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Worst sex you've ever had?

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I'm married now, but before I met my wife (post first divorce) I dated a few ladies. One girl I was with for a little while was great in bed. The only thing that kind of bothered me is that she had a negative attitude when it came to giving a guy some head. I explained oral sex is very important to me several times but she didn't seem to respond to those messages.

She LOVED having sex, all the time. So one night we have been going at it for a little while. We switch positions to doggy and I'm straight POUNDING her. She comes hard, yelling (I'm worried about my damn neighbors she was so loud). Now what I noticed is that her vaginal muscles must have relaxed after she came because it didn't feel as tight. Maybe she was just that much wetter. Anyway I couldn't reach orgasm like that, so I thought maybe she would finish me off with oral. So I casually said "your pussy's a little loose since you came, do you mind going down on me until I come?". BIG MISTAKE. She gets pissed and moves off the bed (I pop out of her). She puts her clothes on, says "how would you feel if I told you 'hey your dicks a little too small for me'?". Then she left. It was about 3 am. I didn't answer her calls for a week, then I gave in and told her I'd see her again. I was really mad. We broke up a month later when I got asked out by another girl. She was crazy anyway.
 

teh_pwn

"Saturated fat causes heart disease as much as Brawndo is what plants crave."
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I should really stay away from threads like this. :p

That could be with just 1 girl. :p With the right woman you'll go through condoms faster than you'd like. And 3 times is like one session. 5 or more if it's a sleepover. So you're talking about 4 nights.

You also need to be reasonably fit in your core, and her too. Otherwise you won't really be able to various positions without it being a workout more than sex.
 

airblade

Banned
4. hot chicks cant fuck #2
my latest worst sex experience
this blonde woman, by far the hottest woman I´v ever met, like a model, but curvy, damn she was hot when I think about it and had probably the best boobs I´ve ever seen/touched. to make it short, we drove to her home, told me to wait a few minutes and BAM she switched into some ultra hot lingerie... like the hottest porn you can imagine..
well the fun started and it was okay, I had a condom on, and then she wanted to suck it... with the condom still on... which was weird for me.. well I could life with that, but it felt meh... then the insane happend, I fucked here so hard, she started to bleed down there, like something was broken.. well we tried a few time again, but blood was everywhere, turned me off...then she said this to me "please put a mask on, a pig mask prefered and rape me"

WHAT IN GODS NAME! I want naughty sex and not a freak rape Play, she said, it turns her on...

I´ve never met her again

Queue to exit.
 
Tried anal with my current girlfriend. Lots of lube. Dick slipped in slowly and she gave up at its half-length. She fell forward from doggy style, said "ow." That sex lasted about 4 seconds.

Sorry this story wasn't exciting, but my sex life hasn't had anything really bad at all! Except this one time during phone sex which I won't get into.

If it was her first time, lube is wonderful but doesn't help as much with the not hurting as you'd imagine. Anal sex done properly is not easy. Do some research and do it properly. Totally worth the time.
 
Oh, oh man...I can remember my worst sexual experience like it was yesterday.


Me and an ex of mines back in high school were hanging out in downtown Indianapolis. Great atmosphere, lots of shit to do, you guys should definitely visit XD. But anyways, I know she always had a thing for me, even after me breaking up with her via Myspace over some bullshit reason (I was heartless, lol). She was infatuated with every minute detail about me. We went to Buffalo Wild Wings, where she proceeded to drink...a lot. I was 20 at the time, so I couldn't indulge myself in any liquor, just Sprite, lol. She was touching all over me, telling me that she wanted me, every part of me, she even went to the restroom and sent me a picture of the "goods". Thank God we sat in the corner of the restaurant in booths. Upon seeing that she was visibly drunk, our waitress stopped serving her drinks, so we left there and went to this brewery/restaurant called the Rock Bottom. She drunk more, and more, while I sat awkwardly sober. Her words were getting more dirty, her hands were everywhere. After we had enough, we left. This is where the fun begins

She was extremely trashed, and undoubtedly horny. She said that she wanted to fuck me, and I was sure that it was going to happen, I just never though it would be at this location. Downtown Indianapolis has a lot of dark, narrow, and long alleys.....upon her seeing one, she dragged me into it. We started making out...heavily. My hands start rubbing her pussy from under her pants, and she is just moaning, moaning oh so loud. From there, she pulls my pants down and starts giving me oral, and she was pretty good, only downside is that it was cold as shit (it gets really cold here in the winter). She finishes and tells me to fuck her....in a cold, dark, dirty downtown alley, and I obliged. There was a trash can near, so she rested her arms there and I fucked her doggy style. After like a minute of that, I said that we should stop, due to me seeing a police car in the street. She put her pants back on, I pulled up mines, then we left and went our separate ways (thankfully she got home)...

