Awkward Sexual Experiences

[pancake man]

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I'm guessing you grew up in the midwest?

[close]

no, not even close. i grew up in a small city outside of Boston where every member of the city council and school committee is also a real estate agent who profits off of low income housing, which, for a myriad of reasons, brings/fosters a lot of crazy drug use to town. At one time, there were a ton of jobs in the factories and mills, now they're all closed and there is nothing to do but take drugs, live at home, go to the bar, and waste the unemployment/SSI/disability check.

I ran into a dude I hadn't seen in 11 years a few nights ago and he said "you know the first thing that struck me when i came back here? it was all the broken TVs on the side of the road. Broken TVs and syringes."

This screams south shore or right outside of Worcester, fuck almost as depressing as Pittsfield

[Big Bush]

steve, you must be from lowell there is no other place around or close to boston i can think of. Maybe lynn but I'm hoping lowell for you're sake.

[KOOL MIKE]

the KOOLEST MIKE is worried fam, i fucked the shit out this girl 2 nights ago than this morning i went to take a leak and noticed i got these little red dots just below my knob with like one or two on the knob, yo what the fuck, i been doin the google and haven't found too much, someone tell me what the fucks up, do i got the STD's? someone tell me sumthin, do i just go to a normal doctor or some special dick doctor? yo

[Grubby Mits]

What like around your pubes? Doesn't sound good man, just go to the doctor. Remember to think about stephen hawking if the doctors hot (happened to me). Are you sure it's not a physical injury though? Could be a friction burn. I thought I had an STD when my bellend looked all fucked up once, but it just because the chick was terrible at blowjobs and scraped me up

[KOOL MIKE]

What like around your pubes? Doesn't sound good man, just go to the doctor. Remember to think about stephen hawking if the doctors hot (happened to me). Are you sure it's not a physical injury though? Could be a friction burn. I thought I had an STD when my bellend looked all fucked up once, but it just because the chick was terrible at blowjobs and scraped me up
[/quote


hmmm she did blow me for like an hour and there was a bit of scrapeage, lol i fell asleep thru that shit and woke up and she was stil going, but they aint anywhere near the pubes they are on my shlong just bellow my head if ya know what im sayin and than a couple  on my knob, i did jerk off this mornin aswell, im hoping to fuck it got somethin to do wit that, like i work this litlle motherfucka red raw or some shit

[twitchflip]

sounds like it could be a yeast infection, dude. either way, consult your doctor and get tested. ask for both urinal and blood tests and cover all the bases. good luck

[LambShank]

there's a story that i've been waiting to post for a while but it never feels like the right time. i'll bust it out today in celebration of my one year anniversary with the girl its about.
my girlfriend is an actress (plays and stuff, not movies) and called me one night around eight o'clock to pick her up from a rehearsal. niether of us had any money on our person so there wasnt much to do, so i drove down to the beach to hang out until we though something up. we hung out in the car for a while since it was february and cold on the jersey shore so push came to shove and we started banging in my front seat with her on top and myself sitting just as though i were driving and i was checking the rearview mirror every minute or so to make sure we were alone. around nine fifteen i was feeling good, definitely the longest id ever lasted at that point, and i was holding her from the bottom. things were feeling wetter than usual but i disregarded it as and figured it was from how long things had been going for. a few minutes later i checked the rearview and this was when i saw a blacked out car with some extra bright lights cruise by extra slowly. i've always been paranoid of cops and suddenly had a huge pit in my stomach. the car slowed down, turned on its lights and k turned right behind us as i threw my girlfriend off of me and we scrambled to get our clothes back on. 
in our mad dash to get dressed she had put on her pants and my thrasher sweatshirt that was ten sizes too big for her and left me with just shoes, socks and jeans due to my lack of foresight and habit of wearing sweatshirts without a shirt underneath. here i am, shirtless and out of breath, when an officer comes and knocks on my window. we talk for a while and he was actually pretty cool and didnt give us any trouble, just told us to get out of there and not be such idiots in the future and half jokingly asked my girl if i was holding her against her will. we collected ourselves and headed over to my friends house to hang out for a while and on the way out i realized that there was some dark brown grime all over my hands. i washed it off and brought my lady home. when i got home and turned my car off the interior lights came on and i got up to notice an enormous bloodstain on my front seat, and another on the back of my pants from sitting on it all night.
turns out she had her period while we were fucking just before the cop came. i guess this isnt as awkward as a lot of other stories but i kind of thought it was worth sharing.
 

