Your Worst Sex Stories and Moments

IDKFA

Gold Member
But the smell
Man
The Smell

The site of period Blood doesn't bother me but sometimes the smell is just rancid

But the smell...
money coins GIF by Ashlyn Anstee

The smell? I'm suggesting having sex while your girl is on her period. I didn't suggest sticking your face in there and eating out the bloody axe wound.

If it's bad from just sex then crack open a window, put a peg on your nose, give a few sprays of John Paul Gaultier etc. Don't give up God like sex for something as minor as a smell.
 

TheInfamousKira

Reseterror Resettler
As a teenager, my first experience with cunnalingus was with a chick who apparently couldn't tell when her period started. I could. Oh, Heavens, I could. I ended up throwing up some combination of sprite, pizza rolls, and this chick's shed uterine lining all over the floor, rushing to get towels and water while she sat spread legged in shame in my parents' living room. Any time I taste blood or metal since, I physically tremor for five seconds until it dawns on me that this experience was in the past, and can't hurt me anymore.
 

anthony2690

Gold Member
Got a few I guess, thanks to the Myspace days.

Met a girl in Birmingham, we go somewhere quiet and she performs oral on me, and demands that I unload on her face, this was a pretty public place, but I obliged, she definitely needed to wash her knitted sweater though.

Got a bus home, got a message on MySpace and some girl I was checking out, had added me, I went hers that night. (No idea how she found me so fast, but whatever)

Went Middlesborough, courtesy off a rather attractive suicide girl model, I was still pretty young/not overly experienced at the time, she suggested I have her legs on my shoulders, so there I am going at it, but I'm literally hitting my head on the wall at the same time, but was too polite to say, I was half concussed by the time I was done.

Had an asian girl round that I was very attracted too, claimed she was a virgin/waiting for marriage, so I didn't make no moves and just being nice/friendly, but holy crap did she take advantage off me (she was a filthy liar, I tell you)

Was dating someone in Leeds for a little while, we got a hotel, and some "booty relax lube" from Ann Summers and she had a butt plug too, she was riding me and had the plug in, and I accidently pushed it in a bit too far, I went panic mode, she was laughing her head off, at how worried I was, went toilet squeezed it out, and the mood was kinda dead for the night, I genuinely freaked out.

At a friend's house party, got head off a girl I was crushing on, woke up with bruise on my penis :(

In Lutterworth in some little village and me and my girlfriend at the time were getting it on early hours off the morning, and her mum casually walks through and asks if we want a coffee :l
Funnily enough, the pub in the local village had condom vendors and the condoms were captain condom, I'll always remember them!
Truly horrific moment for myself though, but she was giggling away :/

Myspace days were pretty wild, as people just threw themselves at you, I was with pretty much with a different person or two each week & I got to travel all round the UK.

Now I'm old, boring, settled, happy? I guess haha.
I do regret it a bit, as people start to have a negative reception of you, and I let down some absolutely wonderful people, I don't think I was a good person, I was caught in the moment and didn't know how to control myself.

I don't think any off my stories or gross/weird like others here though, some of you are animals (looking at you skidmark guy)
 
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BadBurger

Is 'That Pure Potato'
In high school I was having sex with a girl in my car, on a street near her house around 3 AM. We're going at it in the passenger seat. Me on top.

Queue a sudden banging on the window. I pull out and awkwardly turn to look, having to kind of contort my waist because my rock-hard schlong was in the way.

It was her furious mother.

It sucked at the time of course but with the hindsight of years it is one of the funniest nights of my life.
 

Pallas

Gold Member
Well a long time ago, while having sex with an ex. She literally pissed on me(or squirted?) after having an orgasm. It went everywhere and yeah… awkward for me and embarrassing for her.

Same chick, and we did anal. I ended up with a brown colored condom. It was pretty gross but I didn’t freak out, wasn’t trying to make her feel bad but I really needed to shower asap after that crap.
 

Zelphyr

Gold Member
Here's another tale where sex was heavily implied yet shot down in a Blaze of Glory.

Again in my 20's back around 1990 me and my buds in Montreal used to go to the Blue Dog bar. We showed up around 9 and got shitfaced 'till closing time at 3.

