One Night Stands


Most Embarrassing Sex Ever?

Lets hear everyone's most embarrassing sexual encounter or hookup story...

Give a thumbs up to the best stories (or should I say the worst lol).

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BlackAndYellowover a year ago

Answer 1 of 10

Boyfriend's Mom Sees My ...

Sooo my current boyfriend and I were upstairs at his house. He has a very large house and he has the third floor to himself, so we can usually get pretty noisy. Well, on this day, we had only been dating for about a year, and I was 17 and he was 19. We were fooling around in his bed, and we forgot to lock the door. My boyfriend undresses me and starts to go down on me. He is eating me out so good, and fingering me so perfectly, and I am being kind of loud. In the middle of this, his mom bursts in the door and sees me laying on her son's bed, BUTT NAKED, with her son's head between my legs licking and flicking away. Sean keeps going at it as his mom is staring me in the face with a horrified look (his bed faces the door) and Sean did not hear her so he keeps going and I am frozen there and his mom is frozen there and he makes me squirt and his mom sees and screams and then Sean jumps up and his mom is still there starring right into my vag, with my boobs out and everything! After she left, Sean sat with me while I hyper ventilated for a good hour. At dinner that night, his dad was asking him for tips on how to get a woman to squirt like that, and my face was beat red, and his brother kept making jokes about how he wanted to go "eat out" and how he wish he had some "fresh juicy cake to eat tonight like Sean does". OMG so awful. They still make fun of me for it.

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Kyle Miracle

Kyle Miracleover a year ago

Answer 2 of 10

Take off your socks!! When I first star...

Take off your socks!!

When I first started developing my social skills a few years ago, I really admired a recent acquaintance - we'll call her Meg. Well Meg was one tough nut to crack...she would flirt and tease and send mixed signals like it was her job! And Meg is gorgeous too (and she used to ride a crotch rocket, see what I mean!? She's so cool!)

Finally the moment arrived, I manned up, made the move and kissed her. I was so proud of myself! :) A couple dates later, and we were in my bed. Everything was going much better than I could have even hoped for...then in the middle of it all - out of nowhere - Meg wants to stop. It came as such a shock so I asked her why. She gave me a bs reason and we talked for a while, then she went home.

A week later, she told me the real reason was because I left my socks on and when she thought about that, it turned her off! Crazy huh? I didn't even think of it at the time. With some people, it's just got to be a perfect moment right down to the minute detail.

Now, we're still very close - not intimate in that way - but great friends. I value our friendship above any other relationship we might have.


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BritishGuyover a year ago

Answer 3 of 10

Some funny situations: Scenario A: So ...

Some funny situations:

Scenario A:

So I go camping with my family. Now one of my uncles had twins and I knew one of them didn't like me but I knew the other was crazy about me.

Anyway its late night, dark outside and I'm in my tent. I feel something creep up by my side and then next thing you know I feel a tongue down my throat.

It was the longest, nicest kiss ever. I turned the light on and it was my uncle.. he'd gone into the wrong tent!

Scenario B:

When I was very young I didn't know much about sex.

One day I was making out with this girl and she put her hands down my pants and started playing with my penis.

I was getting a strange sensation but I didn't quite know what it was.

A couple of minutes later(which is still my personal record) I ejaculated. Now at that time I had no idea what had just happened.

I was scared out of my mind and demanded she tell me what she did.. I was upset and running around all over the place.

About an hour later though I was like can you do it again?

Those are both made up but I'll get down to my diary sometime for real ones :P

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Simone de Boudoir

Simone de Boudoirover a year ago

Answer 4 of 10

Ok, I mentioned this elsewhere, but once...

Ok, I mentioned this elsewhere, but once I invited a guy to my house with the intention of smoking the herb and hooking up. I was mislead by his internet photo, in which he was not smiling. He arrived on my doorstep and was missing most of his teeth. Think, like a pekingnese dog. A couple of lower teeth and that's it! We hung out for a bit and then I explained that I wasn't interested and sent him on his way.

I guess that was more of a bad date? OK, I've got sex ones, I know I do.

A dude farted pretty much in my mouth once. I was licking the taint and yeah, that was gross. I'm a trooper though, and I kept going.

I once aimed poorly and got cum in my partner's own eye.

