LELO’s Bad Sex Awards: Everyone Has a Story to Tell

Whoever tells you they don’t have an embarrassing story of a sex-related nature is lying through their teeth. Here at LELO, we all have our cringe-worthy anecdotes and we own them. Show us yours and we’ll show you ours.

Bad Sex Awards

There is a saying that comedy equals tragedy plus time. With this, the same rules apply. They might be mortifying at first, but the cringe wears off after a while and so every ridiculous sex story morphs into a hilarious anecdote You know, the one you reach for when you want to impress or entertain your friends with the new levels of awkwardness you’ve managed to achieve.

It’s time to really kick the shame out of the equation and just take these things as they are – funny as hell. Remember, there is no such thing as perfect sex. There is no such thing as sweat-free sex. Everyone pulls funny faces. There are thousands of funny sounds the human body can produce. There are millions of potential ways to end up with the dumbest of injuries, just ask your nearest E.R. doctor, they’ll agree. If there is no judgment, there can be no shame.

So doing what we do here at LELO, we have developed such an appreciation for these tales that we decided to start our own Bad Sex Awards, but we’re definitely not the first ones to think of this. In case you have never heard of the Literary Review’s Bad Sex in Fiction Awards, check them out here. As we all know, sometimes life truly does imitate art, but when it comes to awkward sex, real life can be so much worse. For every single award-winning fictional scene you’ll find there, we’ll bet you a pretty penny that someone out there has a real-life story that is so much worse.

It might even be you. And guess what? You’re definitely not alone.

Join in our mission to show sex for what it is – a desperately and completely human experience meant to bring you joy without worrying about the way you look, sound or bend.

We’ll feature the cringiest of cringes in our newsletter, on our blog and social media, so make sure you subscribe and enjoy your monthly dose of sex-gone-hilariously-wrong episodes. To submit your own story, e-mail us at volonte@lelo.com with the subject BAD SEX. Our copywriters will be choosing the winning entries on a monthly basis and deliver them straight to your inbox.

Written by: Katy Thorn

Katy Thorn
Katy Thorn is a post-grad writer with a passion for writing about sex, sexuality, and all things rated R. She received her degree in Women’s Studies with a focus in Intersectionality at the University of California, Berkeley (Go Bears!). She has a cat named Yoko, drinks too much black coffee, and hates writing bios.

19 comments

  1. Decades ago, I got involved with a co-worker. It was also a clandestine affair, neither of our spouses knew about it, so we had to find places and times to have sex, spur of the moment. One evening ( after an unexpected early closing of the shop) we found a spot in a park that had been closed for repairs. I was balls deep when things lit up and an amplified female voice told me …”Put your pants on and come here!” We’d been spotted by a patrol car cruising the park. They kept the spotlight on us as we dressed, checked with her that it was consensual (someone had reported a possible rape in progress, according to the lady cop) and told us to get out of the park. My lover took it remarkably well…she insisted we find another spot immediately after the police car left, so she could finish. I did my best to accommodate.

  2. My man and I were getting really into it one night and I was riding him and he spanked me for the first time and it was so good I kept saying spank me harder and he ended up spanking hisself in the balls.. instant soft and I was laughing so hard we both lost it and that was it!

  3. A few years ago I was going down on my significant other in a 69, doing all the right things I’m guessing because she was making all the right noises. My tongue was flicking her clit and I had two fingers in her pussy and one in her ass. She was loving it and I was loving making her juices flow. I wanted more of the tasties and so I removed my fingers and got right in there with my nose right at her asshole and my tongue mercilessly flicking her clit until she grabbed my head and pushed me right into her pussy as her orgasm started. She was really bucking hard against my face and I had to grab her butt cheeks hard to keep my tongue in the right position while she came. Except I made the mistake of pulling her cheeks apart a little too much. I guess my finger fucking her ass had filled her full of air and she farted right up my nose. It didn’t stop her orgasm but she was totally embarrassed afterwards. We still laugh about it today and I joke with her about trying to gas me while I was eating her. She can see the funny side now.

  4. This is a hysterical story of my husband and I ( at this time we were only dating). So my husband works on the ambulance as a very well known medic. He knows everyone, policemen, firemen, etc. , wherever we go. So this one day, we were on a date and we ended up parking behind some vacant buildings parking lot. We used to park between these two tractor trailers that were set up side by side. So anyway, the one night we start undressing and start throwing our clothes all over the place, we were between making out and starting to get very dirty. As we were having sex, I see this black vehicle pull up behind us and start flashing the bright red and blue lights. The officer starts to walk towards the car as I’m trying so desperately to put my clothes back on, the officer starts talking to him and starts asking what we were doing and just making sure we weren’t trying to steal anything. This whole time I was in a panic, just to find out that my husband knew the officer and just worked a night shift with him the previous night. So after he clears the area, the officer, slaps the back of his truck and says “get her tiger!” and drives away. My husband was the talk of the night shift the next night he worked. And can you believe that same officer high fived him??!! Talk about embarrassing!!

