Awkward Sexual Experiences

[Hercules Rockefeller]

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wait, you fucked her while sitting in a wheelchair?

[close]

yeah man


problem?

pretty much the opposite! congrats.

[Justis]

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wait, you fucked her while sitting in a wheelchair?

[close]

yeah man


problem?

[close]

pretty much the opposite! congrats.

internet high five

[Hypemhesh]

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yes her step mom was bangin, but i'm not a complete barbarian,i was just trying to make a good impression. regardless i still got punched in the face in the stairwell and shunned by she and her friends later at the party atop said stairs.  dolo at the party i went into the kitchen and grabbed some crepes they were making (yum) and a beer from the tap.  i have no problem just getting back to the basics when the nonsensical is just too too manifest.  and nothing like a female getting violent on you for having conversation with her visiting step mom at dinner, to put one in the mood to be lone wolfin it.  so that's what i was doing. in one room they were playing a wii, and in the main room (where psycho and co had posted up) they were dancing a little and drawing on some canvas on the wall (nothing heavy was drawn that day).  i went back into the kitchen to cop another crepe, this one was more dessert-like...

[close]

This sounds interesting, but I', strapped for a clue as to what the fuck is actually going on in here.

Seems like it's only a 1/3 of the story... I'm really curious to see what other types of crepes will be eaten in this endeavor

[jimi420]

him breaking his leg:

I literally yelled "Fuck!" when I saw your leg bend. fuck that.

I've been talking to this girl I dated when I was 16 (no she's not a juggalette,) and she's been talking about how she needs a secret fuck buddy. Not one to pass up an opportunity to feel ashamed of myself, I told her I could come over after babysitting my nephews. I drive over to her house and we watch BET for a little bit then I go to her room and lay down on the bed. We start talking about people that we've fucked and she mentions that she's fucked like 2 guys in the past few days. she gets pretty detailed and I start to regret coming over but I'm already there so I might as well go through with it. We start making out and she takes off her pants and says "Is this weird that we're just now fucking and we've known each other for so long?" I tell her it's not and she says that I have to wear a condom (which is cool with me because she's a skank.) The only problem is is that I've never worn a condom in my life. So I tell her to put it on because I'm not really sure how to. She puts it on the head and tells me to do the rest. I do and we start fucking. While we're fucking she says "Oh you're so much better than Dillan," which is a friend of mine she fucked right after we broke up. I ignore it and keep going and she starts to sing "This Place is a Prison," by The Postal Service (It was our song whenever we were dating.) At this point it's kind of hard to focus because she's being so weird. After like 20 minutes her Mom comes home and we have to hurriedly stop. After we put our clothes back on her Mom asks "Oh I'm so glad it's Noah! I thought it would be one of  your ugly boyfriends. I hope you wore a condom." I tried to play cool and said I had to go home and just walked out. She texted me and said "We should do that again " I never replied. Second worst sex I've ever had. 

[Joe Pesci]

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him breaking his leg:

[close]

I literally yelled "Fuck!" when I saw your leg bend. fuck that.

I've been talking to this girl I dated when I was 16 (no she's not a juggalette,) and she's been talking about how she needs a secret fuck buddy. Not one to pass up an opportunity to feel ashamed of myself, I told her I could come over after babysitting my nephews. I drive over to her house and we watch BET for a little bit then I go to her room and lay down on the bed. We start talking about people that we've fucked and she mentions that she's fucked like 2 guys in the past few days. she gets pretty detailed and I start to regret coming over but I'm already there so I might as well go through with it. We start making out and she takes off her pants and says "Is this weird that we're just now fucking and we've known each other for so long?" I tell her it's not and she says that I have to wear a condom (which is cool with me because she's a skank.) The only problem is is that I've never worn a condom in my life. So I tell her to put it on because I'm not really sure how to. She puts it on the head and tells me to do the rest. I do and we start fucking. While we're fucking she says "Oh you're so much better than Dillan," which is a friend of mine she fucked right after we broke up. I ignore it and keep going and she starts to sing "This Place is a Prison," by The Postal Service (It was our song whenever we were dating.) At this point it's kind of hard to focus because she's being so weird. After like 20 minutes her Mom comes home and we have to hurriedly stop. After we put our clothes back on her Mom asks "Oh I'm so glad it's Noah! I thought it would be one of?  your ugly boyfriends. I hope you wore a condom." I tried to play cool and said I had to go home and just walked out. She texted me and said "We should do that again " I never replied. Second worst sex I've ever had.? 

stopped reading right here

[steve]

not really awkward, well for me anyways...

in 07 i was kicking around NC, just skating and partying under the pretense of trying to figure my life out and look at UNCG. Never happened....

I had been sleeping in my car for a while but through skating, music, bars, and good fortune i was graced with the kindness of the South and offered many places to stay after only a few weeks of kicking it around in one particular city.

The cat who offered me a place to stay was also a Mass transplant and had said that if i washed dishes and mopped the kitchen I could eat, drink, and sleep at his place- no way was i turning this down. His roommate was a shitbag from Jersey City. However, his roommates girlfriend was a great looking "goth" chick. Now, this style of female isn't generally my thing, but a hot slut is a hot slut- Snookie or Morticia Addams....

So as a week or so passes the roommate, Ray, starts to grate my nerves more and more. This leads to me ignoring his presence in his own home and hanging out with his goth girlfriend more and more.

Eventually, well very much with the quickness, we start fucking, Amy and I, that is. Ray would go to his shitty dishwashing job and she would pick me up, buy me lunch, smokes, brews, and drive me to her parents house. We would smoke some buds, maybe she would give me a foot massage with lotion, and a blow job before feeding me dinner and fucking me. She would then drive me to the bar where her dude washed dishes and buy me drinks. things were kosher, Ray seemed to like that i kept her out of trouble.

Well, one day we drive out to Asheville to spend some of her money. It was a cold and shitty day. I was broke and aggrevated. Whilst driving home, down some winding mountain roads, Amy starting sucking my cock. It was great, as road head from a girl with 2 tongue piercings is bound to be. Well, i bust my nut shortly before we pull off the highway. She suggests that we go to the bar where Ray was washing dishes, Las Palmas.

We walk into the bar and Ray is sitting there eating dinner. We approach him and extend greetings. First he thanks me for taking her shopping for the day and tells me to order dinner, on him. I naturally ordered a steak, taters, and PBR. He buys me a tequilla shot.

Amy then leans into him and slaps him with a full on 30 second make out, about 15 minutes after gargling with my jizz.

Kinda felt a little awkward.

Amy has a sister too....

[saucy ragu]

not really awkward, well for me anyways...

in 07 i was kicking around NC, just skating and partying under the pretense of trying to figure my life out and look at UNCG. Never happened....

I had been sleeping in my car for a while but through skating, music, bars, and good fortune i was graced with the kindness of the South and offered many places to stay after only a few weeks of kicking it around in one particular city.

The cat who offered me a place to stay was also a Mass transplant and had said that if i washed dishes and mopped the kitchen I could eat, drink, and sleep at his place- no way was i turning this down. His roommate was a shitbag from Jersey City. However, his roommates girlfriend was a great looking "goth" chick. Now, this style of female isn't generally my thing, but a hot slut is a hot slut- Snookie or Morticia Addams....

So as a week or so passes the roommate, Ray, starts to grate my nerves more and more. This leads to me ignoring his presence in his own home and hanging out with his goth girlfriend more and more.

Eventually, well very much with the quickness, we start fucking, Amy and I, that is. Ray would go to his shitty dishwashing job and she would pick me up, buy me lunch, smokes, brews, and drive me to her parents house. We would smoke some buds, maybe she would give me a foot massage with lotion, and a blow job before feeding me dinner and fucking me. She would then drive me to the bar where her dude washed dishes and buy me drinks. things were kosher, Ray seemed to like that i kept her out of trouble.

