3 Awkward Sexual Encounters That I Still Can’t Believe Actually Happened

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awkward sexual encounters

Very absurd things can happen when you’re getting intimate with a relative stranger. Here are three of my funnier hookup moments from the past year.

1. The Eye Lick

I had met a girl over the weekend and we decided to go on a hike during the week. At one point in the hike, when we were fairly isolated in the wilderness, we sat down on a blanket and started hooking up. Now, I had learned from the previous weekend that this girl was incredibly licky. Too licky. Like golden retriever with a jar of peanut butter licky. And I’m not talking about on my dick; I’m pretty sure no guy has ever complained about his dick being licked too much. I’m talking all parts of my body: stomach, shoulder, and I’m pretty sure my elbow even got some tongue action.

Anyway, she had made her way up to my left ear and was doing some cyclone maneuver when she rapidly changed course and did a ninja tongue slash across my face, licking my eye in the process. And I don’t mean that I closed my eye and she got my eyelid; I’m saying that she moved so swiftly that I didn’t have time to blink and my eyeball got a tongue lashing that fucking hurt. I immediately sat up and spent the next five minutes rubbing my poor eye. Who the hell licks an eye? When would she think that’s even remotely appropriate in a sexual situation? I guess if we were doing some Lord of the Rings roleplaying and I was Sauron and said, “Yeah, lick my eye, you filthy hobbit,” then yes, in that extremely specific scenario, the eye lick would have been appropriate. But, as a future reference for any girls reading this, never lick a man’s eye.

2. My Budding Porn Career

In this story, it’s not the sex that was awkward but the aftermath. There are only three significant details that you need to know.

The first is that the girl I hooked up with was incredibly vocal and loud.

The second is that I live in Spain, where the apartment buildings are constructed with a big, hollowed-out square in the center. This means that sound ricochets around and echoes to all of the apartments in the building.

And third, the elderly woman that lives beneath my apartment detests my roommates and me, and had previously called the police numerous times to complain about noise.

Unbeknownst to me, while I was having sex, my downstairs neighbor held her phone out the window to record the sound. I’ll let that sink in. There’s an old lady living in Spain who has an audio recording of me having sex — an audio recording that I can only hope never sees the light of day.

Now, my neighbor did this not because she was trying to get into the niche porn-for-the-blind market, but in order to play the recording to our doorwoman, Conchi, and complain about the noise. I’d like you to fully visualize the oddity of that moment: two eldery Spanish women huddled around a phone listening to an audio recording of me having sex.

I didn’t know about any of this initially, so when I walked out of the building later that day, I didn’t understand why Conchi was looking at me with such a mischievous grin. She proceeded to call me over and tell me what had happened. I was mortified, but she just laughed and gave me a high five. Conchi is a terrible gossip, and over the course of the next few days, the entire building was told the American guy sex story. Elevator rides with my neighbors were uncomfortable for a little while after that.

3. The Big Black Vibrator

I was visiting a friend’s hometown and met a girl at a bar. When we got back to her place, she went to the bathroom to freshen up. So, alone in her bedroom, I naturally began to explore. I didn’t have to look far before I found something of interest. On her desk was the ‘BDSM Boardgame,’ complete with a picture of a tied-up sexy girl on the front. I thought it was odd to have something like that so openly displayed. I opened the box and began to sift through the materials: rope, tape, clamps, a ball gag — tonight could be a weird one. Then I looked behind the box, and that’s when I saw it:

The big black vibrator.

I should’ve just left it there, but I’m like a perverted curious cat — I had to touch it. I poked the button on the bottom and immediately jumped back in shock, afraid that the desk would collapse from its sheer vibrating power. It was like I had just revved up a chainsaw. It was loud as hell, so I picked it up in an attempt to shut it down. Each time I pressed the power button, however, the thing shifted gears into a more intense vibration. I don’t know if NASA or Elon Musk has been working on vibrators, but this thing was the size of… well, the size of an above average penis, yet had the raw engine power of a Vin Diesel muscle car. My fingers were starting to go numb. It was at this moment that she opened the bathroom door. In the commotion, I had moved myself onto her bed and was on both knees, holding up the vibrator like I was Rafiki presenting Simba to the African Serengeti.

We both sat there in a silence (minus the rumble of the vibrator), which I broke by saying, “Uhhh, I warmed it up for you.”

Thankfully, she laughed, and all was well.

Image via Shutterstock

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Hey my name is Nick Holke, and I write my own comedy blog at Stories on my site vary from: buying the morning after pill in Vietnam, almost shitting myself on a bus, and everything in between.

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