  5. 30 years ago when I was 17. My new companion and I went to local park that was relatively small. She had some new lingerie she wanted to show off. And things heated up and the buckets seats in the front weren’t the best so as it’s going hot and heavy in the back seat of my K-5 Blazer I hear something I look up it was US mail truck turning around. Looking like he went on out, moments later we hear something again and there he is back again watching. After we finished she flashed him and we rode off laughing our ass off.

  6. Years ago, my gf and I were trying out lube to aid fun times. In the past, sex could sometimes be painful so to enjoy slippery, smooth fucking was a treat. We were able to try some positions that let me go deeper/harder, culminating in some prone boning that we were both really, really getting into. She started voicing encouragement – to go harder, faster.

    I obliged, my thrusts becoming longer each time to the point I was exiting and re-entering. This was a bad idea.

    The mixture of her juices and my lube had accumulated in the area and all over my dick…things were slipperier than I guess we might have anticipated, especially with her being so relaxed and into it. Upon one of the exits, my trajectory readjusted and I hit the wrong whole upon re-entry, somehow managing to get about a third of my length (sheer speed/ferocity can get you places) up her rear before I noticed the alarming tightness, simultaneously joined by her sudden silence and stillness.

    That moment, probably a second or two long seemed to last an eternity. I remained frozen as her mouth turned into a scream, pivoting on her hips to smack me across the face and body, yelling “wtf are you doing? GET OUT GET OUT GET OUT!”

    I retreated to the other side of the bed, confused, blue balls and trying to console a highly irate gf. She never accepted it was an accident. 🙁

  7. Generally

  8. I just want to say generally speaking that bad sex and bad pizza have something in common. When either one is kind of bad, it’s still kind of good.

  9. Many years ago I was fucking my girlfriend in the back seat of my car in a restaurant parking lot. Suddenly spotlights and police lights go on right next to us! Totally ruined the moment but cop eventually let us go.
    2 days later I had just dropped her off at her house and was heading home when flashing lights go on right behind my car. Just another instance of police harassing young drivers in that town. I pull over hand cop my documentation. I instantly recognise him. He takes the documents starts to move then doubles back. “Hey do I know you from somewhere?” I answer Uh, yeah……

  10. My girlfriend and I went to a gloryhole for our first bi experience. The house looked abandoned. The yard was overgrown and there was a place for a padlock on the outside of the door. We got up the nerve to go in, and found the door where the member would come out. We knocked and a flaccid member dropped out. We got all excited, stroking it and licking together until it got hard. She grabs me by the back of my hair to push my head into the cock, only to find out that it didn’t fit in my mouth. We still had plenty of fun riding it but to this day I’ve never had a penis in my mouth. Oh and the guy wouldnt stop texting for like 6 months.

  11. Growing up in the late 60’s you had to have a fast car, and a hot girl to go with it. We usually wound up in one of the many parks in Queens, NY.in the late hours of the night. This night we wound up in Cunningham park, in the back seat, all windows totally fogged. Minutes deep in to the action, headlights drive by. don’t think much about it, we keep going, back then police cars only had red lights came on. Then that dreaded knock on the window. I wiped the window to confirm it was the law, rolled down the window, and the first words out of my mouth were “BUT OFFICER I WASN’T SPEEDING”, He couldn’t stop laughing, and told us to be on our way.

  12. My bad sex story . . . In the early 80s I was a boy toy before they had a name for it. I can’t say it was something that intrigued me as a means of getting into it with a woman. We were both divorced. Me, I married too young and she, her husband needed her to raise his kids from his first wife and when they were grown, he turned her in for a younger model. In any event, we were both still reeling from our pasts. She made the first move one night I was sitting on a bar and she just sat right on my lap and I, after getting over my shock began to pursue her. We both worked together – made things interesting.

    So, one beautiful June afternoon, lying naked on the bed with the breeze blowing though the windows making the curtains flutter and the air seemed like vanilla, she goes down on me. Friends and neighbors let me tell you, she had no where to go and all day to get there. I start to worry – I’m afraid my resulting orgasm would land me in the hospital – for weeks! Just as the top of my head (big AND little) is about explode, leveling a small suburban village – she comes up. I say, “what’s up?” She says, “oh, I don’t do that.” I jump out of bed, pacing up and down the hall. She asks, “what’s wrong?” I don’t recall what I said, wan’t mean. She makes a general reply, “guess we know why I’m divorced twice…” The odd part – her and her first husband were swingers with one other couple long before that became popular. She commented that there were “rules” that well, her and her playmate didn’t keep. Also odd – we had sex on a not unpopulated beach once – no real attempt to cover up what we were doing – I rolled on top of her – her only words were, “I was ready for this an hour ago.”

    Just unusual where some folks draw the line?