Well, one day we drive out to Asheville to spend some of her money. It was a cold and shitty day. I was broke and aggrevated. Whilst driving home, down some winding mountain roads, Amy starting sucking my cock. It was great, as road head from a girl with 2 tongue piercings is bound to be. Well, i bust my nut shortly before we pull off the highway. She suggests that we go to the bar where Ray was washing dishes, Las Palmas.

We walk into the bar and Ray is sitting there eating dinner. We approach him and extend greetings. First he thanks me for taking her shopping for the day and tells me to order dinner, on him. I naturally ordered a steak, taters, and PBR. He buys me a tequilla shot.

Amy then leans into him and slaps him with a full on 30 second make out, about 15 minutes after gargling with my jizz.

Kinda felt a little awkward.

Amy has a sister too....

DON'T LEAVE US HANGING. And Jimi,

Not one to pass up an opportunity to feel ashamed of myself

<3

[Donkey Lips]

This page is definitely keeping the thread live. Steve & Jimi...well done.

[augustmoon]

rocking an ileostomy for another couple weeks.  staying with my homegirl in NY for the next week, sharing the same bed.  i'm sure "awkward" is going to be an understatement....

[BraveUlysses]

Good for you Justis. Is it illegal or just unethical if some older dude watches some young kids fuck? I don't wanna do it but I'm just curious.

[saucy ragu]

Good for you Justis. Is it illegal or just unethical if some older dude watches some young kids fuck? I don't wanna do it but I'm just curious.

Go ahead and watch.










Then tell us how it went from your cellblock computer.

[sexualhelon]

Alright, so I had a pretty good one happen not too long ago and figured I'd grace the slap awful sexual experiencesthread with it:

     This night started off as most nights do - having a few beers at a friends place then heading to a pub. We were going to this couchsurfing meet up if you've ever heard of that website. So everyone grabs a drink at the bar then settles in at the table with all the couchsurfing people. I soon realize it's just a bunch of boring, awkward individuals so I gaze around the pub looking for ladies to talk to. Spot some, head over. They're both Polish - as most girls here are seeing as how I'm living in Poland. I ask them if I'm interrupting a girls night out or if they mind me joining them for a drink. They tell me I kind of am but since I'm cute to stay - so I do. One of them is really shy and the other one is just eye fucking me the whole time asking inquisitive things such as: Why talk to us of all the other girls here, tell me the most interesting thing about yourself, are you a boob or ass man, etc... My friend then walks up and tries to join but they completely blow him off. There's a bit of silence at this point and she has this strange look on her face so I decide to reciprocate the drilling of questions and ask her what's on her mind. She says It's really bad and she shouldn't say it but if I want her to she will. And I do so she does. She tells me how she was thinking she really wants to watch me fuck her friend if I don't mind. Funny how she asks me this before her friend. Her friend isn't too keen for this on the day she just met a guy so it doesn't happen we just go to some all night club.

     This is where it get's interesting. So maybe the threesome could have happened this night but it didn't, although it did later, for one particular reason. This insanely drunk Canadian guy decides to join us and he's an alright guy so I talk to him for a second. Bad Move. After this I discover he's the most awkward individual I've ever met and won't leave. This results in the girls eventually being over it and deciding it's time to go home. At that point I was pretty over it myself but decide to walk around this cheesy club for a bit and end up bumping into these gay French guys I know who have a french girl friend with them. It was obvious this girl just wanted to fuck and since I was in with her social circle she sides on me. She wasn't really my type - a short little petite girl with frizzy red hair, green eyes, and peculiar glasses. We dance for a bit and then we go for a cigarette. I carry a little notepad around and she flips through it then wants me to draw something on her arm. Seeing as how I'm drunk it's not the greatest thing I've ever drawn, quite bad actually. I think it was an Alien. After that we start making out. Shortly after I start egging her on about just coming back to my place. She's trying to play it off but knows she wants to. Eventually she agrees and we leave to walk back to my place

