Awkward Sexual Experiences

[nice weather]

A friend of mine once told me about losing his virginity in a weird outdoors gangbang. The girl supposedly was kinda crazy and let like 8 dudes bone her behind a bush one after another. He was second to last in line and it was getting dark and starting to rain. BUMMERRRRRRR, not romantic at all  ~ ~ ~

[odp]

a few years ago i met this girl at a party that i went to out in the mountains 2 weeks before i was slated to hit the road and head south. We ended up having sex that night, if you could call it such; asphyxiation, holes in the wall, a leather belt and a painting of christ all played pivotal roles in their own right. Somehow, after this all went down and we recapped over my bottle of wild turkey and a pack of turkish royals, it was decided that i would spend some more time with this girl danie, living in her shit stain apartment. Now, as the days and nights passed we fucked quite a bit. Her body was tight, she had only recently quit the college swim team; whoring, drugs, and alcohol hadn't yet ravaged her body. One day she asked if i wanted to go for a ride out to Burlington VT to her parents home for the night. I agreed as i'm not often the passenger on a road trip and i was going to leave for the south in a few days. We get there to be greeted by a pack of small children running around the front yard,nearly  naked in the rain. So apparently her mom was babysitting many nieces and nephews. this pissed me off to no end because after having been given hand sex on the ride up i was promised the real thing at the parents house. Sex at the parents house is always interesting too, there's just so much that can go wrong that when the nut comes, it's usually of epic proportions. Anyhow, we're hanging around, eating, drinking grape juice, and watching two and a half men when mom comes and says "ok, i need you guys to watch the kids because i'm going to the store for a while."
The kids are still outside in the rain, the mother is leaving... all i can think is "ace in the hole." As soon as mother leaves, Danie grabs my cock through my shorts and pulls me into the back room, apparently she was thinking the same thing. There is a giant tent of couch cushions, blankets, and sheets extending from the fire place to the couch, she says "lets go in there." We go in and she starts sucking my cock. then she takes her pants down to around her knees, starts pushing her ass onto my pelvic area and pulls me into her. At this point i'm not thinking much about the kids outside, not at all. after a while, a few minutes anyways, we heard the door open and the tribe of wild youth are in the front of the house. she keeps fucking me. i tell her im about to come, she pulls away and in one motion picks her pants up and crawls out of the living room blanket tent as i bust a big nut onto the ceiling of the tent. I rolled away to prevent any backlash drip and walked into the kitchen. i walked past the kids and they run into the room with the tent. i could only think of how gross that dripping glob of jizz was going to be when it fell on one of their heads. that shit was awkward

[everypennyfedcar]

AHAHAHAHAHA!

[MFS]

i was completely wasted, like 8 beers in 3 hours 5.5%,

This made me laugh for sure. Hardly a recipe for a buzz.

[Crazy Ralph]

a few years ago i met this girl at a party that i went to out in the mountains 2 weeks before i was slated to hit the road and head south. We ended up having sex that night, if you could call it such; asphyxiation, holes in the wall, a leather belt and a painting of christ all played pivotal roles in their own right. Somehow, after this all went down and we recapped over my bottle of wild turkey and a pack of turkish royals, it was decided that i would spend some more time with this girl danie, living in her shit stain apartment. Now, as the days and nights passed we fucked quite a bit. Her body was tight, she had only recently quit the college swim team; whoring, drugs, and alcohol hadn't yet ravaged her body. One day she asked if i wanted to go for a ride out to Burlington VT to her parents home for the night. I agreed as i'm not often the passenger on a road trip and i was going to leave for the south in a few days. We get there to be greeted by a pack of small children running around the front yard,nearly  naked in the rain. So apparently her mom was babysitting many nieces and nephews. this pissed me off to no end because after having been given hand sex on the ride up i was promised the real thing at the parents house. Sex at the parents house is always interesting too, there's just so much that can go wrong that when the nut comes, it's usually of epic proportions. Anyhow, we're hanging around, eating, drinking grape juice, and watching two and a half men when mom comes and says "ok, i need you guys to watch the kids because i'm going to the store for a while."
The kids are still outside in the rain, the mother is leaving... all i can think is "ace in the hole." As soon as mother leaves, Danie grabs my cock through my shorts and pulls me into the back room, apparently she was thinking the same thing. There is a giant tent of couch cushions, blankets, and sheets extending from the fire place to the couch, she says "lets go in there." We go in and she starts sucking my cock. then she takes her pants down to around her knees, starts pushing her ass onto my pelvic area and pulls me into her. At this point i'm not thinking much about the kids outside, not at all. after a while, a few minutes anyways, we heard the door open and the tribe of wild youth are in the front of the house. she keeps fucking me. i tell her im about to come, she pulls away and in one motion picks her pants up and crawls out of the living room blanket tent as i bust a big nut onto the ceiling of the tent. I rolled away to prevent any backlash drip and walked into the kitchen. i walked past the kids and they run into the room with the tent. i could only think of how gross that dripping glob of jizz was going to be when it fell on one of their heads. that shit was awkward

