What’s Your Most Embarrassing Sexual Encounter?

bogart4017
wrote on October 27 2009 @ 12:50 pm: [report]

Years ago i was with this woman for the first time and i’m really going to town when i suddenly got a major cramp and my left thigh and another in my right foot. I pulled out to roll over in agony and shot a load all over the room. Not a good look.

C.Munro
wrote on October 27 2009 @ 01:00 pm: [report]

My first encounter with whiskeyd*ck was fairly embarrassing.  It was my 27th birthday, and I’d spent the day overeating and basically gargling with Glenfiddich.  That night I went over to see the girl I was dating, and for some reason when we transitioned from foreplay to the deed itself my boner vanished, not to return for several hours.  She was upset, to say the least, and asked me for a bit of oral as compensation, but I’d already attempted penetration and the taste of the condom lingering in her ladyparts made me gag uncontrollably.  Of course, she thought it was a comment on her own body instead of the unappealing flavor of a Trojan with spermicidal lube. 

She never spoke to me again after that night.

ChoJinn
wrote on October 27 2009 @ 01:06 pm: [report]

I dropped by to see a girl who was house sitting.  One thing leads to the next and we’re having sex on the owners’ bed.  Turned into a particularly rough encounter, and we broke the bed; not a bracket or screw but part of the lower left beam.  Tried to fix it for a couple hours to no avail, and just bolted.

Actually, that’s more awesome than embarrassing.

Secret Story Time
wrote on October 27 2009 @ 01:13 pm: [report]

Finding out 2 people were watching me during an entire half hour of lovemaking.  They saw the man and me inside and out.  And we KNEW the people.

Secretia

brandyalexander
wrote on October 27 2009 @ 01:13 pm: [report]

Getting fingered after he cooked with habeneros.  Almost an emergency room night…

Queen Frostine
wrote on October 27 2009 @ 01:28 pm: [report]

1. Handcuffs + lost key

2. Living with his parents. Mom came down to the finished basement to do laundry, and found us passed out post-coitus with the Hershey’s syrup, whip cream and cherries bottles arranged along the dresser.

SueSue
wrote on October 27 2009 @ 02:26 pm: [report]

*Warning* Mine is embarrassing and gross - I was a teenager with my long-term boyfriend and on the rag, not knowing what the consequences could be.  We had great sex, then when he pulled out, my crimson wave shot out projectile style all over the place and scared the crap out of me.  I thought I was hemorrhaging or something.  Gladly, since we were young and committed, we just laughed it off.

racethesun19
wrote on October 27 2009 @ 03:19 pm: [report]

He was a virgin. And nervous. Which led to the following situation…
Twin bed. Star Wars figurines looking on. He put on 2 condoms, going for the layered look I guess. Then the real trouble started. He would get hard, then go soft, then start to harden, then go soft. He wouldn’t let me help, so he was sweating & trying to masturbate with the condoms on and me, naked and bored, next to him. Needless to say, sex did not happen. His parting words? “We’ll get better.”
No, we will NOT get better. Because we are NEVER attempting that again.

SCRMOM
wrote on October 27 2009 @ 03:31 pm: [report]

Not only having one of our children witness us having sex, but actually having him climb into bed with us before we realized he was in the room.

Can 529 accounts be used for therapy?

hannahsguy
wrote on October 27 2009 @ 03:48 pm: [report]

I didn’t do this, but from a friend.  He told me that he was soooo drunk that, after sex, he wound up peeing on her while spooning.

ewwwwwwwwwwwwwww!

Ally
wrote on October 27 2009 @ 04:59 pm: [report]

I was so drunk I actually fell off when I was on top. Cringe. I ended up with a massive bump on my head and a sense of wounded pride.

Lilly
wrote on October 27 2009 @ 06:05 pm: [report]

A guy I recently dated…...when we first hooked up, things were getting hot and heavy, but we both were pretty drunk as well. He ended up peeing on me! I’ve never been more grossed out before in my life! And that clearly put the stop on any action that night.

