Awkward Sexual Experiences

[The Claw]

The first time I had sex I didn't know you were "supposed" to stop after you came. I had been going for a good twenty minutes and then i came with out pulling out or breaking my stride. I figured since i had a condom on and it felt super good i might as well keep going. I kept going for another twenty minutes or so and this girl was down for every position and didn't want to stop either. I came again while still inside her and after a little more humping decided to stop. I pulled my dick out to see the condom was broke and I had released two  excited virgin loads into this girl. I didn't tell her i came twice and I also didn't tell her the condom broke. I wasn't really worried because she was kinda a skank and I was sure she was on the pill and also she probably had a stock closet of plan b pills at her house. She came over again two days later and we did the same thing. I miss being young dumb and full cum.

[ThugWaffle]

If anyones interested I can keep writing, had a funny car head experience the other day and will be fucking the girl over the next few days.

Let's hear it.

[Gertrude Stein]

I was with a teacher at a bar in New York playing it as cool possible

Was drunk enough to propose a night cap on the roof

Soon enough this petite blonde teaching lil kids the next day

after like an hour of savage of sex

just bent me over and rimmed me for like a half hour.

I thnk she was fingering herself at the same time and

I did not know what to do. It was weird kissing her goodbye

at the subway with her lil elementary school outfit and

attache. COuldnt believe those lips would b instructing

lil city kids all day. I realized life was fuct. N that I should

enjoy it by any means necessary. I bin. Its chillin now.

[Made In China]

Dude above me should get some kind of writing award.

[few123456789]

Dude above me should get some kind of writing award.

[sexualhelon]

I'm in Ukraine right now - Kiev to be exact - and the other night I had sex with a genuine alcoholic. The women here are all fucking gorgeous and this one's no exception but aside from looks she really wasn't my type. She's a friend of a friend so I stayed with her for a few days and made the mistake of having sex on the first night.  It was alright at first and I was pretty drunk too but she chain smokes like no other - if I had to guess at least 3 packs a day but probably more since it's literally one after the other ALL day. The first day I got there I arrived at 8am and she was already drinking and offered me a beer at well so I took it thinking, "when in Rome" but after I took a nap for a few hours then woke up and she was still drinking. I think maybe I had another glass of wine but kept it tame so I could save myself for that night after that so we just hung out for a bit then went to a movie in this film festival where she fell asleep before it even started. After that we went out for drinks again then headed back to hers which resulted in some odd sexual conversations followed by drunken sex. Afterwards she was saying things like, "I don't want you to ever put clothes on again" and "I want to rape you again in the morning". She then dragged me to her bedroom but was pretty well pushing me out of the bed in her sleep so I went to sleep in the living room. The next morning I woke up at 7am to this girl smoking cigarettes and blowing smoke in my face with a glass of wine in her hand just watching me sleep. Shit was weird.

[Matze]

this sounds like good times. nothing awkward right there.

[redhatchet]

Was with an (ex)girlfriend, and I can't remember exactly the chain of events but we basically had a talk and decided we were going to break up. I was probably 19 at the time, her 18 or so. But us being horny youngsters decided we would have going away sex.

This was not the best idea for emotional teenager(s). We are getting it on as usual, I definitely have learned a few things since but it's getting close to the end. This particular girlfriend was on all this gnarly effective birth control so I would raw dog and cum inside her everytime. Damn do I miss that... Anyways, she's on top but bent over with her chest pressed on mine. I finish inside her and I notice something is off. She is making a noise, very quietly at first. And it all clicks. She's crying. Not blubbery mess tears but quietly crying. So here I am, completely naked, soaking in my own man fluids inside my now EX-girlfriends pudding as she lay crying on top of me and I am at a loss of what to do. So I basically give her the bro back pat until she stops. And we kissed and that was that. Not much compared to some of the shit in here haha. Filthy animals.

[JB]

Was with an (ex)girlfriend, and I can't remember exactly the chain of events but we basically had a talk and decided we were going to break up. I was probably 19 at the time, her 18 or so. But us being horny youngsters decided we would have going away sex.