Not show up at 1 AM because it was "cool" to be late. Just 6 hours of drinking, debauchery, community and happiness.

Around 11 I spot a cool chick with short black hair giving me the eye at the bar.
I tell my boys I'm going on a mission.

Now back then I looked like Matt Dillon in "Rumble Fish". Today I look like Matt Dillon got slapped by the fish 20 times but I digress.

I sit down at the bar next to this minx and introduce myself. She says she's visiting from Boston. It's her last night in town.

She is gorgeous and charming. I smell & tell her perfume, "Eau de Rochas" . She is intrigued. She has grey blue eyes like Roger Daltrey had sex with a husky puppy.

We talk & drink and talk. Time passes. She's buying me drinks. We talk some more. About trivial shit and meaningful stuff. She's buying me more drinks. Boston Red Sox bla bla bla more drinks. Superman is faster than The Flash gettafuckouttahere. More drinks. Gun control oh Lord help me. MORE DRINKS.

Around 2:45 AM she wiggles her hotel keys in my face and asks me to come with her for the final night in town at her hotel.

I politely say as I'm drunk off my ass "Naahh izzz ok I'll just get back to my boyzzz".

She replies " What the hell ARE YOU GAY?!?"

I then said in a verry slurred speech while my hand was resting on a stool for balance "Lisssen Missy I have sum standards and yurrr not just there yet!"

And I stumbled back to my buds.

I had accomplished my mission to get as many free drinks from a woman to balance out the universe for all the men who bought drinks for women but never got any.

Me and the boys went and got some burgers and all was good in the world.
 

nush

Member
My embarrassing sex stories, for her..

The clumsy girl. She walks in the bedroom trying to show off a sexy walk but she was wearing a long cardigan, the pocket of which caught on the door handle and stopped her sexy walk as she jerked backwards. Then she got undressed but the top she was wearing was zippered on the back and she was twisting around trying to get it off, so I helped her but my metal watch strap got caught in her hair. So I spent a few minutes picking the hair out as I didn't want to rip off a clump of her hair. Finally she walks out the shower, the floor was wet and she slipped landing right on her ass. It took everything I had not to laugh and cockblock myself with this girl.

Different girl, finished with a titty fuck. What I didn't notice until I was saying goodbye to her was that a string of my cum had shot up a bit higher and landed in her hair. I hope she checked herself in the mirror before going out.


Another girl, always gave great head and would take a shot in the mouth (Spit not swallow before you ask). Anyway one time she came off my dick a bit too early and I had a couple of squirts left in in me and as she took her mouth off my dick they hit her right in the face.
 

Pallas

Gold Member
Here's another tale where sex was heavily implied yet shot down in a Blaze of Glory.

Again in my 20's back around 1990 me and my buds in Montreal used to go to the Blue Dog bar. We showed up around 9 and got shitfaced 'till closing time at 3.

Not show up at 1 AM because it was "cool" to be late. Just 6 hours of drinking, debauchery, community and happiness.

Around 11 I spot a cool chick with short black hair giving me the eye at the bar.
I tell my boys I'm going on a mission.

Now back then I looked like Matt Dillon in "Rumble Fish". Today I look like Matt Dillon got slapped by the fish 20 times but I digress.

I sit down at the bar next to this minx and introduce myself. She says she's visiting from Boston. It's her last night in town.

She is gorgeous and charming. I smell & tell her perfume, "Eau de Rochas" . She is intrigued. She has grey blue eyes like Roger Daltrey had sex with a husky puppy.

We talk & drink and talk. Time passes. She's buying me drinks. We talk some more. About trivial shit and meaningful stuff. She's buying me more drinks. Boston Red Sox bla bla bla more drinks. Superman is faster than The Flash gettafuckouttahere. More drinks. Gun control oh Lord help me. MORE DRINKS.

Around 2:45 AM she wiggles her hotel keys in my face and asks me to come with her for the final night in town at her hotel.

I politely say as I'm drunk off my ass "Naahh izzz ok I'll just get back to my boyzzz".

She replies " What the hell ARE YOU GAY?!?"

