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16 of the Most Awful and Hilarous Sexual Encounters

Sex can be an amazing experience, and it can sometimes be a nightmare! Here’s a compilation of 16 embarrassingly bad sex stories!

funny sex

Do you feel like you’re the only one in the world who has funny, odd, or disappointingly bad sex? Guess again. One British condom maker conducted a sex survey and found that only 44% of their participants were satisfied with their sex lives! This low number shows that more and more people are having underwhelming sex that we believe must be shared!

Sex is a magical experience shared between two consenting partners, or at least it can be when it isn’t a gut-wrenchingly bad, yet hilarious nightmare. Admit it, even while you’re deep in the middle of some primo bad sex, in the back of your mind, you know you’ll be sharing this epic fail with your friends sometime down the road.

Feeling like you’ve got the kingpin of bad sex tales? We’re sharing some truly awkward sex stories to make you feel less alone!

*Some names have been changed to protect the bad sex lives of the storytellers!

Which hole was that again?

During one sex program, a husband and wife were both asked if they’d ever had anal sex together. The husband responded with a vehement “No!” while the wife responded with a coy “Yes.” The truth? He’d been putting it in the wrong hole and not even knowing it!

The truth is, a wide majority of men will have popped it in the wrong hole at some point or another *hey, things can get pretty slippery down there!*. Here are some similar “wrong hole” experiences.

#1 “I once had a boyfriend where once, during morning sex, he kept talking about how dirty it was that he was in my bum and what a dirty girl I was because of this. I didn’t have the heart to tell him that he was in my vagina, and couldn’t understand how he could confuse the two!” -Melissa [Read: The 10 biggest misconceptions about anal sex]

#2 “This one time, I was with this girl and she told me to put some lube on it while I was playing with her backside. I thought she meant my penis, but apparently she meant my finger? That’s the story of how we both had our first, but not last, accidental anal. I ended up marrying this girl. Coincidence?” -Mark* [Read: The curious guy’s and gal’s guide to first time anal sex]

#3 “This is more of a no-hole tale… The worst experience I had was with one of my earlier girlfriends. She was extremely attractive, and on our first time, I was way too excited… So excited that I didn’t notice I wasn’t inside her anymore! I kept humping away until she finally said, “Babe? You’re outside me!” Ugh!” -Gary*

#4 “I was in cowgirl with my boyfriend, and he wanted some more bounce and a little less grind. I bounced a little too high, his penis slipped out, and I came crashing down on it! I don’t think I have ever heard a guy scream as high and as loud since then. Luckily, it wasn’t broken!” -Deborah* [Read: 19 moves to own the cowgirl and make it so much hotter!]

#5 “Like Deborah, my husband wasn’t a fan of grinding during cowgirl, either. So I bounced, and I hate bouncing. Eventually, I bounced too high and heard a sickening sound when I landed. Unfortunately, his did break! He’s never let me forget it. Needless to say, we don’t bounce anymore!” -Cassandra

He couldn’t get it up

According to a recent study, performance anxiety affects up to 27% of men, making it difficult for them to get or stay hard in sexual situations, or may even prevent them from achieving orgasm! With a little practice and a lot of patience, sexy performance anxiety can be conquered… Unfortunately, that wasn’t the case in these exploits! [Read: 15 naughty ways to last way longer in bed]

#6 “I had been asking the girl I was dating to bring back another girl for a threesome for some time. We were at a music festival one day, and I was insanely drunk, and she told me to come back to the tent because she had a surprise waiting for me.

I stumbled back to the tent to find her and another woman going at it. I started to join in, but after a few minutes, it became clear that my penis was non-operational. They tried for a long time to get me hard, but nothing could bring life to my poor limp penis. After a while, things started getting really awkward. Not exactly a dream come true.” -Devin* [Read: 20 things you need to know before getting into a threesome]

#7 “A friend of mine had confessed his love for me earlier in the day, and my boyfriend had witnessed it. I turned him down, obviously. Well, what happened must not have truly hit my boyfriend until much later, as that night while we were humping, his penis suddenly went limp, and he started yelling about the love confession! We laugh about it now, but at the time, it was a total downer!” -Tayla

#8 “I suffered from performance anxiety when I was new to sex. Many women usually have to comfort the guy for not being able to get hard, but in my case, I had to comfort the girl! She cried because she thought it meant I wasn’t attracted to her. I had to draw attention to the anxiety I had, so that she could feel better about not thinking it was her fault.” -Adam* [Read: 13 ways to overcome sexual anxiety and perform]

#9 “I don’t recall feeling embarrassed over what happened either. I did not freak out as I knew what the issue was, and I knew I’d get my mind right and resolve it. I think the worst thing a guy can do is pout about not being able to get it all the way up due to performance anxiety. He shouldn’t draw more attention to it than necessary!” -Matthew* [Read: 20 ways to keep an erection up for longer]

It’s TOO big!