[Grubby Mits]

Update for my 21st century pussy project: 3 girls replied so far, one isn't a looker (haven't replied yet and feel bad), another one is hot but a muslim (hard mode?) and the final one is hot, in her mid 20s, a dom and most likely going to murder me

[Harem]

This would've been 2 years ago. I remember going back to this girls house who was really into classical style music. I impressed her with my knowledge of Igor Stravinsky and she made reference to this all night. We get back to her place and she remembers she left her house key at her friends house. Not a issue, her housemate will let us in. Average dude wearing a Angry Birds t-shirt. We get to her room, and get into it straight away before she asks if she can could slip into the shower quickly, I say sure. By this time I needed to take the biggest shit. I'm talking like shitting out a cement block. I use the only toilet in the house, which is a couple of meters away from the bathroom she was in. I don't know why I did this, but I decided to take a shit with the seat still down. Like there was no reason for me to do it, I was just like 'fuck it'. Being drunk as fuck I thought I'd be a good idea to wrap my hands in toilet paper and then proceed to smear it all over the seat, so it was covered. I didn't know this girl, I was never going to see her again? I literally get back to her room just as she is about to walk out and pretend I'm going through her record collection. We fuck for the next 20 minutes, and the whole time I'm thinking how funny it would be if she needed to use the toilet and see what was in there and blame her house mate. Went back to the toilet to see my art work. Holy shit that smell (Dhal & Spinach curry the night before will do that) Ended up taking a packet of Mozzarella cheese from her fridge, and eating it as I walked to find a cab.

[steve]

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I'm guessing you grew up in the midwest?

[close]

no, not even close. i grew up in a small city outside of Boston where every member of the city council and school committee is also a real estate agent who profits off of low income housing, which, for a myriad of reasons, brings/fosters a lot of crazy drug use to town. At one time, there were a ton of jobs in the factories and mills, now they're all closed and there is nothing to do but take drugs, live at home, go to the bar, and waste the unemployment/SSI/disability check.

I ran into a dude I hadn't seen in 11 years a few nights ago and he said "you know the first thing that struck me when i came back here? it was all the broken TVs on the side of the road. Broken TVs and syringes."

[close]

This screams south shore or right outside of Worcester, fuck almost as depressing as Pittsfield

508, homie.

Pittsfield sucks too. I lived in North Adams 10 years ago, and visit often. Fuck, it's a shitty area to live in. At least out there, though, you've got the mountains. down here all i've got is the taunton river.

[Filip]

This would've been 2 years ago. I remember going back to this girls house who was really into classical style music. I impressed her with my knowledge of Igor Stravinsky and she made reference to this all night. We get back to her place and she remembers she left her house key at her friends house. Not a issue, her housemate will let us in. Average dude wearing a Angry Birds t-shirt. We get to her room, and get into it straight away before she asks if she can could slip into the shower quickly, I say sure. By this time I needed to take the biggest shit. I'm talking like shitting out a cement block. I use the only toilet in the house, which is a couple of meters away from the bathroom she was in. I don't know why I did this, but I decided to take a shit with the seat still down. Like there was no reason for me to do it, I was just like 'fuck it'. Being drunk as fuck I thought I'd be a good idea to wrap my hands in toilet paper and then proceed to smear it all over the seat, so it was covered. I didn't know this girl, I was never going to see her again? I literally get back to her room just as she is about to walk out and pretend I'm going through her record collection. We fuck for the next 20 minutes, and the whole time I'm thinking how funny it would be if she needed to use the toilet and see what was in there and blame her house mate. Went back to the toilet to see my art work. Holy shit that smell (Dhal & Spinach curry the night before will do that) Ended up taking a packet of Mozzarella cheese from her fridge, and eating it as I walked to find a cab.

Dude, seriously, fuck you.

[Harem]

Were you the banal ass dude with the Angry Birds shirt who probably posts on the Game of Thrones IMDB forum and gets turned on by the underpass scene in Irreversible?

