Embarrassing sex-related stories

[richd213]

I once had premature ejaculation when having sex with a bird of prey.

Hawkward

 

[auron200004]

So... this is one of those stories that NOBODY should be proud of.

It was a few years ago when Runescape was still a thing. Me and my girlfriend were really into it. One night, while we were doing something around Lumbridge, she started private messaging dirty things to me. I responded, and it got kind of heated. Like, as in my pants were down heated.

Anyway, in that game if you forgot to click on your friends name in the friends' list, it would type in public chat. Let's just say that right as I was close to finishing...I forgot to click on her name...and there were other players around.

Anyway, I sort of became more concerned that I would be banned from the game for vulgarity. I didn't, but it's funny how I was willing to stop and freak out about it while my girlfriend was still messaging me.

And that, dear friends, is that. Now I can finally forget about it. Forever. *shudder*

 

[marcooos]

I have a couple, both with the same girl.

First story:

Spoiler

First, my first time. Not hers, but mine. So I was giving her a ride home from my house, which is about a half hour drive. We'd been dating for about three months at this point, and I was ready to get beyond just groping. As we were passing the local CVS, she said "You know, we should probably keep some condoms on hand, just in case..." Me, being the calm, cool, collected guy I am, cut across a lane of traffic, cutting some very upset person off, just so I wouldn't miss the parking lot. I dashed in, like a kid at Christmas, and ran back to the condom aisle, took a moment to get over the initial shock of how many there were, and just grabbed a box. I paid for it, dashed back out, and quickly got back on the road. We got back to her room, spending the remaining 20 minutes in mostly silence. We got back, got into her room, and I was ready to just get down to it. She, on the other hand, stuck the box in her dresser, and said "We'll just leave these in here for when we need them." I moped to the bed, and sat down as she turned on the TV. Flipping through the channels, she kept trying to strike up a conversation, but all I could think of was "I just bought condoms. I'm supposed to be making the sex right now." More importantly, my dick was at attention, wondering when the fun was going to start. Finally, the gf settled on Scarface, since I'd told her it was pretty good, and she'd never seen it. So she laid down in bed and managed to get me in a horizontal position. I was watching the movie, and my mood started improving. Eventually, my train of thought went something like "Y'know, this is a pretty good movie. Al Pacino's a badass, can't beat the tacky shirts, they're running around with a chainsaw, I have a hand on my dick, Al Pacino's accent is pretty coo...wait...hand on my..." at which point, I glanced back to see her smiling at me. We commenced with the kissings, the gropings, the strokings, and finally, she told me to go get a condom. I jumped up, sprinted across the room, grabbed one out of her dresser, and dashed back, ripping open the wrapper, and putting it on. She positioned herself accordingly, as did I, and it happened.

Now, up to this point, she had sworn that she had been with two guys, and I had believed her. What it felt like, though, was that she made a habit out of being fisted by the Hulk. I continued though, getting no traction whatsoever, but I was playing the good sport, and she seemed to be enjoying herself.

Cut to an hour later. She's still having the time of her life, and can't believe I'm nowhere close to finishing. I didn't have the heart to tell her that it felt like I was thrusting into an oversized hole in the wall. Finally, I let out a grunt, tell her I just finished, then removed the condom and threw it away before she could investigate. I felt REALLY bad afterwards, since she was singing my praises, but I was getting seriously winded, and she wasn't all that interested in getting on top. And thus, Dan lost his virginity.

Funnier second story:

Spoiler

So, before we get to the funny, some not-so-funny backstory. The gf had been raped by her step father when she was younger, and was taking part in regular therapy sessions to get over it. I was sympathetic, and was always ready to throw on the breaks and come to a full stop at the first hint of tears, no matter what we were doing.

So one day, she said she was going to be having a therapy session, and it was going to be pretty intense, so she'd appreciate it if I could be around, and possibly even stay the night. I was cool with it, and I hung around while she was off at her session. When she finally got out, after a couple hours, she seemed pretty well put together. In fact, she walked in and immediately started kissing me. I resisted at first, thinking maybe she was just trying to compensate for the negative feelings of the session with some positive ones, but she was pretty insistant, so I cautiously proceeded, telling myself that I would follow her lead. I wouldn't push her at all for anything. Good move on my part, since she went from full on tongue wrestling, and she was winning, to end of the world kind of crying. I dutifly switched to the caring boyfriend and comforted her. She wanted to talk to her mother, so I ventured into the forbidden land of "the purse" got her cell phone, got her mom's number dialed, and handed it to her. After a bit of talking, she hung up, threw herself on me, and sobbed into my shoulder. I just listened to her pour her soul out. After a couple hours, she laid down and started drifting off. I asked if I could borrow a pillow so I could sleep on the floor, because I figured, after such a traumatic evening, the last thing she needed was a big guy like me draped over her while she slept. So I curled up on the floor, and after a while, slipped off to sleep.

Now, for the record, that WAS NOT meant to be funny. That was there so the next part would make sense.

I woke up the next morning, and didn't even open my eyes. I just laid there, and enjoyed how nice and soft the bed was. Then something clicked. I wasn't supposed to be in the bed. I was supposed to be on the floor. I sat bolt upright, looked around, and saw my gf at her computer.

"Oh," she said, without looking at me. "You're awake."
"Uh huh..." was all I could manage.
"Do you remember what you did last night?" Her voice was flat. I couldn't read anything in it. Was she angry? Sad? Upset?
"Um...nuh uh..." At this point, I realized, much to my dread, that I was not wearing my pants. I was ready to throw myself in front of an oncoming 18 wheeler.
She turned around, finally. "I woke you up at about 2 in the morning and told you to come to bed." Alright, well, I was seeming like less of an asshole. At least I had a reason to be in the bed.
"..Kay..."
"You got up and crawled into bed. By the time I got your pants off, you were already asleep."
"...Kay..." It was getting a bit clearer, though I still could remember a damn thing.
"I straddled you, and you didn't wake up. I shook you and told you that you were forgetting something."
"...Kay..." She was silent. "...Did I do something bad?"
She stood up and thrust a finger in my face. "You asshole! You pushed my horny ass off of you, got up, and picked up the goddamn pillow you borrowed, appologized, and went back to sleep!"

And that, fair audience, is how I cockblocked myself.

That second story is funny as fuck.

OT: I don't have any (forever alone) but I have a fuckton of stupid ones from my best friend, one of my favourites is this...
He was lying in bed with his girlfriend, she starts getting frisky asks him if he wants head, to which he replys "No I'm tired it's to much effort".

Or the time he had sex in a bush, at a key roundabout, by a major ferry port, whilst me an a couple of mates were watching house of flying daggers on a psp

 

[ICantBelieveItGoesBoom]

I consider myself a virgin but there was one awful night...

Basically, a couple of days before a pretty big party, one of my (female) friends introduced me to this friend of hers who I later found out has had sex with numbers of people in the dozens (she's only 16). I later found out we were introduced because she found me attractive so she talked to me on Facebook for a few days then the party came...

I'll be the first to admit that I'm a bit of a lightweight when it comes to drinking so I was pretty happy and I tend to get kinda cuddly with people when I'm drunk. So, she leads me off at some point pretty early in the party to somewhere secluded and just sort of expected me to start getting off with her but I didn't (she's not exactly good looking, even forgetting her personality) so I just walk off but later when I'm just too drunk to help myself she drags me to the same spot and starts making out with me and puts my hand down her skirt.

I don't really remember the rest but I've been told by many people that she had sex with me and was really creepy with me the whole night and it was obvious that I didn't really like being there but anytime someone talked to me she flipped out at them.


So yeah, pretty creepy.

 

[Owen Majkowski]

Let's see, there was my first time, just this past year (18), in which nothing remotely odd or funny happened. And then there was the next time (with the same girl), about a month later. It turns out, she had a bit of a fetish for a certain golden fluid, and asked if I would indulge her just once. I agreed, and so she made me drink at least a gallon of water while I was at work, and I forced myself not to go to relieve myself at all for 8 hours. That's not the worst part.

As I was driving to pick her up and take her to my house for the act, she says that she was hanging out with a mutual friend (we had both dated this girl at one point) and asked if I would be ok with her joining us, and of course, I said as long as she wanted to, it was fine by me. Fun times ensued, until the point where I had to fulfill my obligation. The third member of our menage a trois just watched the event, and afterwards burst out laughing and saying that that was so gross.

Still, after we cleaned ourselves up we ended up continuing the fun, so no harm done. And we're all still really good friends. so alls well that ends well I suppose.

 

[itsausernamewhatofit]

just heard a friend complain that when she had sex with a guy last night, that was so drunk he drew a line with his sperm on his forehead and whispered "simba!".

thought i'd share. xD

I think you win best story in the thread, that gave me a good laugh trying to imagine it.
As for myself, I've got no real stories to share, maybe I should join the club I've been hearing
about in this thread.

Although come to think about it I do have one story, but not about myself. So when I was in ninth grade there was this girl who everyone kind of known as the class slut. She was dating this really obnoxious guy who never really showed up to classes and was always being suspended for something or other. Anyway she, not being incredibly bright, was head over heels for him and talked about him all the time. Constantly mentioned having sex with him etc. So apparently one day she mentioned rim jobs in one of her stories regarding him and this spread around like wildfire. After that whenever anyone ran into the guy from then on they would just look at him and go RIMrimrimrimrimrim (if you imagine someone revving a motorcycle, it sounded sort of like that). This went on for close to a year with the teachers completely oblivious to its meaning until the principle caught wind of it and enacted a school wide ban on saying it near him. What struck me as funniest thing about it was just the scale of it. Pretty much everyone, his friends, people who hardly knew him, upperclassmen, people he had never spoke to would say it when they saw him. He and his girlfriend would be making out in a hallway and people would run up and, as a joke, yell "PDA is not okay!"
She has since broken up with him many times although it looks like she's learned her lesson.

 

[PureChaos]

while in bed with a girl, i roll over and accidentally head-butted her

 

[Generalissimo]

i was 15. she was 31.
i don't think that would have worked. plus, i'm not one for adultery.

Um... that's... kinda screwed up.

What's the age of consent in Bulgaria?

15, surprisingly. i was kinda shaken for a day or two after.

 

[The Clown]

Tell please! I've read this entire thread and I have it bookmarked. Believe me, I'm reading at least.

Ok then.

Last year me and my girlfriend decided we wanted to try something new and she came up with the idea of doing a threesome, she told me she had a friend she had done lesbianish things with in the past and as a guy I was up for it. Being busy people the only time we could actually find to do it would be at the second girls house at a gathering a friend of ours was having. During the party I was very nervous and was a bit hasty, we couldn't wait so me and my girlfriend retired to an upstairs bedroom sending a text to the second girl asking her to join us. We got pretty into it and due to drunkenness on my part she finished quite quickly and I didn't, knowing the night would hold more for me I wasn't phased really, not long after we had finished a drunk guy bursts in and shambles up to me asking for a condom which I supply him with mostly to get him out. Turns out the second girl didn't get our text and had decided to have sex with this guy (a bit of a skinny guy who apparently just had his second time with her). Eventually we get the thing together and I'm in bed with these two, but still drunk and unaware of our plans the other guy follows her in. We had some fun, myself especially, the feeling of laying inbetween two girls with a hand on each... well, it's something else. But half way through all this the before snoozing guy to my right starts fondling the second girl which she wasn't a fan of so my girlfriend decided to swap places , she does and the guy continues and after some fun the guy becomes very annoying, both of the girls are telling him to leave and he won't so out of frustration I end up wrestling him naked out into the fully lit hallway where I am greeted by who I can only assume was the hosts mother and I just came out of her bedroom, running happened.

 

[srm79]

I fell asleep "on the job" once.

I was about 20, living with my first girlfriend, had no kids and a job that offered me a comfortable lifestyle. We had been partying pretty hard for a week and a cocktail of alcohol, energy drinks, and some other stuff best not talked about just took over and knocked me clean out, literally "mid-stroke".

I woke up the next afternoon at about 1pm with absolutely no idea why I had bruises all over my ribs. It all came flooding back about 2 hours later in the pub...

 

[Jaeke]

Funnier second story:

Spoiler

So, before we get to the funny, some not-so-funny backstory. The gf had been raped by her step father when she was younger, and was taking part in regular therapy sessions to get over it. I was sympathetic, and was always ready to throw on the breaks and come to a full stop at the first hint of tears, no matter what we were doing.

So one day, she said she was going to be having a therapy session, and it was going to be pretty intense, so she'd appreciate it if I could be around, and possibly even stay the night. I was cool with it, and I hung around while she was off at her session. When she finally got out, after a couple hours, she seemed pretty well put together. In fact, she walked in and immediately started kissing me. I resisted at first, thinking maybe she was just trying to compensate for the negative feelings of the session with some positive ones, but she was pretty insistant, so I cautiously proceeded, telling myself that I would follow her lead. I wouldn't push her at all for anything. Good move on my part, since she went from full on tongue wrestling, and she was winning, to end of the world kind of crying. I dutifly switched to the caring boyfriend and comforted her. She wanted to talk to her mother, so I ventured into the forbidden land of "the purse" got her cell phone, got her mom's number dialed, and handed it to her. After a bit of talking, she hung up, threw herself on me, and sobbed into my shoulder. I just listened to her pour her soul out. After a couple hours, she laid down and started drifting off. I asked if I could borrow a pillow so I could sleep on the floor, because I figured, after such a traumatic evening, the last thing she needed was a big guy like me draped over her while she slept. So I curled up on the floor, and after a while, slipped off to sleep.

Now, for the record, that WAS NOT meant to be funny. That was there so the next part would make sense.

I woke up the next morning, and didn't even open my eyes. I just laid there, and enjoyed how nice and soft the bed was. Then something clicked. I wasn't supposed to be in the bed. I was supposed to be on the floor. I sat bolt upright, looked around, and saw my gf at her computer.

"Oh," she said, without looking at me. "You're awake."
"Uh huh..." was all I could manage.
"Do you remember what you did last night?" Her voice was flat. I couldn't read anything in it. Was she angry? Sad? Upset?
"Um...nuh uh..." At this point, I realized, much to my dread, that I was not wearing my pants. I was ready to throw myself in front of an oncoming 18 wheeler.
She turned around, finally. "I woke you up at about 2 in the morning and told you to come to bed." Alright, well, I was seeming like less of an asshole. At least I had a reason to be in the bed.
"..Kay..."
"You got up and crawled into bed. By the time I got your pants off, you were already asleep."
"...Kay..." It was getting a bit clearer, though I still could remember a damn thing.
"I straddled you, and you didn't wake up. I shook you and told you that you were forgetting something."
"...Kay..." She was silent. "...Did I do something bad?"
She stood up and thrust a finger in my face. "You asshole! You pushed my horny ass off of you, got up, and picked up the goddamn pillow you borrowed, appologized, and went back to sleep!"

And that, fair audience, is how I cockblocked myself.

You sir, have just made this man's day today.

 

[Bara_no_Hime]

i was 15. she was 31.
i don't think that would have worked. plus, i'm not one for adultery.

Um... that's... kinda screwed up.

What's the age of consent in Bulgaria?

15, surprisingly. i was kinda shaken for a day or two after.

Oh.

