Post your most embarrassing sexual encounters Vol. 2012

[airforce1king]

Originally Posted by remix

Originally Posted by HOOD17

Originally Posted by Rusty Shackelford

Im in so much pain right now

greatest gif execution ever omfg

I've been trying to reply for 5min but I can't stop effing laughing!!!

 

[kramer]

Originally Posted by Stay Lurkin

Originally Posted by Tero

Originally Posted by Rusty Shackelford

This dude isn't even denying anything

 

[twizzi]

op let me live

 

[airforce1king]

Originally Posted by DajonDondo

Originally Posted by KanyeWest101

So this was back in 2006 summer and I had just graduated highschool, I had this chick over my crib that I use to mess with once in a while, I smashed once before, and this would of been the 2nd time around. The first time was almost impossible because her ****y was sooo tight I couldn't even get it halfway in before she started crying for pain.

So we in my room and start to get it popping now, and I am prepared for this 2nd time now, and I have it in my head that I am NOT STOPPING FOR NOTHING! Going to just keep going, crying or not.

Missionary wasn't really working out so I tell her hop up on top. She climbs on top while I'm laying down in my bed and it was really tight again to get in, but I finally made it happen, and finally made it FULLY inside, and on that initial trust I made to get it in, all I herd was a 'pop' noise... In my head I'm just thinking like... "wth was that? That doesn't sound good"

So shorty get's up, and I can remember the sight I saw to this day in vivid slow motion 3D picture, I seen a POOL OF BLOOD just gushing & dripping from out of her ****y onto my stomach, and everywhere else.

I freaked out, and spazzed on shorty, "I'm like *#* IS GOING?!" Blood was everywhere, I had to throw away my bed sheets, undershirt, socks, everything in sight had blood all over it. She quickly got up and ran to the bathroom. She couldn't explain what happened, and I sure as hell was lost to the point of no return.

Possibly it could of been her hymen breaking? I might of been her first, didn't really ask her or care, and the first time we did it I didn't really fully penetrate so that's probably why it didn't happen then. She didn't say anything about being on her cycle either.

This was my worst and most awkward sexual experience with any female, although not really embarrassing on my behalf.

Ew..

Ummmmmm..

only embarassing 1 is when these 2 chicks told me that they were down to have a 3sum. I was 17 and they were 19....... I was talking to one of them and somehow they both came together to my crib... So they told asked me if i eat the box... i said NO... i asked them if they suck ... they said Yes , but only if the guy goes on them first... so..... skip over to where they wanted to experience a 3 sum.... so they both said eat us out.. start it out.. i said 

 .. ok we...  im adventerous... i like to try new things... so i ate both of them out.. 1 by 1... I didnt know how to eat @%*%@, so i did it the way i ate my ex's butt... than i go get the condom... and they say that was the 3sum.... and left 

 ... i was puzzled, lost , confused, terrified, scared, embarassed, and had the taste of @%*%@ in my mouth.... they basically set me up....

LMFAO! HAHAHAHA!

 

[jordanscrub]

9 days in and we already have the best thread of 2012 
Craigslist story had me on the FLOOR.

 

[twizzi]

re-reading through the posts hilarity in everyone good stuff guys, props to those not afraid to dish on themselves

 

[blackcease]

Originally Posted by AirForce1King

Originally Posted by DajonDondo

Originally Posted by KanyeWest101

So this was back in 2006 summer and I had just graduated highschool, I had this chick over my crib that I use to mess with once in a while, I smashed once before, and this would of been the 2nd time around. The first time was almost impossible because her ****y was sooo tight I couldn't even get it halfway in before she started crying for pain.

So we in my room and start to get it popping now, and I am prepared for this 2nd time now, and I have it in my head that I am NOT STOPPING FOR NOTHING! Going to just keep going, crying or not.

Missionary wasn't really working out so I tell her hop up on top. She climbs on top while I'm laying down in my bed and it was really tight again to get in, but I finally made it happen, and finally made it FULLY inside, and on that initial trust I made to get it in, all I herd was a 'pop' noise... In my head I'm just thinking like... "wth was that? That doesn't sound good"

So shorty get's up, and I can remember the sight I saw to this day in vivid slow motion 3D picture, I seen a POOL OF BLOOD just gushing & dripping from out of her ****y onto my stomach, and everywhere else.

