My Most Embarrassing Sex Stories To Remind You That You're Not Alone

Amanda Chatel
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From the first time I had to sex to the very last time I had sex a couple weeks ago, my sex life has been riddled in embarrassment. Why? Because I'm a walking catastrophe for the most part. I'm that woman who, if I dared to try a striptease, would somehow manage to turn it into a disaster — and I know this because I tried and smacked my head on the fireplace mantle in my quest to be sexy. Luckily, for both my partner and I, we could laugh it off, but it didn't erase the moments of embarrassment. There's nothing worse than trying to be sexy and confident, than watching it, or rather experiencing it, as it backfires... like all the times I've strut uptown in heels and felt my ankle give out. Total. Catastrophe.

But while my list of sex-related embarrassments is fairly long, I've always been able to laugh at them. Well, laugh them off 98 percent of the time, because if you want to be an awesome lay, you can't take yourself too seriously. And, obviously, I am an awesome lay. (Actually, jury is still out on that one, but I digress.)

So while I'd never suggest that my embarrassing sex stories trump yours or anyone else's, because life isn't a competition (or so we tell ourselves), I will say, I have some doozies and they're worth sharing. Not just because sharing is caring, but because you're not alone in your embarrassing sex moments and nothing proves that like commiserating... and laughing together.

1That Time I Fell Asleep While Receiving Oral

I briefly dated a bartender in my 20s who excelled in giving oral sex like nothing I'd experienced before. But since he was a bartender that meant two things for me: free drinks and waiting until last call so we could go home together. Both of which, of course, can lead to exhaustion.

So there we were, his head between my legs doing his thing when I fell asleep. Unfortunately for me, I didn't wake up the next morning to realize I had fallen asleep, but I woke up when I farted in his face. Why, yes, I am the classiest person you'll ever meet.

2That Time I Made A Guy Cry — While Giving Him A Blow Job

Amanda Chatel

Although I would never brag about my blow job ability, I think I do an OK job. (Pun!) I'm communicative, I'm open, and despite my disdain for authority outside of the bedroom, I'm really good at accepting direction inside the bedroom.

On one occasion, with a short-lived fling (I've had a lot of those), we were engaged in a 69. Everything was going really great until he spanked my butt so hard that my immediate instinct was to clench my jaw so tight, that I actually bit down on his penis, leaving bruises. But even before the bruises could form, he yelped in a way I had never heard a human yelp before, which was followed by sobbing. We both apologized profusely — he didn't realize, in his excitement, that he had spanked me so hard and, apparently, my mouth decided that was the part of my body that was going to react to his action. We were both equally embarrassed, but that didn't stop me from running a scenario over and over in my head where I actually DID bite it off.

3That Time A Guy Fell Asleep Inside Me

Whether it was karma because I had fallen asleep, then farted in the face of the bartender or because my exhausted partner had hit the whiskey too hard that night, at one point, mid-sex, I realized he'd fallen asleep.

Now, falling asleep during sex happens, so that's not the embarrassing part for me, especially since he was the one who decided it was prime siesta time. The part that made it embarrassing was the fact that we were having anal sex and he fell asleep in me, while I was flat on my stomach. In other words, I had the dead weight of a 5'11" guy on me and his penis was still in my butt. Try as I might, I couldn't wake him and had to lay there waiting for his penis to go flaccid so I could sort of throw him off my back. I'm so grateful I did yoga several times a week back then, because without proper arm strength to do a plank, I could have been there even longer than the 10 minutes or so that felt like easily an hour.

4That Time I Bruised My Tailbone While Running To Get Condoms

I have bruised my tailbone three times in my life. Once during a sledding accident when I was in high school, once during a skiing accident in college, and once while running to get condoms. Although I'm the type of person who probably wouldn't run even if I was being chased, when it comes to sex (or pizza), it's a different story.

So, on the night in question, when I realized I didn't have any condoms in the nightstand, I got up to sprint to the bathroom to retrieve more, but I never made it to the bathroom. Instead, I slipped on a National Geographic, my legs went up in the air, and I came crashing down on my lower back. Instead of having sex, my partner spent the rest of the night holding face cloths full of ice against my tailbone area. If you've ever bruised your tailbone, you know it takes several weeks, sometimes months, for the pain to finally go away. It was awful and, yes, a bit humiliating.

5That Time One Guy Found Another Guy's Condom In Me

Amanda Chatel

Although sex in my 20s wasn't all that great, I still had my fair share of it. And, always, always, always practiced safe sex. I figure if anyone is going to get an STD, it's probably me, so I should use a condom every single time.

During one of my safe sex moments, a condom got stuck inside me, which happens sometimes, and is totally normal. But the problem here was that I was having a quickie with an ex on my lunch break, so when we realized the condom was still lodged in me, I decided I'd deal with it when I got back to the office. But then, thanks to work, I forgot. So I went about my day, got home, took a shower, and completely forgot about the condom. Later that night I went out with some friends and met up with a guy I would occasionally have hot make-out sessions with after a couple drinks. I brought him home for our makeout session, and he reached a couple fingers into my vagina and — voila! — found the condom I had forgotten about. What followed wasn't just embarrassment, but me assuring him that I didn't sleep with "too many" people, although my sex life was none of his business — especially since we weren't even sleeping together.

6That Time My Dog Ate A Used Condom — And Bit My Partner

Keeping with the condom theme, once upon a time I was hooking up with a guy I would eventually date on and off  for a few years. Things were getting really hot and heavy, but he couldn't climax during sex, so he took off the condom and we tried some oral instead. Unbeknownst to us, my dog had swiped the condom from the floor and had made it his new chew toy. When my partner got up to go to the bathroom, he noticed what my dog had and tried to take it away. Refusing to give up his new prize, my dog viciously attacked him, almost taking off a few of his fingers.

The first wave of embarrassment came from my condom-eating dog, the second wave of embarrassment came from the fact that he had to go to the ER for the attack, and the third wave of embarrassment came the next day when my dog pooped the condom out on a New York City sidewalk. Thanks, Hubbell!

7That Time I (Accidentally) Had Period Oral Sex

First and foremost, I'm an advocate for period sex. That being said, I hooked up with a guy while I had my period, but didn't know I had gotten my period. We were in a dark room, we started messing around, and he asked me to sit on his face, which, honestly, I'm not a big fan of, but I try to be a fair partner, and that involves giving and taking. After spending far too long straddling his face, he got up to go to the bathroom, and that's where the screaming started.

He wasn't screaming because it was period blood, he was screaming because the blood on his face led him to believe he lost a tooth, of all things, despite not feeling any pain in his mouth. It took a fairly long time to convince him that he hadn't lost a tooth and that I had just gotten my period. Like, a scary amount of time considering all the evidence that I presented him.

While my list of embarrassing sex moments is longer than this, these are the ones that will always stick out in my brain and will forever make me cringe. Like, I'll be on my death bed still running these seven over and over in my head, obsessively. But while they were indeed embarrassing, it's the risk you take when you have sex — embarrassment and sex sometimes just go hand-in-hand. The most important thing is to be able to laugh it off, chalk it up to experience, and realize no one is without at least a couple embarrassing sex stories. The key to having great sex, is not taking yourself too seriously, and being able to have a giggle when appropriate.