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Adventures In Accidental Anal Intercourse

Welcome to Great Moments in Drunken Hookup Failure, where we showcase four heartwarming true stories of drunken love gone horribly awry. Off we go.

Bizarro Bowl:

In college several years ago, there was a girl that I was seeing for a few weeks. We hadn't yet consummated our relationship, but I had a feeling it was coming soon. One night after a night of moderately heavy drinking, we go back to my room and sexy time begins. After about a half hour of making out, heavy petting, etc..., she decides that tonight is the night. I put on a condom and surprisingly, she wants it doggy style. However, between the booze, the darkness and my excitement, my aim was off by about two inches to the north. It wouldn't have been that bad if I had stuck just my tip in, but due to my excitement, I went, ahem, balls deep in her ass. She made a sound not dissimilar to what a dog sounds like when you step on its tail, a high-pitched yelp. Nothing kills sexy time more quickly than accidental sodomy. We dated for a weeks after that, but I never sealed the deal. The next time I was with a girl, some soft mood lighting made all the difference.


Yeah, women never think that's an accident either.


First week of my last semester of senior year of college. I end up at a party hooking up with a friend of mine, Liz, that I'd known since freshman orientation. Our mutual friends had been trying for years to get us together. Apparently regular sized people can't stand the thought of two tall people (I'm 6'6, she's 5'11) being in the same vicinity of one another without being in a relationship. I always resisted because I happened to be into other people whenever the suggestion was made and besides, no one likes to be told who the fuck they should or shouldn't be with.

So back to the party. I run into her and we end up talking. After a few drinks the cobwebs in by brain clear and I realize I'd be a complete moron if I didn't at least try to see if this beautiful, awesome, height-appropriate chick isn't into me. I lay it all on the line and tell her how I feel. She feels the same way. Sweet. We start making out and things move quickly. I think because we had known each other so well it brought a comfort level to everything that got things moving faster than they would have normally; like we were making up for lost time. I ask her if she wants to go back to my room. She does, and we leave together.

I lived in a six person suite; three bedrooms (each with its own bathroom and shower) and a common room. Only problem was there were five of us who signed up to live together, so one of us ended up having to get a randomly assigned roommate. I knew my roommate (one of the five friends) wouldn't be back for another day, and when we got back to the suite I yelled out to see if anyone else was there and got no response. So I thought we had the whole place to ourselves.

Back in my room, we began going at it. Clothes come off, foreplay commences. After going down on one another she asks if I have a condom. I get up to go to my desk to get it, put in on and crawl back into my bed where she's waiting for me. I'm beginning to slowly ease inside her when all of a sudden we hear a deep, guttural, moan coming from the other side of my paper thin wall. It's Lou, the rando added to our suite that lived in the room over from me. Jerking off. And talking to himself. Loudly. He must have thought he was alone, too. Apparently repeatedly assuring himself how large his penis was and how badly it could destroy any woman that got in its path really got him off. And the greatest part was he doing all this while talking in a voice not unlike Christian Bale's Batman. We ended up spending the next ten minutes trying our best to stifle our laughter until Lou finished, which he did while proclaiming loudly "GAHHH FUCK TAKE THE DRAGON! THAT"S WHAT THE FUCK I'M TALKING ABOUT!" After that, we both knew nothing was going to happen. So we just ended up making out a little bit more and spent the rest of the night laughing quietly about what just happened until we went to sleep.

It all actually ended up working out great for me. Liz and I are coming up on three years together in January. As for Lou, I never spoke to him or tried to contact him in any way after we graduated; so for all I know he's still out there looking for someone to take the dragon.

Rex Grossman feels your pain, Lou.


I lost my virginity at the end of freshman year of college. Fast forward through summer, and its the second week of sophomore year and I had just moved into a fraternity and we were throwing lots of "beginning of the year let's get as many freshman girls into the house as possible" parties. After one of these parties where I didn't land a woman yet again I challenged my roommate to a shot taking contest. Mind you this is the end of the night not the beginning. After 5 shots we decide that we would rather smoke bongs. After about 3 rips a girl I had met earlier in the night comes stumbling into the room. She clearly wanted to get it on. So I kick my roommate out and show this girl how to climb the ladder into my lofted style bed. Before you know it she's blowing me. After a few minutes I sit up to put a condom on and get on top of her. And that's when I felt it all spinning. Instantly I knew I was going to barf, and it would be really really hard to clean up barf in a loft. So what did I do? I leaned over and barfed onto my coffee table from 6.5 feet in the air. Then I rolled over and passed out. I woke up to find out the girl left, barf all over the table and floor, a 5 inch gash on my leg and a condom on my dick.

Two days later (Monday) I talked to the girl and shockingly she invited me over to her dorm room the next day to finish what we started. The next day? Tuesday, September 11th 2001.


The sexiest day of all!


I live in an apt in San Francisco and I was drinking some beers and taking some shots with my roommate, as we prepared to head out for the evening. My third roommate and a group of about 10 guys and girls were already at the bar, so we were trying to play catch up and get out of the house. Shortly before we were about to leave, my roommate got a call from a mutual friend of ours, who was in the neighborhood with two girls. He came over, the girls were decently cute, though one had a boyfriend, and we proceeded to get even more hammered. We head out the bar and I'm doing pretty well with the other girl who was single. We consume god knows how many more drinks at the bar and I guess we left. I remember walking out of the bar with her, into the cold, but that's it. At this point, my memory is 100% gone.

The roommate that I was out with, wasn't in quite as bad of shape as me, and so he had some vague recollections and told me that we got back to the house without incident and also that I began to make out with the girl in the hallway and then walk down to my bedroom. I woke up the next day with most of my clothes on, so I was reasonably sure we didn't have sex, but slightly confused as to why it didn't go further. I figured it was no matter though, I had a great time, got hammered and made out with a cute girl in my bed. Good enough, right?

So, the next day, I talk to the mutual friend that had brought the girls over and he had a sordid tale for me. Apparently, my roommate was correct in his description: we did indeed start kissing in the hallway and then moved it down to my room. It gets a little weirder though. Apparently, things were going fine, when I said I had to go pee real quick. Rather than walk out of my bedroom door and into the bathroom, which is about 3 feet away, for some reason, I decided to stand in my doorway and piss out onto the kitchen floor. After I was done, I sopped it up with a t-shirt from my dirty clothes pile and put it at the bottom of the pile. All while this girl is looking on, horrified. Again, I don't remember any of this, but the girl certainly did. Anyway, she immediately left, went to sleep on the living room floor near her friend and they left at like 8am, well before I was conscious. The worst part is, I didn't know about this until way later in the next day, so not long after I woke up, I sent her a friend request on Facebook. Needless to say, that was not accepted.

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