We’ve asked over 700 people and counting to open up their bedrooms (and wherever else they’re having sex) to us for our ever-popular “Sex Diaries” column. Every week, an anonymous city dweller divulges to writer Alyssa Shelasky — who has helmed the column since 2015 — every date, horny text, orgasm (or not), and more in unapologetic, NSFW detail to comic, tragic, often sexy, and always revealing results. These are the diaries (ranked in order from tamest to wildest) that blew up our group texts, inspired an internet conspiracy or two, and still make us blush all these years later.
69.
The 25-Year-Old Hooking Up With 6 Guys in 7 Days
5 p.m. We make plans for him to come over soon. “What about tonight?” He asks. Even though I’m horny, I hesitate, thinking about the fact that I’ve had guys over the past two nights. But then realize I’m slut-shaming myself. “Sure!”
68.
The Computer Scientist With a Sugar Daddy
8:30 a.m. R we still meeting, the text reads. It’s my … well not exactly sugar daddy. T is very religious and thankfully can’t consummate our “relationship.” He’s recently divorced and I predictably met him at the club. Sometimes he takes me shopping, pays for dental visits, and meets me at velvet-booth restaurants where I order diver scallops and glasses of 40-dollar Riesling. Tonight I need money — a lot of it. Between manic spending sprees and slow nights at the club, I woke up to a low-balance notification.
67.
The HR Manager Who Likes Being Called ‘Master’
7:30 a.m. My morning text from Leslie is more sexual than normal. She’s feeling horny. Over the last eight months she’s gotten to know my likes and dislikes and I hers. We like to play, and sexting has become part of our routine; she says something to get my motor running … we have dominant/submissive roles. She enjoys when I tell her I will spank her when we’re together, and she knows I love when she responds, “Yes, my master.” I always had this type of fantasy, but was never able to actually fulfill it; as Leslie and I started communicating, it came to light more and more.
66.
The Ambitious Young Creative With a Sugar Daddy
6:30 p.m. As everyone starts to leave, I tell my co-workers I’m just finishing a few things up. I’m actually not. Daddy is picking me up in an Uber, so I’m waiting for most of my team to leave so that no one sees me walk out of the building and jump into a cab with a man 20 years my senior.
65.
The Single Mom With a Boyfriend and a Girlfriend
12:45 p.m. Lizzie is coming over tonight. Almost all my dates happen at home — babysitters are expensive. Home dates mean a lot of fooling around in my bedroom. Which fortunately is on the opposite end of the apartment from my son. So far, it’s not an issue. I get the tingles (there’s really no other way to put it) when she texts me.
64.
The Student Obsessed With Their Ex’s New Celebrity Fling
6 p.m. I’m signing out of my work email and into my personal one when I see the option to log in to another account. My ex accidentally swapped computers with me for a week last winter break. I know I shouldn’t but I do. I find Zoom links. Receipts. Then a boarding pass.
63.
The Mom Breaking the Rules of Her Open Marriage
8 a.m. Work is nuts today. I’m the director of programming for a retirement community. With the holidays coming up, the residents are needier than usual. Plus: I’m horny! I’m hoping my dom will sext me soon — he’s in tech and just turned 50. We’ve been seeing each other a few months, but have been too busy for the last three weeks to play. I’ve missed him.
62.
The Married Woman Who’s Been Cheating For Six Years
7:50 a.m. Wake up and check my phone immediately to see if M sent me an early morning text. Nothing. I hate the weekends. His wife checks his work phone and personal phone like a lunatic (we’ve always communicated on his work phone). I find it bizarre — if you’re that insecure, why are you married? Time to take my basal body temperature, I guess. The thing about M and I is we’re both married — to other people. And my husband, D, and I are trying to get pregnant.
61.
The Married Woman Trying To Keep Up a Covid-Free Love Affair
2 p.m. Take a little break to call John. John is the man I was having an affair with before COVID. We’ve been seeing each other on and off since before I had kids. I have three kids now, so it’s been a while. We worked together at a fashion label before I quit to be a stay at home mom. He was married too, but now he’s divorced, and he has no kids. The affair has been going on so long that it’s just a normal part of my life now. My husband thinks John is gay. They never met so I always just referred to him as my gay BFF from work, so he doesn’t blink if John calls or texts. Anyway, John and I can’t fuck around during COVID because I can’t put my family at risk so we’re just really missing each other right now, and talking all the time. Today I call him just to tell him I love him and to escape my life for four minutes.
