The stories had my jaw on the floor. Here’s what people said:
1.
“I slept with my father’s fiancée. It was a long time ago, and she’s no longer alive, but I’m still not telling.”
2.
“I slept with my college professor. Not once, but twice. Two different professors. They were both married. I should also mention—I’m a lesbian. They were females married to men at the time. One was an excellent hook-up; the other was okay. I’ve never told anyone due to my being actively in both of their classes at the time. What a time to be alive.”
3.
“I slept with my stepsister. Let’s call her Jennifer. Jennifer was the daughter of my dad’s second wife, from her first marriage. We were adults, there was alcohol involved, but it was still good.”
4.
“I slept with my mother-in-law. I was separated from my wife at the time, and she, my MIL, asked if I could paint her apartment. She would pay me, and I agreed. It was a three-day job, and I lived on the other side of town, so it was agreed that I would stay over. It was summer and really hot, and I worked in just shorts while she was hanging around in next to nothing. She was a widow, she wasn’t a bad sort, and we had drinks at the end of the day. Anyhow, we slept together. She was better than her daughter.”
5.
“Well, I slept with my ‘first cousin’ at my grandmother’s funeral. But it’s okay because my mom and her sister were both adopted from an orphanage, so we aren’t actually blood-related. She was cute, and I was sleeping around a lot in those days. We hadn’t seen or even spoken to each other since we were young. We just laughed when we saw each other at my grandfather’s funeral. Of course, we hooked up that time too. A couple of years ago, my brother died, and she was there—ready—but I didn’t have it in me.”
6.
“I slept with my Year 10 English teacher 10 years later, after a school reunion. She was married. In an awkward and interesting plot twist, her youngest child and my eldest were in the same grade 1 class years later. I met her husband at a Father’s Day thing at the school. I can’t imagine the look on her face when he told her he’d met one of her former students.”
7.
“I slept with my best friend’s sister. I used to spend the night often at my best friend’s house since he had a pool, hot tub, trampoline, and super cool parents who didn’t really care what we did. One weekend, I got up in the middle of the night to get some water, and I received a text from her asking if it was me in the kitchen. I said yes, and she responded, ‘Come to my room, I need to tell you something.’ I went into her room, and we started talking. That evolved into making out, then to her going down on me. It went on for a long time and eventually evolved into having sex every time I went over. We did it for years, and my buddy never knew.”
8.
“I slept with my best friend’s twin sister. Twenty-two years ago, I rented a room in their house, and she worked the afternoon shift, so she’d get home around 10 p.m. She would come into my room, and we would do literally everything other than intercourse because I was a ‘gentleman’ and didn’t want to take her virginity. To this day, it was still the best head I’ve ever had.”
9.
“I slept with my wife’s twin sister, 15 years before she became my wife. Yes, they are identical. I slept with her sister in high school and married my wife in our 30s. I did not cheat on my wife. My wife and her twin hate each other and barely speak these days for completely unrelated reasons. Their relationship was shattered long before I even started dating my wife. My wife does not know and hopefully never will. Their personalities are night-and-day different. My wife—let’s call her A—is quiet and reserved, smart and classy. Her twin—let’s call her B—is wild, loud, and outgoing. I knew them both in high school as friends. I wanted to date my wife in high school for personality reasons, but she was dating my friend. I was at a party with drinks and recreational drugs when I hooked up with her sister. It was a one-time thing, and we were both messed up.”
10.
“A coworker once bragged to me that he was sleeping with his wife’s sister. His reason? ‘She does everything my wife won’t do.'”
11.
“I slept with my ex-girlfriend’s younger sister. My ex and I broke up near the end of 2012 and we have always remained friends and stayed in touch. Whenever we are both single, we casually hook up a few times every couple of years, and it has never affected our friendship. In 2019, I was hanging out with both her and her sister at a karaoke bar, and my ex left. The younger sister and I drank a little too much, and she ended up taking me home. It was amazing. We started seeing each other for five months, a few times a week. We both knew it was forbidden fruit, though, and eventually stopped. I then casually went back to sleeping with my ex here and there.”
12.
“I slept with my best friend’s wife. I mean, we all know. It happened before they met. As a matter of fact, my friend and I were roommates at the time—he met her when she was leaving one morning. But we’ve all just decided to forget it ever happened.”
13.
“I slept with my mom’s best friend. They’d been friends for, like, 10 years. For reference, I’m 24. We were drinking one night, and out of nowhere, she told me she was a squirter. That was, in fact, my first squirter.”
14.
“My junior year in college (1991), two of my friends had been dating since freshman year. One day, they got into a big fight and broke up. A couple of days later (Friday night), she showed up at my apartment with a bottle of rum, saying she needed someone to talk to. My roommate was out of town for the weekend, and a few rum and cokes later, we were naked and shagging. She didn’t leave until Sunday afternoon, and we spent the entire weekend fooling around. They got back together a few days later. We never told anyone, and we’re all still friends to this day. They’re married now with two adult children.”
15.
And finally, “I slept with a customer AND his dad, after I sold them the son’s first car. I was 22 at the time. Son was 18 and in his freshman year of college. Dad came in, picked out the car. I took the son on a test drive without the dad. Son immediately started flirting with me. He texted me later that night and asked me to go to his dorm. I went and we hooked up on and off for about three months. I called his dad a few days later to thank him for the business. He came by a week later and told me he would like to take me out. I went out with dad several times. To this day, I still can’t decide which one of them was better.”
Who is someone you slept with that no one can ever know about? Tell us us the comments or use the anonymous form below: