Awkward Sexual Experiences

[saucy ragu]

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My ex-girlfriend threw up on me a couple times from gagging while giving me head. One of the times she threw up right when my brother walked in the living room...





Throw up in your butt crack isn't pleasant.

[close]

Man, this isn't about sex, but my ex-wife threw up on me on her birthday.  I was the DD so she could go out and drink with her friends and when we left she seemed fine, she was in heels and she only had a little wobble, but she was walking ok and not even slurring.  She stayed up the whole way home, got in bed just fine and then she woke up in the middle of the night and threw up all over my neck and chest.  Fuck, I was so mad, but I didn't flip on her.  I just cleaned myself up, stripped the sheets and slept on the couch.  She was pretty embarrassed the next day and I couldn't stop giving her shit about it.

[close]

You and the Mrs split up? Shit, I'm clueless man. When did that happen?

I think he means his first wife.

[Lance]

I was bangin this chick steady for a while when I was 18, I was all fucked up on mushrooms 1 night and we just went at it and it was the wierdest sex ever, like trying to shove a clam in a quarter slot, anyway she was saying wierd shit and had she had no idea i was tripping face, so I couldnt finish and made her leave.  I never spoke to her again...Present day, she now works 3 doors down from where I work and I have to see her walk by twice a day we made eye contact and it was the most awkward shit ive expeirenced in a while...A friend of mine knows her husband, guess shes married with 3 kids now.

[saucy ragu]

I was bangin this chick steady for a while when I was 18, I was all fucked up on mushrooms 1 night and we just went at it and it was the wierdest sex ever, like trying to shove a clam in a quarter slot, anyway she was saying wierd shit and had she had no idea i was tripping face, so I couldnt finish and made her leave.  I never spoke to her again...Present day, she now works 3 doors down from where I work and I have to see her walk by twice a day we made eye contact and it was the most awkward shit ive expeirenced in a while...A friend of mine knows her husband, guess shes married with 3 kids now.

Scisorring? Que?

[Mark Renton]

Not awkward but funny..
I was banging in my car with my ex like 2 months ago. My car is one of those small cars with just 2 doors, so if someone needs to go seat in the backseat you have to pull one stick located in the front seat (not the drive one).
When we finished I went to the drive seat, she is in the one beside me trying to put the backrest back how it was..couldn't, so I pull the stick the other way too heavily and the upper part hit her square in the face. I started laughing like and idiot, she got all mad.

[Cockaigne]

So yeah. This just happend when i was skating around the city today. I got hit on by a perverted spanish dude of about 40.

Actually I just moved to this city, and i was just cruising around with two non-skater friends. As i was rolling around these two guys just disappeared into some shop, but i didn't know. As I was lost, without friends and without money, there was nothing to do but skating around. At a certain moment i was stanting at some corner, when a dude on his bike passed me, smiled and said something i couldn't quite hear. So i asked, "whats did you say?", after which he said the same thing which again i didn't understand. He spoke with a lisp, a dirty spanish lisp.

So he told me he just thought i was good looking guy, and he enjoyed that. I'm not homophobic in any way, so i told him thankyou, expecting he was a decent gay. I spoke with him about just moving into the city, and just some random shit. He was kinda obviously gay for me, and told him he didn't have a chance and he should know. We discussed intimacy in the streets, whether its apropriate to kiss in the streets and such. So he actually seemed decent.

But not much later he started talking about partying and stuff. "Are you interested in partying? In fucking girls? Using xtc? Cocaine?". Actually i am very interested in these topic, so i listened to what he had to say. The dirt told me he knew a lot of girls, and could take care of women for me. Actually promising me to have beautiful women for me in his house. I'd be able to come by, have sex and drugs, under the condition I'd be "his" one day in the week. He promised me to buy me presents, get me two grammes of coke, just for free. Also i was offered a thousand euros to show him my dick.

So y'know....i wasn't feeling it. I had told him I was thirsty from smoking and hundry and poor. He could have been a good loverboy and offer something to drink. He just said "money is no issue"/dirty smile. But he never came through with his presents or promises. I don't know. It sucks. I could have been some rich dudes sex slave....or have thousand euros. I'm still kind of in doubt about the whole thing. But there's one thing to say, it was akward.

