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Worst sex you've ever had?

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Unicorn

Member
So this girl I was with finally granted me permission for some anal lovage.
I'm warming up her ass with a vibrator, slowly pushing it to and fro with my left hand whilst playing with her pussy with the right, two fingers in and my thumb working her clit.
She's getting very excited by what my right hand is doing, so I momentarily lose focus of the careful actions of my left hand.

"Ploop."

The vibrator disappears up her ass.
No biggie I figure, I can just dig it out.
So I reach in deeper with my left hand whilst stopping what I'm doing with my right.

"What are you doing?"
".....Oh nothing just grabbing this thing."
"What!?"

She leaps up off the bed and begins to panic. I sit her back down, explain, make a couple of jokes and begin my second excavation attempt.
The problem now is between her getting up and sitting back down it's become lodged in at a strange angle and seemingly won't come out.
I pull firmly.
A sudden warm sensation.
Blood.
Lots of blood.

She runs to the toilet, leaking blood over my cream carpet whilst I run after her beginning to freak. I don't like the sight of blood.
She sits on the toilet and begins having what sounds like a very heavy, manly piss.
I look into the toilet and it looks like a prop bucket from Carrie.
So much blood.
I'm trying my hardest to pull this vibrator out but it won't budge.
The blood is making my attempt to get a decent grip on it difficult.
She's crying.
I suggest going to hospital to remove it and she cries more, shouting at me for thinking of putting her in the situation of explaining to the doctor what's wrong.

After a huge amount of blood (repeated flushes were needed), tears and struggles I finally wrestle this vibrator from her ass.
It's still on and vibrating happily.

The downside is this experience has put me off from ever attempting anal sex again.
The upside is I kept the vibrator and gave it to her as a gift a few months later.
She smiled.
I don't know how I initially missed this thread, but dear lord. Holy shit. I just kept saying, "no, NO... nononononononononononono" aloud.
 
The worst sex for me had to be was when I had a 103 degree fever, a nasty cough, and I had a boil on my rump the size of a softball. Antibiotics weren't doing the trick, and I was an idiot to wait so long before getting it lanced and cleaned,(I went and got it done a couple of days after this whole ordeal) and my girlfriend at the time wouldn't stop because she was greatly in the mood. I didn't want to, but I said fuck it as we were in a bit of a dry spell.

I remember the whole ordeal being excessively exhausting, and I don't even remember how I was able to maintain an erection for the whole half hour of intercourse. All I could think is, "Thank god it's over." After we finish, 10 minutes pass and she wants to go again. I said I can't but apparently she was hard of fucking hearing and started playing with my junk and got pissed because I couldn't get it up again. I was sick as a dog and wanted to do nothing but sleep.
 

Snuggles

erotic butter maelstrom
Drunk. Waiting for my late friend to show up to the party. Go into to the bathroom to give him a call and she busts the door open. Fuck.
 

JBourne

maybe tomorrow it rains
I bet this thread is gonna stop some people from getting it on tonight.

Yeah, I read some of the better stories to my gf as she was getting into bed. She had been really anxious all evening, but that killed it. Very much intentional, as I had to go to work and didn't want to be all tired.

I feel like my story has been told a couple times in here already: my first time after a 2 year absence, I couldn't keep it up. Mostly my fault, but she was just unable to be sexy. She was cute and I liked her, but very awkward and goofy when it was time to get down. It was a miserable night, and I ended up driving home around 4 in the morning. We went on a couple more dates after that, but I had no urge to get down. We parted ways after 2 weeks and never spoke to each other again.

A couple years later, after I was firmly back in the saddle and doing pretty well for myself in the bedroom, I went out with a girl who turned out to be friends with her despite living on different sides of the state. We went on a few dates and eventually ended up making out on my couch, where I found out she purred when she got worked up. Not a subtle little hum, but this loud-as-fuck, hilarious purring noise. It was distracting to the point of keeping me soft, and every time she went for my cock she seemed surprised that I was completely flaccid. I think she must've talked to her friend and swapped stories of my limp dick, because a few days later what little spark we had was gone. She ended up getting married a couple months after, so I feel like I dodged a bullet there.
 

Lazyslob

Banned
I was super tense and that made me sweat like a mad man. I was on top of her and some of that shit went on her face and eye. It probably stung. That and it took me fucking forever to finish.....Well, it wasn't that bad for me because I thought sweating on her was pretty funny, but it was probably weird for her.
 
