Naked And Ashamed: 50 People Confess The Most Embarrassing Thing That Ever Happened To Them During Sex

Illustration by Daniella Urdinlaiz.
Illustration by Daniella Urdinlaiz.
Found on AskReddit.

1. I lost a dildo in my wife’s ass.

“Lost a dildo in my wife’s ass. Thought it was a butt plug, but I guess it was too narrow, and it got lost up there. Had to have surgery to get it out.”


2. I set my own hair on fire lighting candles for ambience.

“Lined the room with candles for ambience. Set my own hair on fire during the act.”


3. Don’t yell “Daddy” while your dad’s in the house.

“This one girl I started hooking up with liked to call me daddy during sex. Well the one time we had had sex in her house she started to call me daddy as usual. Her dad hears her though and runs up the stairs, knocks on her door, and tries to come in an ask if everything was all right. Thankfully the door was locked but she said yeah, no, everything is OK. Never again did I have sex in her house with her parents home.”


4. His jagged fingernails scraped my insides so hard, I needed stitches.

“Oh Jesus OK, so me and my S/O were still virgins trying things out. He decided to finger me, bit his nails beforehand and scraped my insides so hard. He thought he broke my hymen but in reality I needed to go to the hospital. Ended up having to get stitches.”


5. Giving cunnilingus after anal is a shitty, sticky mess.

“Learn from my fail: Giving cunnilingus before anal is great! Giving cunnilingus after anal is a shitty, sticky mess.”


6. I accidentally punched myself in the nuts.

“Banging in the backseat of a car, she was sitting on top facing me. Went to give her a big ole ass-smack and missed. Landed my palm right on my nut sack harder than I’ve ever hit myself in the nuts before. Took a minute to cry and then continued banging.”


7. Her puppy started playing with my swinging balls.

“I was getting it on with this girl on her living room floor. Apparently swinging balls look like something fun to play with if you’re a puppy…”


8. I accidentally lubed my dick with hand sanitizer.

“Ex-girlfriend had two nightstands on either side of her bed. We kept a small bottle of lube on one all the time. One week when I came over I was doing my thing , impaling her with all my strength. I decided to lube up, so I do my normal routine and grab the lube off the nightstand. ‘OHHHH shit fuck shit!’ I yelled at the top of my lungs. I turn the lights on and notice she had a small bottle of hand sanitizer next to the lube. A healthy dose of hand sanitizer on your manhood stings very much. We had a good laugh and decided to take a break and try again later on. Later on that night , I managed to grab the hand sani again haha…”


9. I tried to cum on her but pissed on her instead.

“For a little while in my early 20’s, I took Paxil. One side effect was that it was very difficult to cum. We’d be going for so long, to the point where my wife would tell me to wrap it up or stop because she was getting raw. Well one time, we’re going at it, and I felt that I was close. Told her I was close, and she said to pull out and finish on her stomach. So once I was just there, I pull out, only to piss all over her. After the initial shock of just receiving a golden shower, she just started laughing. Somewhat surprising, she still lets me do things to her with my penis.”


10. Her Pomeranian dropped my used rubber at her dad’s feet.

“My GF and I had just recently started having sex so we’re using condoms regularly… One of our first times doing it, I got off right away…RIGHT AWAY…Well, I didn’t want her to know I had finished so quickly so I tried to be a hero and just limp-dick it until it got hard again. So I’m trying like hell to finish this off with a halfy and after we finish I look down and the condom is gone… Of course it is. I didn’t say anything because I was too shy and figured it would work itself out naturally. Not 10 minutes later I hear her dad, from downstairs, yell ‘What the hell!?’…As their Pomeranian dropped my used rubber at his feet as if it was a prized possession.”


11. Girlfriend’s dog licked my asshole immediately after I started cumming.

“Girlfriend’s dog licked my asshole immediately after I started cumming.”


