47 People Confess Their Most Awkward And Embarrassing Sexual Experience

Illustration by Daniella Urdinlaiz
Illustration by Daniella Urdinlaiz

1. WRONG time to ask ‘Who’s your daddy?’

“I said, ‘Who’s your daddy?’ and apparently her dad died of cancer 2 weeks before that and she started crying.”

2. I told her I loved her while losing my virginity

“Telling her I loved her while losing my virginity.”

3. My wife fell asleep while I gave her oral

“My wife fell asleep while I gave her oral.”

4. I accidentally said ‘Fuck you!’

“I was making love to my then-girlfriend and it was really hot that she was thrusting her hips up to meet me so I wanted to say ‘Yeah, fuck me back’ but I ended up saying ‘Fuck you!’ She kept asking ‘What? What did you say?’ And I kept trying to not talk about it and continue having sex.”

5. Micropenis

“Micropenis. Didn’t even get to the actual business. I took one look and noped on out of there. A girl has needs, too.”

6. Sharted at a gangbang

Sharted at a gangbang. Didn’t get invited back…the lack of another invitation was awkward, I was still part of the FB group.

7. Fell off the bed and dislocated my knee

“Fell off the bed and dislocated my knee.”

8. Well, it FELT like a boob…

“Well, one time I was with this chick who was kinda overweight. We were makin’ out, she was kinda leaned over and straddling me. She had some pretty decent boobs, so I move my hand to try and grab a handful. I get some of that sweet boob and start kneading that shit like some Silly Putty, mmm yeah. I was doing this for a good thirty seconds before she reaches down, grabs my hand, and moves it up to her ACTUAL boob. Turns out I was just grabbing at a roll of tummy flab. She didn’t say anything about it, and I never called her back.”

9. I stopped to use my inhaler

“Nothing too serious, just had stop and use my inhaler. It was cool, she wasn’t really in to it anyway. But she oughta see me now, I don’t even have to carry an inhaler anymore.”

10. He put his dirty toes into my vagina

“The first most awkward was when an ex told me to close my eyes. Suddenly I felt this weird rough feeling in my vagina. I open my eyes and he is putting his dirty toes in there.

11. I could almost wrap my hand around it twice—and I have tiny hands

My second ex constantly bragged saying his penis was 8″ long. He later said he admitted it was actually 6″. Once the pants were off and we were ready to go he was actually 4″ long and below average in girth. The most awkward part was when he asked, ‘It’s huge, huh? I bet you have a hard time wrapping your hand around it and fitting it in your mouth.’ I could almost wrap my hand around it twice and I have tiny hands, and my prior and first ex had him beat lengthwise by a little over half an inch. I just had to awkwardly say nothing since I didn’t want to hurt his ego.”

12. He meowed as he came

“He meowed as he came. I think he thought it was cute or something.”

13. Got our lip/nose rings stuck together

“Got our lip/nose rings stuck together. We couldn’t get unstuck for a while and we were very close to calling her mom to come help (while we were halfway through doing the business).”

14. All of a sudden she jams this pink rubber dong monstrosity straight into my gooch

“I met a girl online, we talked a bit and then we decided to meet. Well she was quite a bit larger in person, but fuck it, sex is sex right? So she starts giving me a blowjob, I close my eyes, I hear buzzing. All of a sudden she jams this pink rubber dong monstrosity straight into my gooch. It hurt and led to some pretty awkward sexing.”

15. A pinworm was wriggling on my poopshaft

“Was fucking my high school girlfriend in the ass on her dad’s bed. I pull out and notice something white on the tip of my dick, fucking pinworm. Fucking disgusting. And she was denying it the whole time, saying it was a piece of wayward toilet paper even when it was clearly wiggling on my poopshaft.”

16. Lost my boner (and the condom) inside her

“Losing my boner and then losing the condom…inside her. There’s no coming back from that friends, let me tell you.”

17. Twenty people watched us from the food court

“Having sex outside of a mall behind a wall when we noticed about 20 people watching us bump uglies from the food court above us.”

18. Cold dog nose on my taint

“Cold dog nose on my taint. 1/10, even on a hot summer night.”

19. Furby couldn’t stop talking

“Long story short: Knocked a Furby over which promptly rolled under the bed and couldn’t stop talking. ’Ah! ah! weeeeeeee!’ said the Furby.”

20. Some guy keyed my car while I was having sex in it

“So I met this chick at a reddit event in my city. Hit it off real good and decided to get some tacos. She wanted to ride with me and we proceeded to go get some tacos. Got to the place one thing led to another and we started to do it in the car. As we were doing it some guy decided to key my car. Apparently the guy that keyed my car had a crush on the chick from the event and followed us to the parking lot.”

21. She would cum so hard when I gave her head that she would sometimes fart

“This one girl would cum so hard when I gave her head she would sometimes fart. We are dating. For 8 years now.”