After he made many, many amends (weeks worth of I’m-sorry-phone-calls, flowers, etc) we continued dating. Then weeks later, on the night we ended up first sleeping together, I was going down on him and felt my nose get runny. I’d been getting over a cold, and didn’t think too much of it. Fast foward to post-sex-bathroom trip. I looked at my face….I had streaks of blood all over. Apparently my runny nose was actually a bloody nose - I haven’t had one of those since I was 10! Talk about awkward.

Laurel
wrote on October 27 2009 @ 08:59 pm: [report]

Honestly, I think I must have blocked them out. I can’t remember any. Though when I lost my virginity, after we had finished my bf at the time asked me what it felt like, to which the only thing I could honestly respond was “an uncomfortable tampon”. Heh.

janiejones
wrote on October 27 2009 @ 11:46 pm: [report]

A one-night stand with this hot older guy in a band… when I was 18. I tried to act so cool and sexy and suave. Until he was in me, and I farted. I tried to laugh it off—I thought it was funny, but he kind of just frowned and kept going. Yeah, I couldn’t really have a conversation with him for longer than five minutes, after that happened…

effing hickster
wrote on October 28 2009 @ 03:33 am: [report]

I made the mistake of eating a dish consisting of mostly black beans and rice when I’d figured she wasn’t going to call like she said she would. Well, she called. At her house, I must have gotten out of bed at least fifteen times to go to another room and fart.

When I was a teenager, a couple who hung out in my circle of friends had oral sex after a particularly heavy bout of drinking. She wound up puking all over his package. Ewww.

adamjs
wrote on October 28 2009 @ 05:56 am: [report]

@lilly: I’ve had the accidental nose bleed thing happen once too. We were in a hotel room in poor light - there was so much blood everywhere on the white sheets/pillow cases it looked like someone had been killed :-|

ollieisapollie
wrote on October 28 2009 @ 09:50 am: [report]

my boyfriend loved blowjobs (duh) but I have always had a bad gag reflex, and he was bigger than my previous boyfriend- a recipe for disaster, as I remained committed to working on him and ignoring the gag reflex until I actually threw up on him.  He mercifully laughed his ass off.  I was half laughing and half crying.  I’ve never been more embarrassed, but we were in a loving, committed relationship and so it became a funny memory for us.

majicksand
wrote on October 28 2009 @ 10:33 am: [report]

Getting caught by his mom.  I felt like such a whore.

Jenn27549
wrote on October 28 2009 @ 01:58 pm: [report]

I was 18.  One night stand with a fairly popular guy in my circle of acquaintances.  Had been wanting to hook up with him for a while.  Nothing was going on pre-sex, but I apparently started my period DURING sex.  He was fairly disgusted at the end and told me I should have told him, he wouldn’t have had sex with me if he’d known!  Oh well…he turned out to be quite the ass anyway.  We never spoke to each other again.  I’m fairly certain he told plenty of people.

tubbyhumptydance
wrote on October 28 2009 @ 04:53 pm: [report]

I have had a girl (and her dad) walk in on me with her sister. Her dad said just one sentence I’ll never forget.

“your car keys are on the floor of the living room”

Antiquity
wrote on October 28 2009 @ 09:28 pm: [report]

Oh god… I thought I killed this memory… lol. Thanks Frisky for making me remember. >_<;

I went back to this guys place for a one night stand. Well we started getting hot and heavy when his “room mate” threw open the door and started fighting with the guy I was with. I start pulling my clothes on as the two yell back and forth. It turns out it wasn’t his apartment and he was just bumming off this guy. I got the hell out and the guy followed me trying to make all kinds of excuses.