I freaked out, and spazzed on shorty, "I'm like *#* IS GOING?!" Blood was everywhere, I had to throw away my bed sheets, undershirt, socks, everything in sight had blood all over it. She quickly got up and ran to the bathroom. She couldn't explain what happened, and I sure as hell was lost to the point of no return.

Possibly it could of been her hymen breaking? I might of been her first, didn't really ask her or care, and the first time we did it I didn't really fully penetrate so that's probably why it didn't happen then. She didn't say anything about being on her cycle either.

This was my worst and most awkward sexual experience with any female, although not really embarrassing on my behalf.

Ew..

Ummmmmm..

only embarassing 1 is when these 2 chicks told me that they were down to have a 3sum. I was 17 and they were 19....... I was talking to one of them and somehow they both came together to my crib... So they told asked me if i eat the box... i said NO... i asked them if they suck ... they said Yes , but only if the guy goes on them first... so..... skip over to where they wanted to experience a 3 sum.... so they both said eat us out.. start it out.. i said 

 .. ok we...  im adventerous... i like to try new things... so i ate both of them out.. 1 by 1... I didnt know how to eat @%*%@, so i did it the way i ate my ex's butt... than i go get the condom... and they say that was the 3sum.... and left 

 ... i was puzzled, lost , confused, terrified, scared, embarassed, and had the taste of @%*%@ in my mouth.... they basically set me up....

LMFAO! HAHAHAHA!

  son, you only know how to eat butt tho!?

 

[boi]

I feel bad for dude..

 

[ajmasta]

I just spent the past 2 hours reading this thread and laughing my A off hahahahahahahahaha this thread is platinum

 

[airblaster503]

Made it to page 8 and am dying, going to have to read the rest later

 

[coolgraymemo]

Originally Posted by ar916

I met up with my ex we were fighting, I was just trying to smash and dip outta there, I kept trying to convince, for at least an hour finally i got her to but she didnt wanna I can tell but I was like w.e lol, we get to the bed I put it in took two strokes felt like I was coming I came in the condom and just laid on her she didnt know I came and she was like whats wrong, I said nah if your mad we shouldn't do this, lets talk about what happened, she was happy I was happy until she saw the condom lol

lol wut?

 

[mytmouse76]

Originally Posted by BlackCease

Originally Posted by AirForce1King

Originally Posted by DajonDondo

Ew..

Ummmmmm..

only embarassing 1 is when these 2 chicks told me that they were down to have a 3sum. I was 17 and they were 19....... I was talking to one of them and somehow they both came together to my crib... So they told asked me if i eat the box... i said NO... i asked them if they suck ... they said Yes , but only if the guy goes on them first... so..... skip over to where they wanted to experience a 3 sum.... so they both said eat us out.. start it out.. i said 

 .. ok we...  im adventerous... i like to try new things... so i ate both of them out.. 1 by 1... I didnt know how to eat @%*%@, so i did it the way i ate my ex's butt... than i go get the condom... and they say that was the 3sum.... and left 

 ... i was puzzled, lost , confused, terrified, scared, embarassed, and had the taste of @%*%@ in my mouth.... they basically set me up....

LMFAO! HAHAHAHA!

  son, you only know how to eat butt tho!?

tongue in the butt all wild all crazy

 

[41239]

Originally Posted by ToLiveandDieinNJ

Met a chick online. Told me she was 33, but she looked pretty good. I get to the crib, and she must've used pics from when she was 25 or something. Anyway, she made me dinner, but it took me longer than anticipated to get there, so she had ate already. She stared at me and watched me eat. She also failed to mention that she lived with her cousin and 7 yr old nephew. Also failed to mention, that her bedroom was the living room with a big curtain, and that the cable that the curtain hung on was broken. So I'm there about an hour and we're watching a movie on the couch with the lil kid, doing kid things. Her cousin offered up her bedroom to us and slept on the couch. So we smash, and I must admit the P was super tight, she told me she hadn't been w/ a dude in 2 years. IDk about all that, but the P was def nice.