I then said in a verry slurred speech while my hand was resting on a stool for balance "Lisssen Missy I have sum standards and yurrr not just there yet!"

And I stumbled back to my buds.

I had accomplished my mission to get as many free drinks from a woman to balance out the universe for all the men who bought drinks for women but never got any.

Me and the boys went and got some burgers and all was good in the world.
Wait so you’re gay?
 

Northeastmonk

Gold Member
I don’t usually get this vulgar, but I will share some of my NSFW stories.

One time I was cutting jalapeños and didn’t wear gloves. That night I was finger blasting and the lady I was with starting saying something was burning down below. We put two and two together. She ran to the kitchen and grabbed some milk, went into the shower, and started to wash herself with it. It burned the whole night and into the morning. Lessons learned from that experience.

Two things happened during high school. One was with a girlfriend of mine, we tried anal and she wasn’t prepared. I didn’t bother wearing a condom cause it was now or never type of thing. I remember the moment I pulled out and it was like rocky road ice cream all over. I ran to the bathroom and put it under the water. I think I’ve shared that story before, but I’ll never forget. Same girl forgot that a condom was tucked inside of it vagina. I grabbed it when I asked if she had a diaphragm in. When she said no, I got kinda sick to my stomach. She ended up getting a yeast infection from it. Thank god I didn’t get one.
 

Northeastmonk

Gold Member
So dear Gaf tell us of some of your most awkard sex stories that happend to you within the last year or so.

I'll share to kick things off and break the ice. For your info I reside in South Florida so majority of the women here are Cuban, Puerto Rican, Dominican and so on. And I like it that way.

Had sex with this 1 hot Cuban chick. This was our first time together, I hit it from the back and then start seeing quite a bit of a red puddle on the white sheets. I freaked out a bit in my head but kept a straight face and asked her if she was okay.

She turned around and looked over, her face got super red and she started to freak out and then apologizing. She then said proceeded to tell me that I must be super turned off now. I remained respectful with a surprise pickchu face while she looked away. We both moved on and finished to a happy end.

Ok 2nd story

Hot Columbian chick. Massive beautiful ass. One of those girls who put on a tight dress will instantly drive you nuts thanks to her bum. I am an ass man, the issue with this one was that stuffing my face down below was NOT a good idea. A) She either got out of a gym and didn't shower.

Or B) something else was happening, but the smell was sweat and heat. Couldn't do it from the back, too smelly and I almost started gaging. Had to opt for a different position. Saw her 3 times. 1 time it happened, 2nd time it didn't and 3rd time it happend again. If there is a 4th time I suggested to her we both start with getting in a shower and told her it was always a fantasy of mine (so I could play it off without confronting her directly about it) she willingly agreed. Gaf wish me luck please.

Your turn!
I almost forgot the reply to this. Happened to me a lot more back in high school. I’d just grab a towel and wipe her. She’d ask me what was up and I’d just brush it off. If she gets mad then it’s not meant to work. That’s at least what I did.
 

chromhound

Gold Member
Here's another tale where sex was heavily implied yet shot down in a Blaze of Glory.

Again in my 20's back around 1990 me and my buds in Montreal used to go to the Blue Dog bar. We showed up around 9 and got shitfaced 'till closing time at 3.

Not show up at 1 AM because it was "cool" to be late. Just 6 hours of drinking, debauchery, community and happiness.

Around 11 I spot a cool chick with short black hair giving me the eye at the bar.
I tell my boys I'm going on a mission.

Now back then I looked like Matt Dillon in "Rumble Fish". Today I look like Matt Dillon got slapped by the fish 20 times but I digress.

I sit down at the bar next to this minx and introduce myself. She says she's visiting from Boston. It's her last night in town.

She is gorgeous and charming. I smell & tell her perfume, "Eau de Rochas" . She is intrigued. She has grey blue eyes like Roger Daltrey had sex with a husky puppy.

We talk & drink and talk. Time passes. She's buying me drinks. We talk some more. About trivial shit and meaningful stuff. She's buying me more drinks. Boston Red Sox bla bla bla more drinks. Superman is faster than The Flash gettafuckouttahere. More drinks. Gun control oh Lord help me. MORE DRINKS.