SaucyBrunette
wrote on October 29 2009 @ 01:34 am: [report]

A couple years ago I had gotten a procedure done at the gyno where they snip out a piece of tissue to check for cancerous cells. She told me not to have sex for a few days after. Well, the weekend came around and my bf and I had been partying with friends and one thing led to another that nght.
During sex, I noticed I felt a little more wet than usual, but thought nothing of it til we were done. I turned on the lights, and it looked like a murder scene on his bed! Tons of blood everywhere.
The only funny thing? The big bloody handprint from him. Of course we had a major cleanup job ahead of us.

onewriter
wrote on October 29 2009 @ 02:22 am: [report]

@bogart4017 I’m sure she understood…really.  And you have to be highly into “fight or flight” mode for the male to climax, so your sudden pain just put you over the edge.  it wasn’t your fault.

onewriter
wrote on October 29 2009 @ 02:25 am: [report]

@brandyalexander what is a habaneros?

Quixotic Lass
wrote on October 29 2009 @ 10:32 am: [report]

I was bent over a tall bed and he was in me from behind when he just hit my g-spot right on and I squirted like a gallon of fluid all at once.  It all hit the carpet in a really loud wet splat. He jumped back like he was totally grossed out, but said, “Damn girl!  What are you, a porn star?”  Now I think of it as more complimentary, but at the time I was so mortified…  I had no idea I could do that!

_jsw_
wrote on October 29 2009 @ 11:14 am: [report]

TheFrisky: Come on. You did this exact topic less than two months ago.

No, wait. That one was “What’s Your Most Embarrassing Sex Moment?” This one is “What’s Your Most Embarrassing Sexual Encounter?” I suppose there’s a difference, as the former implies a specific moment, and this would imply the entire encounter, so I suppose my awkward moment could be having a steel ball bearing fall out of my ass and break a glass coffee table top but otherwise be part of a great experience, whereas an embarrassing encounter could be having a bland sexual encounter with Gwyneth Paltrow and then having the video show up on YouTube.

Got it. Sorry for thinking it was just a recycling of an article from twelve weeks ago.

_jsw_
wrote on October 29 2009 @ 11:16 am: [report]

My bad. It was less than three months ago. But really, that’s almost an entire season.

_jsw_
wrote on October 29 2009 @ 11:26 am: [report]

Odd. Using the “link” button didn’t seem to work correctly. Clicking it doesn’t take me to the article. The link is this:

http://www.thefrisky.com/post/246-whats-your-most-embarrassing-sex-moment/

catmcroy
wrote on October 29 2009 @ 11:42 am: [report]

Hands down, it was my first night with a new guy, the lights are off, he’s going down on me, it’s amazing and amazing and amazing…the lights go on after and it’s an abattoir. Yea. My period started during it and we didn’t notice. He was a real champ about earning his red wings that night and we left a HUGE tip for the hotel cleaning crew.

spatula
wrote on October 29 2009 @ 11:51 am: [report]

why bother to not only read, but post three comments on, an article that you think is sooo terribly irrelevant/redundant??!? Come on.

This might be my favorite ever post at the frisky, not only because of the awesome and hilarious stories, but they way they are written! Yall are f*ckin funny! I’m literally sitting here lauging out loud.

I fell off the bed once, with my college boyfriend. We were really drunk, and somehow in the course of the action we ended up at the foot of my bed. We’d been together a long time, so the only reason it was embarrassing was because my room was right off the living room in our townhouse, so my roommate and all the other late night partyers heard me say “I’m gonna fall off the bed!” and the ensuing crash, and then we heard the laughter and cheering.

_jsw_
wrote on October 29 2009 @ 12:22 pm: [report]

@spatula: The three comments were due to the lack of ability to edit comments.

Why read it? Because the stories are good.

I just wish there would be less recycling around here. Or at least an acknowledgement of it. You know, like “I was reading an earlier article here, and it reminded me of a time when…. How about you?” Just something other than pretending that an almost identical article had been posted not all that long ago.