     The walk was fairly awkward. Neither of us really had anything to say and I definitely started to sober up a little too much. Then we're at my place. All the awkwardness starts now. We start to make out and when I'm taking her clothes off she doesn't even help unbutton a button or unzip a zipper. She told me she had a thing for guys undressing her. There's a little foreplay but not much because I'm not really into her. In fact, I'm pretty sober at this point and it's hard for me to even have sex with this girl. First she blows me and the strange thing is that as she's sucking my dick she lights up a cigarette. Doesn't even ask me if it's okay to smoke in my flat - which it's not but I don't care at this point. She's French so, eh...and for a French girl she was really bad in the sack. For how tiny she was, there was a lot of room in that vagina. I fake cumming to get it over with and then she gets up and puts her clothes on again. Starts saying how she doesn't think it was any good for me and the proof is that I let her put her clothes back on. Truth was, it was horrible for me and I let her put her clothes on because her leaving seemed fabulous. I try to be considerate though and figure she's going to leave anyway so I say something like, "well I didn't figure I had to stop you from putting on your clothes, that it's understood since we just had sex you could stay if you wanted." Another bad choice. So with this undressing fetish of hers she tells me to undress her again and then wants to have sex again. So we do, but it's worse this time and while she's completely controlling everything I'm laying there noticing the odd shapes of freckles on her body. She can tell I don't want it so gets up and does the same thing again. This time I'm not undressing her and I just tell her how I'm not that into her. I was drunk at the bar and now I'm not. She starts crying and then she storms out. I'm relieved and get up to take a piss, grab some lotion, pour a glass of wine, play some porn on the tv, and start jerking off because at this point I really need to get off. Then there's a knock on my door. It's this girl and she says she forgot her scarf. I didn't really think about it and just open the door naked with a  raging boner, porn still playing, lotion and a glass of wine on my table - I live in a studio so everything's just there to see. She sees this and just starts balling. Storms in to grab her scarf and the leaves, slamming the door behind her calling me an asshole.

[Justis]

that was amazing^

[skate_bored]

that was so fucking good.

[GISM]

Got drunk with this girl I've been seeing. Start boning and it's cool and she asks me to choke her. This is new to me but I went with it just pressing my hand on her throat. Wasn't doing much for me and it was hard to balance so after a minute I put my hand back on the bed. Then she starts thrashing around and pushing me away so I stop but she tells me to keep going. Now I feel like I'm wrangling a crocodile and realize I'm play-raping this girl. It was messing with my focus but I was too drunk to be fully weirded out. She must have tired herself out because after a while it went back to non-rapey sex. She was really stoked on it the next day. I woke up feeling really fucking weird because now I know what it looks like to rape someone... Not into it.

[redhatchet]

Shoulda just choked the bitch. ^^^

[smokecrack]

+1 for sexualhelon.

damn that was a story.

GISM, you need to man up and learn how to properly choke a bitch.

[Matze]

Got drunk with this girl I've been seeing. Start boning and it's cool and she asks me to choke her. This is new to me but I went with it just pressing my hand on her throat. Wasn't doing much for me and it was hard to balance so after a minute I put my hand back on the bed. Then she starts thrashing around and pushing me away so I stop but she tells me to keep going. Now I feel like I'm wrangling a crocodile and realize I'm play-raping this girl. It was messing with my focus but I was too drunk to be fully weirded out. She must have tired herself out because after a while it went back to non-rapey sex. She was really stoked on it the next day. I woke up feeling really fucking weird because now I know what it looks like to rape someone... Not into it.

it's always awesome if girls are into that stuff.

[sexualhelon]

Got drunk with this girl I've been seeing. Start boning and it's cool and she asks me to choke her. This is new to me but I went with it just pressing my hand on her throat. Wasn't doing much for me and it was hard to balance so after a minute I put my hand back on the bed. Then she starts thrashing around and pushing me away so I stop but she tells me to keep going. Now I feel like I'm wrangling a crocodile and realize I'm play-raping this girl. It was messing with my focus but I was too drunk to be fully weirded out. She must have tired herself out because after a while it went back to non-rapey sex. She was really stoked on it the next day. I woke up feeling really fucking weird because now I know what it looks like to rape someone... Not into it.

