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The 50-Year-Old Fooling Around With a Polo Player in the Hamptons


Photo-Illustration: Marylu Herrera

This week, a woman heads to the Hamptons to sext with a new love interest and reconnect with last summer’s fling: 51, single, New York. 


8:32 a.m. On my laptop reading emails from home on the UWS. It’s been a busy week trying to put a project to bed. I’m a casting agent, and I’ve been searching for attractive pediatricians in Southern California for a TV commercial. I love my job because I can work from virtually anywhere in the world.

9:03 a.m. I open my apartment door and pick up the Starbucks bag that’s waiting for me. Every day, I get two venti cappuccinos with whole milk, an extra shot of espresso, and one raw sugar. I like the extra fat and the caffeine jolt.

11 a.m. Zoom with my client, who wants to make sure we will have a diverse and interesting selection of doctors for that commercial.

12:15 p.m. Text from X just to say he’s looking forward to seeing me tomorrow. He’s around my age. We met a few months back at a museum gala and slept together a few weeks ago. He’s my current love interest, even though we haven’t spent substantial time together romantically. Lots of sexy texts and a quick night at my apartment, which was really just a late-night blur. He texts that he’s fantasizing about me in a slip dress. We have plans to see each other tomorrow, so his fantasy might just come true.

7:06 p.m. Dinner at a French bistro with my daughter, who’s in her 20s, before she leaves for a weekend in Nantucket. She’s very independent, but I slip her my Platinum Amex card just in case. I’ve been divorced nearly a decade. I’ve been in two long-term relationships since my ex-husband with rather vanilla guys. Kind, super-smart, successful, but not very exciting or sexy. So I’m eager to see what happens with X.


7:26 a.m. Wake up wet thinking of X. I don’t know if I should be happy or afraid that he’s awoken the needy little monster in me. I haven’t seen her since I married my ex.

11 a.m. Check into a Park Avenue hotel because I’m throwing a lunch here for my friend’s 50th today, and even though I live in the city, I figured I’d get a room to add drama to my night with X later. It’s a nice suite on a high floor — spacious, great modern design, and a huge comfy bed. Perfect for my needs.

1 p.m. The girls arrive. I should say “women.” We’re all over 40! We head up to the rooftop pool with views of the city — what a great spot to kick off this beautiful sunny party. We have lunch and a few cocktails to celebrate my friend. The party is a success, but the entire time I check my messages to see when X will be arriving.

4:45 p.m. Everyone has left the party, and I’m ready to relax. It’s hot enough to put on a bathing suit, which is crazy for May. The sun on my crotch is like foreplay. A delicious aphrodisiac. I can barely wait. A buzz, a breeze, and a boy! What could be better than that?

5:40 p.m. In my room, I have a hot bath and moisturize every inch of my freshly waxed body. I consider staying in just my hotel robe but think that would seem too available, and it’s always fun to be undressed.

5:50 p.m. There’s a knock on my hotel-room door. And there he is with that huge grin and adorable face. His curly ginger hair is as bright as his blue eyes. He’s dressed boyishly in shorts, a T-shirt, and sneakers. It’s kind of awkward when you don’t know someone too well; you’ve only slept together once, 14 days before, and are suddenly alone in a large room with basically just a big bed smack in the middle.

6:15 p.m. Quick catch-up and some hot kissing, then I suggest we explore the hotel. He likes looking at architecture since he’s a builder and developer in D.C. We take in the views and look around the rest of the floor when he pulls me into an empty conference room that says “Private” on the door. He pins me up against the wall and kisses me intensely. Things quickly get really heavy with his hands down my white pants. I am so close to coming when a male voice from the doorway says, “You can’t do that here.” We skulk to the elevator.

7:20 p.m. Back in my room, our clothes are off in record time. He practically throws me on the bed and kisses me from my neck to my toes. He’s ravenous — I remember why I like him so much! I have my first orgasm of his visit. Then he enters me with a burst of energy, and after a few minutes of pounding, I have a second. Still inside me, he collapses in my arms.

8:59 p.m. I suggest room service. We eat in bed in the nude — my second-favorite thing to do in a hotel room! We talk about life, our families, summer plans, and that sort of bonding stuff while we snuggle, kiss, tickle, and massage each other. He likes to be touched as much as I do. Another plus.

11:11 p.m. I don’t know if he wants to sleep over. I also don’t know his relationship status — does he have a partner in D.C.? I don’t ask. I don’t really care. It’s awkward. I had a great day, some outstanding sex, a solid meal, and fun company. He excuses himself to make a phone call in the bathroom. I can’t hear anything — he must be whispering. A few minutes later, all minty fresh, he announces, “Well, it looks like you have a roommate tonight.” I’m very happy that he’s staying.

11:25 p.m. I’m not a good sleeper, especially with someone new beside me. I take a Tylenol PM. The lights are still on as I watch him get under the sheets — he is naked and nearly fully erect. He smiles at me with that boyish grin and grabs my ass. I am once again horny. The sex is so smooth … he is magnificent all over again.


6 a.m. I use the bathroom, freshen up, and sneak back into bed, hoping I don’t wake X.

7:15 a.m. We get up. I have to get out to catch a train to the Hamptons, but I tell him that I’ll arrange a late checkout if he wants to sleep in. But instead, the quick kiss heats up, and I notice his obvious erection.

9 a.m. Post-sex, with no time to wash up, I get dressed, kiss him passionately one last time, and fly out of the hotel room. I head straight to Penn Station.