jizz hats for everyone

[jeremyrandall]

jizz hats for everyone

AAAAAAAHAHAHAHAHAHAHA!!!

SIG'd

[HoneyBear]

 i think the next day i realized i had been fingering her asshole half of the time. it wasnt getting all juicy like normally so that must have been what was going on.

Thread is chalk full of laughs

[everypennyfedcar]

 i think the next day i realized i had been fingering her asshole half of the time. it wasnt getting all juicy like normally so that must have been what was going on.

Thread is chalk full of laughs

Yo rawb, you probably gave that girl a urinary tract infection.

[macgruber]

i got surprise rawdogged a couple weeks ago. it was weird. i'm making out with this girl and whatever and go to take it to the next level when she throws up the brakes. i'm like, whatever. we make out a little bit more and i'm over it and just trying to go to sleep. then she starts rubbing her twat all over me. like grinding against my stomach and leg and shit. then on the dong. then she's got me up in her. and i was basically asleep, like in that, "am i awake starting to dream" part of sleep. but then she's bopping away and i'm like "oh shit, i'm having sex." so after getting worked up prior to this and getting ambushed, i obviously don't last all that long. a couple minutes at most. so by the time i'm ready to finish, i'm awake enough to realize i'm rolling the dice as it is with this girl, so who knows her deal. so i pull out and blow it on her leg. she asked if i came. i'm like... yeah, i came. and she's asks "and you didn't come inside me?" and i'm like, no, no i did not. then she asks if i have an std. i'm like, no, do i now? things didn't work out with her.

[Goblinshark]

then she asks if i have an std. i'm like, no, do i now? things didn't work out with her.

well played, sir

[Watson]

Oh fuck. Where to start?

Well, one time I was fucking this chick, sitting on the couch facing the TV, and she was sitting on the cock facing the same way. All of a sudden her little brother walks in the door and straight down the stairs beside the door so we grab a blanket and throw it over ourselves. He starts having some long ass conversation with her while she sits there and squeezes her pussy muscles and starts lifting up and down turning to talk to me and then talk to him.

Same chick I was fucking her in the basement of my parent's house when I lived at home and we got in an argument because I was fucking her on the chair and she wanted to fuck on the bed but the bed is too noisy. It ended up in a full on fight with me hate fucking her while pressing on her mouth as hard as I could whisper-yelling "SHUT THE FUCK UP! YOU NEED TO SHUT THE FUCK UP." It just turned her on more because she had rape fantasies. That whole incident was just the tip of the iceberg for that night.

Same bitch slimed my cock with shit cream while I was ass fucking her. Already told the story before but I wiped my dick off on the face towel in the bathroom and folded the shit stain to the inside and neatly hung it again.

First time I convinced my first girlfriend to let me bust in her mouth she choked like hell on it and was basically dying. Ruined the nut for sure. Selfish bitch.

One time this chick I just met that night was blowing me and then I was too drunk to come, but I kissed her after and she said "So let me ask you something? How does your cock taste?" I think I said "Not bad."

One time I was starting to get into it with this chick and we were dirty talking and she accidentally said "God I love touching my cock." instead of "your cock". That was the end of that.

Hardcore make out session interrupted by a mother. Sweatpant shorts. Enough said.

Fucking a girl and I told her "I love your ass." And she said "It loves you." So I said "Okay." And she was like "It's talking to you." And I was like "Is it?" And she was like "Yeah. What's it saying?" And I was like "I don't know. I'm hungry?" That girl was consistently an awkward dirty talker. Best I could figure is that she wanted to be raped by her dad.