Of course, if I were actually having embarrassing sexual encounters, I’d be unlikely to be worried about such things.

rhoades
wrote on October 29 2009 @ 12:52 pm: [report]

first time having anal and not enough lube. ouuuuuuuuuuch.

cooldad
wrote on October 29 2009 @ 02:43 pm: [report]

Skinnydipping in a river, then having sex on the bank & succeeding in knocking our clothes in without realizing it & having to drive back to the dorm naked and then run inside.  Actually wasn’t really that embarrassing, but it was memorable

kevinh
wrote on October 29 2009 @ 04:13 pm: [report]

driving to the dropzone with my then wife. she was giving me roadhead on the way there. i had to slow to go through the neighborhood prior to getting there, and on a spot where the sides of the road was higher than the road a black gentleman was walking and looked at us through the window as we passed. the only thing i remember was him pointing and laughing in the rear view mirror as i drove away.

jstavixxxen
wrote on October 29 2009 @ 04:59 pm: [report]

Hmm, I suppose mine would be the time my ex begged me to give him a blowjob while he drove, we were on a long country road that was all but deserted and so, as I did my best, he would accelerate, and slow down over and over again, weaving here and there, it was pretty hilarious, that is, until the farmer who owned the land on either side of the long country road came to investigate the car that was weaving all over the road and busted us just as he….....*smile* well you get the picture!!

bronzebuttercup
wrote on October 29 2009 @ 06:06 pm: [report]

I hooked up with this kid and everything was fine until when it was all over and he was taking the condom off it was covered in blood. He was cool about it and didn’t even say anything. I blushed and apologized repeatedly but he didn’t make a big deal about it.
The next day I found out that our whole shared group of friends and the entire water polo team knew exactly what had happened. Occasionally guys still tease me about it. I just shrug it off.

*sam*
wrote on October 29 2009 @ 06:16 pm: [report]

@_jsw_: you know it’s bad when you miss half of the articles on here because you think the people commenting are just revamping an old post… I think the fact that we can pin point when they’re just recycling something so soon is an indicator that it’s high time we move on…

rrtt11
wrote on October 29 2009 @ 06:46 pm: [report]

I had to join just to share this story of which I still cringe when I think of it.

I was 18, first semester in the freshmen dorm and a bunch of people are partying in a room down the hall.

After about 10 minutes of getting there a very hot girl asked to go back to my room. I was now someone to be admired by men and women alike and I have to say I enjoyed the drunken adulation as we walked out hand in hand.

We get back to room with the usual kissing and after about 5 minutes she goes down on me so no problem there. She makes a second stop a little bit lower, okay business as usual so everything is going great.

She makes a third stop even lower to fifth base (from another article). You wouldn’t believe the electric jolt that made my whole body stiffen like someone had touch fifth base with a cattle prod (from another article). 

I lasted maybe 3 or 4 seconds before expending myself loudly and physically

I had never heard or conceived of pleasuring ones most private of places with a tongue no less.
I think maybe my instant furious yelps of surprise and pleasure as well as my entire body stiffening like, well, someone to a cattle prod to my backside.

I tried to hide it but there was no hiding what had just happened in just 3 “or maybe 4 seconds if I was lucky” I had an very shocking and loud orgasm.

The worst part was her returning to the party just 5 or so minutes after my triumphant exit and announced to everyone that I was a premature ejaculator. 

For the record I have never prematurely ejaculated before or after that incident and those were extenuating circumstances.

I am still embarrassed by the whole thing.

Although I haven’t done much with it I have a healthy respect of pleasure of the backside.

retro chic
wrote on October 29 2009 @ 07:14 pm: [report]

@jsw:

Why read it? Because the stories are good.

Uh huh. Just like those other mags with “good stories” we find under the bed…

Bravo and amen to posts 1 & 2, Mr J O’Snarky
Love, Ms R McSnicker.

Nora
wrote on October 29 2009 @ 07:58 pm: [report]

Oh god…. My most embarassing moment ever is.. truly.. shamefull!

Not long ago, I was at a houseparty. I am a student, so at this party all the crazy #&@$% went down. I’ve never done more drugs than weed, but this night, after getting absolutely smashed, I ended up doing lots of weed, three stripes or whatever you call it, of miaow and one E.