So... it was totally legal then. Huh. That story was much creepier when it sounded like Statutory Rape.

I'm from the prudish US of A, so I usually assume 17-18 as age of consent.

So yeah... I have to agree with the previous poster... she was trying to get you to have sex with her. And it was actually legal for her to do so. Not very nice to her husband, but less screwed up than I originally assumed.

 

[Bara_no_Hime]

Tell please! I've read this entire thread and I have it bookmarked. Believe me, I'm reading at least.

^^ I love how we've totally corrupted you. You were all "oh no, I can't look away" earlier, and now you're like "more pleaz!"

I am proud to have been a part of it. I hope you're enjoying yourself.

 

[Crimbo23]

How on earth do i delete?!

Don't worry, I'll do it.

Next time, edit your posts saying "Please delete" and report them. =P

Cheers dude

 

[game-lover]

Tell please! I've read this entire thread and I have it bookmarked. Believe me, I'm reading at least.

^^ I love how we've totally corrupted you. You were all "oh no, I can't look away" earlier, and now you're like "more pleaz!"

I am proud to have been a part of it. I hope you're enjoying yourself.

LOL... *blush* It's a little entertaining... I guess that's why I clicked in the first place.

I guess I just wasn't expecting the public excursions at first. And I think when it comes to being a prude, that's my trigger you could say.

But I guess I got over that pretty quickly. Huh.. *shrugs* I probably wouldn't care about reading much if I wasn't a virgin. LOL.

 

[The Thinker]

EDIT You could say it is still of topic as we are talking about wood...

*rimshot*

Heh heh. "Rimshot".

I have no stories, only tasteless jokes...

But this thread is so entertaining! Let me live vicariously through you, internet dwellers!

 

[Thaa'ir]

Hm...when I was a sophomore at university, me and a freshman snuck* downstairs looking for a place to do it. We discovered a music room used by the local residential college of arts and whatever for practicing that was by some miracle still open.

Well, he was really new to the whole deal and he finished pretty quick, but he let out a lot...more than either of us had expected and we needed to clean up.

So in essence, in a place where students being awake and roaming around at every hour of the night was not in any way weird, we frantically ran to the men's bathroom clutching our shorts and hoping we could make it without being seen or getting jizz all over our clothes. We escaped notice though.

I wanted to laugh every time any of my friends used that room, but I bet that it has seen plenty of such use.

You know, I know that a good amount must have gotten on the floor, but none of my friends who used the room ever mentioned discovering anything gross. I laughed every time they used it though. I suspect, however, that it has seen plenty such use.

*Spell-check marks "snuck." Is that not an acceptable past tense form of "sneak"? Is this just some American thing that I thought was normal?

 

[ozium]

I had a chance to nail a really nice looking girl once but I didn't go through with it. The reasons being that it would have ruined our friendship and I was drunk (mostly because I was drunk). Now that time has passed and I am able to look back and reflect on the event, I wish I had nailed her. Silly me.

 

[Caligulove]

Was helping my girlfriend house-sit for her parents. Had only briefly met them once before when helping her move out of her dorm. So last day of house-sitting, there I was, alone, reading or watching a movie in their living room- waiting for the gf to come home from work. Intended to make dinner for her parents when they got home later that night.

However, when my gf got off work earlier than expected, she had other plans when she got home...

Long story short, we had (some of the best) sex on the couch in her parent's living room. Very angry, loud sex, I should say.

We get dressed, take a shower (during which, familiar themes transpired) and made sure the couch was clean, without any traces of our clamorous coital congress. Made dinner, nothing deviant or rambunctious happened. Her parents arrive, we are finally introduced and chat with each other. The subject of their eccentric extended family comes up- and to my horror, her mom decides we should all sit down and look through the photo albums. To put pictures to stories, and whatnot.

All sit down... together... in the living room.. on the couch.

Most awkward 40+ minutes of my life. Gf and I looking at each other occasionally to see if their parents notice anything... off.. about the couch.