60.
The Woman Sexting Her Married Coworker
9 a.m. Sitting at my desk. My phone vibrates. It’s a text message from an unsaved number, but one I recognize nonetheless. I don’t hear any footsteps coming toward me, so I unlock my home screen. It says, “What r u wearing today?” I text back: “How about I tell you what I’m NOT wearing instead?”
59.
The 23-Year-Old Chasing Middle-Aged Men in the Suburbs
10:00 p.m. I’ve been talking to Ben, 38, for a few weeks now, and our schedules have finally permitted an evening together. He lives in Greenwich too. We’re having a really nice time chatting over a drink at his house, and I’m trying not to lose myself in his Newman-esque baby blues. We make out on the couch for a solid 15, shed a few layers, and then move to his bedroom where I blow him, then he blows me. He’s demanding that I come on his face. But those eyes!
58.
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 possibly going to be — an innocent one-night stand.
57.
The Assistant Who Wants a Sex and the City Experience
11:30 p.m. We’re in the back seat of the cab, making out, hands everywhere, lots of hair pulling, lots of neck kisses, and then he unzips my pants and starts fingering me. I start moaning, not really caring that the taxi driver is there.
56.
The Publicist Who Loses His Underwear on Fire Island
10 a.m. Wake up to W shouting at us to get breakfast. It’s eggs with some meat and peppers mixed in. Tastes glorious. When I get to the kitchen I realize I’m still in my black underwear from last night. Except they’re not mine. They’re a different pair of black briefs. Fuck. Nothing gets between me and my Calvins — except another dude, apparently.
55.
The Aspiring Podcaster Making the Most of His Open Marriage
8:30 a.m. My husband and I met about ten years ago at a gay bar in Brooklyn. We’ve always been open. The week we got married (at a beautiful restaurant in Manhattan), we both fucked other people. We laughed about it then, and we still laugh about it. As for our own sex life, it’s very tame. We have sex with each other once a month or so and not much else in between. I mean, we’ve been together ten years … what do you expect?
54.
The Mom Having Second Thoughts About Her Lover
7 p.m. He’s here, in my arms. I love kissing him. I love being in his embrace. Our connection is sexual and emotional. It’s perfect. I will never pressure him to leave his wife because I don’t personally care about paperwork and/or whether he’s officially divorced. I do think he needs to confront her about the fact that the relationship is over though.
53.
The Architect Asking Out Random Men on the Streets of Boston
11:30 a.m. I stop someone cute on the street and ask him where I should go for lunch. “Any good sandwich shops?” I say. He’s actually cuter than I realized. Really nice eyes — blue. A nice suit. He smells good … somehow I know that even from an arm’s length away. He suggests a place nearby. I love his accent.
52.
The New Mom Whose Husband Turns Her Down in Bed
6 a.m. I’m dreaming about hooking up with a cute, shy chick … then Baby L wakes me. I groan and ask Peter if he’ll change L. Peter obliges immediately — I have a great husband. He lies in bed with me, holding my hand while the baby feeds. Once I lay L down, Peter starts rubbing my back. I’m still kinda aroused from my dream. I spoon Peter and start touching him but am met with a soft “no” of rejection. It doesn’t faze me; sometimes, one of us is just too tired for sex.
51.
The Woman Having Sex With Two Men in One Day
6 p.m. Uber to fuck buddy No. 2, The Gymnast, who I also met the night before on an app. This one is my age, extremely tall at 6-foot-6 and absolutely handsome as hell. I wanted him to film me while he fucked my mouth, but he clearly hasn’t done that before. We have very different definitions of what “naughty” means.
50.
The Married Trader With a Sugar Baby
4:30 p.m. Every other Tuesday, I go to physical therapy for an old back injury. But the wife thinks I go every Tuesday. This is not a PT Tuesday. This is a Brie Tuesday. Brie is my special ladyfriend: We met at a fund-raiser about six months ago, and she is 24. It is pure sex. And money.
49.
The Woman Whose Fiancé Cheated in Nantucket
11:20 a.m. I call Tad and tell him I don’t want any of Natalie’s friends at the wedding — Natalie is the woman Tad cheated on me with a year ago. He says it was a stupid, wasted mistake in Nantucket, that it meant nothing. He actually swears that he can’t even remember what exactly happened.