9:54 a.m. I meet Randy, my best gay friend, on the track. We’re going out East for a weekend together. He doesn’t usually like to hear my sex tales, though. It’s a shame. I found the one gay man in NYC who doesn’t like to shop, style me, or dish.

10:17 a.m. As I sit on the train, thinking about X, I feel tender and tired and realize I smell like us. Not such a bad way to kick off the weekend.

12:44 p.m. We arrive at the former mansion turned hotel with a first-rate spa. It’s my great escape when I don’t have the time to be too far from home.

8 p.m. We go out for dinner. Randy is chatting up a busboy he remembers from last summer.

11:58 p.m. It’s been a long few days for me. It feels lonely in my king-size bed at the inn. I wonder where X is sleeping tonight and if he’s alone.


8:17 a.m. I see a missed call at 8:10 a.m. and a text at 8:11. Both from X.

I never answer calls before nine, and I don’t take phone calls after 10 p.m. I try to live a civilized life. I look out the window. Clouds.

9 a.m. Randy knocks on the connecting doors. Breakfast in my bed or the buffet? If he were X, I’d opt for bed. He is not, so I suggest the buffet and a bike ride.

10:30 a.m. The skies open up. We are about a mile from the hotel.

11:15 a.m. We finally make it back to the hotel. My white T-shirt, now transparent, is sticking to my skin. My phone pings — it’s a video call from X. I never called him back earlier. I pick up laughing. He sees me and smiles his massive, toothy smile. I tell him I’ve never been this wet in my life. “I’ve always wanted a woman to say that to me,” he says. “I just always imagined it would be in bed, not in a downpour.”

I like a man who can make me laugh. I flip the phone around and introduce him to Randy. I promise to call him later, but I have to go to my room and dry off.

8:07 p.m. Dinner with Randy. He’s in his best shorts, a freshly ironed dress shirt, and Gucci loafers. He’s preoccupied for some reason. Ahhh … guess who’s working tonight? The busboy. Randy’s feeling randy! By dessert, I realize Randy will likely be having a guest later tonight.

11:04 p.m. Back in my hotel room, I look at my phone. There’s a text from X. I still haven’t called him back! I look at the time and say fuck it, rules were meant to be broken. I don’t want him to think I’m playing hard to get. I text him good night, but he wants me to call him.

I dial. He picks up immediately and asks me what I’m wearing. And just like that, we have phone sex. It makes me miss him more than before!


9:17 a.m. I slept late. More rain. I consider going home. The hotel is fine, but I miss my bed, my good feather pillows, my D Porthault linens, and healthy food. I’m also tired of room service and the same predictable breakfast buffet.

10:50 a.m. I drag Randy to the spa to see what services we can schedule. He wants to have his asshole bleached, but of course they don’t do that here.

12 p.m. On the massage table waiting for my massage therapist. I like strong hands, so I always request a man. After 90 minutes of heaven, he tells me to take my time getting up from the table. I use the opportunity to bring myself to orgasm as quickly as I can. I wonder if he knows what I’m doing? That’s my favorite thing to do after a massage. Now I’m really relaxed.

8:06 p.m. We go to a country club for drinks followed by dinner. I’ve never been a huge fan of their chef. I’m doing this for Randy. The poor man works like a dog in the entertainment industry. He works harder than I do and makes more money. He deserves a little fun.

9:08 p.m. A well-known polo player who I slept with last summer stops by our table to say hello. He asks where I’m staying and when I’m headed back to Manhattan. He suggests I stop by his stables so he can show me his new ponies. I like ponies, but I’d like to see something else. I feel very frisky since my massage.

11:37 p.m. Randy wants to hang out. I’m ready to leave. I walk over to polo guy’s table and ask him if he can drop me off at the hotel on his way home.

11:44 p.m. He helps me into his car carefully, running his warm hand along my back and down to my thigh. Every hair on my body is at attention. He kisses my cheek and closes the door.

I’m tingling as I remember those hands. As he starts the car, I put my hand on his thigh. I smile. I tell him how much I missed him all winter. He says we should go somewhere, but I tell him to just pull over and we fool around, right there in the car.


9:05 a.m. The phone wakes me. X sent a photo from his rooftop terrace. It’s gray and wet in D.C. too. Good to see he’s checking in regularly. I text him a sexy selfie.

2 p.m. Randy and I have a late boozy lunch at the hotel pub. I take a nap while he takes a Peloton class.

8:16 p.m. Dinner at a small, family-owned beachfront restaurant. My family has been coming here for decades. I know the staff and see lots of familiar locals. Always a good feeling coming back here.

10:30 p.m. I take an Uber back to the hotel while Randy goes to the club to see the twinks. One wants to fuck him in the men’s cabana. It’s after-hours and he has the key. I’m a little jealous.


9:05 a.m. It is still raining. Ugh. I have my last breakfast in bed and do a little work. I need to prepare for a meeting tomorrow morning.

1 p.m. Late checkout. Even though Randy is usually pale as a ghost, he’s glowing from all the sex he’s had with the busboys. Going to get the 2:14 train back to the city.

3:05 p.m. My phone pings. It’s X. We talk about my workweek and various meetings I have going on. We say the weekly weather report looks rainy in both New York and D.C. He sounds like he has something to say but is hesitant. We hang up and agree to chat later.

8 p.m. I’m home and all settled in. X calls me back. He tells me to come to D.C. “There’s plenty to do here in the rain. And if we’re going to be wet, we might as well be wet together.”

10 p.m. I go to bed, unsure what to think about any of it.

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Alyssa Shelasky , 2024-05-25 01:00:02

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