Around 2:45 AM she wiggles her hotel keys in my face and asks me to come with her for the final night in town at her hotel.

I politely say as I'm drunk off my ass "Naahh izzz ok I'll just get back to my boyzzz".

She replies " What the hell ARE YOU GAY?!?"

I then said in a verry slurred speech while my hand was resting on a stool for balance "Lisssen Missy I have sum standards and yurrr not just there yet!"

And I stumbled back to my buds.

I had accomplished my mission to get as many free drinks from a woman to balance out the universe for all the men who bought drinks for women but never got any.

Me and the boys went and got some burgers and all was good in the world.
I went to Blue dog with my ex 2 years ago lol. Weird place
 
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Here's a couple

2) First time I fooled around with a girl, it turns out she was in a relationship. She immediately told her boyfriend, and I had to deal with that. That was fun. The trama (and trust issues I got from that experience caused me to not really look for any sort of relationship for 10 years)

3)First time I tried hooking up with my wife, I couldn't get hard. I was too nervous about the environment and all sorts of things. I couldn't get hard. My wife gave me this hateful look. For some reason she kept going out with me, but sex stopped being a priority real quick due to repeated issues. Last time we had sex was about a month before our marriage. It's been over 3 years since then. My wife says she doesn't see the point since she knows I'll just fail to satisfy her.

I've never had what I would call a positive sexual experience. I want to correct that, but I just don't think it's possible at this point. I'm kind of asexual these days.
 
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killatopak

Member
Quite a few but I was just a kid that didn’t know anything. It was embarrassing for the both of us. There was both dick on dick and dick on vag action that was messy and clumsy.
 

Bartski

Gold Member
my WORST sex story tho...

At my lowest low, going through full PEP after assfucking an ultra trashy goth hooker that was likely on heroin. It was dark, my condom broke and I didn't notice. Immediately ran for a checkup and did the whole treatment.
On the upside I have learned I have no STDs, but waiting for the final HIV result (12 weeks incubation time...) was a nightmare and I almost fainted and cried when I opened that envelope and saw it was a minus.
 

StreetsofBeige

Gold Member
Nothing mindblowingly bad I can remember.

But all I know is half the chicks I've banged stink. Wash up or spray some perfume. Or gargle with some Scope.

One thing that did piss me off was I came in the rubber and she sucked me off. She literally ripped off the rubber and threw it against my wall. Splat. So I had come dripping down the wall and the lube from the condom too. I had faint white paint on my bedroom walls, so now I got some man paint on it too, which discoloured it.

I was never able to completely clean it off. No matter how much I tried I could tell there was crusty come depending on the angle I looked at it with the light from the windows shining on it.

I sold that place way back.

If the new owner ever wondered what those weird streaks are in the summer light, well sorry lady but that's my jizz which Lillie threw on the wall. lol
 
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anthony2690

Gold Member
Last time we had sex was about a month before our marriage. It's been over 3 years since then. My wife says she doesn't see the point since she knows I'll just fail to satisfy her.

Ouch, are you filthy rich?
Or does she just not do it for you?
Try a blue pill or Viagra I guess?
Or atleast something, I think satisfying your other half is important.
 

nush

Member
On the upside I have learned I have no STDs, but waiting for the final HIV result (12 weeks incubation time...) was a nightmare and I almost fainted and cried when I opened that envelope and saw it was a minus.

You needn't have worried that much HIV transmission rates from female to male though vaginal intercourse are less than 1%. You can google it if you don't belive it. Anyway you have a higher chance of a regular STD so you should always bag up.
 

TheInfamousKira

Reseterror Resettler
Okay, I've got another one. Terrible in a different way from the first. Again, in my teenage years, I was friends with a man from London who was incredibly into FFVII and Tolkien. We hit it off, and he ended up moving to my town in Pennsylvania. He had trouble finding housing, but eventually got accepted into an apartment above the local Chinese restaurant. Eventually, his visa ran out and he had to return to the UK (or get married, but we weren't THAT good of friends) so he left me his keys and asked me to clean out whatever was left in the apartment, because he wasn't going to be able to take everything with him.