Tried to bone some chick's ass one time and she started crying in pain to the point her cousin or aunt or someone came in the room. I'm still naked, she's still naked ... awkward.
 

neorej

ERMYGERD!
Picked up a MILF at the gym, boned her. Ran into her daughter the next morning. She's my age so we chat over breakfast. She's making remarks about the the noises we made and we laugh.

Fast forward to the evening, I'm meeting the MILF to go to the movies, but she tells me she's been called away to work. She then asks me to show her daughter whay I did to make her come so hard that night. The daughter is smoking hot, I'm horny as fuck, so I'm like 'sure no problem.'

If that's not weird enough, shes constantly asking if she's better than her mom. It was fucking awkward and not as hot as porn makes you think.
 
Sex with someone I should had split from months prior if I was being honest with myself. Thought I could at least enjoy the act even if the emotion wasnt there. Ended up crying after - full out sobbing. We broke up that night.
 
mines a short story (no pun intended) Dated a girl, we finally started having sex, I came in 15 seconds, I said it was the condom...it wasnt... I then tried to put on a "new" condom and do it again, limp as a noodle. Took her to walmart for her sister to pick her up (sounds white trashy) ....after that we broke up and i have been forever alone ever since.
 

Amon37

Member
Halfway through a handjob it started to hurt a little, I notice she has a thumb ring on. I don't want to break the mood so I don't say anything. She finishes me with her mouth as usual and it hurts worse. I zip up and don't say anything

The next day chaffed to hell and it's so sore. I told to remove all rings next time.
 
finally getting a semi-limp dick into a really hot girl. knowing that you might be able to turn it into a decent erection if you can keep it in the vagina. the dick slips out, and you just say, "yeah, this isn't gonna happen."

both people are insecure and sad
 

Bowler

Member
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.
 

soepje

Member
It didn´t even get to actual sex, but i ones made out with someone that kissed like a mechanical fish on dry land, just kept biting me at regular intervals while simultaneously squeezing my butt as if bread dough was being prepaired. I can´t really explain it right, but it was weird... Lost my crush right there and then.
 

Batigol

Banned
Sex with a girl I met on OKCupid.

Fit as fuck, but man, her pussy smelt of fish and I ain't even joking. Literally smelt of cod.

What do I even do here? Ain't gonna tell her 'cause it would destroy her, plus my cock was already out.

But man, it was making me limp. When she was on top I was tasting the smell and she'd ask what's wrong and I'd say nothing.

I finished on top of her, but I buried my head in the pillow so I wouldn't have to breathe in any more fumes.

I stopped texting her after that
 
One night stand with a chick I met in a bar. She wasn't the best looking, but wasn't ugly. I was pretty drunk, and it had been a while for me, so I just said fuck it and we went back to her place. My first warning sign should have been the filthy ass apartment. We start making out, she goes down on me for a bit, and when I go to take her clothes off, I smell the worst stench. Just like her apartment, I don't think she'd cleaned herself anytime soon. Like a trooper, though, I slap on that condom and go to work. That's when I realize she just lays there. No noise, nothing, Just laying there. Thank god my phone rang. It was my buddy Thomas. So I pick it up and fake it out.

"Hi Mom. What's that? Your car broke down and you're stranded downtown? I'm on my way!"

I throw on my clothes on, tell her I call her, and run out the door.

I sat in the shower for like an hour.
 

Stet

Banned
Sex with a girl I met on OKCupid.

Fit as fuck, but man, her pussy smelt of fish and I ain't even joking. Literally smelt of cod.

What do I even do here? Ain't gonna tell her 'cause it would destroy her, plus my cock was already out.

But man, it was making me limp. When she was on top I was tasting the smell and she'd ask what's wrong and I'd say nothing.

I finished on top of her, but I buried my head in the pillow so I wouldn't have to breathe in any more fumes.

I stopped texting her after that

She must have been doing something really wrong in the shower.
 
It didn´t even get to actual sex, but i ones made out with someone that kissed like a mechanical fish on dry land, just kept biting me at regular intervals while simultaneously squeezing my butt as if bread dough was being prepaired. I can´t really explain it right, but it was weird... Lost my crush right there and then.

Oh my god I literally just lost it and spit all over my screen.
 