The sex itself wasn't bad at all, its just the fact that I had sex with my completely trashed ex in a damn alley with a police car like 100 feet away. Kinda makes you feel horrible inside and not too intelligent.
 

Jack_AG

Banned
Dated a girl for a few weeks. When we decided it was on and her panties came off... I was greeted by neanderthal-like foliage and a smell so horrid I can recall that shit to this day. I mean... it was rancid. REALLY fucking bad. Weird because she always smelled great, super clean place, breath minty fresh, etc. Caught me off guard.

Needless to say I bolted as quick as I could. Used the "we should wait" line and never went out with her again.
 

airblade

Banned
The sex itself wasn't bad at all, its just the fact that I had sex with my completely trashed ex in a damn alley with a police car like 100 feet away. Kinda makes you feel horrible inside and not too intelligent.

You're lucky that she didn't throw up while you two were going at it.
 

MickeyPhree

Member
I was 20 and only gave a shit about getting pussy. I met this girl off some chat room on aol, picked her up and brought her to my house. On a scale of one to ten she was about a four, not fat or anything, just not a good looking girl.

I bullshit with her for Alittle bit then it comes time to do the deed. She couldn't kiss for shit, the blowjob I got from her was just awful; lets just wrap my lips around a dick and bob my head.

I don't know why but I decided to go down on her. Panties came off and I was greeted by an Afro of reddish gold pubic hair. This shit was everywhere. I still put my face there. And the smell was disgusting. It didn't smell till literally my face was two inches from the lips. Did it for a couple minutes and I just couldn't go anymore.

Slapped a condom and started fucking her missionary. I fucked her for maybe five minutes; the entire time she was just looking at me and smiling. She also kept repeating "(my name) you're so wonderful". Again after a couple minutes I just couldn't take it. I faked an orgasm, told her some bullshit that I needed to leave, drove her back home, then hauled ass back to my house to take a shower.

Yeah that sucked.
 

Peaky

Neo Member
Morning after going out with a few friends clubbing.

The whole point was to hook me up with one of the girls going, since it had been a long while since I had seen any action and she was always up for it. We slept together that night before waking up at 6am to do the deed. Fingered her for a good 15 minutes, put it in and half-blew after about a minute of rough, painful sex.

Felt kinda bad so fingered her for another 10 minutes before losing any motivation to try again so I rolled over and went back to sleep. She got her money's worth with a good half hour finger pounding I guess.

Hadn't fapped for ages, had been a very long time since my last root and no condom. I didn't stand a chance..
 
I was 20 and only gave a shit about getting pussy. I met this girl off some chat room on aol, picked her up and brought her to my house. On a scale of one to ten she was about a four, not fat or anything, just not a good looking girl.

I bullshit with her for Alittle bit then it comes time to do the deed. She couldn't kiss for shit, the blowjob I got from her was just awful; lets just wrap my lips around a dick and bob my head.

I don't know why but I decided to go down on her. Panties came off and I was greeted by an Afro of reddish gold pubic hair. This shit was everywhere. I still put my face there. And the smell was disgusting. It didn't smell till literally my face was two inches from the lips. Did it for a couple minutes and I just couldn't go anymore.

Slapped a condom and started fucking her missionary. I fucked her for maybe five minutes; the entire time she was just looking at me and smiling. She also kept repeating "(my name) you're so wonderful". Again after a couple minutes I just couldn't take it. I faked an orgasm, told her some bullshit that I needed to leave, drove her back home, then hauled ass back to my house to take a shower.

Yeah that sucked.

That's just... dirty.

I have a few more stories, but I would have to skim back through the thread to see what I've posted.

From flat chest led to limp dick; Steamed windows, flashing lights, Cops are the ones who knocks; Oh Shit!! mom walks in on us. Chaos ensues, girl out the window; Almost Raped by a big girl, but rescued by the skinny one,only to be damn near raped anyway; But you said you weren't a virgin.... why is there blood everywhere; 4-some gone wrong for all the wrong reasons; Ooops, wrong hole [trollface.jpg]; 2 girls, wild night; and probably more that are slipping my mind at the moment.
 

airblade

Banned
That's just... dirty.

