What makes a bad sex story the worst sex story? There is so much disappointing virginity loss, so many intrusive animals or parents, untold semi-public sex encounters foiled by police. There are many UTIs, though maybe only one involved orange squirting. Surprise anal probably could be its own anthology, as could “ejaculate in unexpected places.” (Eyes. Ears. Emitted from one’s nose mid-giggle.) So much of it is lubricated or utterly spoiled by alcohol.
But the below 10 stories managed to make even those sexual misadventures pale. Make your brutal choice among herculean feats of awful sex. Surely not as brutal as actually experiencing it.
1. The Unexpected Exclamation. While the man who wanted to be called Clifford the Big Red Dog — doggie style, get it? — during sex was a strong contender, as were the ladies staging their own sexual non sequitur contest, it was hard to beat this particular episode of dirty talk:
I met some guy at a party, and ended up going to his house… Mid-thrust, he started laughing manically and yelled “I am fucking an alien princess! I am fucking an alien princess!” I, far too sober, immediately stopped, and then had to listen to him say, with wide eyes: “your vagina looks like the fridge scene in Ghostbusters.” I fell asleep and woke up in the morning to him eating a whole key lime pie in bed. Not even looking over at me, he said: “you can’t have any.” I walked home.
2. Bent Out Of Shape. There were many physical contortions and injuries that hurt to read about, but even for a lady, this one was most painful:
While riding me cowgirl, an ex bounced up too high, I partially slid out, she came back down and my penis kinked in the middle, to the left. I felt the snap echo through my entire body.
Horrible screams. A shame, it was pretty fun up until that point. It stayed like that for nearly a year when one day it miraculously straightened itself.
3. The Full Release. It would be easy to stack the list entirely with gross-outs, but not everything can be about poop. (Or vomit. Or pee.) But it can sometimes!
I was fifteen. My first boyfriend had talked me into giving him a blowjob, his and my first one. After some hesitation, I began and everything seemed to be going as he described it would be. Half way through, I noticed my chest felt really warm and wet. I looked down and to my horror, there was an indescribable amount of diarrhea covering my white shirt. To this day, I’m not sure what happened. Of course the real fun part was when I had to left my t-shirt over my head to get it off.
4. The Brass Ring. Never again will we doubt whether Farrelly brothers-style slapstick ever happens in real life. Bonus points for urination add-on.
It was the first time I had sex with this guy, and he was hitting it from behind on his big brass bed. At one point, I was getting tired, so I went to turn my head to make eye contact (I had read that that made guys crazy) and I realized that my head was stuck between the brass posts. I was like a kid in a banister, and kept imagining firemen having to save me. My date sure couldn’t save me – he, in fact, laughed so hard that he peed on the floor.
5. The Sweaty Political Fetishist. This contender, salvagedgrace, made it based on a buffet of transcendent terribleness, all in a single, epic romp.
the first (and last) time i ever had sex with this boy, he managed to go wrong on just about every level:
1. five minutes in, he was sweating so much that he had to stop to ask me for a towel- my room was not hot, and it was definitely not a strenuous five minutes. sadly, he was on top, so i can empathize with victims of waterboarding.
2. the dirty talk came in full sentences- each one had a subject and predicate. such as…
3. “you are my sexy little socialist.” (he is a republican and i am not) definitely not the venue for political discourse of any kind, let alone when said during one of the many time that he….
4. stopped f*cking so he could stare into my eyes. no joke, at least a dozen times he pulled back to give me this puppy dog face because somehow during this farce he’d decided we were soul mates.
5. he kept going soft, which wouldn’t have been so god awful if he didn’t stop to blame the condom each time. and in the manner of a stand-up comic. “what, are these condoms made out of lead or something?!”
5b. extra obnoxious when it’s followed, almost immediately, by “i love how good it feels inside you.”
6. he not only tried to jackhammer during our inaugural romp, but he actually tried to force the mattress to spring him. all this did was result in a really uncomfortable series of thrusts where his rhythm didn’t match the mattress and his cock just stabbed me a few times.
