16 Embarrassing Sex Story Confessions That Will Make You Cringe

March 15, 2019

“We were going at it when I heard a voice ask, “What are you doing?” Somehow, his grandmother had wandered into the bedroom. 

Sex can really be a beautiful thing; two people connecting with one another on a physical and emotional level, coming together in one of the most intimate and fun ways two human beings can.

However, this idyllic experience isn’t always what transpires – because life (and sex) doesn’t always go to plan.

Most of us know all to well, you can be well on your way to having the orgasm of a lifetime, and then, in an instant, the sex takes a turn for the worst and ends in the kind of embarrassment no amount of post-coitus cocktails will ever wipe from your memory bank. We’re talking red-faced, stuttering apologies, never-talk-about-it-again humiliation. We’ve all been there.

But while most people are happy to chalk the experience up as a non-repeatable blunder in no need of sharing, we live in the age of the internet; where the guise of anonymity gives people the chance to share their most embarrassing sex stories with the world. And where else but Reddit would people go to do just that?

From epic dirty talk fails to the release of bodily functions when you really don’t want them, the following tales will make you cringe, laugh, and pray something like this never happens to you…

1. Blast off

“I was doing missionary with my ex while in high school. We were in the gym and I was so turned on I pulled out and blasted in my own eye. I turned around because my girlfriend had this terrified look of embarrassment on her face only to stare into the angry face of her gym teacher while the spooge dripped down my eye onto my lip.” – csoimmpplleyx

2. Birthday surprise

“It was about 12:30am on my 18th birthday and my girlfriend of the time and I were laying on the couch watching a movie. My family had gone to bed earlier, and my girlfriend turns her head and says to me “I’m going to give you your birthday present now”. We start going at it on the couch, and everything’s going well. We’re in the spooning position, and there is a blanket covering us up from the waist down. Not too much motion at the time, just some good grinding, but I was balls deep in her. The room suddenly got lighter, but a very natural non-electric light. My eyes look up to see my mother, father, and sister with a birthday cake walking into the room. Singing happy birthday. While I am balls deep in my girlfriend.” – DavidisGoliath

3. The slip-up

“My wife and I were going at it in the shower one night. For some reason, when I was about to slam my dick back in, she moved and I thrusted my dick directly into the tile wall and compressed it a good inch before it finally bent damn near in half. It swelled up and turned purple almost instantly. I couldn’t walk or function for over a week.” – Anonymous

4. It burns

“I was having very passionate sex where we were just tumbling all over the bed until we fell off the bed. My dick slipped out and I landed on my stomach and got a pretty nasty rug burn on my dick. Blood came pouring out so fast. I panicked and ran to the bathroom with a trail of blood behind me. It’s pretty amazing how fast my boner went down since all the blood had made an immediate exit.” – whattodoes

5. News travels

“My girlfriend at the time and I were making out in my mom’s. Earlier that day she mentioned she got a bunch of money from her parents for munchies and movies. That night, I decided it was time to make a serious move. I looked her in the eyes and said, “Just so you know, I picked up some condoms the other day.” It was on, and it was my first time, so there is nothing to write home about. Classic fumbling and uncomfortable positioning and rhythm-less thrusting, you know the story. It wasn’t until after our festivities that I noticed a lot of money sitting on my bed which had fallen out of her clothes while undressing. I gathered it and handed it to her while we were both post coital, still catching our breath. Suddenly, she went super red and got dressed really quickly, leaving without a word or the money. Now, me being the 17-year-old knuckle head I was, I didn’t even think about the money and texted her saying, “was I really that bad?” She wasn’t a virgin, but I was, so I felt a lot of pressure. It wasn’t until almost midnight when I got a call from her. She thought I had tried to pay her for the sex. She forgot she had gotten money earlier that day and had already told her friends about what happened, who in turn, told everyone else in our friendship groups how I was a scumbag. It turned out okay afterwards because she REALLY wanted to make it up to me.” – ThumbsAtWork

