Awkward Sexual Experiences

[skate_bored]

i was fucking this girl doggystyle on a rickety old futon.  it was bouncing all over the place, and we started to get a little out of rhythm.  somehow my dick slipped out of her pussy and went all the way up her ass without me realizing it.  she let out this death yodel and ran and locked herself in the bathroom for hours.  she was freaking out because the sudden shock caused her asshole to stay dialated open.  anyway, this chick just about fucking killed me.  she thought i did it on purpose, and it took months to finally convince her otherwise.  i did think it was pretty funny though. 

one night i took a girl home from the bar, a girl i only met once about 8 years prior in high school. hadnt seen her since but we talked, came home, started fucking. she had gotten a little thick and had big tits. they were too big. it grossed me out. i was pretty much blacked out but i vaguely remember having to hold them together to not be grossed out. then i remember her laying next to me crying and then i woke up the next morning. she told me that i'd stuck it in her ass completely and it hurt her so she was crying and i passed out. then she said "if you wanted to do it there you should have just asked, i had lube in my purse". what a slut. anyways, i fucked her again the next night and she texted me nonstop for 3 days until i told her to stop and she went nuts. girls are weird.

[mock nugget]

This one happened to my friend when he was in high school. No sex involved, just jackin, which always seems to make the story funnier. He told me about it a few years later when we were drunk and talking about embarrassing shit. He was at his dad's house, in his room jackin it, and he had the stereo on loud. And his dad was calling him cause dinner was ready but he didn't hear. So I guess his dad got fed up and went down the hall, opened his door and was like "DINNER JON!" and my friend looks up at his dad right as he busts his load. I think his actual words were "we made eye contact at the moment of no return".

[CigaretteBeer]

I'm pretty sure I've told this story, but I'll tell it again. It seems like all my awkward sexual experiences involve quiefs. Well, once this asian girl came over and I was kind of drunk and we ended up fucking. I asked if I could fuck her in the ass and she said yes, so I pulled my dick out and was going to lick her pussy while she was bent over. As my face got near her vagina and asshole a huge quief erupted right into my face and mouth. She said "oh that was just a quief, I didn't fart in your face". I told her I'd find some lube and when I came back into the room she was dressed and left soon after that.

[drunk]

something's missing

[kilgore.]

one of my buddies was tellin' me this crazy story about a fish and a couch and whiskey dick, went like this.

Okay, I think Im finally going to tell this story, because I dont think she goes on here anymore and also because I don't care.  You may know the person in question as Vicky, or victoria.  This was like 2 years ago when I was going to school in Philly.  I started chatting her up on here via PM, and then AIM.  I end up meeting up with her on this one really rainy day at her school which was a couple blocks from where I went.  We went to like some cafeteria or something and she put on Fully Flared on her Macbook.  It was pretty awkward. All you guys who think that it would be sick to date a chick who is into skateboarding, its not what its cracked up to be.  Any time she would bring up skateboarding it would be like "Oh, so and so is sooo sick!  Did you see that Thunder ad!" It was just weird.  But anyway I hang out with her 1 or 2 times after this, ALWAYS with her annoying friend, who incidentally also posted here but I dont remember his name.   I went over to her friends house where she was hanging out one day after class (she refused to let me in her own apartment, I dont know why), and theyre throwing back rum and cokes.  Its like 4 oclock. Shes already drunk, all sitting on my lap and shit and all over me.  Now, I wasnt even sure if I was into it, but I just let it happen.  She keeps drinking and is basically hammered, Im barely buzzed.  We drive all over the fucking city to the train station to pick up her sister, and the whole time shes just so annoying and drunk.  Finally we get back to this girls apartment, and we go in her friends room and she shuts the door.  We start making out.  Shirts off, titties sucked.  I still pretty much just want tot leave at this point, the whole night had been annoying as fuck.  Her friend starts opening the door and is like WHAT ARE YOU GUYS DOING IN HERE?  And so shes all like "quick go in the bathroom!" because she's half naked.  Im really fucking annoyed right now.  Her friends like "JUST GO FUCK ON THE COUCH" and we go back in the living room.  She takes her clothes off and literally just lays there like a dead fish.  By this point i am woefully aware this isnt the most.. "fit" girl Ive been with.  I could not be any more flaccid.  After like 5 minutes of me hoping shell do some fluffing or something, I say something like "Ummmmmmm....its uhhh not getting...."  We put our clothes back on, I walk to the train station and never see her again.  She texts me a few days later asking if she was the reason I couldnt get a boner.  I tell her it was because I was a virgin and was too nervous.  I never talk to her again.

Moral: Dont try and fuck anyone from Slap.

[drunk]

there it is!

[russ]

A gnar is in order.

[Bobbito]

one of my buddies was tellin' me this crazy story about a fish and a couch and whiskey dick, went like this.

Expand Quote

Okay, I think Im finally going to tell this story, because I dont think she goes on here anymore and also because I don't care.  You may know the person in question as Vicky, or victoria.  This was like 2 years ago when I was going to school in Philly.  I started chatting her up on here via PM, and then AIM.  I end up meeting up with her on this one really rainy day at her school which was a couple blocks from where I went.  We went to like some cafeteria or something and she put on Fully Flared on her Macbook.  It was pretty awkward. All you guys who think that it would be sick to date a chick who is into skateboarding, its not what its cracked up to be.  Any time she would bring up skateboarding it would be like "Oh, so and so is sooo sick!  Did you see that Thunder ad!" It was just weird.  But anyway I hang out with her 1 or 2 times after this, ALWAYS with her annoying friend, who incidentally also posted here but I dont remember his name.   I went over to her friends house where she was hanging out one day after class (she refused to let me in her own apartment, I dont know why), and theyre throwing back rum and cokes.  Its like 4 oclock. Shes already drunk, all sitting on my lap and shit and all over me.  Now, I wasnt even sure if I was into it, but I just let it happen.  She keeps drinking and is basically hammered, Im barely buzzed.  We drive all over the fucking city to the train station to pick up her sister, and the whole time shes just so annoying and drunk.  Finally we get back to this girls apartment, and we go in her friends room and she shuts the door.  We start making out.  Shirts off, titties sucked.  I still pretty much just want tot leave at this point, the whole night had been annoying as fuck.  Her friend starts opening the door and is like WHAT ARE YOU GUYS DOING IN HERE?  And so shes all like "quick go in the bathroom!" because she's half naked.  Im really fucking annoyed right now.  Her friends like "JUST GO FUCK ON THE COUCH" and we go back in the living room.  She takes her clothes off and literally just lays there like a dead fish.  By this point i am woefully aware this isnt the most.. "fit" girl Ive been with.  I could not be any more flaccid.  After like 5 minutes of me hoping shell do some fluffing or something, I say something like "Ummmmmmm....its uhhh not getting...."  We put our clothes back on, I walk to the train station and never see her again.  She texts me a few days later asking if she was the reason I couldnt get a boner.  I tell her it was because I was a virgin and was too nervous.  I never talk to her again.

Moral: Dont try and fuck anyone from Slap.

[close]

love you, nohomo.

[jack burton]

This one happened to my friend when he was in high school. No sex involved, just jackin, which always seems to make the story funnier. He told me about it a few years later when we were drunk and talking about embarrassing shit. He was at his dad's house, in his room jackin it, and he had the stereo on loud. And his dad was calling him cause dinner was ready but he didn't hear. So I guess his dad got fed up and went down the hall, opened his door and was like "DINNER JON!" and my friend looks up at his dad right as he busts his load. I think his actual words were "we made eye contact at the moment of no return".

so tonight i ended up make out with my friend on the down stairs couch and ended up boning. so it comes to time to finish and i ask to finish in her mouth (sorry wilson). so shes giving me a blowie and as im about to finish my sisters boyfriend comes stormin down the stairs as i cover up my dick and finish in my shirt. my friend sat there with pants around her ankles and a smile on her face. sorry if this makes no sense. ive been doin a little drinkin.

[Watson]

she had sucked on my tongue so hard that the part connected to my bottom jaw was sore

Dude, a couple years ago me and 3 friends drove 16 hours to see Danzig in Minnesota. We were staying in this really nice hotel and there was this group of old people walking around and one of them was this pretty hot cougar that we name "Rocket Tits" because they were all pointed and shit. She had to be at least 50, maybe 55, but still hot. (LurkDaddy, please note, that is a cougar. Not a fucking 28 year old.) One night we were down at the hotel bar, and the group of oldies with this hot old slut were down there, and somehow we all end up sitting and drinking together. This old bitch is all over whichever of us was closest, but mainly my friend. He's engaged so he like jokes around with her a bit and then is like "Yo I gotta go to the room, talk to my man Dan." So she starts talking to me and rubbing my leg, all this shit. And all this is in front of my 2 other friends and all her old friends, like guys and girls. She's like leaning in really close and rubbing my whole face intensely, like pulling my skin back almost making my contacts pop out and shit. She's really fucked. So drunk, like sloppy, nasty, embarrassing to look at drunk.

