Awkward Sexual Experiences

[Kanye Omari West]

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i was in a tent fucking my hot girlfriend on a bunch of mushrooms and her older brother came around the back of the tent while i was sucking her tits and started flipping out at us. he was like "if i hear you kissing one more time i'm coming in there and whupping his ass". he was also on mushrooms.

[close]

The fact you had to tell random fools on the internet that she's hot has me suspecting that she isn't

BUT in the case that she actually is hot, then that's fantastic for you man

[close]

she dumped me actually. a long time ago. she had big hooters and a tight vajeen.

last time i had a girl spend the night she wanted to fuck me but i had this nasty grizzly beard and couldn't get into making out with her (even though she didn't seem to mind the gristle). anyways, she slept in my bed and i couldn't pass out and got horny in the middle of the night and started trying to kiss her again and she didn't wake up. the next day she did get naked for me though and let me suck on her tits. her nipples were like devil horns. i never got to fuck her.

[close]

Rusty reminds me of a certain somebody who shall remain nameless...

If you're from the NH/MA area, you may know who'm I refer to...

[close]

well alright den bro. you want a cookie or something den?

He's being ridiculous right now

[Rusty_Berrings]

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i was in a tent fucking my hot girlfriend on a bunch of mushrooms and her older brother came around the back of the tent while i was sucking her tits and started flipping out at us. he was like "if i hear you kissing one more time i'm coming in there and whupping his ass". he was also on mushrooms.

[close]

The fact you had to tell random fools on the internet that she's hot has me suspecting that she isn't

BUT in the case that she actually is hot, then that's fantastic for you man

[close]

she dumped me actually. a long time ago. she had big hooters and a tight vajeen.

last time i had a girl spend the night she wanted to fuck me but i had this nasty grizzly beard and couldn't get into making out with her (even though she didn't seem to mind the gristle). anyways, she slept in my bed and i couldn't pass out and got horny in the middle of the night and started trying to kiss her again and she didn't wake up. the next day she did get naked for me though and let me suck on her tits. her nipples were like devil horns. i never got to fuck her.

[close]

Rusty reminds me of a certain somebody who shall remain nameless...

If you're from the NH/MA area, you may know who'm I refer to...

[close]

well alright den bro. you want a cookie or something den?

[close]

He's being ridiculous right now

I'm just so Ricky Riccardo- Ridiculose.

[the]

Few months ago I told my then girlfriend that I would be buying tickets to travel around china the next day. She wasn`t too happy about this at all because A)She couldnt come B)Few of her friends traveled there, didnt like it and always told her how shit and dirty China is and C)Pretty sure she just straight up didn`t like Chinese people.

That night we ended up back at mine. Usual shit we start cuddling and kissing. Eventually we get down to business missionary position and from what I could gather she was quite into it. Moaning, breathing changed, sweating e.t.c . but maybe im clueless and dont know any better. Anyway, in the middle of all this she tries to say something but shes all short on breath so its hard for her. I dont think twice and keep on keeping on . She continues to try and form a sentence and eventually manages while breathing heavily in between the words. ``Dont.... go... to.... China``, she says while locking eyes with me....

Not knowing how to respond and just simply baffled by the situation I kinda lose focus and rhythm and start slowing down. I say something along the lines of ``The fuck?? can we talk about this later???``

I try and get back into it but at that point I realize im kinda over it. She doesn`t stop there. She continues to tell me that im likely to get food poisoning and waste money on random shit....

so there I am inside a girl talking about how sanitary China is and how much the visa and travel insurance would cost.
We get into a curb your enthusiasm-esque argument where we both are talking over each other while im still inside her.

I pull out and roll over and have a laugh to my self at what just happened. We both fall asleep and have another go in the morning, argument free.


I didn`t end up going to China due to some other reasons and dumped her couple of weeks later.

[jimi420]

Me and my girlfriend of two year just broke up so Ive been on the prowl for rebound pussy. I hit up this girl who lives a few blocks away from me and tell her to drop by. Luckily my parents went out of town for spring break so I had the whole house to myself and I was planning on fucking all over the place. She comes by and I pop in Harry Potter and The Chamber of Secrets and after a few minutes we start kissing and touching but when I go to finger her she stops me and tells me she just had surgery because she had a miscarriage and they had to take something to do with fetal growth out or something idk so we couldnt fuck because she had stiches on her pussy. Im bummed because I already have a boner and everything so she decides just to give me some mouth. Well i guess sucking dick gets her worked up and decides her stiches arent important. We start going at it and maybe 20 minutes in she starts complaining about pain. I feel like im the shit and that my dick is big but no, her stiches ripped and she was bleeding all over the place. She freaks out, calls her mom to pick her up and take her to the hospital to maybe get new stiches and she makes me come along. I had to sit with her mom staring daggers at me and I wanted to fade into the background. She hasnt texted me since, which is a bummer because her head was on point.