48.
The Yoga Teacher With a Food Fetish
7:30 p.m. My partner and I are engaging in another great conversation, but I keep stealing glances at the box. He’s making himself dinner, and I’m not sure if he thinks we need to wait for “dessert.” Finally, I tell him that I’d like him to feed me the cake, small bites at a time.
47.
The Stay-at-Home Mom Turned Foot-Fetish Model
5:55 a.m. When I was in college, I was a foot model for some big designers. A photographer friend clued me into the foot-fetish industry and let me know how much my feet are worth. Once my money problems got big enough, I remembered this … and started dabbling. From time to time I will get mildly aroused — honestly, usually not. It’s a job. At the moment, I’m not in any real sexual relationship …
46.
The Woman Experimenting Before Moving to L.A.
5:45 a.m. We’re in their bedroom and they’re undressing me. I’ve never done more than kiss a girl, but I’ve always wanted to try more. Her nipples are pierced and it’s so hot. I suck on her nipples for a bit and decide I’m going to go down on her. This is so wild. I cannot believe I’m going down on a girl!
45.
The Webcam Model Who Excels at Multitasking
6:30 p.m. I decide to get back online again to see how the cam traffic is. It is steady and I see some of my regulars. I play naughty stepmom for a 21-year-old guy and suck my eight-inch dildo as he tells me how much he loves my tits. He wants me to ride the dildo and bounce up and down like I am riding him. He tells me how hard his cock is, and that it’s throbbing. I love getting these young guys turned on!
44.
The Woman Trying to Save Her Relationship After Cheating
2 p.m. I stop by Jesse’s bar. He gives me a really big hug, even though he really shouldn’t. He can tell I need it. He smells so good. I would have loved to fuck him that night. What are these feelings supposed to mean? Is it normal to want to sleep with someone else when you have a serious boyfriend? Is this a sure indication that Eric is not right for me?
43.
The Woman Traveling to Europe With a Bag of Sex Toys
9 a.m. PB and I met in Switzerland, where I spent most of lockdown, even though I’m a New Yorker. I work in hospitality, so I had to shut down my business for a while. It’s been a little over a year since I’ve seen PB. We met via an app that I was just about to delete. During our initial sexting, he told me how lockdown had left him lonely, super horny, and looking for sex, drugs, or violence. I told him I could offer all three — I’m a former professional dominatrix, after all. Within an hour, we met up and had something of a marvelous mutual masturbation mess. It was wickedly satisfying. Witty textual banter has ensued for a year, and today I’m flying back to Europe — Switzerland, then Italy — to see him and all the other friends I made there.
42.
The Woman Questioning Her Relationship After a Sex Party
8:15 a.m. Harry and I started dating six months ago after meeting at a party and we’ve been inseparable ever since. Things are pretty great, except when they’re not. Which is … often. Harry’s an actor, and while I love being with him, he’s not exactly boyfriend material. He made it clear up front he wasn’t interested in an exclusive relationship but I haven’t been with anyone since him. It’s not as much security as I’d like but I think it’s worth it.
41.
The Poly Drama Teacher Having a Threesome in New Jersey
5:55 p.m. Masked up and taking two trains to a threesome in Jersey City. This will be my first sexual experience with other people since early December. The best thing about poly life is that two things can be true at the same time. You can be emotionally bereft at the staggering absence of someone you loved and still wanna get railed by C, a six-foot-tall, glam-rock–looking photographer, and L, his feisty Tinkerbell-size girlfriend. This is our fourth or fifth time playing together. I’m bringing my strap-on harness and my polka-dot dildo, per their instructions.
40.
The Woman Secretly Moving in With Her Boyfriend in Uganda
7:30 a.m. It’s finally moving day. Last night, I kept wondering if I really want to live with R, or if I just don’t want to live with my brother anymore. If I’m being honest, maybe I just want to have more sex? R was my first, about a year ago. We’ve had sex about 12 times. Yes, I’ve been counting.
39.
The Marriage Therapist at a Tantra Retreat
7:01 p.m. Everyone’s here and I’m fascinated. As a marriage therapist, I’m used to meeting couples for the first time and I frequently find myself wondering what on earth they’re doing together. But here, all the partners match. In fact, if everyone had been standing by themselves, I bet I could have accurately paired each person with their mate. And, with one exception of a couple in their 70s, they’re all around our age.