Hotel dude comes over and tells us that the bar is closing, so we move into the courtyard, and Rocket Tits' old gross-ass friend goes upstairs to her room and brings me and my friends and all of them a smorgasboard of wine, rum, and vodka coolers. We're being too noisy in the courtyard so hotel dude comes over and says we can't chill in there, but we can drink and hang out in the lobby. What the fuck? So we go in there and hang out and drink whatever free booze this other old bitch is giving us. By now it's just me, one of my friends, and like three old ladies. Rocket Tits sits on my lap, and she starts licking my ear and shit, whispering all this stuff in my ear and still pulling my skin so far back I probably looked like a burn victim with no eyelids or lips.

Sidenote: At this point these frat boy douchebags come in and try to hang out with us and start trying to hit on Rocket Tits. The dude asks us if we were in a band (it seriously happened all fucking weekend and we kept telling people we were and our name was The Blood Of Christian Children), and I was like "Yeah we are. What do YOU do?" And he says "I'm a police officer. What's your band's name?" And I told him "Millions Of Dead Cops." He obviously wasn't a real cop because I didn't end up dead in the parking lot, and they took off.

So then Rocket Tits starts making out with me, and she sucked on my tongue so hard that the thing thing that connects my tongue to the bottom of my mouth literally ripped. Like actually. So I pushed her away and was like "OW! WHAT THE FUCK?!" And she drunkenly slurred "Yerrrr neverrr gonna meet sumwun who ksssses like meee again..." and I was like "Good." So we intensely make out some more in front of everyone and I am feeling up her tits, and then I go for the cooch and she grabs my hand and is like "NO! It's not about the sex! It's about the loveeeeeee, the loveeeeeeee" and starts trying to peel the skin off my face again. So I was like "Yeah it's about the love, but the sex is tight too." THEN SHE STARTS CRYING! "Booo hooo hooo I love my son! He's addicted to meth! But he's a good kid. I LOVE HIM!" Shit don't phase me nothin, and I am still trying to take her to the bone zone, but one of her friends realizes that it's probably not a good idea for her to get slayed by some 30 year old while she's crying about her meth-head son, and takes her away.

When I got upstairs my friend, the first dude she was trying to get it on with told me he was watching the whole thing from the balcony and if I had taken her back to our room he intended to creep into the room and secretly watch me fuck her.

So yeah, that whole thing was sufficiently awkward.

P.S.

She was also the one who took my balls in her mouth and pulled on them, which I found out I'm hesitant about--sorry Wilson, I can't man up to your level.

You're a pussy.

[SFblah]

I think his actual words were "we made eye contact at the moment of no return".

Ugh, that is so shitty and so hilarious at the same time.

[Bobbito]

Expand Quote

she had sucked on my tongue so hard that the part connected to my bottom jaw was sore

[close]

Dude, a couple years ago me and 3 friends drove 16 hours to see Danzig in Minnesota. We were staying in this really nice hotel and there was this group of old people walking around and one of them was this pretty hot cougar that we name "Rocket Tits" because they were all pointed and shit. She had to be at least 50, maybe 55, but still hot. (LurkDaddy, please note, that is a cougar. Not a fucking 28 year old.) One night we were down at the hotel bar, and the group of oldies with this hot old slut were down there, and somehow we all end up sitting and drinking together. This old bitch is all over whichever of us was closest, but mainly my friend. He's engaged so he like jokes around with her a bit and then is like "Yo I gotta go to the room, talk to my man Dan." So she starts talking to me and rubbing my leg, all this shit. And all this is in front of my 2 other friends and all her old friends, like guys and girls. She's like leaning in really close and rubbing my whole face intensely, like pulling my skin back almost making my contacts pop out and shit. She's really fucked. So drunk, like sloppy, nasty, embarrassing to look at drunk.

Hotel dude comes over and tells us that the bar is closing, so we move into the courtyard, and Rocket Tits' old gross-ass friend goes upstairs to her room and brings me and my friends and all of them a smorgasboard of wine, rum, and vodka coolers. We're being too noisy in the courtyard so hotel dude comes over and says we can't chill in there, but we can drink and hang out in the lobby. What the fuck? So we go in there and hang out and drink whatever free booze this other old bitch is giving us. By now it's just me, one of my friends, and like three old ladies. Rocket Tits sits on my lap, and she starts licking my ear and shit, whispering all this stuff in my ear and still pulling my skin so far back I probably looked like a burn victim with no eyelids or lips.