[Andrefosho]

This would've been 2 years ago. I remember going back to this girls house who was really into classical style music. I impressed her with my knowledge of Igor Stravinsky and she made reference to this all night. We get back to her place and she remembers she left her house key at her friends house. Not a issue, her housemate will let us in. Average dude wearing a Angry Birds t-shirt. We get to her room, and get into it straight away before she asks if she can could slip into the shower quickly, I say sure. By this time I needed to take the biggest shit. I'm talking like shitting out a cement block. I use the only toilet in the house, which is a couple of meters away from the bathroom she was in. I don't know why I did this, but I decided to take a shit with the seat still down. Like there was no reason for me to do it, I was just like 'fuck it'. Being drunk as fuck I thought I'd be a good idea to wrap my hands in toilet paper and then proceed to smear it all over the seat, so it was covered. I didn't know this girl, I was never going to see her again? I literally get back to her room just as she is about to walk out and pretend I'm going through her record collection. We fuck for the next 20 minutes, and the whole time I'm thinking how funny it would be if she needed to use the toilet and see what was in there and blame her house mate. Went back to the toilet to see my art work. Holy shit that smell (Dhal & Spinach curry the night before will do that) Ended up taking a packet of Mozzarella cheese from her fridge, and eating it as I walked to find a cab.

Ruthless, can't believe it's for real.

[pancake man]

Expand Quote

Expand Quote

Expand Quote

I'm guessing you grew up in the midwest?

[close]

no, not even close. i grew up in a small city outside of Boston where every member of the city council and school committee is also a real estate agent who profits off of low income housing, which, for a myriad of reasons, brings/fosters a lot of crazy drug use to town. At one time, there were a ton of jobs in the factories and mills, now they're all closed and there is nothing to do but take drugs, live at home, go to the bar, and waste the unemployment/SSI/disability check.

I ran into a dude I hadn't seen in 11 years a few nights ago and he said "you know the first thing that struck me when i came back here? it was all the broken TVs on the side of the road. Broken TVs and syringes."

[close]

This screams south shore or right outside of Worcester, fuck almost as depressing as Pittsfield

508, homie.

Pittsfield sucks too. I lived in North Adams 10 years ago, and visit often. Fuck, it's a shitty area to live in. At least out there, though, you've got the mountains. down here all i've got is the taunton river.

[close]

MCLA? Also Northampton right here, and yeah these mountains rock

[steve]

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Expand Quote

I'm guessing you grew up in the midwest?

[close]

no, not even close. i grew up in a small city outside of Boston where every member of the city council and school committee is also a real estate agent who profits off of low income housing, which, for a myriad of reasons, brings/fosters a lot of crazy drug use to town. At one time, there were a ton of jobs in the factories and mills, now they're all closed and there is nothing to do but take drugs, live at home, go to the bar, and waste the unemployment/SSI/disability check.

I ran into a dude I hadn't seen in 11 years a few nights ago and he said "you know the first thing that struck me when i came back here? it was all the broken TVs on the side of the road. Broken TVs and syringes."

[close]

This screams south shore or right outside of Worcester, fuck almost as depressing as Pittsfield

508, homie.

Pittsfield sucks too. I lived in North Adams 10 years ago, and visit often. Fuck, it's a shitty area to live in. At least out there, though, you've got the mountains. down here all i've got is the taunton river.

[close]

[close]

MCLA? Also Northampton right here, and yeah these mountains rock

hahah yep. MCLA. I was there for a bit in 03. I remember a banking building in Pittsfield, at the bottom of a hill, i think, that had angled ironed ledges around a fair portion of the building. Shit was sick! I've got people who are still up there, so i get out when i can. That NoHo park is awesome. One of my favces.

[NickDagger]

Update for my 21st century pussy project: 3 girls replied so far, one isn't a looker (haven't replied yet and feel bad), another one is hot but a muslim (hard mode?) and the final one is hot, in her mid 20s, a dom and most likely going to murder me

Can you post their pictures?

Please fuck the muslim.

[Dole]

Expand Quote

Update for my 21st century pussy project: 3 girls replied so far, one isn't a looker (haven't replied yet and feel bad), another one is hot but a muslim (hard mode?) and the final one is hot, in her mid 20s, a dom and most likely going to murder me

[close]

Can you post their pictures?

Please fuck the muslim.

Go for the dom and describe us how she made you squeal like a pig. If you make that kind of an effort and finally man up for the task, make it count! 

