Sex is inherently embarrassing—sweat, grunts, involuntary (and voluntary) noises, and body parts pressing together (and sometimes, squelching apart!). Sex is also inherently subjective; all of our bodies and minds are unique in their cravings and reactions. Yet, we continue forth in the pursuit of intimacy and orgasms—and hell, in the name of fun!

Given the complex and kinda risky business of sex, we went in pursuit of real sex-skeletons: stories of sexual bloopers, bumps, and other weird or awkward situations that women have collected in the pursuit of sex-stasy. (Worth it!)

See below for a collection of 15 such stories from real women who were willing to tell all.

Beyond the Impale

“I impaled my ex’s dick with my IUD when I didn’t wait the appropriate amount of time to have sex. He got a small red welt and refused to sleep with me for, like, a week after, and for the month after that would constantly be like, ‘I think I feel it.’ It was clearly a phantom trauma thing—I mean, I went to the doctor to check that it had recoiled enough!” –Tammy, 27, New York City

A Hairy Situation

“My man has a very full beard, and last week when we were having sex I got trapped in it! As in, pieces of his beard got stuck between my teeth like floss. It took two or three mighty pulls to break free—after which we both died laughing.” –Mina, 33, Santa Barbara

Next Time

“During my senior year of college, I had just gotten out of a long relationship and decided to try my hand at casual sex. I woke up one morning horrifically hungover and curiously horny, so I gave this new guy a call to come over. We got down to it and I probably should’ve taken his complete lack of kissing skills as a warning sign, but I like to give people the chance to prove themselves.

We started having sex and, my God, it was the absolute worst. There was ZERO foreplay, and it was like he was a jackhammer and I was the sidewalk. To top it off, right before he came, he said, ‘I’m just gonna finish, I’ll get you next time.’ He proceeded to fall asleep in my bed and I was stuck with him for hours. I was almost afraid to have sex again after that because I thought I was doomed to only ever have horrible experiences like that.” –Sydney, 26, Brooklyn

“I was dating a friend of a friend, and he asked me not to tell our mutual friend about us having sex before we had even done anything. I’m thinking this tall, skinny fellow is probably packing a pencil, but we got down to business and his pants came off and I had to stop him from moving so as to not put a hole in the ceiling. IT WAS AN ABSOLUTE MONSTER: Nine and a half inches of massive, girthy peen, which I have referred to ever since as ‘cockasaurus rex.’

There wasn’t enough foreplay in the world for my nerves, and his attempt at putting me at ease was hovering over me and saying, ‘Let me know if it hurts, my ex used to cry every time, so I want to be careful.’ I had to act like I wasn’t horrified while he tried to ‘make love’ on top of me while I was cringing and on the verge of death. He came as soon as the head made it about an inch in. This was all panic-inducing, not to mention he will go down in history as the guy who exclaimed, upon seeing me naked, ‘It’s so cute how your thighs touch!’” –Anne, 28, London

Pillow Tears

“I was in the early stages of dating my boyfriend, and he was the first man I really liked after one of the most traumatic breakups I’ve ever been through. After a particularly triumphant romp, I broke down crying and let him know I didn’t like him THAT much, and that this wasn’t actually going to work out. To which he responded, ‘Actually, I think you really like me.’ Certainly not my finest hour.” –Margery, 28, New York City

Let Me Get This Off My Chest

“One time when I was having very drunk and sloppy sex, I was on top and I threw up all over this guy’s chest! The worst—or best?—part was how unfazed he was. All he did was take his shirt, wipe up the mess, and kept going.” –Jenny, 33, Los Angeles

Cum Toot

“One time, I was on top and let out the LOUDEST fart just before my climax. Thankfully, it was late and dark and we were both tired, so I was able to roll over and pretend to be asleep before either of us could address what had just happened. Since, though, I’ve relaxed a bit and have coined the term cum toot, as it has happened to more than one girl I know. Ladies, relax and let it goooo!” –Vanessa, 30, Santa Monica

TP Trauma

“I’ll admit I enjoy some doggie style, however, when you’re in the middle of it and your guy says you have toilet paper stuck between your butt? Not good. I’m pretty sure I died. Definitely no orgasm for me. Now I always make sure I’m clean everywhere before getting busy.” –Cassie, 29, Boston

