17 Of The Most Wildly Entertaining Sex Stories Ever Told

SteveHolt9 years ago

Is there anything better than sex? Besides my mom’s homemade chocolate chip cookies of course. Even when sex is bad, it’s still pretty good. Me, myself, have pleasured many ladies from around the globe who can attest to that.

While sex is mainly full of good times, some folks can tell you that things can also go south pretty fast, and I’m not just talking about her. Hi-O! Up top! The dark corners of Reddit dot com bring us some truly horrible stories of sex.

I had a seizure while doing my wife. Neither of us finished unfortunately…

Yet girls always say they want a vibrator.

Drank way too much free champagne way too fast on New Years Eve. Met a girl, ended up hitting it off, dancing, and we caught a cab together. I was already feeling nauseous at this point and wasn’t going to invite her over, but she said “we can go to your place.”

We were making out standing up, started stripping and I pulled her down onto the couch. Sitting down quickly made my head spin and I was on the verge of hurling, barely holding it in. She starts riding but I can’t hold it in anymore. I take off my festive New Years cardboard tophat and vomit into it with her staring right at me. Needless to say, that killed the mood.

I respect his choice in keeping the hat on while she was riding him.

I had just left a 13 year relationship that started when I was 14. I was meeting some guys from online dating sites, and had found a few I really liked. One night I was bored as hell and decided to meet up with this guy I’d been messaging with who seemed nice enough but a little dull. He talked like a hipster but I thought he was being ironic.

I got to his house. Nice place, clean, except… PBR cans EVERYWHERE. We went for a walk, talked, he asked if he could see my tits when we got back. I shrugged and said “sure”, because they’re awesome and I love showing them off. He asked if I wanted to see his cock. I did, because why not? He asked to tit fuck me, and I shrugged. I was kind of surprised he wanted to tit fuck someone so clearly apathetic, but honestly I didn’t have anything better to do, so I let him. He moaned things like “spit on it”, and when he came, he asked me, “Where U want dis nut?”

After I wiped myself off and put my shirt back on, he played me a rap song he’d made and had professionally produced. It lamented things like going to make a sandwich only to find that the bread was moldy. I left, and never spoke to him again.

From that night on, when in doubt, I masturbate.

This is why you can’t bone hipsters.

Was fucking a girl doggy style looking down when I pulled out too far and my dick hotdogged between her butt cheeks and i came in my own face, bout it.

Semen is good for the skin.

The first time I met a couple for a threesome.

I drove to their apartment and we began to fool around. The wife was sucking me when suddenly she stood up, said, “I need to go for a second,” and left the room. Her husband went with her, and they were gone for a few minutes, with me deflating in their bed. He came back in and said, “Nothing to worry about, she’s having an asthma attack. I gave her her inhaler and she’s sitting in a warm bath. She’ll be out in a few.”

He then begins to give me the absolute worst blowjob I have ever received. He gave my head a hickey as he sucked me. I don’t generally like oral sex, but this was absolutely painful. After a minute or so of my politely pretending to smile, he heard her call faintly and stepped out again.

He rushes back in and says, “We’re going to have to finish up quick. Her asthma isn’t getting any better, and I’m going to have to take her to the hospital. So I’ll jerk you until you cum and then you’ll have to go.” WHAT?! Your wife needs to go to the hospital and you’re gonna give me a handjob?!

So I let him jerk me a little, again, horrific. I faked an orgasm through my cringes (claimed that sometimes I shoot blanks and thus I was done) and he rushed me out, saying the words I wish I could forget:

“Sorry, she’s pregnant and we just have to be sure the baby is okay.”

Also I got a speeding ticket on my way home.

Jesus dude. What is wrong with you?

Growth spurt in her mouth, she threw up on my dick. Wiped it off and we finished.

She’s a trooper for still going.

ive had 2 girls start crying like 30 seconds after i put it in. they both wanted to keep going too. sorry but that shit is weird, it totally ruins it for me

Girls cry after they have sex with me too because they don’t want it to end.

Had feelings for a friend of mine, started sleeping with him, he told me he was thinking of his dead girlfriend the whole time.

Banging your dead girlfriend’s image is hot.

Drunken anal sex led to ejaculation followed by bloody jizz fart expulsion onto pillowcase.

That poor pillowcase.

She sharted on my legs and in her panic to get up, kneed me in the yarbles. Talk about a shitty way to get blue balls.

She was just kicking you while you were down.

well, I gagged a couple of times, even though she said she had already taken a shower

so…I wonder what it would’ve been like BEFORE the shower?

I myself have eaten some pretty skunky sushi before.

I was with a girl who had just gotten an IUD that very weekend. What she neglected to tell me was that you are supposed to wait up to two weeks after getting the IUD before having sex, as there is a little copper wire that hangs down into the vaginal barrel, that naturally retracts back in or something after a bit of time. She only waited two days, and things got hot. We start going at it slow, and then I decide I’m about to lay down some pipe. I pick up the pace and almost instantly stab the end of my dick with this copper wire. I pull out in pain to find my dick bleeding, at which point she decides to tell me there may be stray metal inside her. I still have trouble getting up sometimes if that thought decides to pop into my head.

I think she’s liable for your damages.

I had a girl break my nose with her pubic bone. Neither one of us realized it at the time, and kept going for a good twenty minutes of oral.

When we turned on the lights, it looked like a particularly heinous murder scene.

Wasn’t the worst, but certainly the most shocking.

Worst was a woman who just laid there passive and did not much of anything at all in the way of response.

When YOU get murdered by the pussy.

Ate a red head out with gum and got it all stuck in her pubes, had to stop to get scissors and cut it out.

Same girl was on top, same week, and kind of just jumped on my dick, i was not circumscized and it literally ripped the foreskin away from my shaft and blood was everywhere. Not sure if we hung out too much after that.

May the power of circumcision compel you.

He lasted 25 seconds, told me he would have lasted longer if I would have let him put it in my ass, then played “I Just Had Sex” by The Lonely Island loud enough so that his roommate would hear.

This guy knows how to make sex.

My father died two years ago mid-sex with my stepmom, Im not sure if thats the best or the worst way to go out.

That is the best way to go out.

Morning sex is usually the best way to start the day before heading into the office we both work at. I’m down there enjoying my happy meal when I decide to pop my thumb up her bum. Something we’ve done dozens of times before with great success.

It slips in nice and easy, bit of a contented moan from her then she realizes what I’ve done. She panics because she’s positive she carrying a full load and clamps up so hard that I can’t get my thumb out. The knuckle, I have long fingers and big knuckles, gets trapped on the wrong side of her butt clamp.

She’s yelling at me to get it out and I can’t. She thinks I’m goofin and starts trying to shake me loose but is also tightening up her grip. I’m starting to sweat that it’s going to end in an ER trip as my thumb starts losing all feelings.

She does a spin and my wrist is almost broken off but with a tug I pop out with mementos of taco tuesday squirting on the bed.

Needless to say it was a very awkward ride into work that day.

Thanks for ruining Taco Tuesday, jerk.

To read more stories like these, click here.

For the fastest way to keep up with TFM, download our free smartphone app.