Humpday Hookup Horror Stories: The Devil’s Three


If you have a Humpday Hookup Horror Story, submit it HERE. Try to keep it under 500 words. All submissions will be made anonymous. Thou shalt not judge, lest ye be judged…

The Devil’s Three
“Holly” from Milwaukee, WI

There are three things I want out of life: to be happy, to be healthy, and to have a devil’s threesome. I was studying abroad in London when I met a guy, Alex. He was basically the perfect physical specimen. Think David Beckham meets Michael Fassbender. He lived in a penthouse downtown with marble floors, floor-to-ceiling windows with views of the city, and more chandeliers than I had ever seen. He had money, connections, wasn’t hard on the eyes, and was always there when I needed him–at 2 a.m. to get laid.

One night I ended up back at his place (as usual) and after an hour of nightcaps and other substances, we headed to his room to round out the night with the main event. Our routine was usually pretty simple: long, drawn out foreplay, then long, intense sex, then a water (or alcohol) break, and then we’d repeat ’til we were both too tired to go another round.

He threw me on the bed and we got down to it. Just as we were finishing round two, his bedroom door opened and his roommate, Mark, walked in. Alex and I stopped and looked at Mark, wondering why he was standing at the door while we were mid-bone. He apologized and walked out. We shrugged it off (we were significantly wasted, so we didn’t think much of it) and continued. Ten minutes later, the door opened. It was Mark again, but this time he was completely naked. He walked over to the bed and got in next to Alex and me. Alex and Mark looked at me for approval. HOLY SHIT. THIS WAS IT–a devil’s threesome!

I removed myself from Alex and reached over to Mark to start kissing him to indicate I was giving this the green light. It’s everything I ever imagined: two beautiful men (with accents) tending to my every sexual need. I remember thinking I should really emphasize my multitasking skills on my résumé, because this was above and beyond any multitasking I’d ever done before. It began like any threesome porn you’ve seen, but the classy stuff. You know, like X-Art.

I was going back and forth giving both guys attention when Mark got up and moved out of my sight. I was bent over in sort of the doggy position when I felt Mark come up behind me. Then, without warning, Mark rammed his dick into my ass. I screamed so loudly, I was surprised security didn’t show up, concerned that someone was just murdered. I launched myself to the other side of the bed, away from both of them. Mark followed, apologizing and trying to convince me to have sex with him again. Alex flipped out, throwing Mark off the bed and yelling British expletives at the top of his lungs. Meanwhile, I was just lying there with my violated butt hole, realizing I bit off more than I could chew (or deep throat).

Devil’s threesomes. Be careful what you wish for, ladies.

Taking One For The Team
“Clark” from Austin, TX

After moving down to Austin (like one who is aged 23 to 34 does) I went out a ton. I ended up lucking out and finding an awesome friend group. Everyone was really active, nice, and loved drinking, and one guy had a boat that we’d take out on Lake Austin damn near every weekend. The only downside to this was, included in this particular friend group, there was this one girl. For our purposes, we’ll call her “Claire.” Claire was a psycho. I don’t throw around that term loosely. She wasn’t “a crazy girl”–she was legitimately insane, and everyone knew it. On top of that, she was loud, irreverent, rude, and suffered from the worst case of resting bitch face I’ve ever seen.

Claire was the best friend of “Maggie.” Maggie was the most pursued girl in the group. Everyone took a run at her, including yours truly. Maggie was a well-built sweetheart of a brunette from southern California who was in crazy good shape, and I’m pretty sure the only reason our buddy’s boat was full each weekend was so everyone could gawk at her in a bikini.

One day, we took the boat out on the lake. The summer was winding down, and my buddy Chris wanted to finally be the one who closed on Maggie. I’m not suggesting that women are to be viewed as conquests, but it would be quite the feat to get her to even let you hold her hand. Everyone knew Maggie had a thing for Chris, and we were just waiting for him to make a move on her. Sure enough, the two of them were touchy-feely the entire day. Of course, Claire was upset because someone was paying attention to her bestie instead of her, and I reluctantly came to the realization that I would have to jump on a grenade. As we headed back to the docks, I started distracting Claire from Maggie by buying her shots, making her laugh, you know. Chris was going to owe me after this was all done. It went on for HOURS. I’m not just saying an hour and a half. I’m saying we got to the bar and I had to work my magic on Claire for two and a half hours.

Finally, I knew I had to enact home field advantage. My apartment was just down the road from the bar where we were, so I took action. I sucked it up, started making out with Claire, and took her back to my apartment shortly after. I prayed she would soon pass out, but sure enough, she wanted more. I went into the bathroom and mimicked getting sick while I texted Chris: “You better fucking close tonight.”

Claire, wise to my scheme, started gathering her things and said she was going back to the bar. I knew what I had to do. I had to show I was a team player. I had sex with Claire. Disgusting, vile, rude, perma-bitch-faced Claire. I kept her away from Chris and Maggie for an hour. Sure enough, Chris took Maggie home and I was left with the shame of having relations with the most intolerable woman I know.

You fucking owe me, Chris.

The Morning After
“Charles” from Seattle, WA

This was honestly the most awkward morning of my life. It all started on a Tuesday night, my sophomore year of college, when I was still living at my fraternity house. To put things into perspective, this happened toward the end of a month-long bender. Not like an “oh, look at me, I drank so much in college haha wasn’t I great?” bender. It was more of a “fuck me, I might have a problem” bender. This was kind of the turning point when I realized that it isn’t healthy, physically or morally, for a 20-year-old shithead to violently black out every night for a month. So, basically, we all pitched in $5 for our nightly load of booze, which usually consisted of a case and as many $10 handles of vodka as we could afford. The difference was, our $10 handles were actually $8.50 for a while. It’s amazing how reckless $1.50 can be to one’s nightly alcohol budget. This resulted in me bonging vodka, a couple times. And that resulted in me waking up with my face pressed into a back tattoo of a dove. Really classy shit.

At this point, I realized I had at least done something with my black hole of a night, even if she had a back tat of a fucking dove. I inspected the girl and concluded I’ve never seen her in my life. I took a picture of her and group texted all my friends to see if they knew who she was. Nothing. I noticed a purse on the floor, and I grabbed it to inspect for clues. As I unzipped it and reached in for her exposed driver’s license, she started to stir. She opened both eyes to see me sketchily rummaging through her purse like a creep. Or a crook. Either way, I looked like a dick. (I really am a dick, but I make a very concerted effort not to come off as such. Sometimes this works better than others.

Anyway, she caught me, I dropped her shit, she asked me what I was doing, and I told her I wanted to grab her phone to call mine, since I couldn’t find it. She grabbed her phone from under the pillow, and I typed in my phone number only to feel my phone vibrate from under my pillow. So now I looked like a liar. She dressed and we went out to the parking lot, where she insisted her friend would come pick her up. This turned out to be a lie, because for the next hour and 15 minutes, I sat in the bed of my buddy’s truck waiting with her as my entire fraternity house ate breakfast (reminder: this was a Wednesday morning) and gawked at us, laughing their asses off and yelling at us from time to time. My buddies knew I didn’t know who she was, so they kept yelling and asking what her name was. She pretended not to hear them. We talked about our favorite fast food restaurants and the evolution of MarioKart through the years. Her friend picked her up, and I never saw her again.

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