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The Older, The Better
“Ryan” from Tulsa, OK
I was at happy hour with a couple of friends after a particularly long week at work. I was in a seriously self-destructive mood, so I was planning on getting absolutely hammered. I didn’t think I was going to get fired, but it was just one of those weeks where I had terrible anxiety and I was going to hit the bottle to suppress those feelings. Dark as shit, I know.
So we’re at happy hour and I’m just completely gone. Can barely remember anything. Anyway, apparently an older woman, I’m talking like pushing 60 years old, came up to our table and was being highly inappropriate. Highly. Age had certainly taken it’s toll on her, but I could tell that she was once very beautiful and full of life. Since I was already in a self-loathing state, I saw it as a challenge to make myself feel even worse. I went in for the kill on the GMILF.
I bought her drinks, made her laugh, and since she was an older woman, she wasn’t interested in playing games. We were out of there after only three awful attempts at sexual innuendo and two whiskey-sodas. We cabbed it back to her place for a little slap and tickle. I was expecting a nice little place in the ‘burbs, but no. This older woman was loaded due to a large divorce settlement. Typical. She had a really nice downtown loft, complete with marble floors, grand piano and plush furniture everywhere. Thoughts of her becoming my sugar mama started dancing in my head. I’d never have to work again!
She poured us another drink and we skipped over the particulars and went at it. She really wasn’t that bad looking and even had a boob job! Unfortunately, she had a devastating case of pancake ass. I would have to work with it.
I was thrown around her apartment like an abused ragdoll and we went at it all night. Now I know why they call them “cougars.” She had me on the brink of begging for mercy. So we finally finished up and she lit up a cigarette for us to share and we went to sleep. That’s where this turns into a horror story.
The next morning, I woke up in a stranger’s bed (no more terrifying feeling) and heard bustling out in the kitchen area. I had only my boxers on and thought that this older gal was up making breakfast for us. How nice.
Turns out one of her kids had come in town and came over for breakfast. Also, her kids had kids. So there I am, hungover, disheveled and semi-nude, staring a family of four and their grandmother in the face. There were no words that could have come out of my mouth to make that situation any better. I was frozen in terror. So I did an about-face back into the bedroom, gathered my clothes and was on my way out before this older lady came into the bedroom and tried to explain everything, ending with her inviting me to stay for breakfast.
I was not only embarrassed for myself, but for her. Her GRANDchildren just saw that. I probably ruined their innocence forever. FOREVER. They saw my bulge, for crying out loud.
Still half-drunk, half-hungover, but completely famished from a long night of lovemaking, I obliged her invitation for me to stay for breakfast, explaining to her grandkids, who I had pegged for 6 and 8 years old respectively, that I was her plumber and was there to fix her pipes, which caused me to choke on my coffee. She had to have said it on purpose.
I avoided any eye contact with her son, but I could feel his death glare cutting me right to the core. His wife was also scanning over me with her judging eyes. As I sobered up, I realized exactly what kind of ridiculously fucked up situation I was in and made my exit. I spent the next three days in a terrible bout of depression. I had probably ruined at least one childhood and God only knows how awkward the rest of the day was for that family.
What Ryhmes With Gum?
“Mac” from Kansas City, MO
I went out one Saturday night with every intention of getting pretty African-Americaned out. As the night came to a close, I became a textbook example of a man suffering from “Closing Time” syndrome, which in this case worked out okay for me. The perpetrator who would later commit a most heinous crime against me was a girl I had fooled around with before. So thankfully, future events were much easier to laugh off. So once we agreed on how both our nights would end, she decided to make the responsible decision to drive us drunk back to her place. The exhausting five-minute walk wasn’t going to happen.
Essentially knowing what the other person brought to the table sexually, we started getting hot and heavy as soon as we got through the front door. Once we reached her bed, she proceeded with her usual fellatio routine, which to say-the-least, was on point that night. So on point, in fact, that I threw all inhibition to the wind and decided to let myself loose onto/into her pallet. I’m a gentleman and returned the favor orally, but not before she decided spit back everything onto my crotch, including items which did not originally belong to me.
As I went to the bathroom to clean up, I began to notice that my testicles had glued themselves to my leg in a much stronger fashion. This opposed to their normal adhesive behavior during the hot summer months. I will never forget the collage she created on my genitalia, though. To my surprise, she had not only spit semen, but an extraordinary amount of green chewing gum in and around my pubes and package. I have never more regretted not manscaping than I did that night. For the next 20 minutes, I tried not to whimper like a little girl as I pulled apart the gummy, hairy mish-mash off my dick. There is nothing more sobering than ripping off 60% of your pubic hair with your bare hands and using chewing gum as your only tool. I would have gladly accepted duct tape over that shit just for a bit more control over the device used in my torture.
All she had for me was a giggle when I asked if she had been chewing gum. Eventually, all I could do was laugh as well. In this crazy world, I’m just lucky she went with a more neutral flavor. Big Red. A Fireball hard candy. Dip spit. Any three by them-self and/or combined would have been much worse.