Humpday Hookup Horror Stories: Butt Stuff


Butt Stuff
“Rachel” from Boston, MA

A few summers ago, I was staying on Martha’s Vineyard with a friend, her boyfriend (whose family home it was) and a few other lovely ladies. We decided to go out that Saturday night, so my friend’s boyfriend invited a friend picked us up in his blacked out Jeep Grand Cherokee. It was on. We all got blackout to the point of no return. Once the bars closed, we decided to go take a quick skinny dip. We trudged through the dunes and got to the beach where we swam and drank for a while longer.

Back at the house, everyone was pretty spent. After raiding the cabinets and eating some stale food, we decided to go to bed. Adam, made it clear that nobody was to sleep in his parents room (a pristine, well-made bed that looked far too comfortable to pass up). Clearly, I did what any drunk little lass would do, and took Adam’s friend up to the clean bed. What we did in the bed? I don’t remember, your guess is as good as mine. Let your imagination run wild.

The next morning, Adam comes in and violently wakes me up. His friend is gone, and he is pissed at me for sleeping in his parents bed, but even more angry at the fact that I had apparently done butt sex in it. He holds up a towel that he found outside the door, with shit smeared all over it. I instantly begin to cry, because I have no memory of what happened the night before. All I know is that this guy might have sodomized me while I was passed out.

With a ridiculous hangover, and my friends all around asking questions, I notice that my sphincter does seem a little sore. I am livid, mortified and confused all at once. How did I not wake up during that? Why is my anus feeling so funny?

A few hours later, we’re laying on the hammock, waiting for Adam’s friend to return his dozens of texts and voicemails. My friend Danielle finally wakes up and comes out to see what all the commotion is. I explain the whole situation to her, and how upset I am… She starts laughing uncontrollably.

“I stepped on dog shit at the beach last night, I wiped my sandal off with that towel,” she replied.

Still don’t know why my asshole hurt, but I’m just glad I didn’t shit all over a $200 Neiman Marcus towel.

Devil May Try
Brock from Spokane, WA

Of all the cool sex shit I wanted to try in my life, a Devil’s Threeway was not high on my list. In fact, it wasn’t anywhere near my list. This, of course, is what I tell myself when I am sober. When I’m drunk, I become a drunken, tornado demon of bad decisions.

Perfect example: I was at an alumni function for my alma mater and it was just littered with rich folk. I had no idea what I was doing there. I was making $32k a year six months out of college and was somehow thrust into a fantastic networking opportunity with the who’s who of my university. Naturally, I went straight for liquid courage. After a few drinks and embracing the comfort of my own friend circle, I decided to take a lap around the room to see if there was anyone else I knew or maybe gladhand a generous donor at the bar. No luck. I would be finding my fortune at the bottom of a bottle tonight.

After a couple of hours of getting rowdy with some friends, we caught the attention of a couple of older chicks. They couldn’t have been older than 27 or 28, but they loved our style. It was on. Kill switch engage.

One of them was an absolute dime. Former cheerleader, sorority goddess and crazy into me. She touched my arm at one point. I was in. We stuck around for about another half hour and then headed to the bar where the goddess continued to touch my arm and laugh at my jokes. I had no idea what was happening. This was too good to be true, right? RIGHT?

Sure enough, her husband showed up. I was too drunk to notice the massive engagement ring on her finger. Her husband was in his 40s and obviously a very well off individual. My friends told me the look on my face was a mixture of shock, disappointment and sadness. I had never been with a woman as gorgeous as this chick. She wasn’t just hot, she was gorgeous. A knockout.

Her husband was a nice guy and invited me back to their place with a couple other friends. I sat in between both of them on their couch back at the house, which was really weird. Something was happening. They were both touching my leg. Straight Frank and Claire Underwood-style. The hottie pulled me in for a kiss and planted a big, wet one on me and then looked over my shoulder to her husband, who was caressing my shoulders. I shot up out of my chair and whipped around to face him.

“What the fuck, dude?”

“Take a walk on the wild side. Have a little fun with us.”

I weighed my options. On one hand, I’d see this stunning woman naked and be engaging in intercourse with her. On the other hand, her husband would probably be fingering my butthole while I engaged in intercourse with her. OR were they one of those weird swinger couples, who liked watching each other with strangers? I knew they were a package deal. Yes, I would be having a legendary sexual experience with a complete smokeshow, but it also might have my mouth stuffed with some 40-year-old dude’s dong.

They disappeared into the bedroom and I just sat there in the living room, drunkenly debating the merits of what I was about to endure.

I sided with keeping my dignity intact, called a cab and lived to fight another day.

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