Sidenote: At this point these frat boy douchebags come in and try to hang out with us and start trying to hit on Rocket Tits. The dude asks us if we were in a band (it seriously happened all fucking weekend and we kept telling people we were and our name was The Blood Of Christian Children), and I was like "Yeah we are. What do YOU do?" And he says "I'm a police officer. What's your band's name?" And I told him "Millions Of Dead Cops." He obviously wasn't a real cop because I didn't end up dead in the parking lot, and they took off.

So then Rocket Tits starts making out with me, and she sucked on my tongue so hard that the thing thing that connects my tongue to the bottom of my mouth literally ripped. Like actually. So I pushed her away and was like "OW! WHAT THE FUCK?!" And she drunkenly slurred "Yerrrr neverrr gonna meet sumwun who ksssses like meee again..." and I was like "Good." So we intensely make out some more in front of everyone and I am feeling up her tits, and then I go for the cooch and she grabs my hand and is like "NO! It's not about the sex! It's about the loveeeeeee, the loveeeeeeee" and starts trying to peel the skin off my face again. So I was like "Yeah it's about the love, but the sex is tight too." THEN SHE STARTS CRYING! "Booo hooo hooo I love my son! He's addicted to meth! But he's a good kid. I LOVE HIM!" Shit don't phase me nothin, and I am still trying to take her to the bone zone, but one of her friends realizes that it's probably not a good idea for her to get slayed by some 30 year old while she's crying about her meth-head son, and takes her away.

When I got upstairs my friend, the first dude she was trying to get it on with told me he was watching the whole thing from the balcony and if I had taken her back to our room he intended to creep into the room and secretly watch me fuck her.

So yeah, that whole thing was sufficiently awkward.

I have so much to learn. That story is ridiculous.

[raul]

So then Rocket Tits starts making out with me, and she sucked on my tongue so hard that the thing thing that connects my tongue to the bottom of my mouth literally ripped.

Whenever people would play the papercut game--where's the worst spot to get one--I'd pick that spot. Few others can trump it. I can't imagine that without making a direct trip to the hospital, how'd that heal?

You're a pussy.

Ahh.. I know. 

[SFblah]

Wow, Wilson.  A gnar was in order for that one.

And the band thing is hilarious because I had a very cute  drunk girl ask my friends and I if we were in a band once when the bar was closing, and I of course said yea.  She swore she had our CD at home with our photo on the cover but couldn't remember the band name so we played along and talked about how bad the sound was at some place we played down the street.  She was paying FULL attention to us but I noticed the jock guy I saw her with earlier was standing about 6 ft behind her looking pissed waiting for her.  I said, "Hey, is that your date waiting on you?" and she looked back at him and just loud enough for him to hear it said, "Pff, I'm not with him", and waived her hand off in his direction.  He wasn't stoked. 

We didn't hook up with her but seeing her straight blow off her date to talk to two guys she swore was in a band was great.  She did hug on me a bunch and kiss my neck when leaving so who knows if she'd have been down for an afterparty.

[kilgore.]

in like grade 9 one of my best friends invited me over to his house to "run a train" on his girl. I went over, for some strange reason...it was me, and my two friends Hector and Lionel. it was Hector's girlfriend.  my friend Lionel was a horny dude who looked 41 when he was in grade 9 and had severe acne, he was so stoked on the situation. i meet them in the backyard and they are all laying on the trampoline, ha. hector said he was going to go first cause it was his girlfriend. he looks like a giraffe by the way and his girlfriend was not the most "fit" girl i'd ever been invited to run a train on. Hector is just fucking the shit out of her bouncing all around on the trampoline like an animal. Lionel is just smiling, really excited about the whole situation i get severely weirded out by this whole event and walked across the street to my house. god damn that was weird because 5 years later they got married and i was at the wedding, and of course i was thinking of that memory the whole time.

[luc]

in high school i was making out with my girlfriend in the parking lot.. school had been out for a couple hours and we were in the back of the parking lot so we werent worried about anything.. we were down to undies and the windows were really foggy.. then someone taps on the window. it was a cop and he was tripping.. he ran our names and kept us there for a while but then sent us on our way. we just kinda thought it was funny.. we both went home after that and she calls me about an hour later. her dad was listening to the police scanner and he was pissed. he was kinda cool about it though.. i hadnt met her parents before and they wanted to meet me.. so i went over there adn they were like "well since you came over then our daughter must be important to you but dont do that again etc etc"

[jeremyrandall]

in high school i was making out with my girlfriend in the parking lot.. school had been out for a couple hours and we were in the back of the parking lot so we werent worried about anything.. we were down to undies and the windows were really foggy.. then someone taps on the window. it was a cop and he was tripping.. he ran our names and kept us there for a while but then sent us on our way. we just kinda thought it was funny.. we both went home after that and she calls me about an hour later. her dad was listening to the police scanner and he was pissed. he was kinda cool about it though.. i hadnt met her parents before and they wanted to meet me.. so i went over there adn they were like "well since you came over then our daughter must be important to you but dont do that again etc etc"

This just happened to me this summer.  I actually had just finished boning my girlfriend, and had thankfully pulled my pants back on.  Got the tap on the window and the flashlight in the face from the damn cop.  But I think as soon as he saw that I wasn't a highschool kid (I'm 23) he just left.  Wasn't that bad.