It was a costume party, and I met this guy dressed as Tigger. All of him was painted orange with black! As I god more drunk and drugged, I found this quite unattractive guy, for some reason, attractive. So we ended up in the bathroom, where we tried to have sex on the sink (I vaguely remember falling in) and we were butt naked in bright lights (which is embarassing enough really). He had the worst case of whiskey-dick, so it didn’t work at all. (So according to another article here, the guys you can leave out in your partners-list, he’s out. He was actually never on it.)

So get dressed, do some more drugs, and walk down to the girls I came with. They accused me of snogging Tigger, to which I furiously denied, until I saw my face in a mirror.

All black and orange. And he was gross. Hopefully I’ll never see him again! Not that I would recognise him without facepaint.

hittheroadjack
wrote on October 30 2009 @ 07:07 am: [report]

we were in the party with my ex girlF. and starting to having sex in a empty room. but there is 30-50 pp. in the house that night. so that nite every pp at home they came to room to to check somebody that they look when they see we are having sex everytime they said oohhh sorry guyssss. We heared that word nearly 50 times. Hhahahaahahaah and I said oohh ok no problem hahahahahahaaaaah. )

MsMami
wrote on October 30 2009 @ 12:10 pm: [report]

Ok, mine is pretty bad.

My fiancé and I were pretty wasted and decided to have sex right there in his living room, well all I remember was him waking me up and telling me to move, apparently he was giving it to me anal and i pooped.. I will never forget that!! ewwww. Oh well, he is the one who decided to go through the back door. I was left cleaning his off white couches.

Fast Eddie
wrote on November 1 2009 @ 06:59 am: [report]

My buddy’s girl friend and I had been itching to get in each others pants for months.  While he was away for the night she came to my place and we had a little wine I gave her a massage.  By that time we were both turned on to the nova extent.  I mounted her and climaxed on the 3rd stroke.  Of course I apologized and she said it was all right.  We both knew it wasn’t but nothing could be done about it. 

Fortunately we were good enough friends to get together again many times.  Once we tried to do in a hammock.  I’d leave that to professionals.  Another time we did a foursome with the same buddy and another girl.  That WAS fun and everybody had 3 or 4 orgasms.  WOW, two women minutes apart, WOW!

Colinboudreaux
wrote on November 2 2009 @ 12:06 pm: [report]

Many, many years ago I met a girl at a party and we really hit it off. We sat and talked all night and started kissing. She needed a ride home and on the way, we stopped and didn’t have intercourse but pretty much everything else. I really liked her and she gave me her phone number (this was before email) and inexplicitly, I lost it. I searched everywhere but must have tossed it by accident. I bumped into her about 6 weeks later, she was offended I didn’t call and didn’t seem to believe me and that was that. She also apparently was seeing someone new.

About 3 months later I met a girl and really liked her. We started dating and spending more time together. I was over at her house working on some school project and guess who walks into the kitchen? The first girl and it was her sister! We were introduced and we just stared at eachother.

I wasn’t sure what to say and didn’t say anything as I wanted to think about it. When I got home my girlfriend called and her sister told her everything. Anyway, we talked about it and all decided just to forget about it and never really talked about it, but it was awkward. Anyway, we got over it.

vegetarian03
wrote on November 2 2009 @ 08:10 pm: [report]

one time I was with this guy I barely knew and he was trying to go down on me.
I had just gotten over my period so I thought thatd be a bad idea so he just fingered me. I was in a dress and he came up to kiss me and as he pulled away i saw blood allll over his white tshirt. Apparently my orgasm had triggered some extra stuff. Instantly I just stripped his shirt off and as he thought things were about to start going down, I ran to the bathroom to wash the blood off his shirt.
I was stuck at his house with no tampons or anything. and when I finally told him he just laughed.. and then never called me again.