[jimi420]

this girl tongue punched my butthole the other night then tried to makeout with me after she swallowed my load. She was a trooper for doing it but I just can't do that shit.

[PTDK]

I was getting down with my girl on the couch the other evening. I was about to cum and she told me to blow it on her tits, so I pull out and start jerkin to finish off. I look down half way through and realize I am not actually cumming. I was having an orgasm but not cumming. Afterwards she's like "Uh....did you just fake an orgasm." It took me a while to convince her I didn't then we just kept going.....guess it is possible for dudes to have multiple orgasms. She later tells me it was the most confusing thing in her life, and in hindsight if I was an outside party looking in I am sure it would have been hilarious to see a dude who thinks he is cumming on this girls tits and later realizes he wasn't.

[PTDK]

That is pretty weird, dude.

I HEARD an awkward sexual experience this morning!  My upstairs neighbors were fucking loudly and in the middle of it they started arguing about him calling her a dirty bitch.  AWESOME

Maybe they were role playing a role play.

[ice nine]

I'm not sure if I've posted this before, I should have but I don't remember it so anyways, its not nearly as crazy as most shit in here, but I'm a lil suburban bitch who is sheltered as fuck.

I drive a delivery truck usually.sometimes I stop at the only rest stop on my run off the freeway.I eat my lunch or take a nap, its actually really nice, in the forest and everything.

 One time last year(I think) I pull in, and there's a small RV parked on the side, not in the stalls but on the side of the forest/edge of the pavement.an elderly man in the front seat is waving me over from the moment I pull in. I park and look over and he is still doing it. (There are other trucks and buses, other people walking/having a small picnic. I thought it was strange that he waited till I was there if he was in need of help, but I couldn't just ignore him so I walked over. As I am walking I see him scurry into the back of the rv. I stand outside for a second and he opens the sidedoor, and stands at the top of the stairs and says "come on in". Immediately became curiously horny, jk I asked "why would I do that?"He said "I want to suck your cock" in those exact words. I was shocked at his openness, and said no thanks and walked back to my truck. I still wanted to nap but had a 'hard' time falling asleep, and would keep looking over at the RV and if the guy was in the front seat, he was staring at me constantly.I also kept seeing a little wiry dude who looked like flea on crack(probably was him) pacing around the parking lot multiple times. I see rustling in the bushes and flea is there, peeking out at me. He saw me looking, and did the fist to mouth "I'm sucking cock" motion repeatedly at me. I shook my head no. He went back in the bushes. I decide I'm not gonna be able to sleep now and decide to leave. As I am the side door of the RV opens and the old original guy and a disgusting other obese old man, in what looked like a wife beater drenched in cooking oil and sweatpants get out. Creeped me out knowing that other dude was in there the whole time. I don't know what they had planned for me, but at least now I know where the gay casual hookup spot is.

[trannies and mannies]

Seriously, I would have left right there when he asked to suck your dick.

[ice nine]

i barely ever get enough hours at work, or sleep very much. so getting paid to sleep was high up on my priority list, and i'd been busted sleeping on the side of the road before, so this was the only spot i was sure was safe. i even went back one or two more times and did sleep, though it was never the same. the same camper was in the same spot one of those times, but i just ignored it. plus im in a locked truck, in a half full parking lot. if he was so determined to break the window, pull my pants down and suck my cock in front of a bunch of families, i'd probably force myself to cum out of respect for that kind of dedication.

[Donkey Lips]

I HEARD an awkward sexual experience this morning!  My upstairs neighbors were fucking loudly and in the middle of it they started arguing about him calling her a dirty bitch.  AWESOME

Oh no way. I've been there. I don't usually get into verbally degrading a chick during the act, but one girl I used to hook up with in college kept telling me to call her a slut and a whore...do the slapping thing. Sure, I'll play ball. I learned that you can call her "dirty slut, dirty whore, bad girl...etc"every degrading thing in existence....EXCEPT calling her bitch. You know that scene from the Exorcist when the girls head spin completely around with a demonic look? I got that. I also received a complete and full lecture on how unnecessary it was to refer to her as "bitch".