Whether you’re a male or a female, sometimes bigger isn’t always better!

#10 “They say women love a guy with a big dick. Definitely not true, so don’t believe the moaning girls in porn! My second boyfriend’s penis was so large, we couldn’t fit it inside me. He’d push against the opening of my vagina, and we’d both be in pain. So our sex life consisted of me giving him blowjobs and occasionally begging to try sex again. One time, he got so angry at me and shouted that trying to have sex with me is like ramming his penis against a wall!” -Sophie [Read: Big vs. small – why bigger isn’t always better]

#11 “Probably my worst sexual experience was with a girl with a giant vagina. I’m not going to pretend I’m hung, but I am at least average. While inside of this woman, I could stir my penis around in a circle. I felt like I was having sex with a warm bowl of soup or something. It didn’t help that she was dripping wet like a faucet either. I couldn’t feel much of anything inside of her. Only woman I’ve ever met like that. Poor girl!” -Chris* [Read: The Kama Sutra guide to male and female genital compatibility]

Parental walk-ins

Parents can be some of the best life-coaches you’ll ever have, and they offer their advice for free! The one part of your life you probably don’t want your parents inspecting up close and personal? Your sex life!

#12 “My boyfriend and I were dry humping, nude, at my house when we definitely shouldn’t have been. My house was not the “mess-around” house, but regardless, we start messing around, and my mom walked in, no knock!

He got off me immediately and my mother said in a shocked voice: “That’s not nice!” She and I laugh about it now. To this day, she still says she’s never seen a man’s bum raise as fast as his did to get off of me!” -Ashley [Read: Dry humping and the virgin’s guide to orgasms]

#13 “My high school girlfriend and I were going at it, fully naked above the covers at my house. I thought the door was locked, but it hadn’t latched. My mom walked in with a laundry basket, and immediately saw us. She froze, we froze, and we all just sat there looking at each other for a moment. Then mom just said “OH!” and walked out.

By then I was as limp as a wet noodle, but my girlfriend started cracking up. I was really glad she had such a great sense of humor about the whole thing. I was absolutely mortified! Mom never said a word. I wish I had thought to bring that up before she died. We probably would have had a good laugh about it.” -Rob*

Unfortunate miscommunications

While talking during sex is often a nuisance *except if it’s dirty talk*, there are just some things you really need to speak up about.

#14 “My worst sex experience was with my last girlfriend. She had a lot of emotional issues, and during sex was no exception. If she didn’t orgasm within a couple of minutes, she would start to get panicked. Hey, I’m a good guy, never impatient! So I never rushed her and always did everything I could to get her there.

One time, she got so frustrated while riding me cowgirl that she started sobbing and got off. This became an unfortunate habit on her part. Poor Blue Balls Barry…” -Barry [Read: Big blue ball facts every girl’s gotta know]

#15 “I was in Europe and had to buy condoms from a coin machine in the bathroom of a club. It wasn’t until we were getting into it in the darkness of her hotel room that I noticed it was a sparkly pink glow-in-the-dark one. She started laughing, and I started laughing, and because she spoke French, I had no way to communicate to her that these lovely sparkly pink condoms weren’t my preference.

When we woke the next morning, the first thing she did when looking at me was laugh. It was pretty funny. My wife loves this story.” -Garrett* [Read: 10 really easy ways to find a fling when you’re on a holiday]

#16 “This was in 1975, several decades ago. My girlfriend and I were on our way to a fair when we decided, while on my motorbike *half drunk!*, we wanted to get frisky with one another. Eventually, I hid my bike, and we made our way into the pitch black woods.

She started by giving me a BJ and eventually told me she was very wet. I laid her down on a blanket and tried to have intercourse for about 15 minutes, all but ramming my equipment into her with no luck. Goes to show you, you should never go at it drunk because as it turns out, I’d never taken her pantyhose off!

I’d been trying to get through her thick barrier of leggings for so long, pounding, that my equipment started to bleed! I was sore for a week. Married her when I was 17, and we had lots of fun.” -Daniel*

[Read: 30 naughty questions for couples to keep the kinky spark alive]

For better or worse, sex happens! Whether you’re having the best orgasm of your life or experiencing something you quickly want to forget, take solace in the fact that you aren’t alone.

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Waverly Smith

Waverly Smith is a freelance writer who has been getting paid for spreading her sarcastic take on love, life, and sex since 2010. She is many things that peo...

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