Disappearing Act

“My boyfriend and I were in bed together for the first time, and after amazing sex, he asked me where the condom went. I didn’t know. This was embarrassing, since we had just met. I went into the bathroom to look for it myself with no luck. We fooled around a bit more and he managed to stimulate me while finding the condom inside me and pulling it out. I turned beet-red but was pretty impressed at how gentle he was.” –April, 27, Denver

Foot Fun

“On the way home from a first date, my date and I started making out in the cab. Things were getting hot and heavy when suddenly he reached down, flipped off my flats and started cracking my toe knuckles! ‘Do you like that, baby?’ he asked. The truth was, there was only one of us in the car with a foot fetish. That knuckle-cracking action definitely broke the first-date chemistry for me, not to mention gave the cab driver a story for later.” –Marissa, 33, San Francisco

Red in the Face

“During one particularly drunk hookup—the kind where you have mere introductions before inviting them home—my new friend went down on me before we both passed out from the booze. In the morning, when he got up to use the bathroom, I heard him gasp and walk back out. “What the hell happened to my face?” he asked. It was covered in blood. I had started my period, and it had dried all over his face. Needless to say, this was not the start of a great love story.” –Madeleine, 35, San Francisco

Spicy Sex

“My husband and I were getting busy after dinner a few months ago, when suddenly his fingers started to feel good. Really good—I was super tingly and sensitive, and everything was on another level than it usually would be only a few minutes in. Just as quickly as it had started to feel amazing, though, it went south. The sensitive, tingly feeling turned into a burning that turned into a searing pain.

I curled up on the bed while my husband started to panic, and in the chaos we realized: he had made burritos for dinner, which involved dicing fresh jalapeños, and the jalapeño oil was all over his hands, which he then put all over me. We frantically Googled how to fix it, and the best solution was to put full-fat milk or yogurt on the—ahem—affected area, but we didn’t have any dairy in the house. He literally ran to the store at 11pm and brought home four different kinds of yogurt. I spent the night putting it all over my lower half and crying from laughter and pain while he held my hand—after scrubbing them with yogurt and several other jalapeño remedies.” –Roni, 28, New York City

“One Friday night a month or so into dating my boyfriend, we went back to his apartment after drinking and had a typically wild and loud night of sex. He’d mentioned that his brother was coming to visit that weekend, but since I hadn’t met or seen him, I assumed he wasn’t arriving until the next day. Wrong: Turns out that he was out with friends and came back shortly after we did, and slept in the common area outside my boyfriend’s room. I will never forget meeting the brother for the first time, wearing the outfit I’d worn the night before, knowing he’d heard all of my drunken moans. So not the classy first impression I wanted to make!” –Hailey, 29, Brooklyn

Flush Focus

“One time during sex, my face got so red and confused-looking that the guy finally stopped to ask me if I was OK. The truth was I was just concentrating a little too hard on orgasming.”  –Terry, 28, San Diego

A Religious Experience

“I was out at a party with my boyfriend, and after a few drinks, we got a little hot and heavy and realized we couldn’t wait until we got home. We decided that we’d walk a bit and find a spot—luckily for us, we found the perfect place to get down … on the grounds of the National Cathedral. We found a hidden spot and had at it, until we realized that we were definitely being watched. And that our voyeur was very, very appreciative.” –Samantha, 27, Washington, D.C.

Weird and Embarrassing Sex Stories | StyleCaster

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Replies to This Discussion

About the only place I've had sex was in a cemetery.  And then it took us about a half hour to find the car, afterward.

Honestly I like it between the sheets. I have a thing where I can't cum unless I'm comfortable in an environment where familiarity takes center stage. I used to hate sex because I never realized people did this as a recreational activity. I'm disgusted at some of the things people do for pleasure, and you never see this more apparent than this intimate portal to ones very soul. So yeah it's personal to be in a place where the soul is at its most freeing point to regenerate itself in the orgasm of a lover, preferably one with my mark on them.

we actually didn't plan it that way.  lol  And yes, doing it for recreation, or saying it's fun' just doesn't sound right.  Asexual or not, a commitment of some kind should be there.  After all there are trust issues.

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