revised_LIFESTYLE_HUMOR_EMBERRASING_STORIES

Funny Sex Stories

3 months ago by

A few months ago The New Yorker ran a cartoon series about sex I can’t stop thinking about. You can see it here. I’ve never seen the strange and yet common nature of sex so hilariously and accurately described.

Sex is messy, complicated, and above everything else, one of the funniest things we participate in as humans (I think).

Yet we take it so, so seriously. So seriously, that we find it devastating when it doesn’t look like what it looks like in the movies (spoiler alert: it will never look like what it looks like in the movies).

So let’s all relax and laugh a bit at the weirdest things that have happened to us during sex. Below is a collection of a few anonymous embarrassing dating stories we’ve collected and we’d love to hear yours in the comments!

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“A couple of years ago, in an act of trying to be the ‘effortlessly cool girl that all guys instantly fall in love with,’ I decided to do something that’s super unlike me to impress a dude. I went to his apartment to have a drink—having already been out drinking—and when I got there and he offered me a joint, I decided why not?? Let’s be clear. I never smoke pot. I have nothing against it, but outside of trying it once in high school and maybe smoking two more times in college, I’ve just never really bothered with it.

So in my drunken stupor, I got suuuuper stoned. So here I am, drunk and high (the picture of a model citizen) when things get going with this guy. We’re in his bedroom, lights are on and the sheets are white. We’re having great sex when all of a sudden, he thrusts at a slightly odd angle and something doesn’t feel right. We both look down and there is blood. ALL. OVER. THE. BED. We both start freaking out. It’s not my period, but there’s a lot going on. Cut to me sitting on the bed with my hips under a pillow, trying to elevate my vagina (???) while he’s trying to get the blood out of the sheets. But it’s a lot of blood, and we’re both pretty messed up. He looks up at me and his face goes totally white and he runs to the bathroom where I can hear him start to vomit. 5 minutes later, I’m right behind him with my face in the toilet and blood—now more of a trickle—running down my leg. After frantically trying to decide if we needed to go to the hospital the bleeding stopped and we eventually fell asleep.

We’re married now. Anyone that still wants to date you after a night like that, let alone marry you, is definitely a keeper.”

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“My college boyfriend and I had just finished having sex — like ya do in college — when I had a devastating realization, I DON’T THINK I TOOK MY TAMPON OUT BEFORE WE STARTED?! I checked. No string. WHERE THE F*CK DID MY TAMPON GO?!

It was nowhere to be found OUTSIDE my body, so it must be INSIDE my body. Like DEEP inside. A siren was going off in my head, TOXIC SHOCK SYNDROME. TSS. TSS. TSS. YOU’RE GONNA DIE.

For the next hour I made my college boyfriend go “spelunking” for my tampon in the deep crevices of my female nether region, flashlight and all, only to come to the realization that I had indeed removed the tampon and all was right in the world.

Except for my college boyfriend. He never recovered and we broke up a few months later.”

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“My ex-girlfriend is currently engaged to my manny.”

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“I grew up in a small-town and the first time I went to buy condoms, I specifically drove to the Walmart two towns over so I wouldn’t bump into anyone I knew. I sifted through the isles and picked up lube and two different boxes to try out. I got into the check-out line behind a tall man wearing a kippah. He turned his head—it was my rabbi. His eyes went slowly from the condoms up to my eyes. “Happy Hanukkah!” He said with a hand outreached. My eyes went from the condoms, to his outreached hand, and up to his eyes. “Happy Hanukkah to you too, sir.” I tried to transfer the lube and the two boxes into my left hand so I could shake his hand with my right. In so maneuvering, I dropped everything splat across the floor, of course. He saved me with, “You know, I actually forgot something in the store. I’ll run back—why don’t you take my spot in line?” I thanked him, and he wished me well. Oy vey.”

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“It was sophomore year of college when I was sitting in the library, recapping my sex life to my friends over text. I wrote out a long text explaining my escapades–how I met this guy and went over to his place at 3am, how we hooked up, etc. And then, I pressed send only to look down and realize I sent it to my mom instead of my friend, Monica (Mom and Monica are dangerously close together in my phone book, apparently). I immediately sent her a text, telling her not to read it, but it was too late. She already had. She obviously went straight to my dad to tell him what I was up to at college and how horrified she was. His answer: ‘She’s just young!'”