I've told the story before, but I had sex with a guy who kept insisting he couldn't get off with a condom on. Claimed he was sterile and clean. Kept on and kept on, basically begging to remove the condom.

I got off and left. Fuck that noise.
 

Bowler

Member
I've told the story before, but I had sex with a guy who kept insisting he couldn't get off with a condom on. Claimed he was sterile and clean. Kept on and kept on, basically begging to remove the condom.

I got off and left. Fuck that noise.

that is being nice... you could have got off, and then pissed all over him.
 

dark_chris

Member
My ex gf overall was the worst sex. each time we did it was terrible.
She was bushy like all hell (refused to shave it) and she would lay there. I'd have more fun with a blow up doll than her.
 

tornjaw

Member
This isn't my story. This isn't my buddy's story. But it's a story that he told me and true or not, it's fucking hilarious.

So my buddy, Cooper, was in the Navy and he ran a shop where part of his duties were to fix parts of those big ass cannons that go on Destroyers. Well, he had two Sailors that were constantly fucked up. Their attitude: sucked. Work performance: sucked. Hair, boots, uniform, everything about them: sucked.

One morning, after the weekend, Cooper goes into work early, like he normally does and one of those Sailors is already there, looking anxious. He asks him what's wrong. The kid replies that nothing is wrong and Coop tells him that he's there when or if ever he wants to talk.

The work day ends and everyone is leaving to go home and that guy hangs back and says that he needs to talk.

The kid tells him that he got drunk over the weekend and brought a girl back. Not a huge deal really. But the guy explains it -

So towards the end of the night, the bar was shutting down and he'd struck out. He was pretty drunk and horny so he just started hitting on everyone and took the first girl back with him that wanted the D. The girl that he brings back is big. BIG. Easy pushing 250 plus.

They start getting hot and heavy, he turns out the lights and they start removing each other's clothes. She tells him that she's really into tit play so he goes to town. Playing with her nipples, sucking on them, and all around just groping her.

"Are you pregnant" he asks her? This upsets the moment and things stop for a moment and he goes back to what he was doing. "Are you sure you're not pregnant?" No, she says. "Well, you're lactating." I'm not pregnant! she exclaims.

Realizing that she's getting mad, he says fuck it and they have sex. After he's done, he goes into the bathroom to clean up. Coming back out, he turns on the light. This girl is lying on the bed, passed out. As I said earlier, she's big. So her breasts are kind of up towards he head and flopping over to the sides.

Under one of her breasts is a massive boil. In a flash, it all runs through his head : "...you're lactating..." What he thought was her nipple he was sucking on was the head of this boil and instead of milk, he was instead sucking in puss.
 

Grym

Member
This isn't my story. This isn't my buddy's story. But it's a story that he told me and true or not, it's fucking hilarious.

<snip>

Duuuuude.
Not hilarious

jim-carrey-puking-o.gif
 

Oxn

Member
This isn't my story. This isn't my buddy's story. But it's a story that he told me and true or not, it's fucking hilarious.

So my buddy, Cooper, was in the Navy and he ran a shop where part of his duties were to fix parts of those big ass cannons that go on Destroyers. Well, he had two Sailors that were constantly fucked up. Their attitude: sucked. Work performance: sucked. Hair, boots, uniform, everything about them: sucked.

One morning, after the weekend, Cooper goes into work early, like he normally does and one of those Sailors is already there, looking anxious. He asks him what's wrong. The kid replies that nothing is wrong and Coop tells him that he's there when or if ever he wants to talk.

The work day ends and everyone is leaving to go home and that guy hangs back and says that he needs to talk.

The kid tells him that he got drunk over the weekend and brought a girl back. Not a huge deal really. But the guy explains it -

So towards the end of the night, the bar was shutting down and he'd struck out. He was pretty drunk and horny so he just started hitting on everyone and took the first girl back with him that wanted the D. The girl that he brings back is big. BIG. Easy pushing 250 plus.

They start getting hot and heavy, he turns out the lights and they start removing each other's clothes. She tells him that she's really into tit play so he goes to town. Playing with her nipples, sucking on them, and all around just groping her.

"Are you pregnant" he asks her? This upsets the moment and things stop for a moment and he goes back to what he was doing. "Are you sure you're not pregnant?" No, she says. "Well, you're lactating." I'm not pregnant! she exclaims.