[shark tits]

Me and my girlfriend of two year just broke up so Ive been on the prowl for rebound pussy. I hit up this girl who lives a few blocks away from me and tell her to drop by. Luckily my parents went out of town for spring break so I had the whole house to myself and I was planning on fucking all over the place. She comes by and I pop in Harry Potter and The Chamber of Secrets and after a few minutes we start kissing and touching but when I go to finger her she stops me and tells me she just had surgery because she had a miscarriage and they had to take something to do with fetal growth out or something idk so we couldnt fuck because she had stiches on her pussy. Im bummed because I already have a boner and everything so she decides just to give me some mouth. Well i guess sucking dick gets her worked up and decides her stiches arent important. We start going at it and maybe 20 minutes in she starts complaining about pain. I feel like im the shit and that my dick is big but no, her stiches ripped and she was bleeding all over the place. She freaks out, calls her mom to pick her up and take her to the hospital to maybe get new stiches and she makes me come along. I had to sit with her mom staring daggers at me and I wanted to fade into the background. She hasnt texted me since, which is a bummer because her head was on point.

i woulda tried to get some scripts out the deal

[Carrolls Chesthairs]

Me and my girlfriend of two year just broke up so Ive been on the prowl for rebound pussy. I hit up this girl who lives a few blocks away from me and tell her to drop by. Luckily my parents went out of town for spring break so I had the whole house to myself and I was planning on fucking all over the place. She comes by and I pop in Harry Potter and The Chamber of Secrets and after a few minutes we start kissing and touching but when I go to finger her she stops me and tells me she just had surgery because she had a miscarriage and they had to take something to do with fetal growth out or something idk so we couldnt fuck because she had stiches on her pussy. Im bummed because I already have a boner and everything so she decides just to give me some mouth. Well i guess sucking dick gets her worked up and decides her stiches arent important. We start going at it and maybe 20 minutes in she starts complaining about pain. I feel like im the shit and that my dick is big but no, her stiches ripped and she was bleeding all over the place. She freaks out, calls her mom to pick her up and take her to the hospital to maybe get new stiches and she makes me come along. I had to sit with her mom staring daggers at me and I wanted to fade into the background. She hasnt texted me since, which is a bummer because her head was on point.

[JB]

Me and my girlfriend of two year just broke up so Ive been on the prowl for rebound pussy. I hit up this girl who lives a few blocks away from me and tell her to drop by. Luckily my parents went out of town for spring break so I had the whole house to myself and I was planning on fucking all over the place. She comes by and I pop in Harry Potter and The Chamber of Secrets and after a few minutes we start kissing and touching but when I go to finger her she stops me and tells me she just had surgery because she had a miscarriage and they had to take something to do with fetal growth out or something idk so we couldnt fuck because she had stiches on her pussy. Im bummed because I already have a boner and everything so she decides just to give me some mouth. Well i guess sucking dick gets her worked up and decides her stiches arent important. We start going at it and maybe 20 minutes in she starts complaining about pain. I feel like im the shit and that my dick is big but no, her stiches ripped and she was bleeding all over the place. She freaks out, calls her mom to pick her up and take her to the hospital to maybe get new stiches and she makes me come along. I had to sit with her mom staring daggers at me and I wanted to fade into the background. She hasnt texted me since, which is a bummer because her head was on point.

Amazing. +1

[jack burton]

Jimi I love you.

[scorpion1001]

Jimi I love you.

said it for me too

[captainfalcon69]

Jimi I love you.

[Kanye Omari West]

hahahahahaahaha whatttt theeee fuckkkkk sonnnnn

[ttching!]

Jimi, was it the same hospital where the doctor busted you going down on your girlfriend with the broken leg?

[JB]

Jimi, was it the same hospital where the doctor busted you going down on your girlfriend with the broken leg?

fuck, that was Jimi too? i think that story and the last one he posted were the only ones from this thread that i actually had to tell people about because they were so good.