After that, she flipped back into game mode, finished me off and then cooked me manicotti for dinner. We don't talk anymore.

[chillout]

my first night in college me and my roommate ended up hanging out with these girls. i had drank a little and my roommate hadnt at all, and both these girls were pretty wasted so i wasnt really trying to get it in. me and the two girls go out for a smoke and on the way back one of them sprints to our room. me and the other girl continued to walk up the stairs. When i get to the room the girl im with goes over by my roommate and i hear a noise coming from my room so i go check it out. the girl who sprinted up, jumped out from under my covers, and screams "would you fuck me, id fuck me" with the scariest devil face ive ever seen. i just kinda played it of and we watched 5 minutes of a tv before she passed out and i carried her back to her room

[Bobbito]

a couple months ago I was getting down with this chick I had known for years but never chilled with until she moved pretty close to where I live. First night I fucked her was probably the sickest. I think it was the 2nd or 3rd time we fucked that turned sour. the sex was awesome, fucking her from behind against her bed standing and everything, talking dirty, all that good shit. After I nut, I go to slip the rubber off and realize its all torn up. Right then and there I started to think about my life and that I'm gonna become a father now and instantly became sober but still kinda out of it because I had just blown a really mean nut. Worst part was I was 3 or 4 tall cans deep too so I was in heaven for like 15-20 minutes and then ended up with a bad situation. Luckily, she used to work at a free clinic so she had plan b on deck and took it asap. I cured my issues with half a Newport and then passed out.

Here's where it gets nasty....I'm texting with her like 4 days later. A couple hours go by between texts and I get one saying "OMG the nastiest thing just happened to me!". I thought maybe she found a spider or cockroach in her apartment or something but then she tells me "your condom just fell out of me". Since that day, I realized trying to wife that was futile and that I should just casually fuck her because not having a dependable nut, especially during winter, sucks. Last time we slept together was a couple days before Christmas and have only seen each other like 5 times strictly because we have a lot of mutual friends so its inevitable.

Also, as a sidenote, she had this weird fucking tendency that pissed me off. She would sometimes (especially when drunk which would happen after like 3 beers) use this stupid baby voice that was a huuuuuge turnoff. I told all my friends and they laughed about it but I simply just couldn't. I felt like I was laying next to a 10 yr old when she did that. bleeehhhhhh.


best thread ever btw!!

[frisco]

Recently I went home with this chick who was roommates with a chick from my old highschool. Didnt start out well. We get out of the cab, shes wasted as shit, im leaning over paying the cab driver and she yells "PIGGYBACK" and jumps on my back, mind you it was pouring rain, I lost my balance and both of us went down backwards into a wooden fence. The noise was ridiculous, the loudest hollow thud, pretty sure she was concussed but she was just laughing. Long story short she passed out in bed, I waited it out and got it done in the am, pretty haggard actually, had scrapes all over my elbow

[buttpirate]

Recently I went home with this chick who was roommates with a chick from my old highschool. Didnt start out well. We get out of the cab, shes wasted as shit, im leaning over paying the cab driver and she yells "PIGGYBACK" and jumps on my back, mind you it was pouring rain, I lost my balance and both of us went down backwards into a wooden fence. The noise was ridiculous, the loudest hollow thud, pretty sure she was concussed but she was just laughing. Long story short she passed out in bed, I waited it out and got it done in the am, pretty haggard actually, had scrapes all over my elbow

that's not awkward.  unless you got it done while she was passed out and she woke up midway.


I got a semi-bj in a club toilet one new years.  I was so drunk that I couldnt get it up, whiskey dicking hard.  the random girl passed out with my soft cock in her mouth after ten minutes of trying, I had to pick her up and carry her out and panties were still in the toilet bowl.  everyone waiting to take a shite after had a good upskirt look as I walked out.

[jimi420]

I had my first experience with whiskey dick... so disappointing...