Realizing that she's getting mad, he says fuck it and they have sex. After he's done, he goes into the bathroom to clean up. Coming back out, he turns on the light. This girl is lying on the bed, passed out. As I said earlier, she's big. So her breasts are kind of up towards he head and flopping over to the sides.

Under one of her breasts is a massive boil. In a flash, it all runs through his head : "...you're lactating..." What he thought was her nipple he was sucking on was the head of this boil and instead of milk, he was instead sucking in puss.

I want to freaaaaking throw up mannnnnnnnn
 
puss? SUCKING?

nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nopenope nope nope nope nope nope nopenope nope nope nope nope nope nopenope nope nope nope nope nope nopenope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nopenope nope nope nope nope nope nopenope nope nope nope nope nope nopenope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nopenope nope nope nope nope nope nopenope nope nope nope nope nope nopenope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nope nopenope nope nope nope nope nope nopenope nope nope nope nope nope nopenope nope nope nope nope nope nope
 
I've had a few bad experiences, from really bad head, to regretful/boring/painful sex, stank vag and post sex surprises.

There was a time I pulled this white yoga chick. Tall, thin, blond, fit. We went back to her house thinking I was gonna check off another box on my "Fuckit List" (natural blond).
We start going at in her bed, making out, stripping off clothing, touching, feeling, all the usual pre-sex foreplay.
I go to finger her and she is unusually tight, I had to really force my finger in there, like stop what I was doing and concentrate to figure out why it was soooo damn tight. She said she was relaxed, but my finger was starting to hurt (circulation was almost being cut off)
At this point I started to lose my concentration as the only thing I could think of at this point was if my finger hurts trying to bang, how was my dick supposed to fit in there?

So I go in for a closer inspection, a visual one, using both hands and all my attention. I spread her legs and in instantly my nostrils flared and eyes widened and started to water as the stench wafted out of her like I just popped the top off of a bucket of fish heads left simmering in the sun for a week during the hottest summer on record.

It took everything I had to not gag, but I got up went to the bathroom, washed my hands, caught my breath and used the excuse that she was far too tight for me and that I would never fit. She was disappointed and so was I, but this was just not gonna happen. I thought about suggesting a shower, but really I want desperate, so I got dressed and called it a night.



I've also had night where it just seemed like I would never finish, and where my girl had so many orgasms that I literally fucked her dry. But she didn't want me to stop until I came too, she wouldn't take "to be continued" for an answer and would spit on it and just keep going. At this point (now 15 minutes of literal dry fucking) I had to pull out and pretend like I was about to cum. took it to the bathroom and had to let my boy breathe. Chafed/rubbed raw, sore and a little swollen from all the friction, "to be continued" was now mandatory at all necessary occasions going forward, no more forcing it, I'll get mine next time... not a big deal.

There are more stories, 1 or 2 of the horror story variety, but not really sure I want to share those.
 

double jump

you haven't lived until a random little kid ask you "how do you make love".
that boil story is too fucked up to be real. That's some shit you take to your grave if true.
 
I think we as men and women of the human race have a responsibility to tell people when they reek in either the genital area or otherwise.

I'm serious, we need to band together and make people feel bad about something they SHOULD feel bad about, pending any medical reasoning.
 

shira

Member
This isn't my story. This isn't my buddy's story. But it's a story that he told me and true or not, it's fucking hilarious.

So my buddy, Cooper, was in the Navy and he ran a shop where part of his duties were to fix parts of those big ass cannons that go on Destroyers. Well, he had two Sailors that were constantly fucked up. Their attitude: sucked. Work performance: sucked. Hair, boots, uniform, everything about them: sucked.

One morning, after the weekend, Cooper goes into work early, like he normally does and one of those Sailors is already there, looking anxious. He asks him what's wrong. The kid replies that nothing is wrong and Coop tells him that he's there when or if ever he wants to talk.

The work day ends and everyone is leaving to go home and that guy hangs back and says that he needs to talk.

The kid tells him that he got drunk over the weekend and brought a girl back. Not a huge deal really. But the guy explains it -

So towards the end of the night, the bar was shutting down and he'd struck out. He was pretty drunk and horny so he just started hitting on everyone and took the first girl back with him that wanted the D. The girl that he brings back is big. BIG. Easy pushing 250 plus.