[jimi420]

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Jimi, was it the same hospital where the doctor busted you going down on your girlfriend with the broken leg?

[close]

fuck, that was Jimi too? i think that story and the last one he posted were the only ones from this thread that i actually had to tell people about because they were so good.

same hospital, different doctor. After they put new stiches in the doctor came out and told her mother and I that she cant have any sexual activity for at least two weeks. The doctor made direct eye contact with me multiple times. My entire sexual history is a joke

[Joust Ostrich]

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Jimi, was it the same hospital where the doctor busted you going down on your girlfriend with the broken leg?

[close]

fuck, that was Jimi too? i think that story and the last one he posted were the only ones from this thread that i actually had to tell people about because they were so good.

[close]

same hospital, different doctor. After they put new stiches in the doctor came out and told her mother and I that she cant have any sexual activity for at least two weeks. The doctor made direct eye contact with me multiple times. My entire sexual history is a joke

Well, like a good joke, it has brought smiles and laughter to many that were fortunate enough to have read it.  Thank you for sharing.  The broken leg story was so good.

[Radgasm]

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Me and my girlfriend of two year just broke up so Ive been on the prowl for rebound pussy. I hit up this girl who lives a few blocks away from me and tell her to drop by. Luckily my parents went out of town for spring break so I had the whole house to myself and I was planning on fucking all over the place. She comes by and I pop in Harry Potter and The Chamber of Secrets and after a few minutes we start kissing and touching but when I go to finger her she stops me and tells me she just had surgery because she had a miscarriage and they had to take something to do with fetal growth out or something idk so we couldnt fuck because she had stiches on her pussy. Im bummed because I already have a boner and everything so she decides just to give me some mouth. Well i guess sucking dick gets her worked up and decides her stiches arent important. We start going at it and maybe 20 minutes in she starts complaining about pain. I feel like im the shit and that my dick is big but no, her stiches ripped and she was bleeding all over the place. She freaks out, calls her mom to pick her up and take her to the hospital to maybe get new stiches and she makes me come along. I had to sit with her mom staring daggers at me and I wanted to fade into the background. She hasnt texted me since, which is a bummer because her head was on point.

[close]

so good!!!

[Rumpleforeskin]

jimi always comes through with the best stories in this thread holy shit

[Rumpleforeskin]

had drunk sex with a high school cheerleader on a ping-pong table last weekend... the only awkward part was finding out later my friend had been trying to bone her all night... 

[DISTANT RUMOURS]

1)

I met this chick years ago on myspace. She was this fake redhead with small tits but an ass to die for.
I only talked to her on myspace and after a while we met up.

Within 15 minutes she was giving me head behind the busstop. It was awesome.

After a while we started dating and this chick was kinky as hell.

One night we went to a hip hop party at some big club. the place was packed and we were dancing in the crowd.
She starts grinding me, and my dick gets hard. She's wearing high heels and a short skirt.
She notices my dick is hard and "whispers, be right back in my ear". after 5 minutes she comes back and starts grinding again.
She puts my hand under her skirt and I notice that she took off her panties.

So this chick is dancing right in front of me with no panties on. We go to the lounge area and she sits on my lap, with one hand she unzips my pants and starts riding me. The place was packed, I was super embarrassed and shy, but she just didn't care. She sat with her face away from me, and just worked it. After a while I came super hard, but I think no one noticed... and she didn't care anyway if anyone did.

So I zip up, order drinks, and she walks back to the dance floor.
Cum was dripping all on the floor. So a couple of hundred people danced in cum.

Awesome.


2)

The chick was into fucking in public places. For our 6 months, we went to a fancy restaurant and we got some table in the corner of the room. It was actually a very romantic setting. She was drinking wine and getting tipsy. So she got horny and she was rubbing my dick with her feet. At first I could resist, and I was like, "come on Sara, not here!" but man, the girl was hot as hell so I just gave up. I got hard as fuck and she noticed right away. She immediately moved her chair and sat right next to me, and started jacking me off under the table.

When I came, she was holding this crystal wine glass, so I came into the glass.
She moved back across the table, looked in my eyes, and started drinking cum from the glass like nothing happened.

That was probably the coolest image I've ever seen.

