Horrible Hookups: The Funniest Sex I’ve Ever Had
Here are five of my more cringey, funny, and generally awkward sexual experiences. Sometimes sex is weird. But it’s important to roll with the punches and laugh it off. This is me attempting to laugh it off.
Oh, Captain My Captain
It was my first semester of college; I was 18 and recently sexually active. I could count my sexual encounters on one hand, but I was determined to have more.
So when Thea messaged me on Tinder, I was basically down for whatever. I just wanted to have sex.
What “whatever” turned out to be some light bondage. She was adamant about being submissive, so for the first time ever, I found myself in a position of sexual dominance. I told her I was inexperienced, so her solution was to have her laptop open on her nightstand with a shibari tutorial on the screen. I followed along as best I could. When she was satisfactorily tied up, she asked me to hit her with a hairbrush. Despite her enthusiasm about it, I felt awkward about hitting someone, so I did so timidly at first, but as I realized how into it she was, I found myself enjoying it more and going harder.
You know how some people call out names during sex? Or titles? Like “Daddy,” “Mistress,” etc? You know the vibes.
Thea knew I was nonbinary, and in an attempt to be as gender neutral with her language, she called out “Captain!” as I was hitting her with the hairbrush.
I mean, kudos for inclusivity, but also… what the fuck?
Being called “Captain” in a sexual nature while hitting a girl with a hairbrush really set the tone for the rest of my sexual experiences in college.
I will say though, that now, as someone with more experience with impact play and bondage, I generally just have people call me “Daddy.”
Third Base Is When You Have a Panic Attack in Her Truck
The summer after freshman year, I met Gwen on Tinder. We were horny 18 year olds and we did what horny 18 year olds do. Which is to say, we went hiking in a thunderstorm purely to have sex in a forest.
The first time we had sex in the forest was fine. It was wet in more ways than one, and muddy. We then had a picnic (still in the rain, mind you) and started making out again.
The second time we had sex that afternoon did not go well. She was kinky, and wanted to tie me up and hit me with her flogger. (Yes, she had a flogger in the backpack she brought into the forest.)
But after she had tied my hands behind my back and was starting to hit me with her flogger, I started to panic. I had done impact play before, but something about it then set me off and I started freaking out, crying hard as I struggled to breathe.
She untied me and, as I sat shaking with my arms around my knees, cleaned up our picnic. The walk back to her truck was short, but felt like it took forever as I stumbled over tree roots and rocks, trying to steady my breathing.
I continued to panic all the way into her truck and for most of the ride home.
When I finally calmed down, she offered to let me come to her house to shower and later to participate in her family’s board game night.
For better or for worse, I said no, and when she dropped me off, I continued to cry.
That day, I learned an important truth of the world: third base is when you have a panic attack in her truck. Fourth base is when she still invites you to her family board game night.
Give It to Me, Baby!
Derrick was a summer fling. He was sweet and goofy. He lived a few towns over and happily took the train forty minutes each way to see me. He bought me ice cream on dates and kissed me in alleys. He was endearingly stupid.
He liked to put on music during sex. Sometimes, I was in charge of the aux and put on vibey R&B or Bedroom Pop to set the mood, but generally he was on music duty. Once, we were hooking up and he put on Spotify’s “This Is The Offspring” playlist. “Pretty Fly (For A White Guy)” started playing while he was inside of me and, to make matters worse, he thrusted to the beat of the song. I made it maybe halfway through the song before I started uncontrollably laughing and we had to stop. The music was turned off and we continued. I can’t hear the opening notes of that song without cringing, remembering that summer, Derrick, and all the sweaty sex we had.
Find the Clit and Then We’ll Talk…
I must confess: sometimes I am an asshole.
When I hooked up with Ian, I was recently single. I had also recently moved into a new apartment, so recent that my roommate hadn’t moved in, and my only furniture was an air mattress and a bedside lamp. I didn’t let my lack of a real mattress deter me from embracing my sexually free singledom.
Ian was a freshman Theatre major. We matched on Tinder and quickly hit it off, and within a day, he was knocking at my door.
We immediately went to my room and started making out, the air mattress creaking loudly as we rolled around. Clothes came off. The sex itself was mediocre. Too sweaty, too spitty, and he kept slipping out.
At some point, he attempted to go down on me.
Key word: attempted.
Instead of doing anything near my clit, he started making out with my general pubic area.
I don’t know how long I let him do this before I told him to stop. When he came up to kiss me, clearly pleased with himself, I informed him he was terrible at sex.
Making an expression emulating the energy of a sad little puppy, he told me he had never had sex before.
Needless to say, I was shocked and mildly ashamed of being such a dick to someone who had just had sex for the first time.
Not ashamed enough, however, to let him stick around.
He asked if we could try again, and I -- as politely as I could through my visible cringing -- told him no way, please leave.
So he did.
I really hope he’s gained better experiences than me. He’s too cute to not know where the clit is.
Oh Shit (Don’t Hook Up with Your Ex)
My first mistake was going to hook up with my ex. I knew it was a bad idea likely to end in disaster, but little did I know just how much of a disaster it would be.
When I got to my ex’s apartment, we got straight down to it, making out aggressively on their couch before moving to their room. They sat on the bed as I knelt on the ground, starting to help them undress. Their shirt came off, and then their pants, and then, as I was pulling down their underwear, I was greeted with a putrid smell.
They had shit themself.
Their ass was caked with shit.
I recoiled. They caught on to what had happened and yanked their underwear back up and sprinted – and I mean sprinted – to the bathroom.
I sat there, dumbfounded and disgusted, unsure of what to do. I wanted to leave. God, I wanted to leave. But instead, I sat on the floor, in my bra and undone jeans, listening to the sound of the shower from the other room.
Eventually, they returned, their ass clean but their mood soiled.
We both got dressed in silence, fully knowing that sex was off the table. Neither of us wanted to fuck anymore.
I knew that if I left, it would become a capital-T Thing. They were always making me feel responsible for their emotions, and even post-breakup I couldn’t help but feel like I needed to make them feel better with what had just occurred.
So I suggested they play me a song they were working on, in hopes it would distract them or cheer them up or at the very least defuse the tension enough where I could escape.
They picked up their guitar, cleared their throat, and began to play me the song.
Turns out, the song was a slow, sad song about me.
They got maybe two lines in before their voice broke, and they started crying. They quickly composed themself and tried again. They didn’t even make it through the intro before they had to set the guitar down so that they could dramatically throw themself on the bed.
Staring at the ceiling with a dumbfounded expression, pretending the overhead light was a camera and I was on The Office, I let them sob onto my shoulder, leaving tear stains and snot on my shirt.
I played with their hair and made soothing noises while simultaneously wondering how the fuck I had gotten myself into this situation. I had just wanted to fuck around and make a bad decision, but somehow my afternoon had devolved into literal shit and my ex sobbing on top of me.
If anything, take away this lesson: if you try to hook up with your ex, it’ll be a *shitty* time.