12. She projectile-farted a corn kernel to the back of his throat.

“Not me but an acquaintance:
Nerdy guy in college never had a sexual experience beyond the palm of his hand. Went to a big ol’ party kegger at a co-op where a similar and equally nerdy girl with a similar track record.

Well, hosts at the party picked up on it and granted them both a quiet room on an upper level off limits to the main party. Condoms and lube were provided and after about 5 minutes a few of us snuck/sneaked up to the landing on the steps beside the room.

After about 10 minutes of us beaming proudly and holding back from listening in on the door, the door flew open and out came our nerdy guy running like hell, half naked and covered in something. He made it to the bathroom and proceeded to puke and gag and took off for the dorms.

Female friends of the nerdy girl entered the room and that was that until the next morning.

Nerdy guy, who is probably still traumatized from this experience, explained what occurred: He went down on nerdy girl as a gentleman does when one knows he won’t last more than what is a laughable increment of time. While down, between nerdy girl’s thighs, she shifted to a more comfortable position and let loose a fart, a fart so impactful that it shot a lone kernel of corn out of her shooter and through his puckered lips and smack into the middle back of his throat. She then threw up on him and he threw up on/in her lap.”


13. A frenulum-snapping bloodbath.

“I snapped my frenulum, filled my girlfriend with blood, then sprayed blood everywhere while yelling in pain. Then spent 5 hours at the hospital with her sitting next too me and 8 nurses constantly switching out to look at my dick to see an injury they haven’t before. Super-embarrassing.”


14. She emailed me a ton of articles on how to properly go down on a woman.

“Years ago I went out with this woman for a couple of weeks. The sex was pretty OK but one night I was going down on her for a long, long time. She was making a lot of noise and I thought that just meant she was enjoying it so I kept going.

The next day she called me up to let me know I focused way too much on her clitoris and it was all swollen and painful. She then asked for my email address and sent me a ton of articles on how to properly go down on a woman.

After that I just really wasn’t able to do it at all. We stopped seeing each other very shortly after that.”


15. Her mom and sister walked in on us while we were 69ing on the couch.

“She tells me to cum on her face.

My aim was slightly off, so I cum all over her headboard and the pillow and the dribble hits her amazing white satin sheets.

We spent 30 minutes cleaning up the mess.

Another time, not me, but we were going at it furiously, aaaand she queefs. Now it’s not a big deal for me, but she has always had a thing with bodily noises (won’t even let me in the loo even she is peeing or even brushing her teeth), so she was embarrassed as fuck. Still is I guess as she brings it up on occasion.

Another time, we hadn’t locked the door, 69’ing on the couch….and her mom and sister walk in on us…now that was truly embarrassing.”


16. His foreskin caught in my braces.

“His foreskin caught in my braces.”


17. She sharted all over my balls.

“Eating my then girlfriend out, she farts. Another time, a different girlfriend, she is riding me and sharts all over my balls. A woman I lived with loved anal, we were going at it, I pull out to switch positions and a turd chased my cock out.”


18. I yanked out her anal beads like I was starting a lawnmower.

“Was doing butt stuff with an ex GF. It was my first time using anal beads and had no idea what I was doing.

Once I had shoved all the beads up there she told me to pull them out and being the nervous inexperienced guy that I was I ended up yanking them out like I was starting a lawnmower.

She screamed and jumped so hard I thought she was going to hit the ceiling and ended up leaving a major fecal disaster all over my bed. Seriously massive amounts of lube-infused poo-covered me and my bed and carpet.

She waddled over to the restroom clenching her newly prolapsed anus and I awkwardly tried to console her painful sobbing from the other side of the door for almost an hour.

We didn’t stay together long after that.”


19. Nothing kills a boner quicker than a cold wet dog snout on your sphincter.

“My girlfriend and I were having the sexy time when my dog decided to see what all the fuss was about. Nothing kills a boner quicker than a cold wet snout on your sphincter. At least she found it funny.”