3)

AGAIN, public place. We went for late night walk into the fields where I live. And she had a thing with cornfields. So she got horny and pulled me into the cornfield, after 2 minutes we were fucking like crazy. It was dark and I couldn't see shit and she wanted it doggy.
So I made that pussy wet and stuck it in. After a while she sat on top of me and went for it like hell. After a while she jumps up and starts crying " aaaaaaaaaaargh! fucking hell you dick!!!" I was freaking ou and didn't know what happend, tok my mobile phone and her legs were dripping with blood. I stuck in her ass without noticing and she was fucking PISSED. She punched me in the face and I was pissed because I didn't do it on purpose...

Didn't talk for 2 weeks when I one of a sudden I get an email with an attached video. It was her fingering herself and after a while she stuck a dildo in her ass. That she stops and says "I've been practicing..." and blow a kiss to the webcam. I was stunned and fucking horny. I called her up and begged her to come over. But she was at school and could only come over the next day.

The next day she shows up at the door, she acts like tha perfect daughter in law, and my parents are happy that she's back. We go up stairs and within 5 minutes were fucking. She gets on top and sticks my dick in her ass. Rides it till I come like crazy and we cuddled for hours after that.

Best sex ever, hands down.

after a while shit went downhill, she went to college and met some meathead there...

She also has like 3 kids now and she STILL super hot... fucking lucky bastard that got her to marry him.

[Lance]

1)

I met this chick years ago on myspace. She was this fake redhead with small tits but an ass to die for.
I only talked to her on myspace and after a while we met up.

Within 15 minutes she was giving me head behind the busstop. It was awesome.

After a while we started dating and this chick was kinky as hell.

One night we went to a hip hop party at some big club. the place was packed and we were dancing in the crowd.
She starts grinding me, and my dick gets hard. She's wearing high heels and a short skirt.
She notices my dick is hard and "whispers, be right back in my ear". after 5 minutes she comes back and starts grinding again.
She puts my hand under her skirt and I notice that she took off her panties.

So this chick is dancing right in front of me with no panties on. We go to the lounge area and she sits on my lap, with one hand she unzips my pants and starts riding me. The place was packed, I was super embarrassed and shy, but she just didn't care. She sat with her face away from me, and just worked it. After a while I came super hard, but I think no one noticed... and she didn't care anyway if anyone did.

So I zip up, order drinks, and she walks back to the dance floor.
Cum was dripping all on the floor. So a couple of hundred people danced in cum.

Awesome.


2)

The chick was into fucking in public places. For our 6 months, we went to a fancy restaurant and we got some table in the corner of the room. It was actually a very romantic setting. She was drinking wine and getting tipsy. So she got horny and she was rubbing my dick with her feet. At first I could resist, and I was like, "come on Sara, not here!" but man, the girl was hot as hell so I just gave up. I got hard as fuck and she noticed right away. She immediately moved her chair and sat right next to me, and started jacking me off under the table.

When I came, she was holding this crystal wine glass, so I came into the glass.
She moved back across the table, looked in my eyes, and started drinking cum from the glass like nothing happened.

That was probably the coolest image I've ever seen.

3)

AGAIN, public place. We went for late night walk into the fields where I live. And she had a thing with cornfields. So she got horny and pulled me into the cornfield, after 2 minutes we were fucking like crazy. It was dark and I couldn't see shit and she wanted it doggy.
So I made that pussy wet and stuck it in. After a while she sat on top of me and went for it like hell. After a while she jumps up and starts crying " aaaaaaaaaaargh! fucking hell you dick!!!" I was freaking ou and didn't know what happend, tok my mobile phone and her legs were dripping with blood. I stuck in her ass without noticing and she was fucking PISSED. She punched me in the face and I was pissed because I didn't do it on purpose...

Didn't talk for 2 weeks when I one of a sudden I get an email with an attached video. It was her fingering herself and after a while she stuck a dildo in her ass. That she stops and says "I've been practicing..." and blow a kiss to the webcam. I was stunned and fucking horny. I called her up and begged her to come over. But she was at school and could only come over the next day.

The next day she shows up at the door, she acts like tha perfect daughter in law, and my parents are happy that she's back. We go up stairs and within 5 minutes were fucking. She gets on top and sticks my dick in her ass. Rides it till I come like crazy and we cuddled for hours after that.

Best sex ever, hands down.

after a while shit went downhill, she went to college and met some meathead there...

She also has like 3 kids now and she STILL super hot... fucking lucky bastard that got her to marry him.

