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Real-Life Embarassing Sex Stories

Submitted by City Paper readers

Photo: Illustrations by Ben Claassen III, License: N/A

Illustrations by Ben Claassen III


I was living in New Jersey, and I’d just graduated high school. One balmy summer night, I found myself out with a mixture of friends and co-workers from a local cafe I was employed at. We visited a number of house parties, and as the night wore on, people got increasingly hammered and drifted elsewhere, eventually leaving the manager of the café and I (the only two sober ones in the group) to care for one very intoxicated mutual acquaintance. We’ll call the manager George. Though we worked together, George and I had had limited contact with one another until this point. A recent hire, he was 24 years old to my 18, American but with a distinctly European feel to him, and he mostly kept to himself. Also, he was smoking hot, but I’d always read him as completely out of my league, so I’d never bothered pursuing him.

This particular night, however, we were forced to engage with each other and work together to bundle this tragically drunk girl into the backseat of his car and deposit her safely at her home. Afterwards, he proposed hanging out and watching a movie (Snatch—I can’t make this stuff up). Which led to us having crazy hot sex (literally—he didn’t have A/C) for hours before we passed out in his bed. The next morning, I woke up in a horrified daze, committed to trying to sneak out of the house without waking George. I wasn’t regretful, but I was certain this was a one-time occurrence and was bound to make working together awkward, if not impossible. Holding my breath, I gingerly crept over George’s snoring body and began the manhunt for my scattered clothes, catching a terrifying glance of myself in the mirror in the process—my makeup was running down my face, and my long hair was disheveled and twisted in knots.

At the time, I—a true Jersey girl—was wearing hair extensions, fake hair that’d been glued to my head by a professional stylist to make it appear more lustrous. Wincing, I managed to pull on the last of my clothing, and as I opened the bedroom door to escape, I glanced back at George. He’d just rolled over, exposing his naked back to me, and what I saw made my jaw drop: Chunks of hair littered George’s sheets, pillows, and bare back. Apparently, in the “heat of the moment,” our activities had melted the glue attaching my extensions to my head, releasing dozens of them to the bed in clumps like little stray animals. Once I’d taken it all in, I let myself laugh, and accepted the fact that I owed it to George to wake him up and not leave him bewildered, in such a “hairy” situation. We went on to have a very successful and consistent hookup relationship for the next year and a half, and after that experience, I never again let someone glue things to my head.

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When I was 16, I had my first serious girlfriend. I was raised Catholic, although, at that point, I wasn’t really practicing any religion. Due to little bits of Catholic guilt lingering around, I had chosen to stay a virgin a little while longer. My girlfriend at the time was still a virgin but seriously ready to change that. She would beg me almost every day and I would refuse. Finally she called me and told me she had started birth control. For some reason, being the frugal person I am, decided that it would be a waste of money not to put her birth control to good use. Finally, the night came that we decided to have sex for the first time. I was pretty much completely clothed still and we began. I lasted almost seven seconds before orgasm. I then immediately jumped off of her, knelt on the ground and proceeded to start gagging until I vomited on my bedroom floor. The next three days, I was a complete wreck feeling horrible about what I had done. After that, we had sex all the time and it was awesome.

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We are home alone on a very nice summer afternoon. I ask Vicky if she wants to watch a porn while having sex. She’s like, “sure” . . . so that’s what we did. I found a porn from the internet and put it on the television in the living room. We do the damn thing (bump uglys, that is). This act lasted around 30 minutes. When we are done, I exited the porn site and went on YouTube to share, “I just had sex” on Facebook. Then we went out on the deck to enjoy a cigarette. While out on the deck, we hear the alert sound from Facebook on the outside speakers, and it was loud! We were like, “Oh no, if we hear those sounds coming from the speakers now that means the speakers were on the whole time.” So the porn was playing very loud over the speakers outside for almost 30 minutes on a sunny summer afternoon.

 

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A few years ago I met a woman on the internet and we started talking frequently. She lived four hours away, but still somehow we grew close. After some time, she decided to come visit. Our first date and night together went great, but nothing sexual happened other than some making out.The next day she was set to go back home, but before she did, things got hot and we began to get naked for sex. I get on top of her, and things are just about to start, when my little 10-pound dog jumps onto the bed and immediately starts peeing on her head. (We eventually did have sex, after a 30 minute break. . . )We laugh about it now, as this woman is now my wife. . . at the time, not so much.

 

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It was my first year at the Haven Place and it was like every other night . . . until Charlie, my boss, came up on my last song and asked me to do a fourth song because a girl came in late. I said “of course,” because it was a packed house, and at the end of the extra song, I looked to the left of the stage and saw the top of a baseball cap and a hand holding a bill over the railing. I walked over and squatted down (completely nude) and said, “How you doing tonight, hunny?” The guy raised his head and it was my father!

I quickly covered my body and said, “What are you doing here?”

“We need to talk,” he responded.

I was shocked and frozen but snatched the bill and said, “You need to leave.”

He stayed to see if I would leave, but I didn’t. I stayed and did another set and my father left. It took him two months to speak to me again.


The Sex Issue

Intro: The Sex Issue
G Marks the Spot | Baltimore's Sex All-Stars | “It used to be a skill, now it’s a pill”
Waxing Poetic or Otherwise | Real-Life Embarassing Sex Stories | Porn in the USA
Free Love: Reader Valentines | “French Tickler” | Ask First


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