38.
The Unemployed Woman Whose Date Venmos Her $500
4 p.m. Meow, hello “Rob.” It’s a rare occurrence that I match with someone on Seeking Arrangement who is cute and young and willing to pony up. His profile states that he’s looking for someone who is “curious.” Some things to note: If a man writes that he expects “complete discretion” that means he’s married. If he writes that he’s looking for someone “open-minded” that means butt stuff. If he writes that he’s open to “new experiences” that means you’d better prepare yourself to be asked to do group sex. I feel like “curious” will be something akin to butt stuff, but he is really cute …
37.
The Attorney Trying to Avoid Another Office Affair
2 p.m. We’re at the party, starting to drink and play beer pong. David and I have a lot of aggressive banter during the game that I think is making everyone uncomfortable. After kicking his butt he comes over and puts his arm around me and pulls me in for a kiss. Isn’t it a little early in the day for this?
36.
The Mom Trying to Hook Up With Her Ex on Family Vacation
9:00 a.m. We’re both taking the day off work and pulling my daughter from preschool to go see friends in Philadelphia. I have an ex-boyfriend who lives out there and my goal is to see him somehow. He’s divorced and looking good on Facebook. I DM him that I’ll be in town and would love to hang out, but for all he knows I’m just a married mom now. Let’s see if he bites …
35.
The Overwhelmed Mom Still Finding Time for Lots of Sex
8:30 p.m. It’s like my body knows when it’s time for morning sex. I wake up automatically and kinda rustle my husband up. We both have morning breath so no kissing, but I have him fuck me slowly while we’re in a spooning position. We both come and I hop in the shower to start the day.
34.
The Novelist Having an Affair With a Successful Artist
11:30 a.m. We get up from the restaurant and walk down the street. I’m kissing him against a brick wall and I know he’s hard;I need to fuck him. I tell him we need to find a place to have sex. My apartment is so far away, I can’t wait that long, and I want to be more adventurous than that. He has no good suggestions. He’s letting me down here. I’m acting like a spoiled brat. I throw out some terrible ideas like fucking on a quiet cobblestone street midday, or running into a Starbucks bathroom. He denies me. I have to accept that the answer is no. I feel rejected, plus whatever the version of female blue balls are.
33.
The Publicist Sleeping With the Chef at Her Family’s Estate
11:30 a.m. A group of my old friends are visiting for the long weekend from a nearby midwestern city, and it’s the first gathering we’ve had in many months. Everyone got tested before coming, and we’re mostly hanging out by the pool in face masks. I’ve been sneaking around for hours now with the chef at my family’s estate, a man I’ll call R. He kissed me this morning while our friends were otherwise occupied. It was startling and good. We’ve known each other for eight years and he’s been on my ‘maybe’ list for a while now.
32.
The 59-Year-Old Who Has Sex With Her Husband Every Day
6:30 a.m. Wake up early, quick morning fuck. Hubby is proud that this was his fourth time within 24 hours, says he is a super stud and I am super hot. Who am I to argue if he says so?
31.
The Georgia Woman Hooking Up on the River Bank
5:30 p.m. We hike about a mile downhill to the river and lay our stuff out on the beach. We undress right away and practice swimming against the current. S holds me when he sees my goosebumps. I love feeling his cool, wet skin against mine.
30.
The Montreal Guy Sleeping With Two Girls From His Book Club
6 a.m. Rolling in and out of sleep while cuddling with A. Mornings are my favorite time with her. Everything seems less harsh in the morning light. She starts rubbing my chest, and I start to breathe heavily. This is usually all it takes to initiate morning sex. I love when she gets on top and curses at me in French.
29.
The Gay TV Producer Subsisting on Sex Parties
1:30 a.m. We discover the “back room” area (a section of the bar with a sheet separating it and no lights). Everyone is naked and sucking and kissing and fucking. We all stand around one guy on his knees as he sucks us all in turn. As he turns to me I realize he is a friend of mine. We say hi, kiss on the cheek, and then he is back on his knees. My boyfriend comes and leaves the area.
28.
The Woman Taking Off Her Wedding Ring Before a Date
8:35 a.m. I met my husband, M, when I was 15. We dated on and off throughout high school and college. We took lots of breaks, but eventually ended up together for the long haul. I loved his “bad boy” personality and, of course, his good looks. But as a grown-up, he’s a bit boring — in life and in bed. He has no idea that I have affairs … he travels a lot for work. He doesn’t know about my affairs, and as far I know, he’s not having any. I wouldn’t care if he did.