You Sir are a God Damn Street Poet.  Thank you

[ice nine]

ya but that shit seems extremely fake, i aint buying it. unless there are pix

[Chris Hansen is back]

^Ditto.

I was just waiting for...

>spaghetti everywhere.

[PumpkinEsc0bar]

Haven't had sex in like a year and a half.

Nothing more awkward than that

[Kanye Omari West]

Expand Quote

1)

I met this chick years ago on myspace. She was this fake redhead with small tits but an ass to die for.
I only talked to her on myspace and after a while we met up.

Within 15 minutes she was giving me head behind the busstop. It was awesome.

After a while we started dating and this chick was kinky as hell.

One night we went to a hip hop party at some big club. the place was packed and we were dancing in the crowd.
She starts grinding me, and my dick gets hard. She's wearing high heels and a short skirt.
She notices my dick is hard and "whispers, be right back in my ear". after 5 minutes she comes back and starts grinding again.
She puts my hand under her skirt and I notice that she took off her panties.

So this chick is dancing right in front of me with no panties on. We go to the lounge area and she sits on my lap, with one hand she unzips my pants and starts riding me. The place was packed, I was super embarrassed and shy, but she just didn't care. She sat with her face away from me, and just worked it. After a while I came super hard, but I think no one noticed... and she didn't care anyway if anyone did.

So I zip up, order drinks, and she walks back to the dance floor.
Cum was dripping all on the floor. So a couple of hundred people danced in cum.

Awesome.


2)

The chick was into fucking in public places. For our 6 months, we went to a fancy restaurant and we got some table in the corner of the room. It was actually a very romantic setting. She was drinking wine and getting tipsy. So she got horny and she was rubbing my dick with her feet. At first I could resist, and I was like, "come on Sara, not here!" but man, the girl was hot as hell so I just gave up. I got hard as fuck and she noticed right away. She immediately moved her chair and sat right next to me, and started jacking me off under the table.

When I came, she was holding this crystal wine glass, so I came into the glass.
She moved back across the table, looked in my eyes, and started drinking cum from the glass like nothing happened.

That was probably the coolest image I've ever seen.

3)

AGAIN, public place. We went for late night walk into the fields where I live. And she had a thing with cornfields. So she got horny and pulled me into the cornfield, after 2 minutes we were fucking like crazy. It was dark and I couldn't see shit and she wanted it doggy.
So I made that pussy wet and stuck it in. After a while she sat on top of me and went for it like hell. After a while she jumps up and starts crying " aaaaaaaaaaargh! fucking hell you dick!!!" I was freaking ou and didn't know what happend, tok my mobile phone and her legs were dripping with blood. I stuck in her ass without noticing and she was fucking PISSED. She punched me in the face and I was pissed because I didn't do it on purpose...

Didn't talk for 2 weeks when I one of a sudden I get an email with an attached video. It was her fingering herself and after a while she stuck a dildo in her ass. That she stops and says "I've been practicing..." and blow a kiss to the webcam. I was stunned and fucking horny. I called her up and begged her to come over. But she was at school and could only come over the next day.

The next day she shows up at the door, she acts like tha perfect daughter in law, and my parents are happy that she's back. We go up stairs and within 5 minutes were fucking. She gets on top and sticks my dick in her ass. Rides it till I come like crazy and we cuddled for hours after that.

Best sex ever, hands down.

after a while shit went downhill, she went to college and met some meathead there...

She also has like 3 kids now and she STILL super hot... fucking lucky bastard that got her to marry him.

[close]

You Sir are a God Damn Street Poet.  Thank you

[Matze]

got to remember to gnar you for the rest of the week.

[JB]

@DISTANT RUMOURS

[saucy ragu]

The perfect cap to that story has to be a photo of this creator of dreams.

[Ronald Wilson Reagan]

So, I got vomited on tonight by a girl whose deep throat game wasn't as on point as she apparently thought. We were hooking up before going out, and my shirt was ruined. I had to wear my jacket and keep it zupped up for the rest of the night.

[L33Tg33k]

Damn, that sucks dude. I could only imagine something like that. I could only imagine.

[Ronald Wilson Reagan]

This thread should make you realize a lot of what your missing isn't something you want to experience. I really don't think you'd want to be vomited on, then have to sit there for a half hour consoling the girl hidden under her blanket crying from embarrassment as you wonder how you are going to deal with the shirt situation.