So I go in there the next afternoon with my girlfriend at the time, and we start having cuh-razy sex on the floor. About twenty minutes in, there's a loud knock on the door, and I spring up and try to get dressed, but only manage my pants and a Pac Man Hoodie. The locked door opens before I can get to it, and it's my friend. I calm down, but am still half ass wondering how he got into a locked room.

He notices my state of undress, then right behind him comes the elderly Asian landlord. I'm feeling the kind of shame that can only be brought on by facing down a man who was elbow deep in raw chicken all day, when, to my further horror, his elderly Asian wife comes in right behind him. At this point, my girlfriend falls over or some stupid shit trying to put her pants on, and this small Asian woman just starts shrieking. I tell the landlord that I was just cleaning out the apartment, and in his broken understanding of English, he assumed I meant "cleaning it out," like I was just stealing everything that wasn't nailed down. He asks for his keys and tells me he never wants to see me again, and I leave. I can't even recall if my girlfriend came with me or not.
 

Bartski

Gold Member
You needn't have worried that much HIV transmission rates from female to male though vaginal intercourse are less than 1%. You can google it if you don't belive it. Anyway you have a higher chance of a regular STD so you should always bag up.
I know, but it wasn’t vaginal and no lube so way higher risk due to internal bruising
 

chromhound

Gold Member
Here's a couple

2) First time I fooled around with a girl, it turns out she was in a relationship. She immediately told her boyfriend, and I had to deal with that. That was fun. The trama (and trust issues I got from that experience caused me to not really look for any sort of relationship for 10 years)

3)First time I tried hooking up with my wife, I couldn't get hard. I was too nervous about the environment and all sorts of things. I couldn't get hard. My wife gave me this hateful look. For some reason she kept going out with me, but sex stopped being a priority real quick due to repeated issues. Last time we had sex was about a month before our marriage. It's been over 3 years since then. My wife says she doesn't see the point since she knows I'll just fail to satisfy her.

I've never had what I would call a positive sexual experience. I want to correct that, but I just don't think it's possible at this point. I'm kind of asexual these days.
Get some Viagra. You might have a performance anxiety
 

GymWolf

Gold Member
Never paid to fuck in my life, but when i was 19, i was in cuba with my best friend and one of the guy in our hotel was an italian billionaire gay lawyer who worked with 250-500 motorcycle pilots (world famous pilots like valentino rossi etc.), Well this guy took me in high simpathy (not sure if this is the right term) and since it was my birthday (20), we went into a large square full of women and told me to chose who i wanted to fuck for my birthday and he would have paid for that.
I was half drunk so i didn't refused, i chose the most beatiful ebony skinned chick that i could find but my little brother wasn't on the mood for fucking that night, probably a mix of drunkness and awkwardness of the situation.
The lawyer still had to pay 25 pesos to the chick so at least we made her night :lollipop_grinning_sweat:
 
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Winter John

Member
Worst one had to be the night a New Jersey sea beast turned me into a woman. I'd been out drinking with my buddy in Bridgeton and missed the last train out so he made a few calls and we ended up at his cousin's apartment. The minute I saw the thing flowing towards us my first instinct was to douse it with mace and beat it unconscious with a lead pipe. It was at least 240. I realised hand to hand combat was out of the question. No way I was going to be able to take the beast down. I decided to play it smart. No sudden moves. No direct eye contact. Soothing tones.

We had a few drinks and it quickly became apparent what the situation was. I was to be it's chew toy in return for a place to crash. It leered at me through it's greasy fringe. It had the dull, avaricious stare of the sex predator. It knew I was trapped. I decided to drink as much as possible. I figured maybe it would leave me alone if I passed out. No such luck. Eventually I was lead into it's lair. Stale food, cat hair, moths, sweat, unwashed piles of clothes. It lay on it's mound. Tits spilling over it's sides. Thighs hanging down onto the sheets. I lay next to it. Kept saying how exhausted I was and sure couldn't wait to get some sleep. I turned on my side away from it. Then it touched me. I felt it's paw on my back and in that moment I became a woman.
 