27.
The Mom Who Supports Her Family With Sex Work
11:30 p.m. I have a 28-year-old virgin on my bed. He’s so nervous he’s shaking. I tell him it’s okay if he’s not ready … but he insists that he wants me to take his virginity. And I do. It’s funny how the nerves stop after their first orgasm. He wants to keep at it, but unfortunately his wallet has other ideas. He’ll be back.
26.
The Divorced Mom Who Has Sex on a Trampoline
10:40 p.m. Back at my place, I make us drinks. Then Yacht Guy notices my kids’ trampoline in the backyard, and suddenly we’re bouncing around half naked. This leads to incredibly hot and fun sex, like a water bed on steroids, except with the mosquitos nipping at our naked bodies. Yacht Guy definitely checks the boxes for me in terms of adventurous sex in public (well, outdoor) places. That was my first trampoline sexcapade, but I have enjoyed other semi-public sexual encounters, from getting fingered under a restaurant table to having sex in the men’s room at a boutique hotel in NYC. He ends up staying over, which I’m not a big fan of, but I didn’t think I should make him drive the 50-plus minutes home.
25.
The Architect With Multiple Secret Boyfriends
10 p.m. BDSM guy DMs me on Instagram. He’s a guy I met recently at a wine bar who immediately picked up on my kinky side — I mentioned something about ball gags in my drunken stupor. He’s been in my DMs every day since. I’ve dabbled as an amateur dominatrix for as long as I can remember. I’ve never once had to advertise: These men always pick up on the energy I put out. I do it mostly for fun, but it has its financial perks, too. Sometimes men will give me cash just for meeting me, to set the tone of the relationship. If it’s $500 for a 20-minute coffee, then I’ll know they’re serious. Sometimes it’s gifts — a pair of Louboutins, or I’ll bring them out as my slave for the night and they’ll have to pay for everything. My boyfriend knows about this side of me — he likes the money it brings in. At least it’s one thing I can be honest with him about.
24.
The Married Woman Trying Out Candidates for Her First Affair
9:45 a.m. So here’s the thing. I want to have an affair. I’m in a perfectly happy marriage and I think my husband is faithful, but I’m bored, and he’s always traveling, and I kind of just want mind-blowing sex. We have our kids, our home, our jobs … I would like to add a little danger to the mix. But … with who … is the question.
23.
The Musician Who Dumps All His Girlfriends at Once
3:30 p.m. I call my best female friend in New York to update her on the latest with all the people I’m seeing. Before the pandemic, my dating life in L.A. was pretty unbelievable. I was having sex with four different women a week. I’m still in touch with most of them but only hooking up with Sarah, a comedy writer for a late-night show — she’s the one I had the most feelings for anyway. By the way, pre-COVID, I would fuck all of them in one week; once or twice, I’d fuck two people in one day. My friend in New York is always amused by my stories and yet isn’t totally grossed out by me because I am — if nothing else — honest with all of them. They all know I’m seeing a lot of people and am not monogamous with any of them.
22.
The Dentist Trying Not to Think About Her Husband’s Affair
8 p.m. My husband works late on Mondays and comes home with Indian food for us. He’s been on his best behavior since the affair came out. He’s scared to death of what I might do. Divorce him? Take the kids? I don’t know and I don’t mind keeping him on edge.
21.
The Poly Lawyer Who Keeps a Spreadsheet of Her 6 Lovers
10 p.m. I push him onto the couch. He flips me, kneels on top, and holds me down, tickling me until I cry actual tears. I straddle his lap and tie his hands together with an extension cord. I turn the lights low and give him a lap dance. He watches bemused, not exactly turned on but entertained. When the song starts to close, I rub my pelvis in circles on his lap. He gets hard. I am a squirter so I grab two beach towels out of the bathroom and drape them over the couch. He rides me from behind as we do it doggy style and then fall asleep to the sound of the ocean.
20.
The Single Woman Refusing to Feel Guilty for Her Sex Life
11:20 a.m. It’s Friday, so I’m planning ahead to secure some dick this weekend. I swipe right on Tinder until I run out of swipes (a daily habit). I’ve never actually been in a serious relationship — the closest I got was right before this current Tinder rampage. I dated a guy for about five months, but we never became “official” (whatever that means). It wasn’t until it ended that I knew how unhappy I was — it made me realize I need to have fun and figure out what I want before sticking with one person.