22. I had a few fingers in her while she talked to her parents

“My girlfriend junior year was pretty much a high school kid’s dream come true. She was attractive, equally horny, and her parents were super liberal. They believed it was better to just let her lock up in her room with me, then have us get arrested doing it in a car. So every day after school it was back to her house and lock up in her room till dinner. So one time I have a few fingers in her when her mom knocks on the door. It’s locked so we are fine but her mom is trying to talk. I start removing said fingers, but she whispers to me ‘this will only take a second.’ and she holds on to my hand to keep them in. Then her dad joins the conversation. So I’m just sitting there listening to them talk about an upcoming trip while I’m knuckle-deep. Only time in my high school career that I decided to pull the plug and say lets rest for a few hours. Shit just felt wrong.”

23. My nosebleed started dripping onto her cheek

“First time having sex with this girl, I am on top. About a minute into it she stops me. I look down and see blood on her face. Turns out I had gotten a nosebleed and it dripped right onto her cheek. But hey, now I am shopping for her engagement ring, so I guess it worked out.”

24. She puffed a very polite fart right into my face

“Drunk as a motherfucker with a high school fling and I’m eating her pussy like it’s the Last Supper. She got relaxed, too relaxed and puffed a very polite fart right into my face. Nothing grotesque, just ‘Pooooft.’ I stopped munching, looked up and gave her what must’ve looked like the People’s Eyebrow. She was mortified. Nearly crying from embarrassment. I shrugged and went back to the buffet. Awwww, what a happy memory.”

25. Gave a girl a paralytic orgasm

“Gave a girl a ‘paralytic orgasm.’ She literally contorted her face on one side like she was having a stroke and her hands turned in like she was posturing. Lasted about 2-3 minutes. It threw me off at first but was also kinda proud of myself.”

26. Cramped my ass cheek trying to fuck in the back seat

“Cramped my ass cheek trying to fuck in the back seat of my Nissan. Had to open the door and stand on the pavement. Bare ass exposed to the night air.”

27. She kept telling me to choke her harder

“Girl told me to choke her, so I did. She kept saying harder, so I obliged. By the end of it, I had all my weight on this girl’s throat. I easily outweighed her by 100 lbs. She still kept telling me to choke her harder. She was turning bluish and started to choke/cough. I couldn’t do it anymore, I went limp and pulled out. She was so mad at me for ruining her orgasm, ‘I was right there!’ I never talked to her again.”

28. A 15-minute weird seizure-like orgasm

“Recent girlfriend and I were together on and off for a long long time, very comfortable and we had tried a lot of fetishes together. She was really into being dominated, tied up and spanked so we were doing that. She knew she was leaving town for a while, so she wanted to do something special, so she was bent over, hands tied behind her back, blindfolded and as I was putting a scarf in to gag her she said, ‘I want you to cum inside of me.’ Never been a thing for me, but I figured why not? Barring some weird hiccup in her cycle, there was little chance of getting her pregnant. So we were going at it for awhile and she was really into it, more so than normal. When I was just about to pop, I started going harder….pulled back for a deep thrust and she suddenly flattened against the bed because she got cold feet. Now, this wouldn’t be too big of a problem except the timing was such that I was thrusting in as she flattened out and my cock thrust right into a bone. The pain of this made me try to draw back which in turn made both of my hamstrings go into the most painful spasms I’ve ever felt, which then sent me straight forward like I was a catapult. I am no small man, and the force I landed with knocked the wind out of her and broke the middle section of the wooden bed frame. I was also mid-orgasm, but the orgasm kind of just leaked out in an uncomfortable way and it kept going for about 15 minutes and it felt….weird…my whole body was twitching or shuddering and my legs wouldn’t stop shaking but in the worst way imaginable.”

29. Truck started rolling down a hill while I was having sex in it

“I was with my ex-fianceė and we were having sex in the back of my truck under the moon and whatnot near her parents’ house that is adjacent to a corn field and next thing I know the truck starts rolling down a slight grade.”

I thought we just wiggled it a bit because we were going at it pretty good, but turns out my parking brake is faulty and I didn’t leave the truck in gear as we pick up some speed down this incline towards a drainage ditch. My first instinct is to try and hop out of the truck and then into the cab. Of course it turns out to be a dumb ass idea.

I jump out, cock hard as a diamond in an ice storm glistening in the moonlight, and try to reach the door handle but by that point I was already too far behind it and I hear a crunch and a little scream as my back tires wedge into the ditch. So I run over and help her out of the truck and we grab our clothes. As she’s getting dressed she looks at me with the most serious expression she’d ever put on her face and says, ‘I came.’ For whatever reason we thought that was so funny and stood there half dressed for about 5 minutes laughing until we cried. We got dressed snuck quietly into the house and acted all surprised the next morning when her dad used his truck and hitch to pull mine from the ditch.”

