Every week, the Cut posts a new sex diary — anonymous accounts from city dwellers about a week in their sex lives. Below, the nine that resonated with readers most, from a Hollywood assistant with a sugar daddy, to a married mom having sex on her friend’s bachelorette trip, to a Connecticut dermatologist excited about a threesome with her husband.
9. The Southerner Stumbling Into Her First Threesome
3:05 a.m. Spot L at the bar. I walk over and say hi. He seems happy to see me, but the conversation is a bit stilted. He makes me a drink and introduces me to his friend T. T is pretty, but dressed in a very boring outfit. Still, I decide to befriend her so that I have someone to talk to while L is working.
T is telling me how much she likes L and I realize that they’re together (this is unexpected!), but then she shyly propositions me to go home with them. (This is really unexpected!). Read the story …
8. The Woman Getting Back Into Group Sex
11 p.m. Back out by the bar and sufficiently tipsy. I start chatting with a group of guys and mention that I’m a bratty sub, which piques the interest of a cutie — Kyle — who looks to be about 40. Jared, Kyle, and I decide to go up to a playroom, and pretty soon I’m naked with two cocks in my hands. Kyle flips me over and starts fucking me from behind while I blow Jared. We rotate a few times and notice another guy watching us from the doorway. We invite him to join, and I swear he has the biggest dick I’ve EVER seen. My hand can only get three-quarters of the way around it. He starts fucking me from behind while I continue to blow Jared. We flip around again and Kyle stands over me to finish all over my stomach. Pure ecstasy. Read the story …
7. The Author Sleeping With a Not-Yet-Divorced Dad
8 p.m. I’m at a local place where I love to order a burger and a dirty martini. I’m eavesdropping on these two guys talking about their upstate homes. They’re older than me and scream married with kids, but I try to talk to them anyway.
It turns out one of them, Rob, is “separated.” He sticks around and we’re flirting and talking. He only gives vague details of his marriage, and I wonder if he’s lying. I won’t sleep with a married man. Cheating isn’t my thing. He says his “ex” lives in the city, while his divorce pad is in Brooklyn. They have a teenage daughter who shuttles between the two. This guy is attractive and I’d love nothing more than to have sex with him tonight, but his vagueness worries me. Read the story …
6. The Gallerista Getting an Erotic Massage at a Russian Bathhouse
4:34 p.m. I’m alone in the steam room and a guy comes in. He asks if he can put his towel down beside me. We chat for a little — he’s in finance and lives in Red Hook. He then asks if he can give me a massage. I’m kind of taken aback, but I say “yes” and lie down on my belly. It’s like a pornish fantasy come true! Read the story …
5. The Woman Getting Flown Out for a One-Night Stand
1 p.m. At coffee with my friend, trying to explain to her why I’m catching a flight to meet this guy. Here’s the deal: I met R in a hotel bar in West Hollywood about five months ago. He’s 25, lives in Seattle, and was traveling with his friend. He’s not my usual type — blue eyes, wavy golden hair. Happy. I typically go for gloomy, dark-haired, dark-eyed Slytherin types.
Anyway, R and I had a cutesy one-night stand, and I assumed I’d never see him again, but we randomly messaged on Instagram a few months ago and kept in touch. A few weeks back, we were on the phone, and he asked me to visit him in Seattle. He said he’d get me a ticket. I thought he was joking, but a few hours later I had a JetBlue ticket in my email. Read the story …
4. The Literary Agent Who Has an Affair and Leaves Her Husband
10 p.m. Back at my hotel. We’re pretty much immediately naked. I’m extremely turned on by George and the danger of it all. The whole time we’re fucking, I think to myself, I can’t believe I’m doing this … I can’t believe I’m doing this! Read the story …
3. The Married Dermatologist Having a Threesome in Connecticut
10 p.m. We head to the hotel room. The lights are off. I start kissing Ellie and she’s ferociously kissing me back. We are going for it. I’m really wet and take her hand and put it down my underwear. I’m actually afraid I’m going to come. I want to hold off and come when she goes down on me so I enjoy when she moves over to my husband — it means I’ll last longer if she’s not touching me. They kiss and he starts going down on her. It’s all a bit blurry because I’m drunk, but it ends with my favorite position: He’s fucking her while she’s going down on me. It’s truly like a porno. Read the story …
2. The Executive Assistant With a Sugar Daddy in Calabasas
1 p.m. Get a message on Seeking from a guy in his mid-40s who looks hot. He’s straightforward and invites me over to have sex. He also tells me straight up how much he wants to pay me. I ask for a little more money, and he agrees. Usually I wouldn’t meet someone the day they message me, but something about his directness turns me on. Read the story …
1. The Married Mom Having Sex on Her Friend’s Bachelorette Trip
9 p.m. We’re at a club and I’m drunk. I’m dancing with much, MUCH younger men, and no one is really doing it for me, but I’m definitely letting loose and grinding on them and feeling super-sexy. One of the girls had her boyfriend and his friends meet us. When they arrive, I immediately spot the guy I want to have sex with, F. He looks like Clive Owen, who has always been my biggest Hollywood crush. F is reserved and not going to grind on the dance floor, but we start talking at our table, and he makes me a very good drink, and I literally want to sit on his face just because he’s so hot and perfect for me.
We don’t hide our situations. He knows I’m a married American with kids, and I know he has a girlfriend living in Paris. I also know this is a man who would break my heart if I were single, so I’m happy that this is — or is possibly going to be — an innocent one-night stand. Read the story …
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