Sex is one of the best things life can offer, but it’s not always romance and lit candles. Sometimes it’s just totally awkward and cringe-inducing. Read on for some of the most embarrassing encounters ever—whether they make you laugh or blush, just be glad they didn’t happen to you. (Want to pick up some healthier habits? Sign up to get healthy living tips delivered straight to your inbox!)
A Serious Surprise
- “My boyfriend and I were on vacation in Italy and we had just finished a big lunch with lots of wine and went back to the hotel to have sex. We wanted to try something ‘kinky’ so he suggested that he pull out and come on me when the time was right. When the moment came, he pulled out, but instead of coming, he started PEEING all over my naked body! He was mortified and I was initially shocked and then started laughing. I guess it was from all that wine we had—lots of pressure on the bladder!”
Catching Some Z’s
- “It was my fourth year of med school and I was interning at a hospital, working crazy hours. It was tough, but I still tried to keep things hot with my fiancé. One night after a long shift I came home to find that he had cooked me dinner. We ate and then went into the bedroom and started doing it, missionary style. All of a sudden, my fiancé started yelling, “Aileen! Wake up!” I opened my eyes and when I saw the angry look on his face I realized I must have dozed off with him still inside me! We’re married now and still laugh about it.” (Ever ask yourself “why am I so tired?” Here’s what to look out for.)
Dangerous Encounter
- “When I was in my 20s I thought it would be sexy to get my nipples pierced. I had been flirting with one of my professors for a long time, and I purposefully wore a tight shirt to his class hoping he would notice, and he sure did. He invited me back to his apartment to ‘go over some of the reading’ and of course it led to something more. He was super turned on by the piercings but he also had a really hairy chest and at one point when he was on top of me, the rings got snared on him. I was writhing in pain and yelling at him until he finally got a scissor and cut us apart. Definitely not sexy!”
Third Wheel
- “My boyfriend and I were always fantasizing about a threesome, so for his birthday one year I decided to make it happen. A girlfriend of mine who was single and bi agreed to be part of my ‘present.’ When we surprised him things were very hot at first, with the three of us all touching and kissing, but very quickly, my boyfriend and friend paired off, leaving me sitting there alone. I was basically a bystander to some hot sex that had nothing to do with me. At one point I even checked my e-mail on my phone. The guy and I broke up, and I never spoke to the woman again.”
All Tied Up
- “The guy I was seeing was always asking me what my fantasy was, so I finally told him: to be tied up. One evening he came to my house with a bag of goodies, including some rope. With my hands tied behind my back he gave me some of the most intense pleasure I’d felt in a long time. But when the sex was over, we couldn’t get my hands free. I couldn’t find a scissor and he wasn’t comfortable using a kitchen knife so close to my wrists, so we called my neighbor, who thankfully is a close friend and has a great sense of humor. She came by and ‘cut me loose’ without saying a word.”
A Real Mouthful
- “My husband is very well-endowed. The first time I went down on him, I literally vomited up the meal we had just eaten together (bean and cheese tacos). Since then I’ve learned how to handle his sizeable package.”
Technical Difficulties
- “I was in a long-distance relationship with my boyfriend, which meant that we did a lot of sexting while we were apart. One afternoon I was texting with my coworker while continuing a very sexy text session with my boyfriend. Wanting to give him a reminder of the last time we were together, I texted him a pic—a close-up of us having sex! When I realized I had sent it to my coworker I was mortified. I quickly typed ‘disregard’—she never mentioned it and I was thankful.”
A Strong Sensation
- “One night I was in the woman-on-top position when we both heard a distinct snapping sound. My husband pushed me off of him and ran to the bathroom screaming, ‘You broke my dick!’ On the way to the hospital I Googled ‘penile fracture’ and we were both afraid he would never be able to get an erection again. Thankfully the ER doctors assured us that he was fine—and one cute doctor even said to him, ‘You’ve got a good woman there.’ We left the hospital relieved…and mortified.”
Working the Night Shift
- “My coworker and I were having a little fun in the office one night, which included him bending me over the table in the conference room where we spend most of our afternoons. The next day at work we were in a meeting and my boss picked up something from the floor. When he first held it up I didn’t recognize it—but when my coworker gasped I quickly realized it was my NuvaRing! It must have popped out during our vigorous encounter. Thankfully my boss threw it in the garbage and went on with the meeting. We never hooked up in the conference room again.”
Unlawful Citizens
“My husband and I were looking for ways to spice up our sex life, and so one afternoon after taking a walk in the park we dashed behind some bushes and started to make out. I was wearing a dress so it was easy enough to make it happen. It was very hot, until we heard voices yelling. Yes, we were caught by the police and arrested. That ride to the station was the longest drive of my life.”