19.
The Account Executive Who Lives Two Blocks From Her Ex
11 p.m. Small talk doesn’t last long — soon Liam is pushing me against a wall in my bedroom and slipping off my thong. I love that he has to have me immediately.
18.
The Indie Rocker Who Prefers Women With Pubes
9 a.m. This is my first time being single on the road in three years. My ex and I broke up last month, this time for good. I’m really excited to see what’s ahead. I was always pretty faithful, save a few random make-outs on the road.
17.
The Makeup Artist Who Meets a Hot Italian Waiter on Vacation
9 p.m. G picks me up at my hotel along the river. He looks extremely good and keeps calling me “rich girl,” which turns me on. To be clear, I’m not rich. But I’ve saved all my money for this trip so I’m living large and my hotel is quite nice. I jump on the back of the Vespa, scared shitless, and he takes me to a gorgeous piazza where we proceed to have the hottest steamy make-out session like we’re back in high school.
16.
The Finance Guy Hung Up on the One He Can’t Have
9:30 p.m. I walk into Estella’s favorite wine bar by her house. She looks beautiful. She gives me a kiss on the lips and is really warm. Does she not realize how often she blows me off and fucks with my head? Is she a master manipulator, or just clueless? I don’t care. I fucking love her.
15.
The Married Mom Looking for Men at Balthazar
10:30 a.m. I sit at Balthazar for breakfast. I do my emails here, breathe, etc. I also come to look for men. I want to have an affair. I feel like it’s my own chance to have some fun romantically. I can’t divorce my husband for financial reasons. I like the life he’s provided for me, but I hate him. He hates me too. Somehow our hatred for each other has reached a place where it works.
14.
The L.A. Woman Looking Forward to a Threesome
7 p.m. Josh comes over and pushes me up against the kitchen counter before I can even say hello. He turns me around and proceeds to go down on me from behind. I come. I always come with him in seconds. I tell him my room is waiting.
13.
The Massage Therapist Falling for a Guy From His Sex Parties
12 a.m. Mikey arrives, of course. I can’t escape him. He’s drunk or high and being very flirtatious with me. We go back to the bedroom that I was just fucked in and start to fool around. Then he fucks me. I love being with him sexually; our sexual chemistry is off the charts. But as always, once it’s over, I feel sad about myself. I’m not sure why — probably need therapy for that one. I decide to call it a night.
12.
The Graphic Designer Whose Date Is Into ‘Marriage Play’
3 p.m. Addressing his marriage fantasy encourages him, and he playfully suggests that we go around acting like a married couple. Ha-ha, okay, I say, going with the joke. We walk to the grocery store to get food. I think we are getting ingredients to cook, but he picks up several frozen pizzas, some beer, and a pre-made salad. “Let’s go home and cook, honey,” he tells me as we walk out of the store. “Is my wife hungry?”
11.
The Woman in a Sexy Quarantine “Bubble” With Her Neighbors
5:30 a.m. I wake up again so I leave my apartment door and go up the stairs to our neighbors’. Around the second week of quarantine my roommates and I climbed up the ladder to our rooftop for the first time and met our upstairs neighbors (it’s just our two units above a bar in our building). We quickly became best friends and have been hanging out together, spending all our time floating between units. There are three of us and three of them. You can connect the dots on what happens on the messy Friday nights when the six of us drink our faces off and dance in the living room — because what else is there to do when you’re on lockdown.
10.
The Married Swinger at a Weeklong Sex Party in Jamaica
1 a.m. We catch up with the San Francisco couple and the four of us make our way to the nude side. The hot tub is always packed at night. S pulls me into the grotto space behind the waterfall between the pool and the hot tub. F and A don’t follow, but A gives me the thumbs up. Years ago we were a “same room” couple, but these days we go with the flow.
9.
The Italian Wife Juggling Work and Sex
8 a.m. We haven’t had sex in a while, which for two Italians is like torture of the worst kind. But life gets in the way — my husband is having child-support issues with his ex-wife and I am trying for a big promotion at work, since I have my own kids with my own ex. We’re both overemotional people, so stress can get the better of us. Anyway, this day we wake up already excited, already horny, knowing we have the evening to ourselves.
8.