This was not the best idea for emotional teenager(s). We are getting it on as usual, I definitely have learned a few things since but it's getting close to the end. This particular girlfriend was on all this gnarly effective birth control so I would raw dog and cum inside her everytime. Damn do I miss that... Anyways, she's on top but bent over with her chest pressed on mine. I finish inside her and I notice something is off. She is making a noise, very quietly at first. And it all clicks. She's crying. Not blubbery mess tears but quietly crying. So here I am, completely naked, soaking in my own man fluids inside my now EX-girlfriends pudding as she lay crying on top of me and I am at a loss of what to do. So I basically give her the bro back pat until she stops. And we kissed and that was that. Not much compared to some of the shit in here haha. Filthy animals.

the whole idea of going away sex has me giggling at my desk. its like you know its going to end with the girl crying, but what dude is going to turn that down?

"i dont like you enough to date you anymore, but lets fuck one more time. doesnt that sound good?"

i dont know why, but i find this hilarious.

[SodaJerk]

Expand Quote

She jerked sooooooooooooooooo hard that she ripped the skin that's sitting between your knob and the shaft. Yeah... that part....

[close]

I believe the phrase is snapping your banjo string

I've done this a few times and its not fun. If it keeps happening the doctor said you have a choice of circumcision or cutting a V out of the string and stitching until it heals with a scar that will be more tear resistant. Luckily mine scarred enough not to require further medical intervention.

[trannies and mannies]

unfortunately I have nothing to contribute, but I can gnar everyone with a good story.

[Mark Renton]

I'm in Ukraine right now - Kiev to be exact - and the other night I had sex with a genuine alcoholic. The women here are all fucking gorgeous and this one's no exception but aside from looks she really wasn't my type. She's a friend of a friend so I stayed with her for a few days and made the mistake of having sex on the first night.  It was alright at first and I was pretty drunk too but she chain smokes like no other - if I had to guess at least 3 packs a day but probably more since it's literally one after the other ALL day. The first day I got there I arrived at 8am and she was already drinking and offered me a beer at well so I took it thinking, "when in Rome" but after I took a nap for a few hours then woke up and she was still drinking. I think maybe I had another glass of wine but kept it tame so I could save myself for that night after that so we just hung out for a bit then went to a movie in this film festival where she fell asleep before it even started. After that we went out for drinks again then headed back to hers which resulted in some odd sexual conversations followed by drunken sex. Afterwards she was saying things like, "I don't want you to ever put clothes on again" and "I want to rape you again in the morning". She then dragged me to her bedroom but was pretty well pushing me out of the bed in her sleep so I went to sleep in the living room. The next morning I woke up at 7am to this girl smoking cigarettes and blowing smoke in my face with a glass of wine in her hand just watching me sleep. Shit was weird.

That's not weird. That's Ukraine.

[LambShank]

Just posting to try to bump this thread but I went into a sex shop for the first time today. It was creepier yet cleaner than I had originally expected. The dude working reminded me of Jeff Albertson (Comic Book Guy) from the Simpsons if he were really into the Denver Broncos and Lord of the Rings. There was also a wall full of very very expensive butt plugs, didn't see that coming.

Sorry if this wasn't the great piece of literature you were expecting, I'm just trying to keep one of slap's funniest/most interesting/horrifying threads from fading into obscurity.

[InternetDaddy]

I had met this lady off OKCupid like two or three months after my lady and I broke up. We got drinks the first night and had a really cool conversation about GoT and cartoons and shit. She wasn't super cute, and was 4 years older than me, but it wasn't bugging me. We made out in her car like teenagers and she said "I promised myself I wouldn't fuck you on the first date, but I'm off work tomorrow and you should come over." Being a person who possesses a penis, I agreed. Fast forward to the next day, I'm in her room, she's psyched on me and I'm psyched on sex. We go at it for a while, and I tell her (truthfully), "it's always super hard for me to finish with a condom, so this might not work out," to which she replies "well just take it off then!" At first I am psyched, but then I ask the fateful question: "are you sure?" "Oh yeah, it's totally fine, I have a couple plan B pills in my nightstand just in case."

"Oh jesus," I think, "she just keeps those on deck!? Is this a regular occurrence?"

But, again as an owner of a penis, I whipped it off and went back at it, and ended up blasting on her face. (Later on I convinced myself I had AIDS and got tested, clean thankfully). We boned like 5 more times over the next few weeks and then I stopped returning her texts.
Not the best story, but a little awkward and very scary after the fact.

[poorlatino]

Had sex with my ex girlfriends mom like a month ago in Aspen. It was awkward because they both made the same noises when cumming..

[Anti-Hetro]

Expand Quote

I'm in Ukraine right now - Kiev to be exact - and the other night I had sex with a genuine alcoholic. The women here are all fucking gorgeous and this one's no exception but aside from looks she really wasn't my type. She's a friend of a friend so I stayed with her for a few days and made the mistake of having sex on the first night.  It was alright at first and I was pretty drunk too but she chain smokes like no other - if I had to guess at least 3 packs a day but probably more since it's literally one after the other ALL day. The first day I got there I arrived at 8am and she was already drinking and offered me a beer at well so I took it thinking, "when in Rome" but after I took a nap for a few hours then woke up and she was still drinking. I think maybe I had another glass of wine but kept it tame so I could save myself for that night after that so we just hung out for a bit then went to a movie in this film festival where she fell asleep before it even started. After that we went out for drinks again then headed back to hers which resulted in some odd sexual conversations followed by drunken sex. Afterwards she was saying things like, "I don't want you to ever put clothes on again" and "I want to rape you again in the morning". She then dragged me to her bedroom but was pretty well pushing me out of the bed in her sleep so I went to sleep in the living room. The next morning I woke up at 7am to this girl smoking cigarettes and blowing smoke in my face with a glass of wine in her hand just watching me sleep. Shit was weird.

[close]

That's not weird. That's Ukraine.

[peacepappies]

I just moved to a new city a year ago and i hooked up with this girl who' s pretty good-looking, yet pretty annoying. (the reason i only fucked her when i was drunk/wasted). So this one night my best friend and me were fucking drunk and this girl is texting me theres some people hanging out at her house and i can come over if i want (this is like 4 in the morning). So on the way over there we meet this dude who sells weed and wants to sell us some. I'm an occasional smoker but my friend doesnt smoke really, but he's so wasted he's like yo give me 20 euros of weed, which is a shitload. So we arrive at the girls house and we continue drinking and hanging out with the people over there. My friend is like yo we should smoke the biggest pure joint ever and im agreeing since im already really wasted. So we roll and smoke the joint and my friend is so fucking high he starts bursting out in laughter like 10 minutes straight, which makes me also laugh like crazy. We roll another big joint (2nd and last one) and he gets even more high. A little bit later everybodys going to sleep, me with the girl and my friend just on the floor, still high as a kite. So i start fucking the girl on this 2person matress which is laying on the ground while my friend is 2 feet away on the floor giggling all the time, which makes me giggle also like a fucking 15 y/o schoolboy, fucking stupid. Keep in mind the girl is still okay with all this. My friend stops giggling so i just assume hes a sleep and i start banging this girl pretty hard. after a while we change positions and i just look over to check if my homie is still passed out and i swear to god he's laying on the edge of the matress like some hipster girl posing for a picture hanging over a balcony looking at me, it wasnt that awkward but suddenly he bursts out in laughing so fucking loud and i crack up to, still with my dick in the girl. This lasts for about 3 minutes, then he quits laughing while i go to sleep and i finish up.

ill post some more shit tomorrow

[Carrolls Chesthairs]

ill post some more shit tomorrow

looking forward to it

[JB]

Just posting to try to bump this thread but I went into a sex shop for the first time today. It was creepier yet cleaner than I had originally expected. The dude working reminded me of Jeff Albertson (Comic Book Guy) from the Simpsons if he were really into the Denver Broncos and Lord of the Rings. There was also a wall full of very very expensive butt plugs, didn't see that coming.

Sorry if this wasn't the great piece of literature you were expecting, I'm just trying to keep one of slap's funniest/most interesting/horrifying threads from fading into obscurity.

Stoked on this thread.

Sex stores always have the potential for being hilarious. My girlfriend and I go every once in a while and the last time we were there was both the weirdest and most enjoyable times I've been. We were looking at toys and the girl working there, this black chick with dreads wanders over to us. Every other time we would just whisper to each other, never spoke to the people working there except at checkout. Well this girl comes up asking a bunch of questions and starts opening up about herself. The best story's she told us is that she was once at a festival in downtown Detroit and he glass butt plug fell out, but she kicked it way before anyone noticed. The other is that her ex boyfriend called her because the girl he fucked ass was bleeding and he didn't know what do to. She asked him if they used lube and he said he didn't have any so he used crisco. I bought my girlfriend a vibrator and we left laughing.

[dickcakes]

chrissy spit on my head she touch it in miami

[oyolar]

Expand Quote

Expand Quote

She jerked sooooooooooooooooo hard that she ripped the skin that's sitting between your knob and the shaft. Yeah... that part....

[close]

I believe the phrase is snapping your banjo string

[close]

I've done this a few times and its not fun. If it keeps happening the doctor said you have a choice of circumcision or cutting a V out of the string and stitching until it heals with a scar that will be more tear resistant. Luckily mine scarred enough not to require further medical intervention.

