A collection of anonymous confessions detailing various sexual encounters, including affairs with friends, ex-partners' relatives, and experiences exploring different sexual orientations and relationships.
"My best friend in high school got his girlfriend pregnant. She had the kid and gave them up for adoption. We all attended the same state college, a two-hour drive from home. I was only casually acquainted with her, but one Sunday she called me needing a ride back to school.
After arriving at her dormitory, I helped her carry some boxes into her room. On the drive, she had been trash-talking her baby daddy, so I guess I took the opportunity to proposition her, to which she enthusiastically agreed. After we finished having wild 18-year-old college student sex, she asked where I had been all of her life. Then she proceeded to tell me that I was bigger than my best friend, which evidently quite surprised her. We agreed that we should keep our little tryst a secret and never do it again, and that is a thing I often regret.""I slept with my friend’s brother at her wedding. The interesting thing is, she knows about it and is totally cool. What she doesn’t know is that her brother is really bad in bed. I didn't know what to say to her when she asked me whether I would get together with him again.""I was a married man in my mid-30s and had always wanted to see what it was like to be with a guy. So I downloaded Grindr randomly, and within 72 hours, I had started a multi-year, FWB relationship with a 50-year-old guy. It was quite exhilarating, but eventually the rush had subsided, and we parted ways.""We were college friends, and life took us on different paths. We've kept in touch for 16 years. We were both in dark times and helped each other. Then somehow it turned into the best sex of our lives. We're still hooking up now. His wife is awful to him, so I love that he can find comfort in this when life gets rough.""I slept with my ex-wife’s sister when she was my fiancée, before we were wed. She wanted it to continue, but I didn't.""I slept with my first wife’s sister and with my second wife’s sister. Both were pretty good.""I slept with my sister-in-law, my brother-in-law's wife. We have known each other for 37 years as friends. She needed a job done in her house, and as we reacquainted, it slowly became more than friendship. We are both overtly sexual and couldn’t help ourselves. She is a tremendous lover, the best I’ve ever experienced.""I entered a local bar in small-town America and spied an all-grown-up former babysitter having drinks with her younger sister. I hadn’t seen them in years, and they hadn't been my babysitters in decades. My wife had always made the sitter arrangements. She went through contacts from church, so we knew the parents of the sitters from services. In this chance meeting, time had gone on. I was divorced, and those girls had grown up. Still, there was enough of an age difference; I thought it was innocent enough to keep them company and get caught up on how life turned out for them. It wasn’t many drinks when they divulged they had crushes on me back when they sat my kids and fantasized about me then, on the ride home, I would give them, and at church services! In spite of being uncle-age, they still wanted to push through with that. The elder of the two was forward about it, and we left the bar together that evening.""When I was living with my older sister, I slept with her best friend. One night, I walked into the house, and there was my sister, a guy she was dating, and Doris. We had a few drinks and then I excused myself because I had to work early the next day. An hour or so later, Doris walked into my room and propositioned me. It was quite a night.""Let’s just say I was very charming growing up. I slept with my brother’s ex-girlfriend. I slept with both of my best friend's older sisters. I also slept with my high school best friend’s younger sister. I slept with my cousin's wife. I also slept with my coworker's wife. I was a terrible person.""I slept with twins at the same time. We were all three on the same soccer team. I am now married to one of them, and the other is married to a man. We never talk about it.""I asked my professor a question after class. He invited me to his place for breakfast. I knew I was on the menu. He was so much fun, and the sex was great. We went out for a while, but we knew it was just friends with benefits.""This happened many years ago when I was in the police academy for five months. We had this really cute defensive tactics instructor who had this gorgeous buffed body. As part of the training, we had to go on a police ride-along. This instructor was also a sergeant in the local police department, so I got to ride around with him for an entire shift. The chemistry in the patrol car during that 8-hour shift was palpable. As soon as he got off shift, we went to a bar and had a couple of drinks. Later, I was able to show him some of my own physical arrest techniques inside his pickup truck. It was a great one-night stand, but we both knew that’s all it was. He was married, and I had a boyfriend back at home. However, it was just the sort of release I needed for a very stressful period in my life. Needless to say, I passed all of my defensive tactics classes with flying colors. I never saw him again after graduation, and to my knowledge, no one ever found out.""My mom was getting married to this woman, and she had a son around my age. We slept together, even though he was technically about to become my step-brother. He was my first, and nobody ever found out.""I had a threesome with my twin cousins without knowing it. We had a blast that night, and we parted ways after. Months later, I went to my grandparents’ house for Thanksgiving, and I saw them there. It turned out that they were my uncle’s sons that I had never met because they lived in Italy.""I had infrequent, passionate sex with my wife’s mom starting from when I first met her daughter at 19 and up 'til a few months ago. She is a fantastic lover and is beautiful! It doesn’t happen often, maybe twice a year, if that…but it’s extremely erotic and powerful for us both!""A