25 People Reveal The Most Awkward Sexual Experience Of Their Life
1. She called out her brother’s name.
“She called out her brother’s name during her orgasm.”
2. She looks at me harder, blinks a few times and says, ‘oh, thought you were someone else.’
“Met a girl at a party and we were drunk. She can on pretty hard and took me upstairs. Before I realized what was going in she had my penis in her mouth. Not 30 seconds later she asked if I am enjoying myself. I am speechless as this is my first BJ ever. Then her expression changes, she looks at me harder, blinks a few times and says, ‘oh, thought you were someone else.’ Casually gets up and leaves.”
3. During sex he told me that for the last 12 years he was fucking his own brother.
“The sex wasn’t memorable at all but what was memorable was him telling me that for the last 12 years he was fucking his own brother. I just sat there quietly and couldn’t think of anything other than I just handed my V-card to an absolute freak.”
4. Mom drank my cum out of a Coke can.
“When we finished, I put the used condom in an almost empty can of Coke and forgot about it. This would normally be fine, but my mom had a penchant for finishing abandoned drinks….Fuck, that was an awkward talk afterwards.
tl;dr – Mom drank my cum out of a Coke can.”
5. She answered the phone and talked to grandma for like five minutes while I was still fucking her.
“Her grandma called her when I was inside of her. She answered and talked to grandma for like five minutes while I was still fucking her.”
6. I pulled out and spit on her back. I didn’t realize she was looking at the mirror beside the bed.
“I couldn’t get off so I decided to fake it, so I pulled out and spit on her back. I didn’t realize she was looking at the mirror beside the bed.”
7. Homeboy just started fucking chewing on my clit like a dog with a rawhide.
“I was at a party my freshman year of college. I was an awkward kid, barely coming into my own and having trouble accepting that anyone found me sexually desirable.
My friends kept trying to set me up with this guy, Tom—‘Tom’s so great! He’s such a nice guy and he’s really into you! Go for it!’” I was really drunk, but sure enough, someone pushed me at Tom and we started chatting.
The party was in his apartment, so invariably we stumbled into his room. He started tugging my clothes off and begging me to sit on his face. I was still pretty inexperienced and had never been propositioned so boldly before. But fuck it, I was drunk, and I felt sexy, so I did it.
Homeboy just started fucking chewing on my clit like a dog with a rawhide. I yelped and said, ‘Stop it! That hurts!’
He apologized and tried again.
Nope. Gnawing on it full strength.
I just got off of him, silently put my clothes on, and left the room to hunt down the ‘friends’ who’d set me up with him.
‘Sorry!!! We, uh…knew he was kinda terrible in bed, but he was really into you, so…sorry?’
Never forgave them for it.”
8. The Mormon Handjob.
“The Mormon Handjob:
The first time I ever gave a handjob I was with my boyfriend in the woods behind my house. Partway through he starts crying. I am all sorts of wtf-is-happening?!?! Then he starts talking about how Joseph Smith was also led into temptation in the woods.
He came anyway and had no other issues during our relationship. I guess teenage boy hormones win out over religion.”
9. I had a seizure whilst getting a blowjob.
“I had a seizure whilst getting a blowjob. She thought she was doing a really good job until I pissed in her mouth.”
10. When I lost my virginity, the girl kept saying, ‘If only your mother knew what I was doing to you right now.’
“When I lost my virginity, the girl kept saying, ‘If only your mother knew what I was doing to you right now.’
After a little time, she wondered why I went soft.
Was a virgin, though, so I powered through and finished.”
11. He began talking about his insecurities with his ex.
“He began talking about his insecurities with his ex while he was on top of me and began comparing us.”
12. Her dad licked his fingers clean…without knowing his daughter’s juices were on them.
“In my teens, hooking up with girlfriend in her dad’s office for the thrill of it while the rest of her family is out.
I have three fingers on my left hand which are thoroughly coated in lady juice when we realize that we can hear people in the house. We quickly correct our clothing, and to provide a pretense for why we’re in there I pick up her dad’s acoustic guitar and sit it on my lap, but out of consideration for the fact that I don’t want to taint his instrument with his daughter’s gruel I don’t play anything.
Her dad walks in. He gave me permission to play his guitar anytime I’m over at the house, so it’s fine for me to be there, but when he walks in he asks me what I’m playing these days, so despite my misgivings all I can do is briefly play some stuff for him—I was studying jazz guitar at the time so I show him some improvisations I was trying at the time.
This was already awkward enough. But then he asked for a go, and of course I had no choice but to relinquish the guitar, strings now contaminated by his girl’s juices, and watch as he played it for a few minutes. I thought that was the worst of it. I was wrong.
Another few minutes pass and his wife and my GF’s little sister get home. They’ve brought fish and chips. The guitar gets put down, and I get to watch my GF’s dad eat fish and chips with hands that have touched his daughter’s juices and lick his fingers clean.
I wanted to curl into a ball and die of shame. My GF looked like she was going to be sick, which at least gave me a good excuse to go home.
Man, that was an awkward afternoon.”
13. I’ve puked during a BJ.
“I’ve puked during a BJ. More than once. Don’t suck dick on a full stomach, kids.”
14. Fire ants.
“Take a drive in the country with the full moon out, stop by the dam, start getting cozy, decide the ground was going to work out…10 minutes later: fire ants.”
15. She had a tonsil operation a few days earlier and my dick ripped open the wounds.
“Met a wonderful girl at the grocery store. We started talking while buying vegetables and really hit it off. We parted ways without exchanging names or numbers. I thought about her a lot and deeply regretted that I didn’t ask her out. She randomly found me online six months later, turns out she had thought about me as well.