7. he kissed fine outside of bed, but once in bed the kissing was relegated to tiny pecks in rapid succession, and with his eyes open.
8. i have large breasts, which he often claimed to be a fan of. given that he’s a big, rough and tumble kind of guy i expected some decent groping out of this combo. no such luck. instead of quality love and attention, my breasts were delicately patted with an open hand even after the third time i told him that he wouldn’t break me.
9. during sex he actually apologized for being ‘inappropriate.’ i’m not a subtle girl- you’ll know when i want an apology from you, and it’s a really slim chance that it’ll ever be while you’re inside me.
10. when i had exhausted every other trick in my book and this still wasn’t over- i asked him to bend me over so he’d feel more comfortable objectifying me and i wouldn’t have to see his face. i positioned the requisite hand to guide him into place, and after a couple minutes realized that he still hadn’t made contact, despite all his talking. it wasn’t until i moved my hand away and he made a joke about ‘falling out’ that i realized he’d didn’t know that he’d been fucking my hand instead of me.
6. The French Connection. Parental walk-ins are a popular part of the sexual horror story pantheon, as are trips abroad, but only this one included an unexpected parent, transnationalism and a champagne bottle up the ass.
A few years ago, my French bf-at-the-time took me to Paris to meet his family….His mother, a haughty Parisienne who believes that her only son is GOD, and that no girl could possibly be classy enough to deserve him. Their regard is mutual – he worships her as much as she worships him.
One evening after a champagne-soaked dinner, she left to go to the theater. Expecting that she’d be gone for several hours, we started having regular sex, and then anal sex, on a couch adjacent to the table at which we’d had dinner. Things kept getting hotter, and my b.f. started f*cking my ass with the slim end of a champagne bottle. This felt good at first… but then I realized that something felt off. I slowed him down in an attempt to understand what on Earth my body was doing, and I realized that my bowels were moving. And I kind of realized that it was too late to stop what was happening.
At this already Godforsaken moment, we hear a key in the door and his mother pops into the room. The bitch had forgotten her shawl or something. So there I am, naked, on her couch, while her son, also naked, is holding a champagne bottle that is obviously deeply embedded in my ass. We shriek, and he yanks out the bottle. And immediately out comes a LARGE, dark brown, smelly piece of poop. It just rolls out – this felt like it was happening in slow motion, and I kept trying to stop it but I couldn’t – and lands on her couch.
The French boy and I broke up shortly thereafter. I dumped him – pun intended.
7. The Thwacking One-Hit Wonder. While we are in theory sympathetic to performance anxieties, this tragicomic encounter with an oblivious underperformer makes us pity the girl more than the guy.
The fact that he was a grown man who still called himself Timmy should have tipped me off that this wasn’t going to be the most satisfying experience. So Timmy was a fairly sweet, if dim guy and before we had sex he told me he’d had sex with a few girls, but only one time each and he didn’t know why. I was all, “That’s so weird! You’re totally cute, let’s have sex twice today.”
Half an hour into fooling around, I figured it out. Not only did he not get hard at all, it seems that no one had ever told him that you need to in fact be erect before trying to penetrate a woman. He kept holding his tiny, limp dick and trying to kind of…just…flop it inside of me, I guess. I tried my very best to, um, rectify the situation and get things really going, but he kept saying, “What’s wrong? Why won’t you just put it inside you?” So I just sort of…shoved his flaccid penis inside of me and he started to moan like it was feeling really good for him. Then it promptly just fell out.
I remember how sad and floppy it looked lying against his leg and then how pitiful the whole effort was as he started to rock against me, gently thwacking his droopy, listless penis between my legs as though I must be the luckiest girl in the world. Needless to say, we did not have sex more than the one time. I wonder if he has since broken that streak.
8. The Unwanted Stump. Even the most kink-oriented coupler (or tripler) has boundaries. And for this person, that was one man’s sweaty stump.
