submissives and wanted to pay me ,500 a month to help him realize his fantasies.
An attractive couple wrote me seeking a regular “third.” By the time Darrell, a divorced man in his late 40s worth between million and 0 million, contacted me, I was relieved to hear from a potentially worthy candidate.
Unsurprisingly, Hank made a move on me, and I kissed him for a split second before withdrawing abruptly. I sensed that he wanted a puppet more than a girlfriend, and no amount of gifts or pampering could compensate for having to deal with such a controlling person.
So I scrambled to the front door—thankfully, it was unlocked—and bid Hank good riddance.
Then, matter-of-factly, he said, “Whether I met you on the site or at the Standard, you’d cost me at least 10 grand a month.”The site he was referring to was Seeking Arrangement, an online network that pairs people possessing resources (“sugar daddies” and “sugar mommies”) with those, usually much younger, seeking them (“sugar babies”).
I had become a member a few weeks earlier, partly as a social experiment and partly out of genuine desperation.
The rest of Hank’s profile, which told me that he was middle-aged, played sports, and worked in finance, was of less interest.
We set up a date and specified what we’d be wearing so that we could recognize each other—a navy-blue baby-doll dress and black tights for me, a striped button-down and a maroon cashmere vest for him.
I need a tall, blonde girlfriend.”When the waiter arrived, I ordered a very necessary glass of Sauvignon Blanc. I allowed Hank to feed me a piece of meat and chewed thoroughly.If I had a hefty allowance from a generous benefactor, though, I figured that I could take the leap comfortably. To overcome my reservations about walking the line between dating and prostitution, I told myself that any such concerns were the result of societal conditioning.The idea of wealthy older people supporting struggling younger ones is nothing revolutionary, after all—look what Peggy Guggenheim did for Jackson Pollock or the Tuohys did for N. The idea that mixing money and mating is inherently bad, I reasoned, was a fallacy based on our collective obsession with moralizing sex.(Seeking Arrangement skirts the issue of prostitution by promoting the exchange of “intimacy and companionship” for “gifts.”) I took a deep breath and posted my profile, determined to focus on New York–based single men claiming to be worth at least million. (Throughout this article, I’ve changed the names of the men I dated to protect their privacy.) Initially, he drew my suspicion with the cocky, typo-ridden message he sent me on Seeking Arrangement: “i think i maybe waht you r looking for; read my profile and if you r interested drop me a line.wont be disappointed.” Then I saw his net worth—0 million—and the amount he was willing to spend on a girlfriend: ,000 to ,000 per month.That would be enough to cover my living expenses and leave me with thousands in disposable income.
I was frustrated with my job, which offered little upward mobility, and was thinking about quitting it to pursue my goal of becoming a full-time freelance writer.