[oyolar]

I had my first experience with whiskey dick... so disappointing...

Did you expect it to be awesome?

[saucy ragu]

a couple months ago I was getting down with this chick I had known for years but never chilled with until she moved pretty close to where I live. First night I fucked her was probably the sickest. I think it was the 2nd or 3rd time we fucked that turned sour. the sex was awesome, fucking her from behind against her bed standing and everything, talking dirty, all that good shit. After I nut, I go to slip the rubber off and realize its all torn up. Right then and there I started to think about my life and that I'm gonna become a father now and instantly became sober but still kinda out of it because I had just blown a really mean nut. Worst part was I was 3 or 4 tall cans deep too so I was in heaven for like 15-20 minutes and then ended up with a bad situation. Luckily, she used to work at a free clinic so she had plan b on deck and took it asap. I cured my issues with half a Newport and then passed out.

Here's where it gets nasty....I'm texting with her like 4 days later. A couple hours go by between texts and I get one saying "OMG the nastiest thing just happened to me!". I thought maybe she found a spider or cockroach in her apartment or something but then she tells me "your condom just fell out of me". Since that day, I realized trying to wife that was futile and that I should just casually fuck her because not having a dependable nut, especially during winter, sucks. Last time we slept together was a couple days before Christmas and have only seen each other like 5 times strictly because we have a lot of mutual friends so its inevitable.

Also, as a sidenote, she had this weird fucking tendency that pissed me off. She would sometimes (especially when drunk which would happen after like 3 beers) use this stupid baby voice that was a huuuuuge turnoff. I told all my friends and they laughed about it but I simply just couldn't. I felt like I was laying next to a 10 yr old when she did that. bleeehhhhhh.


best thread ever btw!!

You didn't tell me. Hmph.

[Greg Ostertag]

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I was getting down with my girl on the couch the other evening. I was about to cum and she told me to blow it on her tits, so I pull out and start jerkin to finish off. I look down half way through and realize I am not actually cumming. I was having an orgasm but not cumming. Afterwards she's like "Uh....did you just fake an orgasm." It took me a while to convince her I didn't then we just kept going.....guess it is possible for dudes to have multiple orgasms. She later tells me it was the most confusing thing in her life, and in hindsight if I was an outside party looking in I am sure it would have been hilarious to see a dude who thinks he is cumming on this girls tits and later realizes he wasn't.

[close]

that's happened to me more than once, actually.  i think a medication i take fucks with my kit like that.

Busting placebo nuts...

[PTDK]

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I was getting down with my girl on the couch the other evening. I was about to cum and she told me to blow it on her tits, so I pull out and start jerkin to finish off. I look down half way through and realize I am not actually cumming. I was having an orgasm but not cumming. Afterwards she's like "Uh....did you just fake an orgasm." It took me a while to convince her I didn't then we just kept going.....guess it is possible for dudes to have multiple orgasms. She later tells me it was the most confusing thing in her life, and in hindsight if I was an outside party looking in I am sure it would have been hilarious to see a dude who thinks he is cumming on this girls tits and later realizes he wasn't.

[close]

that's happened to me more than once, actually.  i think a medication i take fucks with my kit like that.

[close]

Busting placebo nuts...

Happened again this weekend. Gonna go see a doctor just in case.

[Monty Burns]

I had my first experience with whiskey dick... so disappointing...

Never happend to me ( knock on wood )  guess my hornyness outwinns my drunkness everytime

[j....soy.....]

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I was getting down with my girl on the couch the other evening. I was about to cum and she told me to blow it on her tits, so I pull out and start jerkin to finish off. I look down half way through and realize I am not actually cumming. I was having an orgasm but not cumming. Afterwards she's like "Uh....did you just fake an orgasm." It took me a while to convince her I didn't then we just kept going.....guess it is possible for dudes to have multiple orgasms. She later tells me it was the most confusing thing in her life, and in hindsight if I was an outside party looking in I am sure it would have been hilarious to see a dude who thinks he is cumming on this girls tits and later realizes he wasn't.

[close]

that's happened to me more than once, actually.  i think a medication i take fucks with my kit like that.

