Three Hookups That I Should Be Too Embarrassed To Tell You About

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Three Hookups That I Should Be Too Embarrassed To Tell You About

Despite the fact that I’m now in a committed relationship, doing ‘grown-up’ things like planning a romantic bed-and-breakfast weekend trip and taking applications for other couples to double date with, this wasn’t always the case. I’ve enjoyed many years of being aggressively single, and in that time have collected a myriad of hookup horror stories that I feel the need to share.

Accidental Anal

It was Halloween night, 2012. I was in Santa Barbara with the girl I was dating. Well, in her mind, we were dating. In my mind, as we had never discussed exclusivity, I was free to do as I please. I was being a douchebag, is what I’m getting at. After drinking our faces off in an Isla Vista mansion all night, we returned back to my buddy’s place with a group of friends to keep the party going. Several more beverages later, I found myself in the bathroom of the house with my girl. At her request, I bent her over the counter, and started “hitting it from the back,” as I believe I called it at the time. It seemed like just our average sloppy hookup, when she turned to look at me and moaned “you like fucking my ass like that?”

In retrospect, this would have been the ideal time to “act like I’d been there before.” However, I had never been there before, and instead of pretending like I knew which hole I was in, my idiot-self blurted out, “Wait, is my dick in your ass?” I immediately realized this was the wrong thing to say as she turned around, slapped me across the face, and yelled, “Can you not feel the difference between my asshole and my pussy?!” She then stormed out of the bathroom and directly into a crowd of laughter because apparently the bathroom was not soundproof. Needless to say, I wasn’t allowed in the back door for quite some time afterwards.

The Trek Of Shame

Spring Break. Lake Havasu, Arizona. The recipe for a perfect disaster of sloppiness. It was a nine-hour drive to the lake and we made the wise decision to use that ride as a mobile pregame. We arrived at the hotel at around 2 p.m. and allegedly got checked in and set up camp in our room. I don’t have a lot of memories from the rest of the day, but I do remember going out to a pool party that night and drinking like I was trying to put the Jack Daniels Company out of business. Sometime during this, I met a girl, took a shuttle ride back to her hotel room, and had sex on her roommate’s bed. A true college love story. When I woke up, I was alone in the room. The clock read 10:15 a.m., an anxious reminder that I was late to the beach to start drinking.

However, I had no phone or wallet, nor had any idea where I was. I walked down to the lobby, clad only in board shorts and flip-flops, and asked the concierge if he could direct me to my hotel. He looked at me with a mixture of sympathy and disgust and told me to follow the main road about three miles and I would run into it. That’s right. Three fucking miles, in flip-flops, in the Arizona sun that was already approaching the mid-90s. That hour long walk of shame was a baptism by fire. My soul was exposed for the world to see, and since Lake Havasu City is a retirement community 90 percent of the year and drunk college kid Mecca the other 10 percent, the cars that passed me had mixed reactions. I had (empty) beer cans thrown at me, countless “walk of shaaaaame” battle cries, judgmental grandparents scowling at me, and a woman that looked like my grandmother even try and convince me that I needed to read the bible. I declined the request and got back to my hotel just in time to take some shots and go to the beach.

The ER Visit

After a long night of pounding gin and tonics (strange how these stories all start the same way), I had been unable to attract any girls at the bars, so I decided to fire off a classic “u up?” text to a former hookup of mine. Surprisingly, the Hail Mary worked and an hour later we were back at my place getting down to business. All seemed to be going well as I hit her with the moves (straightforward missionary, because I was too drunk for anything else) until, all of a sudden, I heard glass shattering. I heard the girl tell me not to stop and figured we had knocked over a glass or something. I thought we would just deal with it later. You can imagine my horror when I turned on the lights several minutes later to survey the damage and my girl and the bed were covered in blood.

“What the fuck?” we both yelled at each other, her confused about where she was bleeding, me terrified that I was about to go to jail for the rest of my life. That’s when I noticed the room was definitely draftier than it had been a half hour ago, and I took a look at the window. Well, what was left of the window. Apparently, she had put her entire leg through my window during the act and had sliced up her calf in the process. I immediately wrapped her leg in a towel and called an Uber to go to the ER. Alone in the waiting room, I was bombarded by my thoughts such as, “Will she be okay?”, “Who’s fault is this, legally?” and “Is it bad that I’m taking this as a compliment on my sexual abilities?” I never got the answers to the last two questions, but she turned out fine and didn’t even need any stitches.

I wish I could say those are all the stories I have, but I’m sure there’s more that I’ll remember later. To all you single people out there, cherish your awkward and disastrous hookups because your stories are all everyone looks forward to at brunch.

Image via Shutterstock

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