I have a few more stories, but I would have to skim back through the thread to see what I've posted.

From flat chest led to limp dick; Steamed windows, flashing lights, Cops are the ones who knocks; Oh Shit!! mom walks in on us. Chaos ensues, girl out the window; Almost Raped by a big girl, but rescued by the skinny one,only to be damn near raped anyway; But you said you weren't a virgin.... why is there blood everywhere; 4-some gone wrong for all the wrong reasons; Ooops, wrong hole [trollface.jpg]; 2 girls, wild night; and probably more that are slipping my mind at the moment.

hahaha classic.
 
The amount of unprotected one night stand stories in this thread is disturbing. Get that "heat of the moment" BS outta here...don't be a fool, wrap up your tool!
 

wsippel

Banned
Worst sex I've ever had was the first time I've ever had sex (with the girlfriend of my best male friend - it sucked, and we're no longer close friends), followed by the second time I've ever had sex just a week later (with my best female friend - sucked as well, but at least it didn't ruin our friendship). Those were also the only two times I've ever had bad sex.
 

Northeastmonk

Gold Member
The amount of unprotected one night stand stories in this thread is disturbing. Get that "heat of the moment" BS outta here...don't be a fool, wrap up your tool!

I agree. I once sat in a hot car while the girl I met took the morning after pill. I was not going to leave until she did.

I've had some bad experiences. I once met this girl who needed someone to talk to her. I went over to her house and she begins to tell me about her life. She had a defibrillator in her chest, her left arm had experienced hemiparesis (paralysis) from a stroke she had a while back. She had a few kids who didn't live with her either. Well when we got on her bed we started to have sex. At this point I'm like okay, this woman's been through enough and I proceed with the sex.Well after we finish I do my business and she swallows. Thinking the night was about over, we continue to talk. She informs me she is "going" through a divorce. So she's basically still married. I think to myself "I can't really be around for sh*t to hit the fan". So I reach in my wallet pull out about $100 and threw it on the table. Then I left.

I had a few where I got my member covered in feces and called it off.
 
Couple things

1)Ladies keep your fucking dentals away from my dick during oral sex. Please. I should be saying "Halleluya! Thank you Jesus!" not "Bitch I rebuke you and yo teeth."

2) Brush your goddamn teeth. Trifling ass got racoon pussy twerking on your tonsils or booty and hotwings.
 
Sounds fake. There's no way this happened. No, don't come in here defending the honesty of your post, my brain will never be able to comprehend the possibility of this being true. Not even hypothetically. It refuses.
Fake or not, I was laughing my ass off. The puking part sounds straight from a Family Guy episode
or a Heavy-R video clip
 

Bundy

Banned
Simple: Sex in a small car (it was her car).
What the fuck?! HORRIBLE!
Don't know how you can enjoy sex in a car.
Second time in a car was shit, too.
Never again.
 

Bradiculous

Neo Member
The worst would had to have been both our first times. I went in way too fast and it wasn't in for more than 30 seconds before she bled all over her carpet so we had to clean ourselves and her floor up before her parents got back to her house in a matter of minutes.
 

Zoolader

Member
Simple: Sex in a small car (it was her car).
What the fuck?! HORRIBLE!
Don't know how you can enjoy sex in a car.
Second time in a car was shit, too.
Never again.

Are you banging in a Smart car? I've had some awesome times in the front seat and back seats of a smallish 4-door car.
 

Kyne

Member
I have nothing comparable to anything in this thread.. (hella good reads though)

.. anyways, someone should make a "your first time" thread. I feel like that would garner a lot of interesting stories c:
 

Rur0ni

Member
4. hot chicks cant fuck #2
my latest worst sex experience
this blonde woman, by far the hottest woman I´v ever met, like a model, but curvy, damn she was hot when I think about it and had probably the best boobs I´ve ever seen/touched. to make it short, we drove to her home, told me to wait a few minutes and BAM she switched into some ultra hot lingerie... like the hottest porn you can imagine..
well the fun started and it was okay, I had a condom on, and then she wanted to suck it... with the condom still on... which was weird for me.. well I could life with that, but it felt meh... then the insane happend, I fucked here so hard, she started to bleed down there, like something was broken.. well we tried a few time again, but blood was everywhere, turned me off...then she said this to me "please put a mask on, a pig mask prefered and rape me"

WHAT IN GODS NAME! I want naughty sex and not a freak rape Play, she said, it turns her on...