Northeastmonk

Gold Member
Here's a couple

2) First time I fooled around with a girl, it turns out she was in a relationship. She immediately told her boyfriend, and I had to deal with that. That was fun. The trama (and trust issues I got from that experience caused me to not really look for any sort of relationship for 10 years)

3)First time I tried hooking up with my wife, I couldn't get hard. I was too nervous about the environment and all sorts of things. I couldn't get hard. My wife gave me this hateful look. For some reason she kept going out with me, but sex stopped being a priority real quick due to repeated issues. Last time we had sex was about a month before our marriage. It's been over 3 years since then. My wife says she doesn't see the point since she knows I'll just fail to satisfy her.

I've never had what I would call a positive sexual experience. I want to correct that, but I just don't think it's possible at this point. I'm kind of asexual these days.
Buy a sex toy to use on her. For a lot of women it’s hard for them to orgasm through straight intercourse and they’ll lie through their teeth if they say they are. I hate when women are blunt like that. They aren’t helping the situation, they’re only making it worse. Sex for me has been a visual thing. If I can’t see the person then it’s not going to go well. I kinda blame it on all the sex I had as a youth too. Honestly, a sex toy might solve the issue. You can satisfy her needs without all the performance anxiety. Just don’t make it a one person show. Do it for her.

Your situation is bad and I feel bad after reading it. That sucks you’re suffering that way. I hope my advice helps. I don’t talk to anyone about sex. It’s a difficult/taboo subject as an adult. Typically sex inside a marriage is a huge priority and can cause major issues. I know for me personal, if sex wasn’t there we’d probably had gotten a divorce years ago.
 

M1chl

Currently Gif and Meme Champion
Quite a few years back I was fucking some random girl against the wall, she suddenly tiptoe (ed) and with full force I nail the wall. Was painful as fuck, even when I typing this it still triggers me. What a horrible pain.
 

Porcile

Member
Worst one had to be the night a New Jersey sea beast turned me into a woman. I'd been out drinking with my buddy in Bridgeton and missed the last train out so he made a few calls and we ended up at his cousin's apartment. The minute I saw the thing flowing towards us my first instinct was to douse it with mace and beat it unconscious with a lead pipe. It was at least 240. I realised hand to hand combat was out of the question. No way I was going to be able to take the beast down. I decided to play it smart. No sudden moves. No direct eye contact. Soothing tones.

We had a few drinks and it quickly became apparent what the situation was. I was to be it's chew toy in return for a place to crash. It leered at me through it's greasy fringe. It had the dull, avaricious stare of the sex predator. It knew I was trapped. I decided to drink as much as possible. I figured maybe it would leave me alone if I passed out. No such luck. Eventually I was lead into it's lair. Stale food, cat hair, moths, sweat, unwashed piles of clothes. It lay on it's mound. Tits spilling over it's sides. Thighs hanging down onto the sheets. I lay next to it. Kept saying how exhausted I was and sure couldn't wait to get some sleep. I turned on my side away from it. Then it touched me. I felt it's paw on my back and in that moment I became a woman.

Isn't this just the story to Moby Dick 2?
 

chromhound

Gold Member
Worst one had to be the night a New Jersey sea beast turned me into a woman. I'd been out drinking with my buddy in Bridgeton and missed the last train out so he made a few calls and we ended up at his cousin's apartment. The minute I saw the thing flowing towards us my first instinct was to douse it with mace and beat it unconscious with a lead pipe. It was at least 240. I realised hand to hand combat was out of the question. No way I was going to be able to take the beast down. I decided to play it smart. No sudden moves. No direct eye contact. Soothing tones.

We had a few drinks and it quickly became apparent what the situation was. I was to be it's chew toy in return for a place to crash. It leered at me through it's greasy fringe. It had the dull, avaricious stare of the sex predator. It knew I was trapped. I decided to drink as much as possible. I figured maybe it would leave me alone if I passed out. No such luck. Eventually I was lead into it's lair. Stale food, cat hair, moths, sweat, unwashed piles of clothes. It lay on it's mound. Tits spilling over it's sides. Thighs hanging down onto the sheets. I lay next to it. Kept saying how exhausted I was and sure couldn't wait to get some sleep. I turned on my side away from it. Then it touched me. I felt it's paw on my back and in that moment I became a woman.
 
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