6. Dirty dog

“When I was in high school, my grandfather asked me to look after his dogs while he was out of town for the weekend. I took my girlfriend over there one night knowing it’d be a safe place to fuck. When we arrived, we took care of the dogs then headed for the guest room in the basement. We quickly started going at it. Since we’d started dating, we hadn’t had a free and clear place to have sex. After we were done, we both noticed an awful dog shit smell. She was laying back on the bed spread, I was sitting up. As she got up, I noticed that solid, dried up pieces of dog shit were stuck to her sweaty back. I went over and flipped the light switch on and only then did we realize that the entire bed spread was covered with dried up dog shit. She was horrified, disgusted, and humiliated. I got her a clean towel and walked her upstairs to the shower while I cleaned up the mess in the bed room.” – HorribleSmell

7. Twisted

“I was using my girlfriend’s small dildo on her while my main attention was elsewhere on her. It was one of the twist ones where if you twist, it either turns it on or off, or you keep twisting to remove the battery. This time, I twisted it too far and the top half got stuck inside of her. It took needlenose pliers to remove the top half from inside of her.” – Apyollyon90

8. Hello, Granny

“When I was in high school, I had this thing going on with a fellow football player. So, we were going at it, standard cowboy style – for two guys, that is – with both his hands in mine at either side of my head. I was just about there, when I heard a curious voice ask, “What are the two of you doing?” Somehow, his grandmother had wandered into the bedroom. Thinking quickly, and noticing the glasses on a ribbon around her neck, I looked at her with what I hoped was a puzzled expression, and pushed half-assedly at my partner’s hands, shifting them upwards. “Calisthenics Ma’am”. I couldn’t believe it worked. My buddy nearly frozen with fear, his arms straight out. If a lucky drift of blanket hadn’t bunched up near his rump, we’d have been done for. I talked him into finishing me off. I felt I’d earned it.” – Anonymous

9. Third time’s a charm

“This story is about the third time having sex. My girlfriend and I are doing it in my room at my dad’s house. We’re in missionary and under the covers, thank god. We hear a vacuum banging around in the hallway outside, but think nothing of it. My aunt and uncle were coming over later that night. They were going to stay in my room, but they won’t be arriving for several more hours. We’re getting into it, when suddenly the door opens, and my dad casually vacuums into my room. We immediately stop, horrified and frozen under the blankets. Meanwhile, my dad’s just calmly vacuuming, not looking at us. He says, “Hey, uncle John’s coming over later, so make sure your room is clean.” Meanwhile my girlfriend is whispering “I hate it! I hate it!” My dad only vacuums about a third of the room before he heads out. On his way out, he says “We should get you a ‘Do Not Disturb’ sign.” He then says “Here ya go”, turns off the lights, and leaves. My girlfriend and I are speechless, and don’t finish.” – mrmagiceyelens

10. Doggy style

“I got incredibly drunk at a college party one night and hooked up with a girl who offered to let me crash at her place. We sat down on her couch and her little white poodle hopped up next to me while the girl rolled a joint. I like dogs a lot and scratched its head / played with it until she led me back to her bedroom. My new friend, the dog, followed. Unfortunately, the damn dog wouldn’t leave. It just wouldn’t stop jumping around the bed while were having some great drunk / stoned foreplay. Receiving a blowjob with a poodle hopping and chuffing all around us isn’t ideal. I started going down on her, but the poodle started licking my ear and climbed onto my back for a better look. While we were going at it, the dog would come around from behind and put its cold fucking nose right in my balls for a couple of strokes and then ran away. We were having great stoned sex that I couldn’t stop, but it was seasoned with this demonic little dog cutting in at the worst times and worst places. The next morning, I tried to sneak out of the apartment, but bumped into the girl’s roommate. She let me know that the dog had carried one of the used condoms into the kitchen and left it on the floor. Would I be so kind as to clean it up? Ugh.” – moose_caboose

