Humpday Hookup Horror Stories: Rogue Finger


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Rogue Finger
“Nina” from Brooklyn, NY

I’ve shared this story with many of my close friends, but I thought I’d share it with my best friend, the internet. I was steadily hooking up with a coworker and we were getting to the point where we were having sober sleepovers during the week. Pretty serious, you could say. We never had the relationship talk, because I never felt it was necessary. We both knew what we were doing and when we were ready to take the next step, we would. The sex was great, we got along well enough and we both had great jobs that we did not want to screw up.

So our sexual liaisons continued for several weeks and never interfered with our work. Until one night.

We were hooking up when he asked me if I would let him do something. I asked him what he meant. He said, “Why don’t I just show you?” His hand crept down the small of my back and towards my asshole. Before I could even stop him from doing what I knew he was thinking about doing, POP. He had plunged his entire index finger into my anus. All the way down to the knuckle. I yelped and smacked his chest, begging him to take it out. He laughed like a crazy person and I finally just slapped the everloving fuck out of him. He reached up to his face with the hand that had previously been fully inside of my body cavity. I nailed him right above the eye and he started swelling up. I felt bad, so I got him some frozen peas and did my best to play nurse. He spent the night and we decided the next morning that it was best we stop hooking up.

I strolled into work on Monday, kind of relieved the whole thing was over and then I saw him sitting at his desk. I figured it’d be best to not talk to him all day. A few hours later, he walked by my desk and I noticed his eye was puffy, but it wasn’t a black eye. His eye was completely red. He had given himself pinkeye with the finger that was plunged ever-so-violently into my crevices.

He took the rest of the week off.

Mile High Near Miss
“Connor” from San Antonio, TX

Ever since I started traveling for work three years ago, I’ve always had the fantasy of hitting it off with a good looking girl sitting next to me and parlaying it into a one-night stand while on the road (Insert Steve Perry singing “They say the road ain’t no place to start a family” here). I fly for work probably three times a month. Some months it’s more. This particular month, I was scheduled to be traveling seven times. Night-fucking-mare.

It was my last flight of the month and then I was taking some much needed vacation time. I was flying to Phoenix on a Friday for some weekend golf and meetings with prospective clients and then was headed back on Saturday evening. It sounds like a vacation, but believe me, it is anything but. As I went through security, i noticed this really cute brunette a few spots ahead of me in line. I stared from a distance, like a creep, for some time. I started walking towards my gate and noticed that the cute brunette was walking ahead of me and gods be good, she stopped at my gate. We were on the same flight. Could Cupid’s aim be this sharp?

The plane started boarding and she boarded with the Business Select crew, while I waited with Boarding Group B. I prayed there would still be a spot open next to her. Fortune once again favored me, and I saw a spot open next to her. I pounced. The flight wasn’t full. She sat by the window and I on the aisle. About 20 minutes into the flight, I decided it was time to make my move and slide up in her DMs.

“How long is this flight?” I asked.

“Ummmm, I think two hours?” she replied.


Then we landed two hours later and she ran into her boyfriend’s arms at the baggage claim. I was that close, guys.

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