We were up pretty late messing around, next morning she wakes me up, and just basically takes it with me on my back, squeezed it at the base and just jumped on. I busted in like 3mins, and wasn't even sure if I came, she was so violent. We went out to lunch and came back and this kid is showing me all his artwork, and they are telling me, he's usually so quiet and doesn't open up to people. So now I'm just feeling awkward,(knowing that I'd never go back there) I also fixed the subwoofer on her cousin's surround sound, it was unplugged, I also fixed the bathroom sink, and thru out the whole afternoon, we're sitting on the couch and she kept saying "I wanna jump your bones", in front of her cousin and nephew, and it just made me so uncomfortable. After about the 17th time saying it, and realizing I wasn't receptive, she started saying, I guess I'm never going to see you again. It was just freaking weird. Oh I also shoveled, the bottom of their driveway, because they did a horrendous job shoveling, and my car got stuck trying to pulling out when we had went to lunch. It was just a bizarre friday night/sat, she also tried to have me stay Saturday night, but I said my boy owed me money and was ready to pay me back, just so I could leave, she was in CT and I live in NJ.

Met another chick online, really cute, a lil chubby and very busty. Anyway, exchanged phone #s and texted back and forth, randomly out of nowhere she texted me a couple shots of her boobs and coochie. I was busy doing something so I didn't see the texts for like 30mins and she thought she offended me and started apologizing, so instead of saying anything back, I just sent a pic of my meat and she told me that she would worship it. (1st warning she is a crazy), so we proceed to text the rest of the week and make plans to meet that Friday for dinner. I offered multiple times to pick her up at her house but she was like nah, I don't sleep with guys on the 1st date. We meet at the restaurant and as soon as she sees me, she says I'm cuter in person and starts pinching my butt. Anyway we eat, and I walk her back to her car, before I can ask if she wants to grab a drink or something, she's like "So are you coming over?" I get to her crib, and she has 3 parrots, and all of them have no feathers but their heads and tails, and she calls them her babies and was feeding them her left over cheeseburger (2nd crazy sign, the birds were tweaked out). she then proceeds to tell me about her miscarried baby she had 5 yrs ago, referring to her daughter and telling me about her ex (3rd sign). Anyway she had said something previously to me about burning, so I brought an eL of some nice bud and got her roasted, next thing you know, we're making out. She randomly starts laughing and says no guy ever kisses her this much and she usually is sucking D by now. I'm like oh jeez, and then just start to strip her and get it in. And after she said all that, I wasn't feeling her anymore, and I just couldn't bust, after about 35mins I finally, nut and I was hitting it doggy and pulled out and literally filled the small of her back with jizz, she starts giggling saying, she's never felt that much on her body. Fast forward, the birds are in the other room making the most loud obnoxious noises, I keep hitting my head on that doorway to her bedroom, bc she lived in a weird apt, we smash again. and it's like 5am, we go out to smoke a cig and I prepare to leave, she's like "oh you're not sleeping over?" and I'm like nah, I'll just zip home, i live about 40mins away from her. So I leave, and about 15mins later she texts me that, she misses me, (crazy sign 4), We keep texting thru the week again, and I just lose interest. She flips the full on crazy switch and said "I can't believe, I thought I could love you" and I just lost it and kept trolling her, this lead to a text battle and she would text me something bananas and then I'd reply and she say stop texting me, and then text again, at one point she told me I couldn't bust because of pot and I needed rehab, lol. This went on for like half a day and I just kept finding it more and more funny so I kept egging her on. She then said she was calling the police and I'm like go for it, you keep texting me idiot and then she threatened to call my parents and tell them I'm harrassing her. Mind you I'm 27, so I google her last name and the town where told me she's from, and find her parent's phone number and just text it to her. After that she just said, I'm sorry and never bugged me again. Chick was nuts.

dude, you put in work like a nice guy tho, but honestly my internet meetups are just like that, theres some kid who likes me in her family, or its some crazy cat/animal girl who thinks we're gettin married, never anything normal

 

[41239]

Originally Posted by bwood056

Originally Posted by KillTheHype

On new years I went to some guys house with my best friend and her cousin (the guy who's house he went to was god-cousin or something with my best friends cousin).