I had finally agreed to a threesome with the man I had been involved in a Dominant/submissive friends-with-benefits situation for the last four months. Since this was largely my fantasy that he had wanted to fulfill, it was going to be a male-male-female threesome. I was nervous, to say the least. He had agreed to write up an ad for Craigslist, let me review it before posting, and screen all the responses…We finally settled on one-not my first choice, or even my second, but he actually followed through.
….I knew that if I could see what was going on, I wouldn’t go through with it, so we agreed that I would be blindfolded and he would take care of me, gauging the situation and making sure the Guest didn’t overstep my limits.
I was kneeling, blindfolded, in the middle of the living room, when the doorbell rang… It didn’t take long before Guest was naked and in my mouth. Nor did it take long after we rolled around a little bit and had changed positions that I started feeling little “feather brushes” against my arms. For the life of me, I could not figure out what the feeling was-they were without pattern but distinct and localized sensations against my skin. It wasn’t until I started feeling them on my face as I was essentially tea-bagging him that I realized that HE WAS SWEATING ON ME. The Guest, this man I had just “met” in the loosest of terms, wasn’t simply sweaty, he was sweating large, gross, hairy man sweat droplets all over my face and torso.
That should have been my clue to stop, but I’m a trooper and a bit loathe to cause a scene. Besides, my Man was there, I knew I was safe, and he and I were having fun.
Fast forward to the end of the afternoon. I’m on the floor on my back after my Man and I finished fucking, kind of spent from all the activities, but still blindfolded. I can feel the Guest’s hands on me, and he asks if he can get me off again. Not one to say no to an orgasm, he starts attending to me digitally. But then the sensation changes-it feels as if he’s trying to fist me, but with his palm or something. The feeling is off…and then it hits me: The Guest is an amputee and is TRYING TO FIST ME WITH HIS STUMP! I don’t go for fisting to begin with, but trying to fit his stump in my vagina was just never going to happen, so I stop the scene, he leaves, and I go to the bathroom to clean up.
When I come out, I turn to my Man and ask, “What he missing a hand?”
“Yes he was. I didn’t think it would be polite to turn him away just because of it though.”
“That’s true, but Stumpy tried to fist me with his stump! Without asking! Had he tried to fist me, that would have been bad enough, but stumping without permission is just poor form.”
9. The Bloodstream Blood is almost never a welcome visitor to a sex scene, be it menstrual blood after a foiled loss-of-virginity attempt, or surprise nosebleeds during cunnilingus — twice. And torn genitals were surprisingly common. Still, this is surely the worst blood-related indignity.
I was “manually prepping” him and thought it was weird that there was so much precum. Eventually, I flicked on the light to grab a condom and he said “Oh my god, you’re bleeding!” I started freaking out. How could this be?! I just got off my period. My hands, stomach and thighs were COVERED in blood…but my nether region was clear. Then, I look over and I see blood literally GUSHING out of the head of his dick. I was so freaked out I just yelled “YOUR DICK IS BLEEDING” and ran out of the room….
He was more mortified than I was…if possible. He told me about a month ago, he was really wasted and zipped the head of his penis in his pants. Being super drunk, he couldn’t dislodge it, so forced the zipper down/yanked his dick out. He then passed out to later find himself on a blood soaked mattress. The doctor told him he needed stitched to close it back up, but didn’t do it…leaving both his penis and me scarred for life.
10. The Would-Be Artist And if that was too much bodily-function misfire for you, here’s an after-sex discovery to end on a possibly sweet, if totally fucking weird, note.
As a freshman in college, I decided to nurse the wounds of a bad breakup with a one-night stand. I should have run in the other direction when the guy told me he was working on his “memoirs” (he was 19), but I was pretty desperate. The sex itself was awkward, passionless, and boring, but the real treat came the next day. I arrived back to my dorm room in last night’s clothes, and as I was changing to head to the showers, my roommate noticed something weird on my ass. Turned out the guy had drawn on me while I was asleep…a sailboat, a cat, and a rocketship, all on my butt, all in highlighter.