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.
“Russ” from Las Vegas, NV
My ex-girlfriend and I had been dating for a while and we decided to spice things up one night, which is to say I finally talked her into doing it in the butt. We had always talked about it ever since we started dating, but since we were well into our second year of dating, it only seemed natural that we took the next step in our relationship.
So I wined her and dined her (did not 69 her) one Saturday night. I wanted this more than anything, but I wanted her to be cool with it. I’m a gentleman. We went out to dinner at a very nice steakhouse and I ran up a $200 tab on steak and wine. She kind of had an inkling as to why I dropped so much cash on dinner. We even went shopping after dinner where I ended up dropping another couple hundred bucks. Then we went out drinking. The perfect storm of drunk occurred and we hopped in a cab back to her place. I wanted her to feel completely comfortable.
We got down to business right when we got in the door and even did some normal sex for a bit. I don’t know how I did it, but I coerced her into letting me use the back door. She smiled at me and said she was ready. Then she reached into her night stand and put a bottle of lube in my hands. LUBE! Man, I miss her sometimes.
I lathered up my shit and probably ended up ruining her sheets with the amount of Astroglide I put on myself, but I wanted this to literally go as smoothly as possible. We were both rookies in the finer art of butt penetration and weren’t exactly sure how it was supposed to go. I saw it in porn all the time, so I just went in full thrust. Foolishly thinking that my girlfriend was as loose as Lisa Ann’s, I shoved it in. She shrieked and tried to roll over, thus pushing myself deeper into her poop-shoot.
The struggle to free herself quickly ended as I realized that she was out cold there in the bed. Oh my god, I had killed her. Not quite (she passed out from the pain), but it was horrifying. She finally came to after a few seconds of unconsciousness. She was alive! I did not have to tell her family how she died. Thank you, lord.
We broke up two weeks later. I’m pretty sure that was one of the main reasons why.
Not Back There, Please
“Kevin” from Denver, CO
A lot of these stories start out talking about how everyone was really drunk at a bar one night, so I’m going to spare you the details.
I was really drunk at a bar one night and this redhead started talking to me. She was almost taller than I was. We hit it off and grabbed a cab back to my place. The entire cab ride home, she wouldn’t stop telling me about how great redheads were in bed and how I was in for the “night of my life.” Fantastic.
We’re having sex and things are going great. She’s doing all sorts of crazy shit that I’ve only ever seen on the internet and loudly moaning my name. At one point, I was on top of her and she’s got both her hands clamped on my ass. She then began spreading my cheeks apart and that’s when I started getting a little nervous.
“Remember what I told you about redheads?” she cooed into my ear, then plunged a finger right into my asshole and then quickly took it out. Look, I’m not all about ass play or anything like that, but I wasn’t about to stop having sex with someone just because they put a finger in my butt. I kept going.
She did it again and I politely asked her to stop. “Not back there. Just not back there, please.” Eventually, she stopped and allowed me to continue with the sex. But that didn’t last long. She gave me this crazed look just a minute later, stuck what felt like her entire fist into my ass. That was that, I climbed off of her and gathered myself.
“I thought you liked it?” she asked me as I stood over my sink in the bathroom, ready to puke. I calmly told her that I did not like fingers in the place that I poop from. I was ready to get back to it, but then remembered that one of her hands was covered in my own shit, so I called a cab and asked her to leave.