This sounds like the worst thing ever.

[saucy ragu]

Had sex with my ex girlfriend mom like a month ago in Aspen. It was awkward because they both made the same noises when cumming..

Necessito mucho mas detail.

[poorlatino]

Expand Quote

Had sex with my ex girlfriend mom like a month ago in Aspen. It was awkward because they both made the same noises when cumming..

[close]

Necessito mucho mas detail.

Well I ran into her on the street and we decided to go out for drink, we talked about her daughter (my ex) over margaritas. We had like three each then left the bar. We decided to go back to her nice ass condo and continue our buzz, so we stopped and got a bottle of patron on the way.
When we go there she gave me like 8 xanax and some percs I popped two xannies and made a drink. She's a hot ass older woman straight up model status she has these nice big perfect breast that are real, I made a comment about them and she was like giggling and she was wearing a skimpy long dress,we started to get closer to each other to the point where were drinking and she's on my lap. I start to feel her up and brought those beauties out and started sucking on them. We made out and I asked for a blow job because she was so horny I knew she would . She went down on me for like 5 minutes then I put it in her and started going for it really rough.  I wanted to show this older hot milf OF MY EX GIRLFRIEND a good time. She was screaming and at times she couldn't even breathe and like I was saying in the post before she made these cute noises when she was about to cum just like me ex girlfriend did. She fell asleep like right after and I grabbed my coat and was about to dip out after I wrote her a nice note. Before I left I went into the bathroom and checked out all her pills, she had like bottles and bottles of really good shit. I ended up taking like 10 80mg oxy's 50 xanax bars, and a shit load of other goods. She would never notice she had like so god damn much. I caught the taxi home and a week later my ex messaged me saying"Hey I head you ran into my mom! miss you love you" and I replied "yeah we had a couple drinks and talked about you for hours she's a really FUN mom"..This story is true. I swear on my ball sack and my little sisters.

[Hercules Rockefeller]

you shouldnt swear on your sisters ballsack.

[poorlatino]

you shouldnt swear on your sisters ballsack.

If she had one I would.

Nice joke tho LOL

[Lance]

Expand Quote

Expand Quote

Had sex with my ex girlfriend mom like a month ago in Aspen. It was awkward because they both made the same noises when cumming..

[close]

Necessito mucho mas detail.

[close]

Well I ran into her on the street and we decided to go out for drink, we talked about her daughter (my ex) over margaritas. We had like three each then left the bar. We decided to go back to her nice ass condo and continue our buzz, so we stopped and got a bottle of patron on the way.
When we go there she gave me like 8 xanax and some percs I popped two xannies and made a drink. She's a hot ass older woman straight up model status she has these nice big perfect breast that are real, I made a comment about them and she was like giggling and she was wearing a skimpy long dress,we started to get closer to each other to the point where were drinking and she's on my lap. I start to feel her up and brought those beauties out and started sucking on them. We made out and I asked for a blow job because she was so horny I knew she would . She went down on me for like 5 minutes then I put it in her and started going for it really rough.  I wanted to show this older hot milf OF MY EX GIRLFRIEND a good time. She was screaming and at times she couldn't even breathe and like I was saying in the post before she made these cute noises when she was about to cum just like me ex girlfriend did. She fell asleep like right after and I grabbed my coat and was about to dip out after I wrote her a nice note. Before I left I went into the bathroom and checked out all her pills, she had like bottles and bottles of really good shit. I ended up taking like 10 80mg oxy's 50 xanax bars, and a shit load of other goods. She would never notice she had like so god damn much. I caught the taxi home and a week later my ex messaged me saying"Hey I head you ran into my mom! miss you love you" and I replied "yeah we had a couple drinks and talked about you for hours she's a really FUN mom"..This story is true. I swear on my ball sack and my little sisters.

Everyone give this man a +1 please, job well done

[Joust Ostrich]

I need to see pictures of both of them.  Then I will shower with gnars.

[poorlatino]

I need to see pictures of both of them.  Then I will shower with gnars.

K I will, I'm just scared someone might know them on slap and tell my ex that I fucked her beautiful mom.

[Joust Ostrich]

You can pm them to me if it'll make you feel better.  No, they won't leave Slap.

[saucy ragu]

You can pm them to me if it'll make you feel better.  No, they won't leave Slap.

^^

Story left me wanting more, thanks for living up to it.