I Had a One-Night Stand With a Wealthy Stranger in the Hamptons

Cosmopolitan

30-06-2025

It was a flawless summer day and I was going to the beach. Did I have any plans to go to the beach? Absolutely none. But, being a modern woman of the world—or at least a woman with access to dating apps—I didn't see any reason I couldn't Tinder some up. I threw on a bikini and got to swiping for the lucky random who would have the honor of escorting me to the coast that day.
Truth be told, I'd been in a bit of a dating dry spell—and thus, by extension, a sexing one—for the past several months. And once it's been a minute, I tend to get a lot pickier. The longer it's been, the higher my standards. Still, I somehow had faith that the dating app gods would bring me the perfect beach date that day. Miraculously, they delivered—a fit, tan, early-50s daddy type who, as a 20-something with a thing for older guys, just so happened to be my type. Within just a few messages, he invited me out to his house in the Hamptons. This beach day had just gotten a lot more glamorous.
I quickly dolled up a bit more than I'd planned to (handsome, rich Hamptons man was no longer just some Tinder rando I was using for a beach day—this man had long-term potential and I was ready to bring my A-game), then hopped in the car he'd called to whisk me away from my apartment in Queens and off to his Southampton mansion, congratulating myself on pulling the last-minute beach plans of my dreams out of thin air.
Now, can I, in good conscience, recommend going to a strange man's house hours away from where you live on a first date? Probably not. But listen, when a hot, wealthy Hamptons homeowner invites you to come dick around his place in Southampton all day, you don't say no—especially if you haven't had sex in five months.
As we neared his high net-worth address, he texted me words I could only dream of one day dropping so casually: 'Just tell the driver the gates will open automatically.' Excuse me? Who was I and how had I suddenly swapped lives with the kind of person entrusted to say things like, The gates of this Hamptons mansion will open automatically, Jeeves?
Inside, the man of the house—who, by some act of God, actually looked like his profile photos—gave me a warm greeting, a chilled glass of rosé, and a jaw-dropping tour of the place. It was exactly the kind of sprawling, sun-drenched, floor-to-ceiling-windowed affair you'd imagine, except all the more stunning because I wasn't imagining it. For one day, if for one day only, this was my real life.
I felt at once wildly out of place and right at home—that confusing feeling of misplaced familiarity you get when you wake up from dreaming about a place you've never actually been to but are certain you've dreamed of before. I had a sudden, childlike urge to run through the halls and try to get lost—to play hide-and-seek with myself in this strange wonderland I'd stumbled into.
He kept the tour of his bedroom brief and rather pointedly unassuming. For a man who invited random women to his house on a first date, he was surprisingly gentlemanly in that regard. And maybe I was just delirious from the rosé or the all-around opulence, but I was beginning to feel a kind of misplaced familiarity for this man, too. I felt drawn to him in a sort of past-life way, as warm as it was thrilling. An hour and a few glasses of Whispering Angel later, when he finally placed his hands gently around the back of my head and kissed me, it was one of those, What if this is really something? kinds of kisses.
I spent the rest of the day in a glorious rosé haze, splashing around half-naked in his shimmering swimming pool. I'd ditched my red bikini top in a sudden stroke of uninhibited bliss, shamelessly showing off for him as he watched from the steps of the pool. Something about him and this alternate universe we were sharing seemed to bring out an almost childlike recklessness in me—carefree and self-indulgent.
'Can I suck your dick?' I asked in another stroke of reckless abandon, swimming up to where he sat on the steps.
'Like, right here?'
'Yeah,' I said. 'I wanna see if I can do it underwater.'
Reader, orally gifted though I may be, it turns out I cannot suck dick underwater and neither can you. Don't try this one at home.
I grabbed his hand and he joined me in the pool, laughing off our little subaquatic experiment as I wrapped my arms around his neck and my legs around his waist, feeling his already half-stiff cock harden against me. You may not be able to suck a guy off under water, but you can certainly turn him on down there.
'Freckles,' he said suddenly, placing a hand on my cheek.
'Oh yeah,' I said, feeling my gaze falter under the realization that the extra layer of glam I'd applied specifically for him had washed off in the pool.
'Never wear makeup again,' he whispered, leaning in and kissing me deeply but softly.
I grabbed his head and kissed him harder. 'I want you,' I said.
We got out of the pool and he wrapped me in a fluffy white towel, taking me inside and leading me by the hand back up to his bedroom. This time, I knew I'd be getting the full tour.
He laid me down on the massive bed and pulled off my wet bikini bottoms, kissing up my thighs before settling his face between my legs. I don't usually like it when guys immediately try to go down on me. It tends to feel a little, 'Let's get your orgasm out of the way so we can move on to more important things, like my orgasm.' But not this time. I got the sense this man genuinely wanted nothing more than me in his mouth.
His tongue on my clit and his finger expertly working a come-hither motion on just the right spot inside me, I could feel myself approaching what may have been the fastest partnered orgasm of my life…until his sex playlist got cut off by an ad, that is. Apparently a man can have a pool bigger than your entire apartment and still not spring for Spotify Premium.
Laughing, I motioned for him to tap out. I've done some ungodly things in bed in my day, but one thing I won't do is get eaten out to a Taco Bell commercial. He laughed, kissing me and letting me taste myself on his tongue.
'I want you inside me,' I murmured into his ear. And I did. Yes, the oral was top-notch, but I was long-overdue for a classic dicking down. And so dick me down he did—in the surprisingly tender, intimate way he did everything. Still turned on from my almost-orgasm moments before, I came quickly, easily, effortlessly, with his warm body on top of me and his hard cock throbbing away inside of me. Like everything else that day, it felt magic, delusional, too good to be true—like I had somehow stolen someone else's life and gotten away with it.
I couldn't get away with it forever, of course. A few hours later, our flawless summer day had faded into a slightly chilly summer night. And, just like Cinderella, it was time for me to leave the palace and return to the humble life waiting for me back in Queens. He put me in a car, kissed me goodbye, and muttered some vague pleasantries about getting together again soon, never to be seen or texted by again. I'd have thought I dreamed the whole thing if it weren't for a few photos I'd made him take of me topless and careless in his pool—photos I've held onto as proof that for one gorgeous, rosé-soaked day, I got to live (and fuck) like the rich.