Welcome to Great Moments in Drunken Hookup Failure, where we showcase three heartwarming true stories of drunken love gone horribly awry. Off we go.
This incident happened way back in '02 when I was in my junior year at San Diego State. I was living in my fraternity house at the time and had just met a lovely girl named Sherice over Thanksgiving break in my hometown of Orange County. Fast forward a few weeks and I was totally smitten with her. Talking on the phone a ton. A weekend visit. Mad texting. I was in love. I thought this was the girl who was going to take my virginity.
Anyways, up pops this fraternity preference mixer one Friday. I was sort of over it at the time, but ended up going cause I really had nothing better going on. The theme was Cowboys and Indians, and I just put no effort into it at all. I wore just a cowboy hat, white t-shirt, and jeans. I show up to the dance and cozy up to the makeshift bar this shithole of a rec center had built for our event. I proceed to get my buzz on and decide to wander around the party a little bit. I get near the dance floor and see this absolutely slamming piece of ass shaking it all over the place. The girl turned around after a minute and she ended up being the Latina girl of my dreams...dressed at Pocahontas in a bikini. She eyes me. I eye her. It was on. We proceed to just dance all over each other. I remember I was getting really sweaty, but she would allow for me to cool down by running to a bar to get us tequila shots. We barely talked. Just a lot of eye fucking, grinding and tequila shooting.
End of the night comes and I take off from her because I had this drunken guilt over Sherice. I hop on the party bus home, but this girl unknowingly ends up getting on the same bus. I was sitting in the back and her in the front. She sees me, gets up and runs at me like a crazed lunatic, and ends up hopping in my lap and giving me THE BEST LAPDANCE OF ALL TIME. Did I mention she did this in front of everyone sitting down without giving a flying fuck? Playing hard to get! We get back to the fraternity and Pocahontas is grabbing my hand (among other things) wanting me to come back with her to her sorority. She whispers in my ear that she wants me "in just the cowboy hat." My response? Run away like a pussy and call Sherice to declare I missed her. I distinctly remember running away (really running) and looking back to see the look of shear confusion on her face. Still haunts me to this day.
Postscript: After about another month of dating Sherice from afar, she called me up to tell me she was getting back together with her ex because they had "unresolved issues." V-card got thrown back in the shuffle. Ugh.
It was the summer after I graduated college, and I was at a friends all day backyard pool-party fraternizing with old high school friends. It was not a rager per-se, but being reunited with old friends whom I had been estranged from (in the mid-west) for so many years made it a drunken night. I had recently broken up with my long time on-and-off again college girl friend and was interested in some strange.
There was one particular girl, we can call her Allie, whom I had always had sexual tension with throughout all the years I had known her. But our previous relationships during high school and college always deterred any real progress towards sexy-time. Fast forward to the night, much alcohol was consumed and people are beginning to shut down. There were several of us stragglers in the hot-tub and byy the time everyone had decided to go in and pass out it was me and Allie left in the tub. There was no conversation, or build up, we just started sloppily going at it; 8 years of anticipation. After about 5 minutes, penetration had been achieved and this was incredible.. However, it may have been the water, or my complete drunkenness but I was having trouble keeping it up, so I suggest we go inside and have some dry-time fun..
I walk inside and two of my best friends, whom I thought had fallen asleep, were in the kitchen and proceed to start a long slow clap. They then direct my attention toward the small TV they had been watching which was hooked up to A LIVE FEED SECURITY CAMERA OF THE HOT TUB. It was literally zoomed in on the hot tub only, and was the only security camera the house even had. To this day I do not understand why it was necessary to have a live feed camera on the hot tub, but I digress.. Allie drunkenly wonders in afterward and for some idiotic reason I tell her that my friends had watched the whole thing and I must have said something like "how funny is that?!" She was not amused and, completely embarrassed, passed out on the couch leaving me dumbfounded in the kitchen with blue balls.
My friends still think it was the funniest shit they have ever seen and were pumped to see her tits. To this day it is the only time I've done it in a hot-tub, albeit a brief experience. It was the last time I ever hooked up with her.
When I was living in Denver, I was dating a girl that lived in Boston. We started dating when I would go out there for work and/or to see friends, but she asked me to come out there for a weekend to spend with just her. For whatever reason, this stressed me out. Between work and that impending weekend, I had some bowel issues that caused some hemorrhoid issues. I figured they would go away by the time the weekend came around and that I'd be fine. No such luck.
On the way to the airport, I bought some Preparation H and Advil to help relieve the agonizing pain I felt anytime I moved my ass (sitting, standing, walking, and even shifting in my seat made me wince). I applied the ointment in the bathroom of the Denver Airport (half expecting Larry Craig to offer assistance). I thought, for sure, that this magical Preparation H combined with the pressure of an airplane flight would have the hemorrhoid pop or go down. No such luck.
She picked me up from the airport, and we went to dinner. I drank a lot at dinner to help numb my pain. I also kept on popping in those Advil every couple of hours. We met up with some of our friends for more drinks (and more Advil) before heading back to her place. Once we got there, she was ready to get down. Through the miracle of alcohol and advil (and pussy), I managed to push through the pain and perform. Afterward, I put on a pair of boxers and passed out on my back.
The next morning, I woke up at about 7:00 and felt something wet under me. I also felt no pain. This meant only one thing. The freaking hemorrhoid popped. I immediately turn over to see if I left a mark on her sheets. There was a brown and red stain on her pristine pink sheets. I immediately go into full on OH FUCK OH FUCK panic mode. It was so early, and she generally sleeps late, so I had about 3 hours to figure something out. I couldn't fall back asleep because (a) my heart was racing too fast and (b) I needed to be awake when she woke up so I could keep her eyes away from my undoubtedly blood and shit soaked boxers. A lot went through my mind during those 3 hours. I seriously debated running out of her apartment never to see her again. This idea came up many times as I sat there facing my own social mortality. Instead, I just lay there on my side like a fucking sloth. But I finally thought of something.
When she finally woke up, she asked me if I wanted to shower. I told her that she should shower first. When she was in the shower, I threw the boxers out the window, stripped her bed down, flipped the sheets, and made the bed. When she saw the stain again, it would be on her side of the bed, and she'll think it was her. She got out of the shower and saw what a gentleman I was and blew me right in the middle of her bedroom. After I showered, I noticed that she re-made the bed. But she didn't say a word to me. That night, after we got down again (pain free!), she was adamant that she put clothes on. When I asked her why, she clammed up and said that she was cold.
Not really a failure, but I'll allow it.