20. I got worms from giving a girl a rimjob.

“Not an immediate effect, but I was dating a girl who had just about the prettiest buttonhole in the world. I was going down on her one day and I decided to throw my tongue into her bum and she loved it. I didn’t mind one bit. Things proceeded as they do, and life went on.

Fast-forward a few months. I had had a couple bouts of crippling gastrointestinal issues, sort of intermittently. Awful diarrhea for a few days at a time, every 3-5 weeks or so. Couldn’t figure it out. Nothing seemed to help. I hit the bathroom and after I flushed and washed my hands, I checked to see if I needed to flush again. To my horror, there was a single tiny worm in the toilet.

Turns out my stomach problems were a result of giving this girl a rimjob. She had the same thing, but also didn’t know what it was. I took some deworming meds and felt like I was dying inside for a couple days. I dropped turds that looked like they had the beard of Zeus, because when worms die in you they turn a ghostly greyish white.”


21. She asked him to spit on her, so he did.

“My buddy was with a girl that was more experienced than him. Mid-coitus she got a little dry and told him to spit on her. He, not knowing what she meant but trying to oblige her, hocked a fat loogie and spit it on her chest.”


22. I shot my own cum into my eyes.

“Girl was on top of me, she got off me right as I was about to cum, the cum shoots out and lands right between my eyes. Gave myself a facial.”


23. What the fuck did you just say????

“I had been dating this girl who loved derogatory dirty talk. She always wanted me to call her a slut, etc., during the action. We dated for years, it basically became part of my routine. First partner afterwards:

‘Yeah, you’re daddy’s little slut!’

‘What the fuck did you just say????’”


24. Each pump of jizz released a fart of differing notes.

“First time sleeping with a girl I had pursued for ages. Farted at point of climax. I had no ability to stop. Each pump of jizz released a fart of differing notes. They stunk, too.”


25. My calves cramped while she was riding me on top.

“She was on top and riding like a champ. When I came, my toes curled and everything in my body flexed and I must have been dehydrated because both of my calves cramped like crazy. I yelled and had to get her to roll off of me. I walked with a limp for a couple days because they cramped so bad.”


26. The ‘taint’ of laughter.

“My ex was really into ass play and I’m pretty experimental by nature so I figured I would indulge her fantasy. We go out to an adult toy store and get an anal vibrator then proceed home for sexy time. As we’re fooling around she starts to play with my taint and is really enjoying it; I’m desperately trying to not laugh because it tickled. The sexy times continue and she proceeds to pull out the vibrator and begins to lube it up as she performs fellatio. The moment of truth arrives and she slowly begins to slide the vibrator into my ass until the entire toy has set up camp next to my prostate. She flips the switch, not realizing it is set to high. I immediately throw my face into my pillow to stifle the laughter I’m experiencing which is only made worse by her repeated use of the phrase ‘You like that??’ She yanks away the pillow to look lustfully into my eyes only to find me laughing like a fucking mad man with tears streaming down my face, completely ruining her fetish forever.”


27. Yep. That was a fart. Didn’t even need to taste it to know.

“Was 69’ing a girl, and she readjusted so her anus was on my mouth instead. She had recently showered, and hairless, so I had no reason to object. Here we go giving my first ever rimjob. She gets pretty into it. Stopped going down on me because she couldn’t keep it together. Then, out of nowhere…

Pffft.

Yep. That was a fart. Didn’t even need to taste it to know. She immediately catapulted off of me and rolled to the other side of the bed. So horrified and embarrassed that she started crying, and trying to apologize through the tears. Me? I thought it was fucking hilarious. I couldn’t stop laughing, but I’m sure that didn’t help with her crying at all. She just lost control of herself on the edge of an orgasm was all, can’t blame her. She calmed down after about 5 minutes and we restarted the action. No more tongue-punching the fart-box, though. At least not that day.”