Back when I had acrylic nails, I accidentally pinched the tender penis skin putting on a condom. I drew blood a little. Nothing kills the mood quicker, let me tell you. Also my primary reason for avoiding fake nails from then on (it was a brief foray into madness for work).

There are probably more, but I can't think of any at the moment.

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wadekid13over a year ago

Answer 5 of 10

So it was my freshman year of college and I was hooking up with this girl in my dorm room. Clothes start coming off, some touching and thing lead to another and she began to give me oral sex. Know I'm the courteous type, so I always ask "do you want me to tell you when I'm ready" or something along those lines.

So after about 3-4 minutes, I said it ...."Ok, I'm ready". Now apparently, she was caught up in the heat of the moment and she lifts her head up slightly, momentarily pausing from the oral sex, and says "what did you say?". Right at that moment, it happened. I came. It was completely out of my control...there was absolutely nothing I could do. Because she had lifted her head up to ask me what I had said, she kind've...uhhh, got a "face wash". She started screaming..."EW, OH MY GOD, OH MY GOD"... meanwhile, I couldn't stop laughing...I mean it was hilarious. After she left, a few of my buddies next door come running in asking "what the hell just happened?!?". I could barely get the story out amidst my laughter, but pretty soon everyone was on the floor too.

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scarlettewiththeropeover a year ago

Answer 6 of 10

Hahaha, I have a terrible story, especia...

Hahaha, I have a terrible story, especially for women. I would call it maybe the female equivalent of a guy looking down and seeing blood on his dick… hard to say since I’m a girl and blood doesn’t bother me one little bit. This is 100% my most embarrassing story, as in only my former roommate knows all the details of this. And I’m a very open person, so that tells you a lot LOL. (I’m finally at the point where I can laugh about it!)

4 years ago I was a freshman in college and I met this guy in a class, and we ended up sitting next to each other and talking all semester. I thought he was really cute and one of the nicest guys I’d ever met, and we’d flirt all the time, but he was in a serious relationship and I was in a weird place with this guy, so nothing ever came of it. The class ended and we lost touch over the summer.

I didn’t see him much for a long time after that, and whenever I did one of us was dating someone. Winter junior year rolls and randomly we both took all the ‘likeness’ quizzes on Facebook, and every time we’d pop up in each others list as being 90% alike. He messaged me about it, saying he’d always thought I was a really cool person and this seemed like a sign to him, and we ended up messaging each other all the time for a few weeks before finally managing to hang out. Things really clicked. The only problem was that even though we had very serious talks all the time about what we liked in the opposite sex, relationships, and we’d flirt like crazy, he never actually asked me on a date or made a move. From all our talking I knew he was a REALLY traditional guy and liked to take it slow, but I’m a very sex-positive person with a healthy sex drive, and I was starting to go a little nuts. My roommate kept telling me I should just make the first move if he wouldn’t.

One night (spring now) we happened to get really drunk, and we were cuddling… and the next thing I remember we were making out, hot and heavy, and his hand was heading seriously south of the border. This went on for a little while, and I told him in this drunken outpour how much I’d always liked him and how horny I was, and he starts saying we shouldn’t have sex, because he doesn’t want me to regret anything because I’m drunk, and he’s a big believer in waiting, and while it was exactly what he wanted to do he was probably too drunk to have sex anyway. My memory gets fuzzy again in here, the next clear thing is him having trouble getting a condom on, and us having what may have been the lamest sex ever. Afterward he said he’d call me the next day and went home to bed. I pretty much passed out. I woke up in the morning after a good long drunk sleep, hung over, went to the bathroom… and the condom was still inside me!

Oh, the horror. There are so many details of what this is like that I could share with you, because this is seared into my memory. I could tell you with specificity what the sensation of pulling a used 9 hour old condom out of your delicate bits feels like, but I think that’s graphic enough right there! I’ll just let you imagine it.

I also have to wonder what the hell he thought had happened to the condom!

Things got really weird with him after this incident… I tried to laugh the whole thing off and move on, so I got him to make plans to hang out later that week, and he immediately felt the need to add that we shouldn’t plan on having sex, because he still believed in taking it slow. After several weeks of is-or-isn’t-it-a-date dates, he admitted to me that he’d been seeing another girl, his first date with her had been a week before we hooked up, and things were getting serious with her! It was awkward, and I was kinda pissed, but I really valued him as a friend and just wanted to move on.