Well anyways, we got really drunk, he was ugly, I passed out, we had sex, in the morning he tried to wake me up for more and I said I was a lesbian thinking I didn't have sex with him already. I kept going at it and going at it until I saw the condom on the floor. I felt so stupid. I can't believe I did that. I hope the sex was at least good.

Oh yeah, and when I looked in the other direction, on the floor was my cousins best friend sleeping. He heard everything. Including my best friend who had sex with the other guy who lived with them in the living room. She was on her period -_________________-

this wasnt in tampa was it ?????

well isnt that convenient, i wish i had the luxury of forgetting what happens when i get plastered, i always remember everything, not in exhausting detail, but no different than when im sober, but at least you didnt cry rape like all those other girls who are too pathetic to cope with their dirt

 

[illmaticblueprint]

I don't understand how my mans started eating butt before !*%%% though 

 

[mr marcus]

Originally Posted by IllmaticBlueprint

I don't understand how my mans started eating butt before !*%%% though 

He a pillow biter...cause if u messing w/ girls eating butt ain't some *!++ u do first if at all unless you nasty like that

 

[horchata kid]

Originally Posted by Essential1

Was getting dome from this girl that had been trying to get with me for a while (I wasn't interested and told her that but was still able to finagle my way into getting dome).. I was laying on my back on the bed. At the time she had to leave is when I popped.. So I'm sitting on the side of the bed. And try to stand up to walk her to the door..

And once I tried to stand up my legs just collapsed and I fell to the ground... Was like in any war movie when it gets all silent and the troops are in the field and then someone gets sniped.. That's how I fell..

Was pretty awkward walking her to the door like I was crippled..

I think she sucked the soul out of my body like the shadow people in the movie Ghost.

 

[eashawty]

Originally Posted by IllmaticBlueprint

I don't understand how my mans started eating butt before !*%%% though 

 word...

 

[Kev93]

I was vacationing in El Salvador last summer with my cousin & a couple of his hoodlum friends at a pent house, having a couple drinks.
So since my cousin knew the ropes around the joint he asks this thick dark haired broad how much she charged, she was like "I only do private dances".
Since it was my birthday my cousin offered to pay for the %!$$%% services & offered 2x the amount...
Anyways once me & her get into the room we start undressing & talking and she puts the glove on me & she start lubricating it.
So then she start giving me head & she want me to 69 with her I'm like NAAAAHH! at first so then she just decides to stand up on the bed & sits on my face giving me head, so then as her ****Y gets closer i smell a nasty sensation of fish Im like oh hell No!! But then again my cuzzo paid for her so i just proceed with the smashin of a stinky vagina. My face was

but luckily 30 minutes is how long i lasted & had shawty moaning the whole time as she is on top. Smelliest vagina I've ever smashed..

 

[10 piece nuggets]

Originally Posted by slickp42189

Originally Posted by ToLiveandDieinNJ

Met a chick online. Told me she was 33, but she looked pretty good. I get to the crib, and she must've used pics from when she was 25 or something. Anyway, she made me dinner, but it took me longer than anticipated to get there, so she had ate already. She stared at me and watched me eat. She also failed to mention that she lived with her cousin and 7 yr old nephew. Also failed to mention, that her bedroom was the living room with a big curtain, and that the cable that the curtain hung on was broken. So I'm there about an hour and we're watching a movie on the couch with the lil kid, doing kid things. Her cousin offered up her bedroom to us and slept on the couch. So we smash, and I must admit the P was super tight, she told me she hadn't been w/ a dude in 2 years. IDk about all that, but the P was def nice.

