We were at the Brooklyn Bridge Park. It was sunset, a summer evening. My girlfriend was on my lap, and I just decided we could get away with it. She didn’t object.
Every time we take the Amtrak train to visit his parents in D.C., my boyfriend would touch me under a blanket. Once, we arrived in D.C., and it was taking me forever to get off. Everyone left, and we stayed put for an extra ten minutes in an abandoned train. His parents kept calling to see where we were.
My ex-boyfriend and I worked hard to find this one spot near our offices where we could lean into this little nook and fool around while standing up. Five feet away would be throngs of Rockefeller Center tourists. We’d kiss for ages, and then I’d put my hand down his pants and he’d try to “aim” away from his work suit and mine. Soon, we had to start bringing napkins.
It was one of those all-you-can-drink Halloween parties, and I met a guy dressed as a flasher. The weird thing was he had a freakishly long penis. I kept asking to see the hose, and soon enough, the hose was inside me. On a pleather couch. In some sketchy bar-lounge. The next day, I took Plan B.
My girlfriend loves Catholic churches, even though she isn’t Catholic. One night, we were walking past a church in Brooklyn, and she dragged me inside. She was insisting on blowing me inside the confession box, behind the curtain. We gave it a try.
I met her outside our kids’ school. One night, someone threw a fund-raiser at their loft for the school. We were both there without our significant others. She looked incredible. Both of us had to use the bathroom, so we waited in line together. Then we went inside.
I had just bought my first apartment in New York, and my boyfriend of five years was about to propose. Then I took out the trash in my little hallway and I met Michael. He had just remodeled his apartment and invited me over. I mentioned that I had a boyfriend, but I played it way down. Nothing happened that night, but I couldn’t stop thinking about him. I’d hear him coming and going. I’d see him enter the building from my window and strategically wait for the elevator, looking as good as I could. In the two years it took for me to plan a wedding, I was sneaking over to Michael’s for wine, laughter, and sex. My boyfriend never found out. And then we got married. Eventually I sold the apartment.
I had an affair with a female associate. My husband knew we had gotten drunk and made out a few times—he chalked that up to my being a “free spirit.”
I’m married, but for the past three years, I’ve been seeing this artist, always in his studio. I try to stop at just kissing, but I leave with bite marks.
My boyfriend doesn’t have a huge sexual appetite, so I started flirting with strangers on Craigslist. I agreed to meet one guy at a hotel in midtown. He’s crazytown in bed. We meet a few times a year, but I still don’t know his name. He’s in my phone as “Dry Cleaning.”
I started seeing this guy. We had kissed, but I had only “petted” him on the outside of his jeans. No nudity. Then he straight-up sent me a picture of his balls at, like, 2 p.m. Just balls. He didn’t even send it in Snapchat. And guess what? I’m still dating him.
My ex-fiancé, who left me at the altar and broke my heart, sends me the filthiest sexts when he’s drunk, but they are interlaced with all this emotional, super-heavy shit. Like, “I remember how it felt to be deep in your mouth.” Then a second later: “I made so many mistakes … can we start over?” One said, “I’ll never love anyone the way I loved you.” Five minutes later: “Must cum in your ass tonight or will die.”
I briefly dated a man with a bad penis problem. The thing was, he would sext me as if we had the most outrageous sex life: “I’m at work, rock hard, thinking of you.” Or, “Lets go upstate and break some fucking beds.” It was completely delusional! Like, hel-lo, our sex life sucks?
After I slept with an older man, he sexted, “I want to stick my hard rod into your wet pond!” That was the end of that.
I’m a straight female with a serious boyfriend, but I like meeting crazy, slutty women on Craigslist and then G-chatting or BBM’ing until we both cum. I’ve never even kissed a woman.
I met this Dutch guy at a Mexican hostel. It was a great holiday fling; he spoke lots of languages and had a really big dick. We never saw each other again, but we’ve been sexting for five years—even though he got married in 2010. When he says he wants to shove his cock down my throat … I don’t like that one. For one, it’s too big.
I was in an LDR: Boston to San Fran. He was great at using emojis to create dirty images. Like: eggplant + doughnut = splash; bananas, cherries, and lots of finger signs into a doughnut. And he could really write: “Let’s go hump in the park”; “You ready to get peed on?”; “I need you to drink from my furry faucet”; “Not one, not 2, but 3 fingers in your ass”; “You watchin a movie? My nuts hurt.”
I lost my virginity at 16 to my best friend’s dad. She found out when she called me a “fag” once, and I told her I had her dad bent over her kitchen counter for three years. Not long after, the parents divorced.
I was about to graduate from high school a virgin and was pretty annoyed with myself for holding out so long. So I called up my friend, who was a total dog. He’d slept with, like, 30 women, so I figured there was a chance he might not suck in bed. It still sucked.
I was on a kibbutz and it was my 17th birthday. I was madly in love; I called him my Jewish Kurt Cobain. I brought over peach iced tea spiked with cheap vodka, and everyone knew what we were up to. It hurt a little, of course.
I lost my virginity to my now-husband. We were high-school sweethearts, and he’d only slept with one girl before me. It’s weird how people feel bad for me, like I’ve missed out on so much. But I love sex with him. I always have and probably always will.
We had a same-sex marriage and felt quite celebratory. During the wedding, we pretended we had more photos to take outside. No one noticed.
We had like two hours in between our wedding and the reception, so we came back to our place and my man aggressively tried to impregnate me. Then he took a nap. He was coming down with the flu.
I was just as tired as my wife, but there was no way I was letting us just go to sleep. So I drew us a bath, with candles and rose petals, and told her sex was nonnegotiable. She got a second wind.
We had sex in the limo from our wedding to our party. I was in my white Vera Wang dress. My only regret is that I think the limo driver saw and heard everything. I wish we gave him a bigger tip.
It was 4 a.m., and it was in our own bed. We got married at home, so it was me in boxers and a T-shirt and him in the same, having a quickie before passing out. At least we had a fat wad of cash on the nightstand.
It was my first job in the film business, and my boss would take me around to places I “had to see” … but no action. He was an Ironman guy, so I called him “Mr. Run-Bike-Swim” to tease him. One night, he went on a long training session. When he came back late in the evening, I was reading scripts at my desk. He called me into the office and, just like that, I had his ass bent over his desk. Now he is an executive producer on one of the most successful shows on TV.
One time, after my boss had been an asshole all day, I fucked my girlfriend hard all over his desk.
At 26, I started working for a rich, powerful, married CEO. My position required a lot of travel with him, so the majority of our sex was inside lavish hotel rooms. Early on, he told me to pull on his dick really hard and tell him it was small and ugly. Soon, he asked that I call him a slut and a whore. His favorite was when I teased that he got his period and was a bad, bad girl (this, followed by tampons inserted into his ass). We’d meet in an office bathroom so that he could “clean” my vagina. He loved the degradation of licking me front to back, as if he were the toilet paper. He’d have me meet him in crowded elevators to hand off my dirty panties—the dirtier the better; he’d beg that I pee a little in them. Then he’d wear them while giving interviews and presentations. I fell deeply in love with him and have never been quite the same since.
My boyfriend had an office with a glass window and a little curtain shielding him from his colleagues. We’d shut the curtain and do it under his desk. Afterward, we’d have the munchies; he’d go to the vending machine in the coffee room and get cookies and chips.
I got a BJ in my conference room at my office two times by two different people. It’s the only place that doesn’t have security cameras. The first was my intern, and the other was a guy who needed my help fixing his résumé.
My ex was a dermatologist. I’d visit him at work. He’d tell the nurses I was getting Botox.
All memoirs collected by Alyssa Shelasky.