TONS of limp beer-dicks. That's always an awkward situation.

And then of course the time I farted in a chick's face while I was coming in her mouth on the 5th time she sucked my dick that night trying to get off my limp beer-dick. That one was a classic.

[lurk daddy]

Last summer i fucked some random 28 year old lady(cougar) i met for the 1st time that night. At 1st my brother was hollering at her or whatever  , some how i started talking to her and she thought i was funny and shit. I ended up snaking her from my brother he was pissed, bitch was pretty drunk , but of course i was blacked out. I told her to come to the room with me and she was down... then i started fucking her and shit my homie walks in the room and gives a blank look and closes the door back. 15 min later he walks all the way in and starts talking to me while im fucking i started laughing = making my boner go down = me unhappy. I told him to get the fuck outta here laughing..he leaves, i guess word got out that i was fucking. My creepy as brother cracked open the door and peeped me fuck away like a peeping tom. Next thing i know my brother go's in the room and is all " yo lemme fuck her real quick" im whispering " nigguh get the fuck outta here. My brother starts taken his clothes off im like WTFFFFF get out (whispering hard as you can possibly whisper) hes like "man thats some weak as shit man" ya continue doing the dew.

Pretty fucking weird fucking a lady and there brother comes in wanting to fuck too. To make it even more awkward me and her woke up together the bed was all sideways and shes like "wheres my earring" we both re trace our steps from the night and couldnt find it. She go's into the bathroom looks in the mirror and finds the earring in her hair! after that ive never say her again

funny part is i chill with her sister randomly and she brought it up and didnt really care
making her the bigger slut

[raul]

^^ I got a headache reading that. Also, as has been discussed, 28 year olds are not cougars.

[lurk daddy]

^^ I got a headache reading that. Also, as has been discussed, 28 year olds are not cougars.

doesnt count if shes a mom? guess i thought she was cause shes like 9 er 10 years older than me

[raul]

^^ I got a headache reading that. Also, as has been discussed, 28 year olds are not cougars.

doesnt count if shes a mom? guess i thought she was cause shes like 9 er 10 years older than me

She'd be a MILF so long as she has kids. A cougar is about 39/40 and above. Any younger and it's a MILF or just your standard hot older lady.

[DevilOnEnzyte]

I had sex with a girl that had this spinal condition where her spine pinched at her asscrack, creating what looked like another butthole.
I was going at it from behind when I saw that, then said "You know you have two buttholes"...
She did not find it as funny as I did....

[RRRRRAD]

one time i had sex in the back shoe room at this skateshop i work at and heard a customer come in and did the good old middle school stick up between the tummy and pants trick then helped the customers and then went back to have more fun.


and for all the dudes who been there while their homeboys railing his gf or a chick and didnt move or anything and took one for the team thumbs up, thats the only thing you should do in that situation or run away really fast

[DevinSB]

oh i have so many haha. okay, so i was like 13, and i was crashing at my best friend's house, who's 5 years older than me, he's always sorta been like an older brother type deal for me and i basically lived at his house. so one night i sleep over, and his girlfriend was there too, i crashed out in the floor. i wake up in the morning, sit up and look over, and he's facing away from me sitting on the edge of the bed, jerking a load off into his girlfriend's mouth, who's facing toward me, her and i made eye contact, i laid back down super quick and tried to go back to sleep. that whole afternoon was sooooooo awkward.

so i met this girl on myspace summer after freshman year of high school. got her to send me nudes yada yada, it was kinda late at night. my mom's outta town and my buddy is squatting on my couch, and she wanted to hangout, so we go pick her up. like 20 minutes after she gets there her and i start hooking up, she started like hinting toward sex(i was a virgin but told her i wasnt for kewl points), so i grab one of those condoms i'd had in my dresser since forever, strap up and try to put it in, which took me forever because i had no idea what i was doing. about a minute and ten seconds later i blew the fattest load ever and my only response was "sorry, its been a while" we ended up having sex like 4 times that night. i took her home around 5 am, went home and went to sleep, she called me the next day, i didnt answer. then we started school again, and she was in one of my classes, i still didnt talk to her, eye contact with one another was extremely awkward.