We met a few days later and the magic was still there. Things heated up and we started to have sex.
A few minutes in I started crying and having a full blown panic attack because of built up sexual trauma from a prior abusive relationship. After I calmed down she wanted to give me a blowjob. It felt really good but after a few minutes there was blood everywhere. She had a tonsil operation a few days earlier and my dick ripped open the wounds. Tears, blood, and a lot of laughter.
Now, four years later we have two kids and are getting married next summer.”
16. I leaned down to kiss her and promptly THREW UP IN HER MOUTH.
“Hit it off with a nice girl at a Christian Summer Camp. We were both counselors at the time, and one weekend both of us got super-drunk and started to get into it in an empty cabin. As we’re having sex, I begin to black out, and the next thing I know, she’s crying and I’m on the floor, covered in strange fluid. Turns out, while I was still inside her, I leaned down to kiss her, and promptly THREW UP IN HER MOUTH. That seemed to have killed the mood.”
17. She fell asleep while sucking my dick.
“My now ex-gf was feeling a bit under the weather. I went to the store and bought her some Robitussin. She takes it and we continue on our night.
Later, in bed, poke her with my boner, thus initiating the sexual behavior. She says that she wants to thank me for helping her feel better and starts to give me a blowjob. Her blowjobs suck. Literally. She puts her mouth around the head and sucks like a straw. But she also works the shaft, so it’s kinda bittersweet. Anyway, she does this for like five minutes and then starts to go slow. Slowing it down makes it way better and I’m into it. After a bit she starts going so slow I can’t take it anymore. I start jerking off and say I’m about to cum. Then she snored. She fell asleep while sucking my dick.”
18. The look of disappointment on my dog’s face dripping in spermicide foam is one of the saddest things I’ve ever seen.
“My girlfriend at the time could not take birth control so we tried everything available since condoms are so lame. She bought the spermicide foam and we used it once successfully, although it’s awkward as fuck waiting for her to stick the applicator thing in and shoot the foam inside herself. So the 2nd time, I turn my head while she’s doing it to hopefully not lose my rager, and I hear a mini explosion. Something went wrong and it blew up covering both of us and both of my dogs who were next to the bed in spermicide. The look of disappointment on my dog’s face dripping in spermicide foam is one of the saddest things I’ve ever seen.”
19. I look at her and realize that she’s starting to go into a seizure.
“Was once having sex with an ex-girlfriend. Things were starting to reach the end and she gets on top of me to ride to the finish line. Just as I think she’s starting to climax, she starts making these grunting noises that she’s never made before and starts kinda shaking; in the moment I think, ‘I’m the fucking man. She is really having an awesome orgasm.’
Finally I look at her and realize that she’s starting to go into a seizure. (I found out later that she hadn’t taken her medication in a few days and had gotten less sleep than she usually gets.) So she’s seizing while she’s on top of me and I’m still inside her. I lay her on her side and make sure she doesn’t thrash about off the bed but eventually it subside after a few minutes. She then passes out.
30 minutes later she wakes up and says, ‘Oh hey, good morning. Man I have a weird headache.’ I explained what happened and she told me that she had no memory of us having sex.
(For the record, I had decided not to finish inside of her seizing body as I felt like that would have been poor form.)”
20. I pee on his face. I’m horrified. He stops.
“Was really tired after clubbing. Beautiful man asks me if I’m okay and offers to get me home. I look and feel crap at so I’m genuinely surprised by my luck. He gets us a cab, we go home, he goes down on me. I starfish and fight the urge to fall asleep.
Then I pee on his face. I’m horrified. He stops. We don’t speak of it. He leaves early and awkwardly next morning.
As a fantastic coincidence later joins my circle of friends. Turns out he thinks he made me squirt and is quite proud of it. Everyone else knows I’ve been referring to him as ‘the piss guy.’”
21. I accidentally kicked my GF under the chin trying to take my pants off.
“I accidentally kicked my GF under the chin trying to take my pants off. At least now I know she’s not into that.”
22. Got walked in on by her dad.
“Got walked in on by her dad. We were doing it doggy-style facing the door, but her face was down in the bed so it was me he made eye contact with. He went white as a sheet and left immediately. She had no idea.”
23. Chemo BJ.
“The girl was going through chemo and was bald but wore a wig. She started giving me road head and I took off the wig. We get to my place, we’re in my car still, and my friend pulled up.
He sees me rocked back and her bald head bobbing in my lap. I see him too late. He gives me a look of disapproval and shakes his head before pulling away. I grabbed her wig, leap from the car, and chased him down yelling ‘She’s a girl she’s just bald.’ But he never stopped.
I feel bad for embarrassing her now. She didn’t let me resume the BJ but we fooled around again later. My buddy thought I was banging guys but the girl beat cancer, so that’s a plus.”
24. I got stung in the abdomen by a scorpion while in the middle of sex.
“I got stung in the abdomen by a scorpion while in the middle of sex. At first I thought my stomach hair got caught or something so I kept going for it. Once everything was done is when I got stung a couple more times and noticed this small scorpion running between us. My abdomen was swollen and I was in pain for about an hour.”
25. He gave himself a bloody nose so my parents wouldn’t question if the blood on his shirt was from me.
“First time I had sex, my parents were downstairs so we had to be very quiet. The guy kept his shirt on; however, I bled a lot, all over his white shirt. He didn’t finish because he was scared of the blood and he ended up literally hitting himself on the nose, giving himself a bloody nose so my parents wouldn’t question if the blood on his shirt was from me.”