28. I came on her face and she slapped me.

“I pulled out, hastily flung the condom off my member, and came on her face. I hadn’t had much sex experience, but since it was common in porn, I just thought that’s what you were supposed to do. Afterwards, I got slapped, and that girl still hasn’t talked to me since that day.”


29. Her ass cheeks fell on my dumb drunk face and knocked me out cold.

“Met up with this girl from POF at a Hooter’s. We had done the deed a few times, but not enough to break the slight awkwardness of touchin’ bits. Stayed there for a while drinking fairly heavily, and then she invited me back to a house she was watching. Turns out it was her grandparents’ house, confirmed by the stanky musk of antique furniture and Metamucil. Anyway, we start going at it (quite sloppily, I might add) and it starts to get hot in the room. She stands on the bed to turn on the overhead fan while I sit up against the cool concrete wall behind the pillows to catch my breath and cool off. Well, she goes for the fan chain and loses her balance. Admittedly, she wasn’t the smallest girl I’ve ever been with, and when she falls, her ass cheeks collide directly with my dumb drunk face, which in turn smacks my head right into the concrete wall. Hard. Bam. Lights out. Woke up to her calling 911 in an inebriated stupor crying, thinking she had killed me.”


30. My 15-year-old son walked in on mommy getting oral from daddy.

“My 15-year-old son walked in on mommy getting oral from daddy. I am sure we will laugh about it someday. But not any day soon.”


31. My leg crashed into his face, causing a nosebleed and subsequent vomiting.

“Was trying out the logistics of shower sex in a very small shower cubicle, my BF at the time was very tall and I am quite short so we decided that we should try it with him sitting down. Well, he sits down in the shower cubicle and I go and try to put my leg over to straddle him. My leg didn’t make it over. Instead I kneed him straight in the face, not only did he smash his head against the wall but I also gave him a nosebleed. The blood mixed with the water proceeded to look like a crap-ton of blood, which in turn made me nearly pass out and vomit. We proceeded to sit for the next 10 minutes, me on the floor by the toilet and him in the shower tray clutching at his nose. Safe to say the mood was ruined.”


32. I came in my own eye, and it burned like a motherfucker.

“Let’s see…I was dating this very nice lady in college. She was home schooled; her parents were really religious but she was gorgeous so I figured why not date her? It’s college everyone will believe we had sex even if we didn’t. Turns out she’s a freak. So we were having sex one night in my dorm room and I’m behind her she’s bent over head in the pillow muffling her screams, I’m about to cum and boom my roommate walks in. I slip out but mid-hump and as I cum. So my penis slides up her butt and I cum in my own eye. It burned like a motherfucker. So I start screaming; she’s mortified. She doesn’t know why I’m screaming and my roommate is standing there at the door laughing his ass off. I couldn’t believe it and a couple weeks later she broke up with me because she couldn’t stand seeing my roommate because she still kept up super religious appearances.”


33. He told me that my asshole had gotten hairy since I became pregnant.

“I was about 7 months pregnant and having sex doggy-style. When we finish he stands up and nonchalantly says, ‘Your asshole has gotten hairy since you’ve been pregnant.’”


34. I blacked out and hit my head on the toilet after shower sex.

“First time having shower sex with my GF in college and I got so into it that when I finished I blacked out and hit my head on the toilet. Had to stay home from classes that day.”


35. Her parents saw me butt-ass naked.

“Was in my teens. First real GF. We were alone in her house and started fooling around. I stopped and went down on her mid-dance. She squirted all over the place. I being a young guy had already seen it in porn plenty so I didn’t think anything of it. I felt a little pride. She, on the other hand, freaked out and got up and pushed me out of the room, then slammed the door and locked it. I’m standing outside of her bedroom butt-ass naked annnd her parents walked in the door. The front door is about two feet from the hall her room was down, so they both got an eyeful. They knew we were having sex but had the ‘out of sight out of mind’ mindset…well, I wasn’t out of sight anymore.”