They start getting hot and heavy, he turns out the lights and they start removing each other's clothes. She tells him that she's really into tit play so he goes to town. Playing with her nipples, sucking on them, and all around just groping her.

"Are you pregnant" he asks her? This upsets the moment and things stop for a moment and he goes back to what he was doing. "Are you sure you're not pregnant?" No, she says. "Well, you're lactating." I'm not pregnant! she exclaims.

Realizing that she's getting mad, he says fuck it and they have sex. After he's done, he goes into the bathroom to clean up. Coming back out, he turns on the light. This girl is lying on the bed, passed out. As I said earlier, she's big. So her breasts are kind of up towards he head and flopping over to the sides.

Under one of her breasts is a massive boil. In a flash, it all runs through his head : "...you're lactating..." What he thought was her nipple he was sucking on was the head of this boil and instead of milk, he was instead sucking in puss.

/winner
 

Mononoke

Banned
I think we as men and women of the human race have a responsibility to tell people when they reek in either the genital area or otherwise.

I'm serious, we need to band together and make people feel bad about something they SHOULD feel bad about, pending any medical reasoning.

Yeah, you just go ahead and tell someone that their genitals smell. Even saying it in a much nicer way, won't go over so well.
 
This isn't my story. This isn't my buddy's story. But it's a story that he told me and true or not, it's fucking hilarious.

So my buddy, Cooper, was in the Navy and he ran a shop where part of his duties were to fix parts of those big ass cannons that go on Destroyers. Well, he had two Sailors that were constantly fucked up. Their attitude: sucked. Work performance: sucked. Hair, boots, uniform, everything about them: sucked.

One morning, after the weekend, Cooper goes into work early, like he normally does and one of those Sailors is already there, looking anxious. He asks him what's wrong. The kid replies that nothing is wrong and Coop tells him that he's there when or if ever he wants to talk.

The work day ends and everyone is leaving to go home and that guy hangs back and says that he needs to talk.

The kid tells him that he got drunk over the weekend and brought a girl back. Not a huge deal really. But the guy explains it -

So towards the end of the night, the bar was shutting down and he'd struck out. He was pretty drunk and horny so he just started hitting on everyone and took the first girl back with him that wanted the D. The girl that he brings back is big. BIG. Easy pushing 250 plus.

They start getting hot and heavy, he turns out the lights and they start removing each other's clothes. She tells him that she's really into tit play so he goes to town. Playing with her nipples, sucking on them, and all around just groping her.

"Are you pregnant" he asks her? This upsets the moment and things stop for a moment and he goes back to what he was doing. "Are you sure you're not pregnant?" No, she says. "Well, you're lactating." I'm not pregnant! she exclaims.

Realizing that she's getting mad, he says fuck it and they have sex. After he's done, he goes into the bathroom to clean up. Coming back out, he turns on the light. This girl is lying on the bed, passed out. As I said earlier, she's big. So her breasts are kind of up towards he head and flopping over to the sides.

Under one of her breasts is a massive boil. In a flash, it all runs through his head : "...you're lactating..." What he thought was her nipple he was sucking on was the head of this boil and instead of milk, he was instead sucking in puss.

Dude no. I'll have my revenge.
 
Picked up a MILF at the gym, boned her. Ran into her daughter the next morning. She's my age so we chat over breakfast. She's making remarks about the the noises we made and we laugh.

Fast forward to the evening, I'm meeting the MILF to go to the movies, but she tells me she's been called away to work. She then asks me to show her daughter whay I did to make her come so hard that night. The daughter is smoking hot, I'm horny as fuck, so I'm like 'sure no problem.'

If that's not weird enough, shes constantly asking if she's better than her mom. It was fucking awkward and not as hot as porn makes you think.

This sounds incredible. Not for for this thread.



My worst sex story isn't all that great because I normally fuck like a champion and have a strong gag reflex. But once when I was in NY for vacation, I was with this girl back at her place, and I can seriously smell her ass. Like real serious shit. I knew it was a fluke since I'd been with her the night before and she was clean and we were both destroyed since it was 3am and we were drinking at 7pm. I flipped her over, closed her legs and fucked her prone until I came. I mean, it was gross but I'm not going to not cum.

That and every BJ I have ever received. I don't think I can cum from them anyways so its always really boring for me. I just sit there and wait a good amount of time until I tap her shoulder.
 
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