We were up pretty late messing around, next morning she wakes me up, and just basically takes it with me on my back, squeezed it at the base and just jumped on. I busted in like 3mins, and wasn't even sure if I came, she was so violent. We went out to lunch and came back and this kid is showing me all his artwork, and they are telling me, he's usually so quiet and doesn't open up to people. So now I'm just feeling awkward,(knowing that I'd never go back there) I also fixed the subwoofer on her cousin's surround sound, it was unplugged, I also fixed the bathroom sink, and thru out the whole afternoon, we're sitting on the couch and she kept saying "I wanna jump your bones", in front of her cousin and nephew, and it just made me so uncomfortable. After about the 17th time saying it, and realizing I wasn't receptive, she started saying, I guess I'm never going to see you again. It was just freaking weird. Oh I also shoveled, the bottom of their driveway, because they did a horrendous job shoveling, and my car got stuck trying to pulling out when we had went to lunch. It was just a bizarre friday night/sat, she also tried to have me stay Saturday night, but I said my boy owed me money and was ready to pay me back, just so I could leave, she was in CT and I live in NJ.

Met another chick online, really cute, a lil chubby and very busty. Anyway, exchanged phone #s and texted back and forth, randomly out of nowhere she texted me a couple shots of her boobs and coochie. I was busy doing something so I didn't see the texts for like 30mins and she thought she offended me and started apologizing, so instead of saying anything back, I just sent a pic of my meat and she told me that she would worship it. (1st warning she is a crazy), so we proceed to text the rest of the week and make plans to meet that Friday for dinner. I offered multiple times to pick her up at her house but she was like nah, I don't sleep with guys on the 1st date. We meet at the restaurant and as soon as she sees me, she says I'm cuter in person and starts pinching my butt. Anyway we eat, and I walk her back to her car, before I can ask if she wants to grab a drink or something, she's like "So are you coming over?"[color= rgb(255, 0, 0)] I get to her crib, and she has 3 parrots, and all of them have no feathers but their heads and tails, and she calls them her babies and was feeding them her left over cheeseburger (2nd crazy sign, the birds were tweaked out).[/color] she then proceeds to tell me about her miscarried baby she had 5 yrs ago, referring to her daughter and telling me about her ex (3rd sign). Anyway she had said something previously to me about burning, so I brought an eL of some nice bud and got her roasted, next thing you know, we're making out. She randomly starts laughing and says no guy ever kisses her this much and she usually is sucking D by now. I'm like oh jeez, and then just start to strip her and get it in. And after she said all that, I wasn't feeling her anymore, and I just couldn't bust, after about 35mins I finally, nut and I was hitting it doggy and pulled out and literally filled the small of her back with jizz, she starts giggling saying, she's never felt that much on her body. Fast forward, the birds are in the other room making the most loud obnoxious noises, I keep hitting my head on that doorway to her bedroom, bc she lived in a weird apt, we smash again. and it's like 5am, we go out to smoke a cig and I prepare to leave, she's like "oh you're not sleeping over?" and I'm like nah, I'll just zip home, i live about 40mins away from her. So I leave, and about 15mins later she texts me that, she misses me, (crazy sign 4), We keep texting thru the week again, and I just lose interest. She flips the full on crazy switch and said "I can't believe, I thought I could love you" and I just lost it and kept trolling her, this lead to a text battle and she would text me something bananas and then I'd reply and she say stop texting me, and then text again, at one point she told me I couldn't bust because of pot and I needed rehab, lol. This went on for like half a day and I just kept finding it more and more funny so I kept egging her on. She then said she was calling the police and I'm like go for it, you keep texting me idiot and then she threatened to call my parents and tell them I'm harrassing her. Mind you I'm 27, so I google her last name and the town where told me she's from, and find her parent's phone number and just text it to her. After that she just said, I'm sorry and never bugged me again. Chick was nuts.

dude, you put in work like a nice guy tho, but honestly my internet meetups are just like that, theres some kid who likes me in her family, or its some crazy cat/animal girl who thinks we're gettin married, never anything normal

Sons 4 hints got me rolling. Especially that one.