36. Huge loud farts started erupting from me.

“I was an inexperienced college freshman, violently drunk at a big party and a guy and I snuck into a room to do the nasty. I was laying down while he was sliding into me and he was putting some pressure on my stomach and the second he was mounted I farted. I tried to let it out slowly as to be undetected, but that just made it squeaky. He stops in place and goes, ‘Did you just fart?’ And I couldn’t help it so I burst out laughing and that just opened the fart floodgate and huge loud farts started erupting from me. Surprisingly enough, this guy and I hooked up one other time, but nothing came out of it.”


37. I ran to the bathroom and started puking.

“I was rather ill but still had the fire in my pants. GF and I were sexing it up and right after I finished, I ran to the bathroom and puked. ‘Was the sex that bad?’ lol good times.”


38. He came on her face and told her it was good for her skin.

“Not me, but my roommate in college. He had just started seeing this girl, and she came over while I was out of town for a little sexy times. He was not the most adept sexual partner, so he never knew that he was supposed to give some indication that he was reaching climax. She was giving him head and he just came square between her eyes. She was obviously startled, and on some kind of weird yet hilarious instinct, he goes, ‘Don’t worry, it’s good for your skin.’ The two of them are still together and I still make fun of him for it to this day.”


39. I humiliated my cuckold boyfriend and then farted on him.

“My boyfriend is into ‘cuckold’ and just general humiliation/degrading talk in bed. So earlier in the day, we were swimming and he can swim but he can’t float or tread water, so he has a floaty noodle all day. He decides to take a break from swimming and I continue… So he’s watching me from the beach when he sees two men start swimming towards me. He goes all protection mode or some shit and decides to swim out to where I am to make sure the men leave me alone…but he brings his floaty.

Later on in the evening, we are having sex. And I genuinely love him so talking to him in a degrading manner is a bit hard for me, and always awkward. This time I say, ‘I need a real man… who can protect me without a floaty.’ At this point we both start laughing at how ridiculous it was that he swam out with a floaty, and how awkward I am for trying to use that for humiliation. But then, I laugh so hard that I let out a huge fart.

It was a pretty awkward day for sex.”


40. I was a two-pump chump.

“The most embarrassing thing to ever happen to me during sex is something that has probably happened to a lot of guys here…

First time with a girl who is now an ex, and about two pumps in, I realize I’m going to cum. To my credit, it had been about 5 years since the last time I had sex and it wasn’t a problem for much longer than that.

I told her that I had to stop (I didn’t tell her that I had started cumming, lol) and she responded by telling me that I could put it in her butt.”


41. I couldn’t take the strap-on seriously.

“I was dating a woman, having only dated men in the past. A lot of what we did seemed awkward at first, but I quickly got the hang of it. Our progression sexually went in stages of new thing introduced, do that thing for a week, master that thing (more or less), move on to next thing.

A month or so into the relationship she bought me a strap on. I was a bit dubious but hey, try anything once right? It was huge. I mean pink-skinned, veiny, a set of balls and everything. She tried to be all sexy with getting me in it. As soon as it was on and I looked down it struck me as the funniest thing I’d ever seen in my life. I am laughing hysterically and it’s all bobbing up and down, which makes it funnier.

Meanwhile she lies on the bed, still trying to be all sexy, telling me ‘how bad she wants my cock.’ That has me tearing up and laughing harder. Once a laugh gets you like that it’s impossible to stop. She is begging for it, I’m laughing. She eventually bursts into tears. I feel bad! So I try to oblige but I can’t stop laughing. I’m pounding away while laughing hysterically. She’s sobbing and saying, ‘oh yeah baby, give me that cock.’

Needless to say, that particular skill was never mastered.”


42. Trying to be suave, I leaned in and fell off the bed.

“Putting the moves on the now ex-wife on our anniversary years ago. I went to lean down on the bed while saying, ‘Hey, Baby.’ When I leaned down, I missed the bed and rolled off into the floor. Rico. Suave.”