TheSugarInYourGasTank
wrote on November 3 2009 @ 08:04 am: [report]

K, so my first serious boyfriend and I went parking. It was only the second time I had ever had sex and things weren’t really working out for us inside the car so we decided to move it outside even though it was raining a little. He laid me on the hood of his car and about two thrusts in I slid off of the car because of the rain and into a mud puddle. To his credit, he did try to catch me.

lazymike321
wrote on November 4 2009 @ 12:00 am: [report]

1. Handcuffed to a girls bed, her riding me backwards, her mom walks in. Awkward…

2. This is not so much embarrassing for me as it was for the girl, I was more horrified. I had been seeing a girl for about 4 months. We decided to get a quicky in before I had to go to work for a 24 hour shift. We got done and I went into the bathroom to quickly shave, get dressed, and hurry out. When the bathroom light came on I realized I was covered in blood. I ran into the bedroom, turned on the light, through the covers off her and could only stare in horror. It looked as if someone had been a victim of a slasher film on my bed. She screamed and ran into the bathroom, not to return. I was locked out of the bathroom, covered in blood, and late for work. Took a quick whore bath and left. Found out the next day from her doctor that she had a mis-carriage during sex. She felt awful and embarrassed.

Yodar Critch
wrote on November 20 2009 @ 09:42 pm: [report]

I was with this young lady.  We were both kinky and I had my usual supply of rope.

To ensure scene security, I made sure the door to her house was locked.  We were upstairs desporting ourselves, when I become aware of something.

1.  Her mother evidently had a key to her house
2.  Her mother evidently had a habit of stopping by and just letting herself in.

It also became evident that her mother

a.  Did not know I was involved with her daughter
b.  Did not know that her daughter was kinky
c.  Did not know that our activity was safe, sane, and consensual.

Hasty explanations from her daughter while I was untying her, probably saved my life.  A quick exit.

Our relationship did not last much longer.  I don’t think her mother approved.

Moral:  Do more than just lock the door.  Put the chain on and ask the resident of the house who else has a key and what their visiting habits are.

It will save a good scene from being interrupted… and possibly being shot by an irate mother.

Boy those mothers can get mad!

iCandy
wrote on December 12 2009 @ 01:37 pm: [report]

I was on my period, but my boyfriend and I had been clubbing and drinking a little, and had taken out the dirty dice. Well, there was no going back. I’m sitting on the edge of my bed, and he had pulled his boxers down just enough, being in a hurry. I didn’t think anything of it. One episode of amazing sex later, I’m horrified to discover that he is covered, from belly button to almost halfway down his boxers, in blood. He actually laughed it off.

ZoosChef
wrote on January 27 2010 @ 07:16 am: [report]

Oooh tough call.

First that comes to mine is the second-or-third time my boyfriend, now fiance, and I had sex.
He had been nailing me on the edge of the bed so that my head was starting to slip off the side, so I suggested in my sexiest suggestion-voice that we switch positions. So he pulls out and sits back for a second, and I sit up trying to push my boobs out at him, and action.
HUGE. LOUD. LONG. QUEEF. It was like a full balloon completely deflating. We froze. I totally panicked and recalling this comment about queefing I’d read on the internet about it technically being the “penis’ fault” i pointed out and YELLED at him;
  “THAT WAS YOUR FAULT, YOU KNOW!!!”
The poor guy. who certainly had not read any such comment for context, stared at me like I was pointing a gun at him. I quickly realized that I was being dumb and apologized, and he reassured me that he understood and that it wasn’t a big deal. Such a great guy. We ended up carrying on.

Runner-up though was the time I woke up to recall that my late night of webcam sex with aforementioned boyfriend had ended with me going to bed and not putting away my vibrator. Which was still on the computer desk. Which was in the dining room. Which was next to my dad and his wife’s bedroom.
As I walked shamefully across the room to claim my prize (it was sitting out, proud and obvious) my dad made sure to stifle a laugh and ask if I’d had a good night.