Love Your Mommy and Daddy: I Gave My First Rim Job to a Dad Who Left His Kids at Home to Get His Ass Eaten by a Feral Sugar Baby
"I was the most obliging of fucktoys, the most diligent of ass-cleaners, the filthiest of Daddy’s filthy little whores—and I was fucking into it."
This essay is part of the “Love Your Mommy and Daddy” series, where writers share times they fucked people their parents’ age. Read the last installment here. If you are interested in submitting, please read the Boyslut zine submission guidelines.
I Gave My First Rim Job to a Dad Who Left His Kids at Home to Get His Ass Eaten by a Feral Sugar Baby
By Stella St. Regis
It was a sunny Saturday in April, and I needed dick. More specifically, I needed attention in the form of dick—and also money. I was 24 and on a sugar-dating hot streak. I’d dabbled in sugaring on and off since I was 21, but that spring, I had really hit my stride. I had a consistent thing going with one Daddy and a few others in the rotation I would see for a fuck and a grand whenever they happened to be in the city. In short, my finances and I were THRIVING.
The only problem with sugar daddies is that, at least in my experience, they tend to be largely unavailable on weekends. That’s when the married ones play house with their wives and children, and the divorced ones have their court-ordered quality time with the kids. (As for the single ones, I don’t trust them. This isn’t a universal truth—spoiler: nothing is—but my general read of single guys on sugar dating apps is either “Desperate” or “Straight-Up Sociopathic Narcissist.” Either way, best avoided.)
This isn’t usually an issue. I’m typically pretty content to do all my working, socializing, and fucking during the week and reserve the weekends for my version of GTL: gym, tidy (the bathroom), and laundry. But something about this particular Saturday was different. It was that frustrating part of mid-April when it’s too cold for bare legs but too warm for tights, so you just end up wearing fishnet stockings everywhere as a compromise. You know, that uncanny valley between spring and summer when you can feel something starting to shift in the air, but the full-blown Summer in the City horniness hasn’t taken hold yet. Which is to say, I was feeling restless—and reckless. I had finished my mundane Things You Have to Do to Remain an Alive Human Who Lives in a Society for the weekend, and the idea of spending my Saturday night in bed with a good book wasn’t cutting it. I wanted to get dressed, drunk, fucked, and paid—in that order.
What’s a girl to do when she’s feeling this particular type of way? Descend upon the men of Seeking (aka Seeking Arrangement, aka the website you’ve read about in literally every article ever written about sugar dating) like a madwoman, of course. If you’ve ever been on Seeking, you’ll probably agree that it’s often a lot more difficult to arrange a same-day hookup than it is on your traditional dating app. There’s a lot of flakiness, a lot of fake or otherwise sketchy profiles to weed through, and lots of people looking for lots of different kinds of setups and rendezvous. Even if you do manage to find someone who seems normal and on the same page, most men on Seeking—at least the ones worth talking to—have families or ultra-demanding work schedules that make it hard to simply drop everything and fuck...
Unless, of course, you’re hot or horny or persistent enough to convince them to do just that. I was some combination of the three when I started talking to Jay*, a divorced fifty-something in Connecticut, late that afternoon.
“I’m bored and need to get fucked tonight,” I messaged him.
“Wow. That’s quite a tempting offer,” he replied. “Unfortunately, I have my kids tonight. Can we plan something for next week?”
We could not. I was in full brat mode. The immortal words of our lord and savior, Ms. Kim Petras, were coursing through my goddamn veins: “If I cannot get it right now, I don’t want it at all.”
Fortunately, it seemed this Daddy liked a brat. Better yet, he seemed to have a specific thing for a brat who likes to take dick for money. When it comes to sugar dating, I like a generous giver—ideally, one who genuinely gets off on the quid-pro-quo power exchange of the dynamic. For a certain kind of man, showering a beautiful woman with gifts, monetary or otherwise, in reward for her gorgeous pussy is a turn-on—and that’s my favorite kind of man.
About an hour of suggestive messages later, Jay was in. He called a last-minute babysitter, sent an Uber to come pick me up in Queens, and told me to meet him at the lobby bar of the J House Hotel in Greenwich.
It was clearly the place to be in Fairfield County that night. Wine moms, WASP date nights, and divorced dads as far as the eye could see. My divorced dad (not the one who literally sired me, he’s actually still married to my mother, believe it or not—sorry to the haters and losers, but I am living, published proof that you can grow up in a loving two-parent home and still end up a horny little weirdo with a Daddy kink) was waiting for me at the bar with the cucumber-vodka-something-or-other I’d requested from the Uber.
I have little to no recollection of what we talked about at the bar that night—largely because it didn’t fucking matter what we were talking about, and we both knew it. We were clearly both there for one thing and one thing only. Two and a quarter cucumber-vodka-thingys in, he was all, “Let’s get a room.” And I was all, “Yes, but my cucumber-vodka-thing…” And he was like, “Bring it upstairs with you; it’s a hotel.”
Standing in the lobby, maybe a little too drunk, sloshing cucumber-vodka-something all over the Louis Vuitton bag I bought with some dude’s money while some other dude paid for a hotel room, I felt like I was fully in character—in the best way possible. The day-to-day life of a sugar baby is a lot less glamorous and scandalous than the 2010s Daily Mail headlines made it out to be. Maybe if you’re playing the game on a certain level, you’re regularly getting wined and dined by aging billionaires on private jets. But in my case, it was mostly nice restaurants, a fuck in a ritzy hotel room or sprawling Soho apartment, then back to my regularly scheduled life as an indebted Queens-dweller with three roommates. You’ve probably seen me on the subway, en route to or from some hookup with some rich guy, and never given me a second thought.
But that night, I felt like I was playing the part. Standing in the lobby of some upscale Greenwich hotel in my mini-dress and too-not-winter-for-tights fishnets while an obviously older man booked a hotel room, I assumed everyone who saw us had to know what was going down—and I liked it. I felt sexy. I felt powerful. I felt filthy. I felt like a dirty little whore, and I couldn’t wait to act on it.
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