Hilarious & True 10 embarrassing sex fails that actually happened to women

Sex can bring about moments of joy, bliss and also a visit to the hospital with laughable and scary moments, here are some.

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I’m sure we all have one weird story about sex, either it happened to us or we heard from someone. For instance, my own first time was as hilarious as it comes. At the age of 21, I had a female friend over, and didn’t even think she would have sex with me, after much puppy eyes and pleading, she agreed.

Now that I think about it, my first sex was mercy sex. It still counts as sex anyway. So, after she agreed, she asked where my condoms are, I didn’t have any so I grabbed my trousers and ran almost 2 kilometers down the road to an Aboki store to buy condoms, praying that she doesn’t change her mind by the time I got back. You know how women are, 2 seconds later, they can change their minds.

ALSO READ: Here is why she called another man’s name during sex

Not sure who to thank for the victory, she didn’t change her mind, so she popped my cherry that day, and she was very nice too. The story of how I bought condoms at a crowded Aboki store is for another day.

This article was originally written by Ronnie Koenig at Prevention, the names of the real people have been changed. The stories are quite embarrassing.

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1. The surprise

"My boyfriend and I were on vacation in Italy, and we'd 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 so shocked that I started laughing. I guess it was from all that wine we had— lots of pressure on the bladder!" —Debra*, 43

ALSO READ: Women with big bum are smarter and healthier says Science

2. The Sleep Off

"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 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." —Aileen, 46

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3. The Piercing Incident

"When I was in my twenties, 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!" —Priscilla, 40

ALSO READ: Should you be sexually compatible with your partner

4. The Awful Threesome

"My boyfriend and I were always fantasizing about a threesome, so for his birthday 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. The three of us were touching and kissing, but then my boyfriend and friend paired off, leaving me sitting 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." —Tina, 34

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5. The tying up Incident

"The guy I was seeing was always asking me  what my fantasy was, so I finally told him that I liked 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." —Clara, 36

ALSO READ: 5 things you should NOT do before having sex

6. The Mouthful Episode

"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." —Beatrice, 39

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7. The Accidental Nudiezz

"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." —Izzy, 30

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8. Case of Broken Penis

"One night I was in the girl-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." —Chelsea, 44

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9. The Office fun

"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." —Drew, 42

ALSO READ: Lessons from the School of Blowjobs

10. The Outdoor Indiscretions

"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." —Veronica, 41