[Hairy Ballsagna]

Update for my 21st century pussy project: 3 girls replied so far, one isn't a looker (haven't replied yet and feel bad), another one is hot but a muslim (hard mode?) and the final one is hot, in her mid 20s, a dom and most likely going to murder me

This is exactly what the teachers at my christian school said secular society was like.

[Will Easley]

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Update for my 21st century pussy project: 3 girls replied so far, one isn't a looker (haven't replied yet and feel bad), another one is hot but a muslim (hard mode?) and the final one is hot, in her mid 20s, a dom and most likely going to murder me

[close]

Can you post their pictures?

Please fuck the muslim.

[close]

Go for the dom and describe us how she made you squeal like a pig. If you make that kind of an effort and finally man up for the task, make it count! 

lmao this nigga said the muslim girl was on Hard Mode! If you look at the two in their extreme forms, I'd say go for the muslim because you'll learn alot from the challenge & if you rise to it, it may be much more rewarding in the end. The other girl may be on some crazy shit & you know never know how that can turn out, lol.

BUT it couldnt hurt to at least go on first dates with both of em. wade the waters a little bit before diving in, lol

[Dole]

This happened last friday. I'm not really even feeling the awkwardness but I guess it had some. So at friday  I went 200miles away for my grandfather's funeral and got hammered that night (the ceremony was at saturday). We were at bar and some fitness chick started hitting on me. Eventually she came to our table to sit with her boyfriend and some of her friend. We let her to stay because of kinda cute girl friend. The girl was totally fuckable but i was kinda bummed that she had boyfriend so i told her I wasn't interested and kept it cool. The night went on and after the bars closed we went to a park across the street for a joint and the chick mysteriously appeared. After about a blurry hour I was there alone with the chick and ended up banging her on the grass. I don't even know how many saw us and i really don't care. Not going to that town for a while. The awkward part is that she asked if i wanted to come to her place to sleep over. I asked about her boyfriend and she was like "let's get him to sleep on a sofa, he don't mind". I mean what the fuck is up with that? Would it be acool moment to let a chick suck your dick at a hangoverish morning while her boyfriend makes coffee at next room. (Couldn't go through with that because of the "How relatioships work"-thread.)

[KOOL MIKE]

girlfriend has friend over to stay with us for weekend. friday night, things almost get weird. after a saturday morning hangover fuck, she tells me she wants to have a threesome, but definitely not with her friend. That part makes sense, and I nervously except because even though I'm not very interested in the idea (sorry dudes), itd be dumb to turn down the experience. saturday night, low and behold, things get weird. I know we said no to the friend staying, but once all 3 of us were hammered, thinks kinda took off. In retrospect, I should have known to stop it but, I was too drunk to say no.

After about 10 minutes of whatever, my girlfriend storms out the room. I quickly jump off the friend, and chase after my girlfriend. Blow out arguement, I go out for a smoke, the other friend comes out and says I just lost my best friend wah wah wah. Bitch, I maybe just lost mine. I go back in. girlfriend is passed out. I thank god for that and lay down. other girl sleeps on the tile in the kitchen.

In the morning, my girlfriend is pissed. I don't say much, cause I'm not that stupid, but she basically starts packing her shit up to move out. I sit on the bed, fairly distraught, but eventually she sits down next to me to tell me what her game plan about moving out is. I listen. within minutes, we're fucking, which transitions to me eating her out, with her trying her hardest not to cum while nearly yelling at me, which then transitions back to what is probably the best sex of my life.

thats the story of my first (and definitely last) 3some, how i discovered a minor fetish, and how i fell even more in love with this bat shit crazy girl. celebrating an anniversary tomorrow.

what a fucking bitch, i fucking hate women and their cuntish attitudes.... what was it about, did you pay a little too much attention to her friend...tell her it was her dumbass idea

[KOOL MIKE]

alcohol is evil

[Rumpleforeskin]

I got head in a Mexican restaurant parking lot.  Nice white family walks by. Made eye-contact. Didn't tell her. Stared and she kept going.

[gaunting]

Not an experience of mine per say, but my friend and his wife (also a close friend) are in a poly amorous relationship with another couple. It is very weird, I'm open to people expressing themselves and whatever, but it's just too damn weird, not to mention, the other couple is downright creepy, they give me an uneasy feeling, I could never be involved in something like that.