Unfortunately, he told his new girlfriend about what had happened, and we weren’t allowed to talk anymore! Then I was really pissed. This past Valentine’s Day they broke up and we sort of started talking again, but it’s never been the same, he’s still awkward about the whole thing, and honestly it never stopped pissing me off that he let his girlfriend tell him who he could be friends with. The worst part is that I still run into him all the time, he’s a bouncer in my neighborhood bar, a favorite spot of me and most of my friends!

This story makes me kind of believe that some things are fated to go badly lol. I don’t know what the worst part is, the actual sex itself and ensuing condom incident, or the loss of my friend! I accept that it’s some kind of karmic punishment for something I did in a past life 0_o

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oohlookasquirrelover a year ago

Answer 7 of 10

I've decided against telling all the bac...

I've decided against telling all the background of my worst sex story because it's just depressing and not amusing at all. But I'll say that breakup sex really is awful, especially if you are the one doing the dumping and you feel really bad about the entire situation. If you're ever close to tears of sadness during sex, you know you've made a bad decision. I do not recommend it, especially if you are no longer attracted to the person you're pity-fucking. I cringe just thinking about it.

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jakedanmanover a year ago

Answer 8 of 10

This was years ago but this was the wors...

This was years ago but this was the worst ever. It was my birthday and my house mates thought they help me through a rough time by bring some ladies over. Kicked it off well with one who was going through a rough time as well. Let's say we hooked up and we were both drinking.

So we are doing our thing (one of the reasons I hooked up with her is because she was producing milk and I always wondered.... Let me just say not as good as you might imagine and I say don't ever try it.... but I digress) and right in the middle of it she started calling me by another name.

As this has never happened to me before (and now I know what to do about it) I kept going and just reminded her of what my name was. I just figured we just meet and she forgot my name. After it happened again I knew it was no longer a slip of the mind. As I was going through a rough time myself and was craving the attention and comfort the a woman can provide, I set my pride aside for the night.

Now let me tell you, this was the worst feeling I ever had after sex in my life. I never felt so used and so dirty after I was done. I was not even sober and could not believe what level I let myself fall to. My birthday ended up being a very dark (short) chapter in my sexual life.

Want my advice? Avoid one night stands altogether and try to do it right from day one. You will thank me many years later!!!

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sexpertover a year ago

Answer 9 of 10

Oh dear... this is going to be TMI, but ...

Oh dear... this is going to be TMI, but hopefully you get some sort of schadenfreude out of this and don't feel so bad!

So I'm in high school and I'm with a real sweetheart. Completely vacant, but a nice guy. I've just ended my first real relationship, and he's my rebound, and he's a nice virginal guy that I'm ready to corrupt.

It was during exams, and since we both lived at our parents' houses, we scheduled a time at his place when his parents would be out. I went, and I had had some cramping earlier in the day, but I was too excited for sex to care. So on goes the condom, the sex starts, everything is working fine, but he loses wood. I look down to see what's the matter, and there is blood everywhere. I just had my period while de-virginating a guy.

He's really nice and sweet about it, but the hard-on never came back, that day, or ever. I had traumatized him so much that he couldn't get hard around me, not even for oral sex. Poor guy!

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Serendipityover a year ago

Answer 10 of 10

My freshman year in college I had surger...

My freshman year in college I had surgery on my foot because of an injury I got in high school volleyball. I was out with some girls in my pledge class (still pledging my sorority) and I was extremely drunk. The girls were watching out for me because I still had a boot on my foot. I met this guy who was really cute and next thing i know I'm back at his place and making out in his bed. Remember I still have this boot on and I'm pretty intoxicated.

One thing leads to another and we begin to have sex. Now my pants are pulled down but they aren't coming off because I got my boot on. So they are at the ankles. Eventually I find my self leaning over his bed with him standing behind me. In the heat of the moment I lift my leg up with the boot on it and not even knowing, stomp it down.......problem is.....I stomped it on his foot.

The guy shouts like I've never heard a man shout. He falls back on his ass (butt naked)...I'm lying there with no clothes on except a boot for my foot and my pants at my ankles. His roommate, concerned that something is wrong, flings open the door and see's all of this.

The guy ends up breaking a bone in his foot and a week later I see him walking around campus with a boot on as well. We saw each other or talked again.

It was one of the worst nights ever but now looking back on it, I can't help but crack up. What a great college hookup story.

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