[Donkey Lips]

This just happened to me this summer.  I actually had just finished boning my girlfriend, and had thankfully pulled my pants back on.  Got the tap on the window and the flashlight in the face from the damn cop.  But I think as soon as he saw that I wasn't a highschool kid (I'm 23) he just left.  Wasn't that bad.

got this in highschool as well. random older chick (she could drive past 9:00pm and i was still 15) that was trying to corrupt my youth and innocence.  she succeeded.  while getting dome i see the blue flashes behind the parked car, followed by the tapping of a maglite on the window.  he awkwardly asks what we're doing as if he doesn't already know.  runs her ID, then asks for mine and I don't have anything since I'm 15.  casually he replies to me "she's 18 and you're 15...nice job" and tells us if we aren't done and out of there in 15 minutes he'll come back.

[LloydChristmas]

Got the tap on the window and the flashlight in the face from the damn cop. 

got this from a female cop, and it wasn't pretty.  female cops are bad enough, but rookie female cops have something to prove.  before getting our id's she's flipping out asking the girl if she was being held against her will and if she consented etc, and me and the girl are just confused as fuck.  even when i said something like "sorry i didn't know this park had closing hours this is my fault"  the officer is like "what? you got something to say, smart guy?". 

they really need to do a better job weeding out these kinds of people in the police academies who have obvious baggage that they carry over into their job.  i'm certain that this officer was probably abused as a child or something, i'd bet my life on it.   

[H8R part 4]

my bartender and his GF asked me if i wanted to do a 3 way with them.  my bartender looked right at me and said, "i'll suck your dick".  she was super cute and all but i turned them down.  i stopped going to the bar because of the sheer awkwardness of it all but i finally realized why he never really charged me for drinks. 


back when i was in HS, my GF was riding me and got off me just as i was about to cum.  she timed it just right that when my dick slid out it was pointing at my head and i shot myself in the neck and cheek.  not so much awkward but gross. 
 

[Bipsmound]

What kind of man cums on his own face?  Sounds like we've got a case of class A certified limp wristed bum dwelling fruit scented Peter Pan daytime TV Andrew Lloyd Webber wenis wizard boystown alley lurking poppers popping dancefloor maven faggotry going on here.

[ed...]

Faster! is a man completely surrounded by homosexuals

[Alan]

...even when he's alone.

[Watson]

It's probably better you didn't go to that bartender's house Faster. Your hand probably would have smelled like cologne for a week after touching the door knob. 

[floop]

What kind of man cums on his own face? 

that is a good question

[floop]

Expand Quote

I think his actual words were "we made eye contact at the moment of no return".

[close]

Ugh, that is so shitty and so hilarious at the same time.

sounds like a scene out of a Todd Solondz film

[Chris Hansen is back]

^

I shudder every time my son orders the tuna fish sandwich at Denny's

I'm Chris Hansen.

[DEDBBIS]

A classmate of mine in high school was porking his girlfriend in his car. She was on top and he asked if he could fulfill manifest destiny and put it in her butt, she grants his wish. As he's about to come, she yells "stop" and he finishes in her as deep as he can reach. She pulls off, and the diarrhea (with white accents of course) comes out all over him. He pukes on himself at the sight of it, and she pukes at the sight of his vomit, leaving them in a sticky situation.

[General Cornrow Wallace]

A classmate of mine in high school was porking his girlfriend in his car. She was on top and he asked if he could fulfill manifest destiny and put it in her butt, she grants his wish. As he's about to come, she yells "stop" and he finishes in her as deep as he can reach. She pulls off, and the diarrhea (with white accents of course) comes out all over him. He pukes on himself at the sight of it, and she pukes at the sight of his vomit, leaving them in a sticky .

 

hahahaha just when you thought it couldn't get any worse....it does

[sven thorkel]

if you've ever worked a labor job you have heard some prole tell some variation of that story. the whole she poops, he pukes, she pukes shtick is probably the number one sexual suburban legend