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“I had been trying to meet up with a boy who I’d been flirting with since day one of college. He was taking too long though, and while waiting for him, I started dancing with Drew. Drew’s dancing was somewhat infamous. He would just stand in one place and lean back almost to the point of touching his shoulders to the ground. Dancing together meant him holding me and guiding me into a similar lean. It wasn’t so much attractive as it was an impressive physical feat…

We went back to his room (which I learned was on the same hall as the boy I had been initially looking for) and immediately started undressing. He kept giving me an uncomfortable grin that was clearly meant to be seductive. The second his clothes were off he, without pause or warning, stood up on the bed (which he informed me later was his roommates because he hadn’t wanted to make his), pointed at his dick while reapplying his grin, and began helicoptoring his dick around.

I left hastily after we fucked but realized right as I exited the building that I had left my underwear. I returned and he found them after a quick search and asked me if I was sure I wanted them. I just took them and walked out the door, immediately running into the initial boy I’d hoped to find and subsequently crawling away.”

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“I decided that I wanted to kiss a girl that night. I made it casual, but it was my first time saying anything like it out loud.

Instead, I ended up at a late-night grilled cheese truck with some friends and plans of going to bed after. All it took to derail plan A and plan B was a random, somewhat skeevy guy to compliment my tie.

I found myself making out with him under a tree in front of some confused friends, and then back at his place. He had two roommates in a dorm-room that was not meant for three people, and they kept knocking on the door as we were hooking up to ask if they could return yet. When he started making moves to go down on me, the most cringeworthy and simply confusing moment I’ve ever experienced in a sexual context occured: he pulled lint from my belly button!! He locked eyes with me and dangled it back and forth for a solid, unbearable 20 seconds. I went from initially embarrassed to horrified and freaked, but apparently I couldn’t let it all be for nothing, so we exchanged no words and he proceeded to go down on me.

Out of kindness to his roommates, I left as soon as he stopped. He messaged me repeatedly for the next week, and I said nothing back until his “you’re not great at responding,” to which I replied “lol,” and that was the end.”

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“On our first date he accidentally made a u-turn on a one-way street.”

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“My sister and I were at Coachella for the first time.

Her friend had been before, so he took it upon himself to meet up with us frequently and show us the ropes, which I of course found extraordinarily generous. In our brief interactions scattered across two days, I learned that he was on the wrestling team (he showed us some moves), had recently received certification to be a yoga instructor, and planned to attend Hampshire College in the fall with the hopes of majoring in a self-designed degree, “Happiness.” To my high school self, he seemed ‘not like other guys’ and thus well suited for being my first.

On the last day of Coachella, that holy 4/20 Easter, my sister and I split up so I could watch the Pixies and she could bask in her new love for EDM. While trying to reunite with her, I nearly got trampled in the throng of teens who couldn’t quite figure out how to enter the tent. I was half-panicking, half-accepting that I might never find a way off the ground, when I heard him calling my name. He pulled me up, asked me if I wanted to get out of there, and bent so I could jump on his back.

He carried me out of the crowd and to another part of the festival where we started dancing, and then I kissed him. He brought me to a nearby tree where we lied down and continued making out. I had previously decided that if I were in a situation where I was going to have sex (which was far-fetched when I’d imagined it), I would play it super smooth and not tell him it was my first time because I didn’t think of it as a big thing and didn’t want him to.

So, we’re making out (it’s getting pretty heated in the middle of Coachella), and I decide now would be the natural time to ask if he had a condom— a slick way to indicate I’m tryna. He just moved away and laughed a little. “Here?” he asked in a way that both implied he knew I was serious and conveyed he thought it was a ridiculous statement. I mumbled something along the lines of “no, just a condom in general… a condom somewhere in this zip code?” He just rolled with it and invited me back to his campsite. He didn’t want to do it in his tent because his friends might come back and have nowhere to go— how thoughtful, I swooned. Instead, he took one of their sleeping bags, and I helped him zip it to his. He then placed it on the ground between two large trucks for privacy, and I had sex for the first time right then and there.

It didn’t last for too long because after a short-bit he stopped and asked if he could go down on me. He did, and I left right after to take another stab at finding my sister.”

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“My senior year of college, I was sleeping with a freshman boy. He was definitely super cute, but still, I thought that I was doing him the favor. I mean, what straight, freshman boy wouldn’t want to be sleeping with a senior girl?? And then he ghosted me! Like seriously, what the hell!?! Embarrassing!”

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“The second time I hooked up with the first guy I’d ever had sex with, we were in the middle of it when he asked “do you want to try it from behind?” I immediately laughed, said “ew, no,” and brushed it off. The next morning it suddenly dawned on me that no, he was not casually asking to do anal. I was embarrassed but mostly just felt bad for calling him gross. We never talked about it until I finally brought it up about four months later, when he (kindly) laughed at me a lot. We’re dating now.”

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