Humpday Hookup Horror Stories: Sent To The Hospital


If you’ve got a hookup horror story, send it in using our submission form, and be sure to select “Column.” All stories will be made anonymous. Try to keep it under 500 words. Thou shalt not judge lest ye be judged.

Sent to the Hospital
Seth from Arlington, VA

I had my girlfriend over for dinner one night and I was going to talk her into doing anal. You can probably guess where this is going. We ate dinner (something light, to avoid any issues later on concerning her back door) and I put on some Dean Martin to set the mood. Ol’ Deano would’ve approved of this method of seduction.

Off to the bedroom we went. I let her know that I wanted to try it, but only if she was cool with it. She was. God bless America. The mixture of port and Dean Martin was the right mix for her, I guess. I lubed up and prepared to insert. Being the clumsy guy I am, I fully inserted myself into her buttocks a little too vigorously, which led to her screaming bloody murder like she had been stabbed in the anus, because she pretty much was.

There was blood. I had torn her anus. Torn it. We rushed to the hospital where she had emergency surgery and I will spare you the details, but the next few weeks were quite trying. The doctor said it best as my girlfriend lay weeping on her side, “Well, that ain’t where a lot of things are supposed to go.”

Couldn’t even look him in the eye.

Shady Switcheroo
Alex from Atlanta, GA

This is by far the most fucked up story I’ve ever heard. It’s secondhand, but I’m 98 percent sure it’s true, because I know the girl and only a piece of trash like her would even think of pulling it off.

My friend’s friend went to a state school in Florida and during his sophomore year, a girl he hooked up with told him she was pregnant and wanted to get it “taken care of.” This was a few weeks before spring break, and it absolutely ruined the guy. He wanted nothing to do with this girl, as she had slept with half of the campus already and was probably banned from an even greater percentage of fraternity houses on campus. He ended up giving her $700 dollars to get it “taken care of.” This is where he went wrong. Shmashmortions don’t cost $700, but he was so desperate to get it taken care of, he hadn’t even thought of what it might cost.

So he thinks she’s taken care of it and he’s not going to become a father. In fact, the $700 bucks he gave her was his spring break money and he ended up going home over break. A couple of days into break, he gets a slew of texts from his friends claiming that they’ve seen this girl on spring break. Sure enough, she had taken his money and had not gotten it taken care of. Instead, she spent the money on her own personal spring break trip. Blew the entire wad in Key West. She was never pregnant. He took her to small claims court, but as you can probably guess, she never showed up.

She dropped out of school after the semester and was never heard from again.

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