11. The Lion King

“I was giving my boyfriend at the time a blow job. He asked me where I wanted him to cum, so I told him I wanted a facial. He cums, and then looks at me with loving eyes. Then, he wipes the cum dripping from my chin and smears it on my forehead while shouting “SIIIIMBAAAA”. Completely killed the mood.” – Vaniii

12. It happened to a friend of a friend

“This didn’t happen to me, but an old friend of mine. He was a really quiet, soft-spoken, polite guy, a total gentleman and a graduate student in the liberal arts. Also, pretty inexperienced, tentative, and vanilla sexually. He’s dating this really cool girl for maybe two months. She is much kinkier in bed than he is and floats the idea of dirty talk. Apparently, she likes to be objectified, even demeaned a bit, from time to time. He’s hesitant, but wants to please her and doesn’t dismiss the idea outright. They decide to change the subject and figures that they’ll revisit the idea another time. Anyway…they have sex a few days later for the first time since the conversation. They are really going at it in the doggystyle position, and she tells him to talk dirty to her. He says that he can’t think of anything to say, so he says nothing, and she then repeats the request, but the second time she is not fucking requesting, but demanding it. He comes up with: “Yeah…you like that, you fucking retard?” He’s never struck me as one for embellishment, so I believe him. He said that was it for sex that night, although they are still together two years on now.” – historymajor44

13. Into the woods

“One time in high school, my boyfriend and I snuck away to a remote area of the woods to get down with each other. I gave him a blowjob, he finished, then I looked up to see an old man staring at us smiling. Creepiest moment of my life.” – fustercluckin

14. Caught in the act

“There’s a gazebo type thing behind the Parliament Buildings in Ottawa, Canada. I was there with my then-girlfriend a few years ago at like 3AM. We had walked there after the bars closed, being drunk, as “let’s go to parliament at 3am” isn’t really a sober thought, and sat down in the gazebo to avoid a sudden thunderstorm that swept through. One thing lead to another and she starts giving me a blowjob. I’m too drunk to care about any consequences and I just let it happen. A few minutes pass and all of a sudden there’s this cough from nearby. Some security guard guy is standing there in a rain poncho, mouth hanging open. My girlfriend and I both start to freak out and apologize. He just nods, once, and says: “well, you aren’t vandals.” Then turns and walks away. We finished.” – WileECyrus

15. A wet surprise

“I was fucking my boyfriend, he finished, and we flop into each other’s arms and snuggle. After a bit, I notice the condom isn’t still on his deflated cock. “Did you take it off already?”, I ask. Groggy, he shakes his head pathetically, “No, it must have fell off when I pulled out.” Panicked, I hunt around in my vagina for the free-range rubber, but I couldn’t fine it. We begin looking around in the bed, but couldn’t find it there, either. I demand he use his long, dexterous fingers to fish way upside of me, but he couldn’t find it. Confused, we shrug and forget about it. Fast forward five days later, I’m waiting tables, begin taking an order and I feel this wet sensation. Shit. Did I just start my period? I hustle to the bathroom, drop my pants and to my HORROR see that a wrinkly, white, still cummy condom has half slipped out of me. I pull it out. It smells like an old Band-Aid that’s been worn in the shower a bunch. I was all alone in that stall, but mortified, nonetheless.” – SavannahSly

16. Unprepared

“We were doing it missionary and I suggested anal. She said she never tried, but said “ok”. I began doing it softly while she was in doggy, then a little harder. We were getting into it, and suddenly, I smelled it. I looked down, and there was shit all over the sheets. I pulled out and shit spurted out onto the carpet as I tried to back away. She ran to the bathroom and, god, just shit everywhere. She calmed down after a while, and we cleaned everything up. Obviously, we threw away sheets, but we never tried again. Learned later that you’re supposed to empty bowels with an enema before trying.” – Anonymous

Image via shutterstock.com.

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