  13. I was on holiday on the seaside, the hotel was nice, girls were pretty. We got a big company there, one night we were drinking on the beach, girls gone mad and went to the sea they started to swim topless, I talked to myself: “Dude, that’s your chance, 2 days till you go home and after the whole holiday you’ve got no sex.
    There was a girl which I liked, I ran into the water we were swimming together we were very close but nothing went further than kissing each other, when we got out the sea girls decided to go change their damp clothes, the one which Iiked forgot her blouse and I took it into my apt., changed my clothes and left the blouse there, I had a plan. Again the whole company met in the bar, everybody ordered drinks, I noticed that my girl(I’ll call her that) was confused and ordered nothing, I thought she could be out of cash or left it at apt. So I ordered beer, and another one and some cocktails.
    Then suddenly she went upset cus her lost blouse, that’s it! That how we end in my room, removing clothes and kissing each other. Than I realised that something wrong with my dick it is soft like a noodle ,too much drinking you know. She started crying suddenly, she thought that I didn’t like her, that’s why I couldn’t hard on. I tried to convince her: “it’s not you , it’s me”
    She took the situation on her hands or her mouth, blowing my dick to get it hard and it worked. Then the worst sex in my life started, she felt good, yes, she came multiple time I guess, but I could not, everything I wanted was to end this i was so drunk i couldn’t came I thought in hours I almost puked few times the dizziness was unbeareble. When I managed to cum I just fell asleep I believe instantly.
    That was my shitty sex.

  14. Hey Can you remove my last name “Buckley” from my bad sex story. I’m the story after Sheree’s comment.
    Thanks!

  15. My husband and I have been married for 23 years. We’re still hot and youthful looking. He has developed a voyeur fetish, and enjoys watching me with other men, and loves to double team me. I’m loving our kinky new sex life, to be the center of attention between 2 men is pure bliss….until an unfortunate event recently.
    Via Tinder, I found a very hot young man in his early 20s. He talked a good game about how he was cool with sharing me with my husband. He arrived, we hung out, got to know each other for awhile, then he nervously pointed to the bedroom.
    To make a long story short, this dude was sporting a very large dick. I was thrilled! He started screwing me, and he didn’t make it past 2 minutes. Not a big deal, I figured, I’d let him rest a bit and get him going again. He wasn’t having that, he wanted to get going right away and directed me to get him hard in my mouth. I obliged. He got hard. I think my husband being present freaked him out, as he was relatively inexperienced, and he could not maintain an erection. My husband would leave the room, we’d get it going, and he’d lose it as soon as my husband returned. Performance anxiety.
    To make matters worse, his Dad was speed texting him constantly to come home because they had relatives visiting for the holidays. Poor guy was visibly stressed by this. What could have been amazing and fun for all turned out to be the worst sex I’ve ever had. He never contacted me after that. Must have been embarrassing.

  16. Can you please remove my photo from this post? It’s very recognizable.

  17. My wife of 30 years never understood sex. To keep me happy she jerks me off once every 2 weeks. But the worst part is, the act is more like pull starting a lawnmower. I am a clean freak yet she tells me she cant give me oral sex, because she doesnt like the taste, even without me cumming in her mouth. I am in great shape, 155 lbs and I work to keep that way. Does’nt help.

  18. In the late 60’s I was a freshman in college. One night I came into my fraternity house and found 2 seniors talking on the phone to a woman. After they hung up they both start laughing. Then they tell me and one other pledge that a woman had called and wanted someone to come and pick her up so she could fuck everyone at the fraternity house. We volunteered to go pick her up and on the way back, we decided to take her up to my pledge brother’s room in the fraternity (he had an escape ladder on the outside of his window in case of a fire) so we could fuck her first instead of sloppy last. After the 3 of us climb up the ladder and entered his room we flipped a coin to see who would go first. It turned out he was so drunk he couldn’t get a hard on so I pull off my clothes and mount her but she was so dry I couldn’t enter her. I turn and ask him if he had any Vaseline and he said it was in the trunk at the foot of the bed, so I reach in the trunk and pull out a jar of what I thought was Vaseline and rub a hand full on my hard dick and I start fucking her. After only two hard thrusts she starts screaming and jumps up and pulls her pants up and grabs the rest of her clothes and starts climbing down the ladder and runs across the campus half naked. I didn’t know what had happened until I turn on the lights and noticed that what I thought was a jar of Vaseline was a jar of Vicks Vapor Rub. We both get dressed and climb down the ladder and go to the front of the fraternity and walk in to see about 10 brothers naked and waiting for us to come back with the girl. After we told them what had happened we all started laughing. True story.

  19. A few years back, I hooked up with a guy from high school with whom I shared a mutual crush.
    I went over to his place, had an obligatory sub-par makeup session, then got undressed.
    We proceeded to have the weirdest POV sex of my life. He would pound me robotically for 30 seconds, then switch positions, pound me again, rinse and repeat. It was like a scripted sequence from a bad porno. I got so dry from the constant switching and the general ridiculousness that we had to stop.
    We had some wine, and got into an hour long debate because he didn’t believe in white privilege.
    I left and never talked to him again.

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