[close]

Dry heaves....

Busting placebo nuts...

[Hercules Rockefeller]

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I had my first experience with whiskey dick... so disappointing...

[close]

Never happend to me ( knock on wood )  guess my hornyness outwinns my drunkness everytime

amazing.

[InternetDaddy]

I didn't have a placebo nut, but I almost wish I did.

I got back home for Spring Break two weeks ago. I went straight to my girlfriend's place, and she gives me head pretty much right away, which was rad. Everything was going great until I'm about to nut, and it's just the weirdest sensation. Like, normally you can feel it kind of work its way up and out, but this time there were two "dry heaves" and then these three big solid globs came out, one after the other. The only way I can really describe them is "cum rocks." They were fairly hard, completely solid, and disturbingly large. My dick hurt for like a day afterwards, too. I looked it up online, and the most likely reason was that I was dehydrated. Now I really focus on staying hydrated, that shit was awful.

[burm]

I didn't have a placebo nut, but I almost wish I did.

I got back home for Spring Break two weeks ago. I went straight to my girlfriend's place, and she gives me head pretty much right away, which was rad. Everything was going great until I'm about to nut, and it's just the weirdest sensation. Like, normally you can feel it kind of work its way up and out, but this time there were two "dry heaves" and then these three big solid globs came out, one after the other. The only way I can really describe them is "cum rocks." They were fairly hard, completely solid, and disturbingly large. My dick hurt for like a day afterwards, too. I looked it up online, and the most likely reason was that I was dehydrated. Now I really focus on staying hydrated, that shit was awful.

Also, protein. If you've had a lot of protein, and haven't cummed in a while, it can start coagulating. Or just the latter, since you always have some protein in it. So basically, you need to jack it more!

[PTDK]

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I didn't have a placebo nut, but I almost wish I did.

I got back home for Spring Break two weeks ago. I went straight to my girlfriend's place, and she gives me head pretty much right away, which was rad. Everything was going great until I'm about to nut, and it's just the weirdest sensation. Like, normally you can feel it kind of work its way up and out, but this time there were two "dry heaves" and then these three big solid globs came out, one after the other. The only way I can really describe them is "cum rocks." They were fairly hard, completely solid, and disturbingly large. My dick hurt for like a day afterwards, too. I looked it up online, and the most likely reason was that I was dehydrated. Now I really focus on staying hydrated, that shit was awful.

[close]

Also, protein. If you've had a lot of protein, and haven't cummed in a while, it can start coagulating. Or just the latter, since you always have some protein in it. So basically, you need to jack it more!

Coagulated Cum would be an awesome metal band name.



This happened last night. Broke in the new table then woke up to find this on it...haha.

[Grubby Mits]

Of all  the stories I've posted in here this has to be the awkwardest. On saturday some slut with a boyfriend invites me over to watch 'friends with benefits' and whilst im on my way she sends me loads of texts like 'what are we going to do if we get bored of the film '. Anyway, I get there and have to end up eating dinner with her mother, which was already awkward because I just fucking ate so every bite of the pizza felt like I was deepthroating Ron Jermy, but what made it more awkward was how her mum wouldn't shut up about watching porn and who she's fucked. She also said she'd rip my dick off if she saw me fucking her daughter, but didn't mind if she didn't see. Anyway she goes out to suck some old man dick in the local pub so we get down to watching the movie and... the fucking bitch fell asleep. Yes you read that right. I sat there and watch Friends with Benefits whilst trying to wake this bitch up for like an hour and a half. Weirdest part is she still keeps texting me, the cheek. 

Nothing to see here folks

[ivegotlevitation]

I had sex for the first time a few weeks ago and lasted about a minute. maybe this should've gone in the real confessions thread. either way, it was awkward.

[Grubby Mits]

I had sex for the first time a few weeks ago and lasted about a minute. maybe this should've gone in the real confessions thread. either way, it was awkward.

Think of dead people. Unless you're a necrophiliac. Actually you'd probably be fucking a dead person in that case anyway so fuck it, keep thinking of dead people.