i was fingerbanging my first like "legit" girlfriend once, like super hard, and outta nowhere she queefed, and we were like face to face when it happened, we both just kinda smiled and i kept going, was definitely weird. a few weeks later she wanted to lose her virginity to me, i was super down, but really drunk, and as soon as my back hit the bed there was no boners happening, she sucked me off for like 5 minutes, i got a chubby at the most. we broke up like a week later, it was really weird after that.


when i was like 17 there was this girl who i used to have sex with on many random drunken nights after random house parties. we would always have like crazy wild 3 hour sex, and one time she yelled "JUST COME IN ME ALREADY" i promptly pulled out, put my boxers and shorts back on, walked out and slept in the living room. was just really weird to be demanded of my come. her and i never spoke again after the next day haha.

[verbal ham]

one time i got sodomized by a horse then i died 

[Bobbito]

I had sex with a girl that had this spinal condition where her spine pinched at her asscrack, creating what looked like another butthole.
I was going at it from behind when I saw that, then said "You know you have two buttholes"...
She did not find it as funny as I did....

LOLOLOLOLOLOLOLOLOLOLOLOLOLOLOLOLOLOLOLOLOLOLOLOLOLLOOLOLOLOLOLOOLOOLOLLLOOLOLLOLOLOOLOLOLLLL

there's a chick I went to school with and rumor was she had two assholes. Must've been in the same situation

[Watson]

one time she yelled "JUST COME IN ME ALREADY" i promptly pulled out, put my boxers and shorts back on, walked out and slept in the living room. was just really weird to be demanded of my come. her and i never spoke again after the next day haha.

Man none of those really seem awkward to me. Especially the last one. I suppose it would be when you're 17. But now, hoo boy I tell ya. That's some hot shit. Go with it homey.

[DevinSB]

one time she yelled "JUST COME IN ME ALREADY" i promptly pulled out, put my boxers and shorts back on, walked out and slept in the living room. was just really weird to be demanded of my come. her and i never spoke again after the next day haha.

Man none of those really seem awkward to me. Especially the last one. I suppose it would be when you're 17. But now, hoo boy I tell ya. That's some hot shit. Go with it homey.

What!! making eye contact with your bestfriend's girl while shes taking baby gravy on the tongue is super awkward! the last one wasn't super awkward, but was weird for me, i'm not trying to blow loads in anyone. she also got pregnant like 5 months later, so i'm glad i didnt.

[jeremyrandall]

God Damn Wilson...I was hoping you would show up.

One time I was starting to get into it with this chick and we were dirty talking and she accidentally said "God I love touching my cock." instead of "your cock". That was the end of that.

Fucking a girl and I told her "I love your ass." And she said "It loves you." So I said "Okay." And she was like "It's talking to you." And I was like "Is it?" And she was like "Yeah. What's it saying?" And I was like "I don't know. I'm hungry?" That girl was consistently an awkward dirty talker. Best I could figure is that she wanted to be raped by her dad.

And then of course the time I farted in a chick's face while I was coming in her mouth on the 5th time she sucked my dick that night trying to get off my limp beer-dick. That one was a classic.

These three stories just made my fucking night!!  But the first one is the absolutely the best thing I've ever heard.

[jeremyrandall]

one time she yelled "JUST COME IN ME ALREADY" i promptly pulled out, put my boxers and shorts back on, walked out and slept in the living room. was just really weird to be demanded of my come. her and i never spoke again after the next day haha.

Man none of those really seem awkward to me. Especially the last one. I suppose it would be when you're 17. But now, hoo boy I tell ya. That's some hot shit. Go with it homey.

What!! making eye contact with your bestfriend's girl while shes taking baby gravy on the tongue is super awkward! the last one wasn't super awkward, but was weird for me, i'm not trying to blow loads in anyone. she also got pregnant like 5 months later, so i'm glad i didnt.

And yeah...first girl I ever boned always let me blow my loads in her...but I was young(er...not really that young) and stupid.  Now I'm so fucking paranoid about pregnancy I won't blow a load in a girl even with a condom on.