I´ve never met her again
That would be a win.
 

tekumseh

a mass of phermones, hormones and adrenaline just waiting to explode
I'm married now, but before I met my wife (post first divorce) I dated a few ladies. One girl I was with for a little while was great in bed. The only thing that kind of bothered me is that she had a negative attitude when it came to giving a guy some head. I explained oral sex is very important to me several times but she didn't seem to respond to those messages.

She LOVED having sex, all the time. So one night we have been going at it for a little while. We switch positions to doggy and I'm straight POUNDING her. She comes hard, yelling (I'm worried about my damn neighbors she was so loud). Now what I noticed is that her vaginal muscles must have relaxed after she came because it didn't feel as tight. Maybe she was just that much wetter. Anyway I couldn't reach orgasm like that, so I thought maybe she would finish me off with oral. So I casually said "your pussy's a little loose since you came, do you mind going down on me until I come?". BIG MISTAKE. She gets pissed and moves off the bed (I pop out of her). She puts her clothes on, says "how would you feel if I told you 'hey your dicks a little too small for me'?". Then she left. It was about 3 am. I didn't answer her calls for a week, then I gave in and told her I'd see her again. I was really mad. We broke up a month later when I got asked out by another girl. She was crazy anyway.

This story reminds me of a great bit that Richard Pryor used to do. Said he and his girl were fighting one night and he was incredibly angry, so finally he just smugly said, "I'm gettin' out of here to find go some new pussy!" To which she replied, "If you had 3 or 4 more inches of dick, you could find some new pussy right here!" To which he had no reply...
 
These first time/blood stories freak me out. Me and my girl didn't have this problem! First time was clean and good. Sometimes I wish I could experience terrible sex just to tell interesting stories.
 
This story reminds me of a great bit that Richard Pryor used to do. Said he and his girl were fighting one night and he was incredibly angry, so finally he just smugly said, "I'm gettin' out of here to find go some new pussy!" To which she replied, "If you had 3 or 4 more inches of dick, you could find some new pussy right here!" To which he had no reply...

HA!
8hxd0Aq.gif
 
I have 2 stories-
Got hot and steamy with a lady 10 years older (me 19, her obviously 29). We were in the car and it was around 1am. We find a kindergarten car park that was very secluded. We started really going for it (mind you, I'd known her for a while but this was our first night out and so obviously first time fucking)...
For some reason she'd never really been good at giving head but she wanted to try please me. Let's just say she used her teeth instead of her lips and my Johnson was as red as a tomato and as sore as you could imagine. Obviously I couldn't finish properly, dropped her off and went straight home to soak it in cold water in the bath tub.

2nd story was me with my girlfriend (now my wife) we were making out one night at a park. Seemed to be too many people around so we got into the front seat of my car. As she was straddling me I undid her bra and she was pulling out my manhood. As all this is happening it had just started pouring and the car started to get steamy. Windows fogged up but seemingly out of nowhere a guy comes up to my window, face planted on the glass and looks right through! We fucking shit ourselves. My dick never went as limp as quickly as that and my wife's bra somehow jumped back onto my wife! It was almost comical. Guy just said sorry and walked off. Always reminded me a little of Zodiac at the start of that film...
 

Jindrax

Member
My first time was the worst...

We were doing it in her mums bed for some reason. But the TV was on. And it was on nickelodeon... Suddenly I heard. "Earth, Water, Fire, Air... ... I couldn't focus anymore and I just turned my head and basically started watching avatar...

Or maybe the first time with my current gf... I took her virginity... And she started crying... as soon as I inserted the captain... I felt like a rapist... I go why are you crying? Does it hurt? She answers: no I just love you so much... I pulled out and hugged her for like 30 minutes while feeling like a massive douche..
 

Bowler

Member
Uh... to your dismay?

I had to use that mattress for the rest of the semester. o_0

My first week into my first semester in college, it was a beautiful warm fall night. Now before school started we had freshmen orientation a few weeks earlier, where I met some new people. I Get a phone call from my friend that I met at orientation, who says he is hooking up with a girl, and she brought her friend with her, and is kinda like the third wheel. He begs me to come over to alleviate the awkwardness of the dorm room third person effect.