43. Little bastard didn’t give a fuck.

“My GF and I had been dating at this point for maybe 3 months. We just recently just started getting into the sexy times, but she doesn’t have the highest libido. Well one day, she’s a fucking dog in heat, and so that night we are raring to go. We got to her place and went to the living room. Her brother was still awake (he’s 15) and watching TV. We wait for him to go to bed and then immediately I slip her pants off and slowly shove my fingers in her fun hole. Maybe two minutes into this, her brother walks back in. The worst part though, is HE SAT RIGHT BACK DOWN ON THE COUCH BESIDE US. His sister, with her pants around her ankles and I just kinda sat up…pulled up our shit…and sat in awkward silence for a bit. Little bastard just didn’t give a fuck.”


44. I met the ex’s mom and grandmother for the first time ever while deep-throating him.

“I met the ex’s mom and grandmother for the first time ever while deep-throating him.”


45. I vomited on his penis.

“I hooked up with this guy a couple of times and one night I go over to his place a little drunk. So we start doing our thing and I go down on him. Well, the combination of alcohol and him pushing my head a little too far made me vomit all over his penis. Now, you would think this is the end of the story but no somehow it gets worse. We then get in the shower for him to rinse off and he for some reason that is unclear to me he still wants it so we start having sex. He stops and goes ‘uhm….’ I had started my period during sex after I puked on his dick. We have now been dating for a year and a half and he still whispers and brings it up when we are with friends to make me turn red.”


46. Her mom tapped on the plate-glass window to alert us to her presence.

“I was 19 or 20. Girlfriend lived at the end of a dead-end street, and being young and dumb like we were, she was riding me on the couch in the living room, in a summer dress with no panties in front of a big plate glass window. Her mom came home from work early and tapped on the glass to alert us to her presence. Right as I was about to cum. GF vaulted off of me, and I painted the couch and coffee table as I tried to scramble to the bathroom with a hard-on and my shorts around my ankles. Good times, man.”


47. She needed knee surgery after I dry-humped her too hard.

“Dry-humped my GF (now wife) too hard and she hit her knee on the bed frame. Two months later she had to have knee surgery to repair the damage… Four titanium screws, two wires, 85% of her meniscus removed and $50,000 bill. She told her dad that she ‘tripped.’”


48. As I came I said, “Here comes Johnyyyyy” with a strange whispering and horny tone.

“It’s not exactly embarrassing, but plain stupid.

It was one of the first times I had sex with my current GF and near the climax I proceeded to ejaculate on her face/chest.

As the sperm was ready to flow I say, “Here comes Johnyyyyy” with a strange whispering and horny tone.

She said nothing.

I said nothing.”


49. Spider! Spider!

“One time my GF really wanted to have sex by this lake and as I was on top of her a see a spider walking up my arm. I quickly rise up to shake it while yelling, ‘Spider! Spider!’ GF thinks it’s in her hair and we’re both jumping around naked trying to shake off this fucking spider. As were jumping we see a boat in the distance approaching us and we bail out of there as quickly as possible. Do not recommend sex in the woods.”


50. I pulled out and shot jizz all over my cat.

“It wasn’t all that embarrassing because I’ve been with my GF for quite a while but still noteworthy, I pulled out and shot jizz all over my cat; he didn’t even move.” TC mark

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  • http://voluptuouscara.wordpress.com Cara

    We were at his place…we had regular missionary-position sex with no toys. Very boring, but that part went without any embarrassing moments. After sex, I go in the bathroom to pee and y’know, wash off my down there. While I’m sitting on the toilet, he shouts very loudly, “What’re you doin’, POOPING?!!!!!” Now, prior to that moment, I thought I was with a grown man…but I realized, and sadl, that I had just made love to an overgrown child who found toilet humor funny.

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