The Family Man Attending a Sex Party With His Wife
11 p.m. Back in our suite with about ten other couples. One lady is getting fingered by some guy as she dances with her husband. A new couple shows up and we start chatting. It is dark and boozy and we’re really getting along. She has soft skin; I feel her back under her shirt. The room clears out until it’s just the four of us. We will call these two Niki and Carlos. They seem more passionate and a bit slower, as opposed to being into heavy banging. Niki is feeling Jax’s large tits; we are all getting naked. Soon enough, we are banging our own spouses side by side.
7.
The Designer Hooking Up in the Steam Room
4:30 p.m. I walk into the steam room and there’s a young guy in there. He flashes me a look and subtly adjusts his junk through his towel. That’s the signal that he’s down to play. I respond and we start jerking off together, then he leans over and starts blowing me. Half the excitement is knowing we could get caught any minute if someone walks in and I come in his mouth pretty quickly. He nods in appreciation, gives me a wink and leaves. I did not see that one coming — I could have sworn he was straight at first glance. My gaydar can be really off sometimes.
6.
The Scientist Playing With Her 4-Person Polycule
12:30 a.m. We’re back at my place, negotiating a scene. Glad I remembered to change the sheets earlier! After going through all the details and getting mutual consent, we’ve all stripped down and P is standing beside N with his hands cupping her breasts with the biggest, dopiest grin on his face while D and I crop her butt and thighs. Later D fingers her, then we tie her to the bed (with the restraints I conveniently left out before) and I can’t resist — I jump in and go down on her, much to D’s and P’s surprise. The three of us are reading each other and feeding off each other’s energy and sharing excited and dumbfounded looks — one of the biggest thrills of the scene for me was seeing my play partners so excited and co-topping on the fly so smoothly with them. The energy was absolutely out of control!
5.
The Novelist Who Always Ghosts After the Third Date
11:20 a.m. One of the girls I always see at Pilates, Clementine, asks if I want to hang out sometime. She calls herself a writer too (no comment). I know how things will play out with Clem. We’ll have a great night. She’ll be charming and I’ll be brooding, and then we’ll fuck and it will be … fine. Then Clem will want to see more of me, and I’ll have to blow her off, and it’s going to get very awkward.
4.
The 50-Year-Old in Her Hottest Relationship Yet
1:43 p.m. J texts me. (Our code for I love you is 143.) We’ve been dating for five years — we met on a dating site while we were both in the middle of divorces, each of us sleeping in separate bedrooms from our spouses for over a year. He’s 64 but in great shape and meeting him was like yeah, he’s the guy I’ve been waiting for my whole life. Whenever I see him across the room when we’re out, I just feel so fortunate. We both hate TV. We don’t have cable and read constantly. Play Scrabble and put on WQXR and guess the composers. He has a son who’s 14. He bikes, I run. It’s a pretty damn good match.
3.
The Woman Who Wants Group Sex for Her Birthday
6:30 p.m. Nudity and kief-honey-spiked cocktails all around. Ace and I have sex while they do the same. He doesn’t come — it’s way too early in the night for that. Then we all hang out together in the pillow-fort tent.
We order pizza and Ace grabs the “strapless” strap-on for Sophie and I to play with together. Then, time for my “birthday present.” Joe leads Sophie from the bathroom. They just staged a mid-play costume change and I couldn’t be more excited. She’s wearing incredible harness lingerie, complete with a choker and leash.
2.
The Pet Groomer Who Thinks She’s Probably a Sex Addict
2:30 p.m. Another cigarette break. I check my Facebook messages. I don’t online date but I flirt with a lot of guys on Facebook. I guess you could say I’m a sex addict. That’s probably the clinical term but I’m also okay with saying that I just love sex. It’s been about ten years of constant sex with inappropriate men. Usually they are much, much older. A few have been married. Today, a guy from the town over is texting about hanging out tonight. We usually get high, fuck, and then I go home. It’s both a completely empty and completely intoxicating experience. I tell him I’ll go home, shower, and be there by 8 p.m.
1.
The Woman Whose Husband Is Sleeping With Her Best Friend
8:40 p.m. Adam decides to kill the mood by mentioning that my best friend, Lana, and her boyfriend, Mason, have invited us around later this week for a game night. He doesn’t know that I know that he’s been having an affair with Lana for three out of the five years we’ve been married, and I always get so jealous when he mentions her.