Remedy to this situation: You stick it in her butt and as soon as you finish run away. Just jolt out the door. If she get's pissed just tell her you were trying to make her fantasy more realistic. Win/win situation.

[Tale Crab]

Don't forget to grab her money on the way out.

[GISM]

..

[Clayton]

I worked for a woman who owns her own jewelry company until she moved. She was in her mid fourties, had a couple kids, an ex husband, dating some turkish dude, kind of crazy, and a full blown milf. This woman kept no secrets and would tell me everything that went on in her personal life. It was pretty normal for it to be just me and her while we worked alone in her house, but one day she started telling me she was breaking up with her Turkish boyfriend who was in Turkey at the time. I didn't really think anything of it. The same day she started playing music on her computer which she probably only had a couple times prior. Mostly shitty soft rock that old people seem to like. One of the songs she played was "Sexual Healing" by Marvin Gaye. I thought nothing of it until the next day she did the exact same thing with the same song. Pretty sure that was her way of telling me she wanted to fuck, but my secondhand embarrassment from the fact that her "game" was to play suggestive songs next to me while she went about her daily routine, her ex-husband went crazy on her and pulled a gun, her boyfriend used to tell me crazy Turkish military stories of him and his friend "Psycho," and the fact that my job would be at serious jeopardy if I whipped it out after reading her wrong prevented me from doing anything other than sit at my computer thinking to myself, "this bitch want me to do something?!"

She's two states away but boning this woman 20 years my senior is currently on my bucket list of things to do before I die.

Sorry this stories actually pretty weak now that I wrote it out. Fuck it. Post.

[Omamori]

Should have went for her.

[smokecrack]

..

i read your original post before you removed it.

i ain't dumb.

i caught chu!

[Kristi Yamaguchi]

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wait, you fucked her while sitting in a wheelchair?

[close]

yeah man


problem?

AHHAHAHHAHA SWAG

[steve]

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Got drunk with this girl I've been seeing. Start boning and it's cool and she asks me to choke her. This is new to me but I went with it just pressing my hand on her throat. Wasn't doing much for me and it was hard to balance so after a minute I put my hand back on the bed. Then she starts thrashing around and pushing me away so I stop but she tells me to keep going. Now I feel like I'm wrangling a crocodile and realize I'm play-raping this girl. It was messing with my focus but I was too drunk to be fully weirded out. She must have tired herself out because after a while it went back to non-rapey sex. She was really stoked on it the next day. I woke up feeling really fucking weird because now I know what it looks like to rape someone... Not into it.

[close]

some choking is usually a good fucking time, man!

the last time i choked a girl she told me to stop saying "i'm not into that" and proceeded to let me face fuck her shortly there after....

one night an ex and i gobbled some percs and had drinks. we were fucked up beyond belief. we had actually gone to dinner with my parents earlier in the evening. anyways, seeing as we were ravaged we ended up having really good sex. i was going on and on calling her a "dirty little whore" and "fucking slut" when she asked me hit her. mind you, i was hitting the poon from behind with a hand pulling back her head. So, i gave a weak slap to the cheek. she started fucking me harder, i mean considerably harder. she yells for me to smack her again; which i did. anyways, to make a long story short, we passed out after a few hours of violent fucking.

the next morning her mom asked if she was wasted and fell down the stairs. she had a brutal shiner... giving a girlfriend a voluntary black eye is awkward.

[Mad Max]

+1 for sexualhelon.

damn that was a story.

GISM, you need to man up and learn how to properly choke a bitch.

There's a funny sketch by a female comedian about guy's choking her during sex, but I can't remember her name. Damn...

[sexualhelon]

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+1 for sexualhelon.

damn that was a story.

GISM, you need to man up and learn how to properly choke a bitch.

[close]

There's a funny sketch by a female comedian about guy's choking her during sex, but I can't remember her name. Damn...

tis whitney cummings
http://comedians.jokes.com/whitney-cummings/videos/whitney-cummings---copying-porn-moves/

[Reev]

Pretty apt name for someone copying porn moves.

[Greg Ostertag]

Pretty apt name for someone who's mouth I wouldn't mind fucking.