Humpday Hookup Horror Stories: Take A Dip


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.

Take A Dip
Jeff from Jacksonville, FL

There was a girl, “Mandy,” that I “dated” in grade school, which is to say that my mom dropped us at the movie theater to go see Spider-Man together. She even ended up touching my leg. It was meant to be. We always slow-danced with each other at CYO dances, and we were destined to date through high school and college, eventually getting married. At least that’s how I saw it in my 14-year-old mind.

Long story short, her family ended up moving after the school year, and I spent a majority of my 15th year on this earth listening to Dashboard Confessional and being a real whiny bitch about it. I got over it, obviously, and went to college, etc.

After graduation, I came back home to find a job and start my life in Jacksonville. One night out at the bars, I was ordering a round of shots for my friends, when I heard a girl shout, “JEFF!” It was Mandy. My heart exploded inside my chest. We shared a warm embrace. She had gone blonde, so it took me a minute to recognize her. We got caught up over a couple of beers and a round of bombs. She apparently was visiting some old friends and was just in town for the weekend.

Closing time came and my chance to close on my first love was right in front of me. Her friends had all left and she needed a ride back to her friend’s place. So, we hopped in a cab and got to her friend’s apartment, which was locked and her friends were passed out, not answering their phones.

I suggested she could stay at my place if she was cool with it, and she was. Holy shit, this was it. When we got back to my place, we had a couple more drinks and shared stories from our youth. It was wonderful. Soon enough, we were making out and headed to the bedroom. A hookup 10-years in the making went down.

The next morning, we both woke up with horrible hangovers and did not want to get out of bed. She asked if I had any water near the bed, so I got up and headed to the kitchen to get her a drink.

Suddenly, I heard a spitting noise, a scream and the sound of violent upchucking. I use smokeless tobacco, AKA dip, and had apparently left a McDonald’s cup full of my dip spit next to my bed, because I’m a disgusting human being. Mandy had taken a swig from the cup, which still had the top and straw in it. She had thought it was some melted ice and had taken a hearty gulp of my tobacco juice, which led to her spewing what had to be gallons of vomit into my bed.

She spent the next half hour in the bathroom puking, while I felt shame and disgust. I threw the puke-stained sheets in the wash and drove her back to her friend’s. We sat in silence mostly and then just both started laughing. She’s coming back to Florida in the fall and we’re planning on seeing each other again. Sometimes, you just know when she’s the one.

Client Perks
Terry from Scottsdale, Arizona

I make my money as a golf pro in the golf hotbed of America: Arizona. Scottsdale, specifically. I played collegiately at a PAC-12 school and played in a couple of pro tournaments, but realized my talents were best suited for teaching soccer moms the finer points of the game on the driving range.

There isn’t a shortage of gorgeous women in this part of the country. I’m not a great looking guy by any means, but I can talk a woman right into bed. Don’t confuse my confidence with arrogance.

Anyway, I had a student come to me asking for lessons one week. She was probably around 40 years old, divorced and had huge, fake boobs. A MILF through and through. She was terrible, but I put up with it, because she would show up to each lesson wearing the most ridiculously sexy golf outfits.

After about a month’s worth of lessons, she finally asked me if I wanted to grab a drink with her after one of our sessions. She talked to me about her kids, which was weird. One was already in college and the other lived with her ex in LA. She was actually a very successful businesswoman, which was a pleasant surprise. Even though I made a good living charging $100 an hour for golf lessons, I was not willing to support a 40-year-old divorcee.

We bonded over several margaritas and took the action back to her place, a huge condo right on a golf course. It was around 7pm and she made me her love slave for a solid six hours before we finally called it quits around 1am. As I was getting ready to leave, she broke down in tears, complaining about her failed marriage and how much she missed her kids. It was quite the script flip.

Next thing I knew, I was consoling her, trying to get her to calm down. She talked on and on and finally dropped the B-word on me. “I just really want another baby,” she told me through her sobbing. She started pulling me towards her again, ready for another go, beckoning for my seed. I began panicking as I realized we had not used protection at all in our quarter-day sex romp.

I bolted out of the house and was absolutely petrified that I had possibly unknowingly impregnated this woman.

I didn’t see her for at least two months, until she showed up at the range again for another lesson, thankfully not pregnant. She apologized to me profusely, but I was sure to keep her at arm’s length for the remainder of our “professional” relationship.

Last I checked, she’s still not pregnant.

Email this to a friend

1 Comments You must log in to comment, or create an account
Show Comments

For More Photos and Content

Latest podcasts

Download Our App

Take PGP with you. Get

New Stories

Load More