[DevinSB]

yeah fuck that noise! i blew a load in a girl, with a condom on, and she didnt have her period for like 2 months, but ended up not being pregnant, and her cycles were just fucked up, i was buggin' out. scariest shit ever, no blowing loads anywhere near a vagina for me.

[jeremyrandall]

Ok...this story isn't so much awkward as just fucking scary.  I'm with my first somewhat long term girlfriend right now...and we fuck ALOT...so I'm ultra paranoid about knocking her up.  Back in the summer time I was telling one of my best friends that I wouldn't even blow a load in my gf even with a condom on.  He couldn't believe I was so paranoid and basically told to stop being so scared. 

So less than 24 hours later, I'm boning my lady from behind, and all the sudden it just feels FUCKING AMAZING!!  Now this is back when were first together and I hadn't really had sex that much.  I could tell I was getting close to busting a nut and was about to pull out.  But then I remembered my conversation with my friend the night before.  I was like "Fuck it...I'm wearing a condom" and just blew my load.  I pull out and the condom is fucking torn to shreds.  Begin hyperventilation.  I just busted a full load into a fertile 19 year old girl.  Not stoked!!!

So basically I'm scared shitless of ever busting inside a girl ever again.  I mean I bought her the Plan B pill...which obviously worked cause she's not pregnant.  But no way I'm ever busting a nut in her anytime soon.

[Donkey Lips]

So less than 24 hours later, I'm boning my lady from behind, and all the sudden it just feels FUCKING AMAZING!!  Now this is back when were first together and I hadn't really had sex that much.  I could tell I was getting close to busting a nut and was about to pull out.  But then I remembered my conversation with my friend the night before.  I was like "Fuck it...I'm wearing a condom" and just blew my load.  I pull out and the condom is fucking torn to shreds.  Begin hyperventilation.  I just busted a full load into a fertile 19 year old girl.  Not stoked!!!

So basically I'm scared shitless of ever busting inside a girl ever again.  I mean I bought her the Plan B pill...which obviously worked cause she's not pregnant.  But no way I'm ever busting a nut in her anytime soon.

Ah yes, I know this story well. You evaluate your life so hard in the coming days. It's amazing when you find out you're in the clear. Food tastes amazing, boring things now mean something to you and you have a complete and total appreciation for everything once you know you didn't knock a chick up.  I used to play in the rain without a coat with one girlfriend...basically the hours of awesome'ness didn't erase the days/weeks of panic afterwards.

[pee]

few months ago i met this girl at the bar and got really drunk. as the bar closed we headed to her friends place. got there being borderline black out drunk and decided to get high. great idea. at one point we decide to go to bathroom to fuck. both being too drunk it didn't really work out that good. i fucked her on the floor for like minute but it didn't really work out. then we thought we should try fucking in the bathtub but that turned out to be way too small. so then we decide to spot and that's  that. it wasn't really that awkward aside from the fact that there were like 5 people in the small apartment and they most likely could here everything we were doing. the girl turned out to be beyond awesome and now i'm in a relationship with her and it's great.

[LloydChristmas]

So less than 24 hours later, I'm boning my lady from behind, and all the sudden it just feels FUCKING AMAZING!!  Now this is back when were first together and I hadn't really had sex that much.  I could tell I was getting close to busting a nut and was about to pull out.  But then I remembered my conversation with my friend the night before.  I was like "Fuck it...I'm wearing a condom" and just blew my load.  I pull out and the condom is fucking torn to shreds.  Begin hyperventilation.  I just busted a full load into a fertile 19 year old girl.  Not stoked!!!

So basically I'm scared shitless of ever busting inside a girl ever again.  I mean I bought her the Plan B pill...which obviously worked cause she's not pregnant.  But no way I'm ever busting a nut in her anytime soon.

Ah yes, I know this story well. You evaluate your life so hard in the coming days. It's amazing when you find out you're in the clear. Food tastes amazing, boring things now mean something to you and you have a complete and total appreciation for everything once you know you didn't knock a chick up.  I used to play in the rain without a coat with one girlfriend...basically the hours of awesome'ness didn't erase the days/weeks of panic afterwards.

...or you are not a father, just as much of a relief.

[Donkey Lips]

i don't think there's any panic on earth quite like a dude wondering if he got a girl pregnant.  ...well, maybe being the chick and wondering if you're pregnant.