30. I broke my ‘banjo string’

“I was having sex with my girlfriend (now wife) and felt a horrible slap on my penis. Well I look down see blood, she’s freaking out because she felt it too. Once we realize the blood is coming from my penis I start to freak out. Called the ER and Googled around. Turns out my frenulum, it’s like some skin that connects shaft to head, snapped while we were going at it. ER doctor said no way to tell how bad it was and requested I come in to get it checked out. Yahoo Answer replies made it seem common, so I just iced it and stayed home. Stung for a few days after but all went well.”

31. I farted with every squirt of my orgasm

“First time having sex with her, and I farted during orgasm. Not one long loud fart. Just a series of little ones. Every squirt of the orgasm had an audible pfft. I could not control it. Pfft. pfft. pfft. pfffffffffft. pfffffffffffffffffft. I was ashamed.”

32. She queefed and farted in my face

“I was going down on this girl I’d been hooking up with for a minute. She was getting pretty into it and accidentally queefed in my mouth. I wouldn’t have been upset if she didn’t rip ass seconds after I went back for seconds.”

33. She fainted in the shower while standing up

“Shower sex and she fainted. Standing up. In the shower. Did not end well.”

34. She did a Fat Albert impression using my fat dick

“I met this girl off Tinder, went on a first date, nothing happened, pretty typical. The second date was the ‘Netflix and chill’ date, I went to her apartment to watch Sinister 2 with her. Pretty quick, things got hot and heavy and we start fooling around. I get on top of her and she slides my pants down and sees my dick for the first time. She looks at it for a sec and says, ‘Wow, you have a really thick dick.’ I thought it was kind of a weird comment, but she was pretty hot so I just said thanks and went back at it. She then grabs the base of my dick and swings it side to side while saying ‘HEY HEY HEY’ in a Fat Albert impression. I fucking died, lost the boner, she thought it was kinda funny too. We never finished the movie. 9/10, never saw her again after that.”

35. She had toilet paper sticking to her butthole

“Had to tell her she had toilet paper sticking to her butthole.”

36. I apparently at some point slid balls-deep into her ass

“Me and my girlfriend junior year were going at it after school, she was really relaxed and I apparently at some point slid balls-deep into her ass and didn’t notice till she said something.”

37. Stray pube caused her to puke on my penis

“Stray pube kicked in her gag reflex and resulted in her vomiting on my penis.”

38. She asked if I was gay mid-thrust

“She asked if I was gay mid-thrust.”

39. An old cat jumped on my back

“A cat as old as I was (early 20s) jumped on my back.
Did you know that when cats get old, they lose their ability to retract their claws?”

40. Girlfriend punched her own vagina because she wasn’t getting wet enough

“Girlfriend punched her own vagina because she wasn’t getting wet enough.”

41. Poor man got his dick twanged

“I kicked my boyfriend in the penis when I moved to sit on his face. Poor man was so excited for a face full of crotch and instead got his dick twanged.”

42. I pooped in his face a little

“A guy was going down on me and I thought I just farted [but] I ended up pooping on his face a little. And the worst part was he tried to keep going and was trying to rub my shit on my stomach I instantly pushed him off and said I need to go wash myself and so does he.”

43. He humped my leg and jizzed all over it

“I was making out with a guy in my dorm room with him on top of me. He asked if we could have sex and I said no. He, fully clothed, proceeds to hump my leg super quickly for like 10 seconds, jizz all over his pants/my leg, get up and say ‘OK, see ya later,’ and leave.”

44. I drooled on her face

“I was titty-fucking this one girl I dated for a few years in high school. She was one of those crazy-but-super-hot chicks. Absolutely perfect tits. Anyways, I was so…in a trance?…while I was fucking her tits that I didn’t realize my mouth was open. Ended up drooling right on her face. Very sad moment.”

45. Some people have a very strong musk odor when sweaty

“Going for a cunnilingus and wanting to puke when I was in between her legs. I stopped everything altogether and went to sleep without explaining. The moment was a very awkward situation which wasn’t really her fault since some people have a musk odor very strong when sweaty which made me sick at the time. The next day was also very awkward when she told everyone that i was a ‘mauvais coup.’ Dunno how to translate that. I couldn’t really explain without seeming really mean and it was really awkward with my group of friend from then on.”

46. My wife threw up while giving me head in the shower

“My wife threw up while giving me head in the shower; she cried…and died a little inside, I think.”

47. Strangest compliment of my life during sex

“We were both drunk with this girl. We just started the sex when she says: ‘Ohh this is soo good, like never before.’ Then she adds: ‘Or am I just too drunk?’ Strangest compliment of my life during sex.” TC mark

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