 

[moreuptempo]

Originally Posted by Galvelocity

Okay so a couple of years ago, my roommates and I lived in this...I don't know what I'd call it. It's like a duplex only it's like five houses attached together? In a big block? Anyway, at the beginning of the school year, we went to a party that was in the big shared backyard. My roommates were encouraging me to go kinda wild. I had just gotten out of a brutal relationship and figured I deserved to have a little fun. At this point in my life, I have never ever gone home with a guy, and due to this incident, I never will again

This guy was kind of a douche but he was cute so I figured whatever. I'm super wasted and so is he. We go back to his house (the one directly attached to mine) and fool around a little. We kinda just made out and I had my top off and so did he but that was about it, I'm kind of a prude unless I'm in a relationship.

 We both pass out. 

At one point I sit up in bed, and look around, and then settle down to go back to sleep. Suddenly, I hear this weird watery sound. On instinct, I barrel roll out of the bed, and stand up. He's out cold pissing EVERYWHERE. Like, I can't explain to you guys the quantities of pee involved. And he fell asleep with a boner so his weiner is at the midnight position, and he's peeing all over his own chest and everything! And it's pooling in the indent in the mattress from his body weight and oh god!

I run out their front door, in only underwear, flee across the yard and burst into my own house. I run to my buddy's room and, still pretty much naked, begin to freak out. After we had a good laugh at his expense. I realized I left all my clothes and some of my favorite rings behind. We decide to go get my stuff.

The front door has been locked since I left, so we climb through his window, which is one of those super small, high up basement windows, so we like tumble into his room. He's still out cold in a pool of his own pee. We carefully reach over him to get my clothes and took what we could find easily. Then we ran back home. I lost two of my favorite rings and my favorite v-neck that night.

We then had to live next door to each other for a year. Every time we crossed paths he would hang his head in shame and walk as far apart from me as possible. And rightfully so. That was a messed up situation

My boy did the same. Only it was her bed that he pissed in.
Left a bill on the desk and dipped in the morning.

Every time we walk past her we laugh.

 

[grup]

Originally Posted by GolfAlphaBravoEcho

I had been chasing this Shorty for a hella long time, like half my life long time and I ha smashed once but I aintbreally get the chance to REALLY get up in there. So like three years later I get another chance. So I'm in there stroke is on point and Shorty says "Make sure you pull out, I cannot get pregnant right now." (Yes, irresponsibly I was going raw.) So I'm like "Yeah, of course." I get to the finish and go for the tummy money shot but I've been churn in and burn in wanting this for too long. It totally clears her torso right into her nose. Must have been the perfect rythmn because she inhaled it and started coughing uncontrollibly. She ended up in tears Ruined the nut, ruined the moment.

!!!

 

[put em up]

Originally Posted by Mr Marcus

Originally Posted by IllmaticBlueprint

I don't understand how my mans started eating butt before !*%%% though 

He a pillow biter...cause if u messing w/ girls eating butt ain't some *!++ u do first if at all unless you nasty like that

I don't understand why youngins gotta lie for Lulz. #$+! don't even make since, you eating crapshooters before the box? Nah...we not buying it.

 

[dajondondo]

Keep the stories coming...

 

[dior paint]

Originally Posted by Af1 Jordan collecterz

I was vacationing in El Salvador last summer with my cousin & a couple of his hoodlum friends at a pent house, having a couple drinks.
So since my cousin knew the ropes around the joint he asks this thick dark haired broad how much she charged, she was like "I only do private dances".
Since it was my birthday my cousin offered to pay for the %!$$%% services & offered 2x the amount...
Anyways once me & her get into the room we start undressing & talking and she puts the glove on me & she start lubricating it.
So then she start giving me head & she want me to 69 with her I'm like NAAAAHH! at first so then she just decides to stand up on the bed & sits on my face giving me head, so then as her ****Y gets closer i smell a nasty sensation of fish Im like oh hell No!! But then again my cuzzo paid for her so i just proceed with the smashin of a stinky vagina. My face was

but luckily 30 minutes is how long i lasted & had shawty moaning the whole time as she is on top. Smelliest vagina I've ever smashed..