friend’s girlfriend invited me to a concert because he had to work. We were both drinking and having a good time, and then she just kissed me. We made out for a while before going around the corner, where she went down on me. We tried dating after they broke up, but the chemistry was different.""My wife slept with her daughter’s first boyfriend. She was 44, he was 19. Ugh.""My cousin was getting married, and I hooked up with her husband's best friend's wife at the wedding. To be fair, I didn’t know they were together and had a child. I only found out after the wedding, when we got together again. I am also friends with her husband. And he doesn’t even know that I hooked up with his wife a few times. She made it seem like they had an open relationship, but later found out that was not true. So now when we see each other, it’s just casual, even though she had asked to hook up a couple of times after we stopped, I just made excuses that I was busy.""My first cousin and I hooked up off and on for about two years after she got divorced.""I hooked up with my cousin's brother-in-law at her wedding. It was sort of a small act of revenge because her husband and I had been secretly dating for a year before my cousin was introduced to him. It was an arranged marriage, so I need to accept my defeat.""My dad's friend was super hot despite being in his late forties. One night, during a family graduation party, we were both hammered, and we had sex in the bathroom, and for the next few months, we hooked up, but I got a boyfriend, so now we stopped. The tension is still there, and we both just don’t talk about it.""I was married to my wife for five years, and she had already introduced me to all her family members, but her sister was in the army, so I had never met her. But one day she came back, so I got to meet her, and damn, I don't know if it was the army work or whatever, but she was hot. We locked eyes as soon as we met. Later, when my wife went to sleep, I went over to her sister who was staying downstairs, and she knew what was up. The sex was great, way better than my wife's. Time has passed, but I'm 25, and I still go over to her sister's for a little 'treat.'""My friend of 10 years got close to me a few years ago. My wife is extremely manipulative and controlling after marriage. I just needed a break. One night, a friend reached out to me to ask if I was okay. No one else cared like her, so I kissed her. I told her there's nothing I can do since we have kids together. We connected on a deeper level and ended up with the best sex of my life. I ended it a few years later, though, since feelings were getting too deep.""My co-worker and I spend a lot of time together. We became close pretty quickly due to the amount of time we spent together. Then one night at work, we were watching a movie, and one thing led to another. His wife is living in a different country, and he said he is struggling with the fact that he doesn't have that intimacy. So I gave it to him. It was amazing. We have done it a few times now, and it's a no-strings-attached thing we have going on. It's so hot.""We met when we were 12 or 13 in middle school and dated. She was my first kiss, and I was a 12-year-old boy madly in love with her. We had off-and-on connections for the next 15 years, where one of us would be with someone, but we’d flirt, but nothing came of it. We reconnected at 27 or 28 when she was married and I was in a long-term relationship. We began to get close and gripe about our significant others. We ended up at a bar in Chicago after a show and started an affair. It happened at her house and mine. At one point, in an alley in Chicago. It was a wild time. My friends saw it as a soap opera. It all blew up from one text that her husband read. We parted ways, and no one knew the details except my friends and my now-wife.""I spotted a sexy man at a work conference, and after hours of relentless flirting, we slept together. It was amazing. I thought that was the end of the story. A week later, I went to a job interview, and he walked into the room with two other people. I’m not sure how we managed it, but we shook hands and pretended it was our first meeting. I found out later that he was the only interviewer who expressed uncertainty about me. Luckily, the others voted in my favor, and I got the job. He was my direct manager for 5 years! We never stopped seeing each other and were an unstoppable team." "It was professionally dangerous and reckless, but incredibly successful and extremely hot! Eventually, I left the company for unrelated reasons, but he is still a dear friend and professional mentor. To my knowledge, no one knows. Thank God!""My long-term partner was part of his best friend's groomsmen party about eight years ago. Fast-forward five years, and a lot has happened in life. I was lonely and depressed, but my partner doesn't believe in depression, so when his friend reached out to comfort me it ultimately led to a kiss. I just let it happen, as if it were a dream. He's married. Being neglected is weird because I gave in to him so quickly, and he got through me so quickly."And finally,"I was working in a restaurant in Tempe, AZ, and waited on him. He was a guitar player in a band. We started talking, and then he left. He began coming in regularly, and before I knew it, he’d wait for me when I got off work. We took a drive and had the first night of the best sex ever! I knew he was married with children, but he wasn’t happy with her. He was going to tell her about us and leave her, but I told him not to. I didn’t want to hurt his kids. We maintained our relationship for over 30 years, and even after I left town, we continued to stay in touch. His family came to my new state for vacation, and we hooked up then. And of course I’d go visit him back in his state. We spoke often on the phone. He recently passed away, and my heart was broken. Of course, I couldn’t show any emotion because I’m married now. He will always be the one who stole my heart."Who is someone you slept with who you weren't supposed to? Tell us in the comments or use the anonymous form below:
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