[iSk84thechicas]

Fucking my ex girlfriend in my living room, we got up and noticed that she left a big red stain of period blood on the couch.  We flipped it over and continued.  Didn't think twice.

[chillout]

Fucking my ex girlfriend in my living room, we got up and noticed that she left a big red stain of period blood on the couch.?  We flipped it over and continued.?  Didn't think twice.

so you got both sides of the cushion bloody? i smell some holes in this story

[iSk84thechicas]

Let me make it clear... I was fucking her missionary. We stopped to start doggy style... She left the blood on HER SIDE.  We flipped over the part she was on, and we continued fucking.....

[Chinaskis underpants]

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Fucking my ex girlfriend in my living room, we got up and noticed that she left a big red stain of period blood on the couch.?  We flipped it over and continued.?  Didn't think twice.

[close]

so you got both sides of the cushion bloody? i smell some holes in this story

bloody smelly holes

[iSk84thechicas]

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Fucking my ex girlfriend in my living room, we got up and noticed that she left a big red stain of period blood on the couch.?  We flipped it over and continued.?  Didn't think twice.

[close]

so you got both sides of the cushion bloody? i smell some holes in this story

[close]

bloody smelly holes

lawl, I just corrected. Bad punctuation

[Donkey Lips]

girlfriend has friend over to stay with us for weekend. friday night, things almost get weird. after a saturday morning hangover fuck, she tells me she wants to have a threesome, but definitely not with her friend. That part makes sense, and I nervously except because even though I'm not very interested in the idea (sorry dudes), itd be dumb to turn down the experience. saturday night, low and behold, things get weird. I know we said no to the friend staying, but once all 3 of us were hammered, thinks kinda took off. In retrospect, I should have known to stop it but, I was too drunk to say no.

After about 10 minutes of whatever, my girlfriend storms out the room. I quickly jump off the friend, and chase after my girlfriend. Blow out arguement, I go out for a smoke, the other friend comes out and says I just lost my best friend wah wah wah. Bitch, I maybe just lost mine. I go back in. girlfriend is passed out. I thank god for that and lay down. other girl sleeps on the tile in the kitchen.

In the morning, my girlfriend is pissed. I don't say much, cause I'm not that stupid, but she basically starts packing her shit up to move out. I sit on the bed, fairly distraught, but eventually she sits down next to me to tell me what her game plan about moving out is. I listen. within minutes, we're fucking, which transitions to me eating her out, with her trying her hardest not to cum while nearly yelling at me, which then transitions back to what is probably the best sex of my life.

thats the story of my first (and definitely last) 3some, how i discovered a minor fetish, and how i fell even more in love with this bat shit crazy girl. celebrating an anniversary tomorrow.

My first threesome was an awkward situation like that but didn't have the blow-out ending. My girlfriend at the time had brought up the idea of bringing home a chick to play with in front of me. The hard exterior of me was saying "Sure...I guess that would be cool if it happened. We'll see when it does.", but the soft inside of me was screaming "HO-LEE SHIT! WE GON' HAVE A THREE WAAAYY".

A few months later, a friend of mine we'll refer to as Kim, was in town and needed a place to hang for a few hours while she waited for some people to meet her. She and my girlfriend played Mario Kart for a few hours while I kept serving them drinks. Around 3:00 AM, we all realize her friends ditched her and she's crashing with us. I go to bed with the girlfriend and Kim stays out in the living room. Girlfriend says "Ask her if she wants to join" and of course I go running into the living room to ask Kim friend if she's down. She doesn't say a word - just gets up, walks into the bedroom and starts making out with my girlfriend. All systems go.

Fast forwarding to the awkward part - I took turns going down on them and they both gave me head. I had been careful to pay more attention to my girlfriend up to this point, to make sure that she didn't spiral into some jealous episode. Girlfriend is on top of me straddling my face, Kim goes from giving me head to straight riding me. The girlfriend turned around to see that and just starts crying. I have no idea what to do, so...I just stay the course and keep the tongue work up while Kim goes to town on me.

Eventually things worked their way back into a less awkward spot and my girlfriend stopped crying. I focused a little more on the girlfriend and things finished in a good place, but the next morning, I could see some dark streaks down the wall next to my bed. Those were the mascara marks from her crying against the wall. I didn't know whether to clean those off the wall right away or keep them there as a trophy of my achievement. It was pretty weird but doesn't matter. Got two girls.