When I get there they had all been drinking, but to my dismay, the girl was stunning. Athletic, Tight in all the right places. This brunette, with her glistening green eyes was mesmerizing. She didn’t have a huge rack, but she was perky with a bit more than a handful.

After chatting for all of 15 minutes, we start making out. Caressing each other. As I look over, the other two are doing the same, appearing as if they are silently letting us know that they need the room to themselves. I wisper in her ear, on how we can go to my room as my roommate is at a party, and we can have some privacy. She agreed, and we made our way up the 6 floors to my room.

When we get there, I notice my door is slightly open, which I assumed was my eagerly leaving towards downstairs and leaving it a jar. We walk in, and there he was, my roommate was back early, in bed snoring. At this point I’m trying to think of a multitude of different scenarios to plant my seed, when my female guest wispers, we can just try and be extremely quiet. I could not say no, even though I thought the bleachers to the football field would be cool, or to a lesser extent, the darkened rec room downstairs in the corner. Nope we are going stealth mode.

She knew how to handle me, her hands her lips, almost put me to the edge. I fought with every muscle, not to overcome the intensive foreplay. I managed to hold off, and I inserted. We started Grinding, holding our breath, almost to a point where we were cutting off our oxygen. It actually felt different in that aspect, and aided to the feeling of the sex. It felt so good.

Then the unthinkable happened. All of the sudden my roommate springs up out of his bed on the other side of the room. We stop, while I was still inside of her. Barely breathing. My roommate, who we now know is completely tanked, starts yelling, in the dark, at his mother to make him some ramen noodles. Still pitch black he enters the closet, yelling “wtf MOM” where is my ramens. At this point my guest and I are trying to contain our laughter. Then my roommate opens the door, takes two steps, pounds on the neighbors door, screaming “ Give me back my fucking ramen noodles!!” We could not hold in the laughter any longer, and burst out laughing, tearing up almost, it was so funny. Now mind you im still inside her, but all of the sudden, she starts saying “oh fuck fuck oh fuck”,

At that point I now know what a golden shower feels like, she laughed so hard, she pissed herself, on me, on my bed, while still laughing. She hurried getting dressed, and ran to the bathroom. I turned on the light, and tried to make sence of what just happened. I removed my sheets, to find a wet spot that was 2 feet diameter. Mind you this was a dorm for freshmen, so it was a twin mattress. I flipped it over and it went right thru. She never returned that night, and I was forced to sleep in the Rec room chair.
I did see her about a week later, we giggled a bit about what had happened, she said she was sorry. She left school to go back home a few weeks after that, at which point I became known as the guy who had a squirter girlfriend.

Golden showers is not that fun at all.
 

Daffy Duck

Member
I've been pretty lucky and not had bad experiences.

However......

A few years ago me and the girlfriend are getting all amorous and we get things cranked up to the level we end up having sex, it's going really well, then all of a sudden I get a slow burning sensation downstairs, but I think to myself, fuck this, it's too good to stop, so we carry on going at it, the sensation is getting worse and really starting to put me off, luckily for me I eventually come and we lay there kissing after, so a few minutes later I climb off her so we can go clean up and I notice blood all over the sheets, and I'm thinking WTF?!? I ask her if she's OK, she says she's fine, I look down at my johnson and it's covered in blood.

I run to the bathroom wondering WTF has happened and after cleaning myself up I notice I have snapped my banjo!! The thing wouldn't stop bleeding (took about two hours to stop) and the feeling was like someone was sticking pins in me for days afterwards.

It took a good week or two before I could do it again, the worst part was getting aroused as when it grew it would stretch it again and bleed.

Going to the doctors about it was also an unpleasant experience.
 
I was having anal sex with my first partner (from behind) and her 5 year old son walked into the room. Never has my penis went from rock solid to flaccid so quickly.

The sex itself was great, just a bad outcome.
 
Pretty much a majority of the sex I had with my ex towards the end of our relationship.

I would try to get really into it but he would always bust it after 15-20 minutes. Hardly ever tried to give me mine after he got his too. He would just lay there once it was done and I would try to coax him into playing with me a little more but he never seemed into it.

He also moans like a girl.

It was pretty awful.
 
Don't believe the story about the guy sucking on a puss-filled boil he thought was a lactating nipple.

The girl would've known the difference.
 
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