Welcome to Great Moments in Drunken Hookup Failure, where we showcase three heartwarming true stories of drunken love gone horribly awry. Off we go.
I love NOLA and I go there as often as I can. I spoke glowingly of it for years to the point that my little brother wanted to go on my next visit. He had just broken up with his fiance, who he found out was a coke whore. He was going through a rough patch and I figured NOLA is as good of place to overcome that as any. I said yes, let's do it. I planned the trip around Tuesday night Rebirth Brass Band at the Mapleleaf and Kermit Ruffins at Vaughn's. I tell him the plans and he starts planning the trip.
My brother also decided to invite my father, with whom I do not see eye to eye, for a little family reunion without telling me. At the Mapleleaf, I make contact with my brother and find out my father and he are at the concert as well. I am feeling good at this point in time wondering around trying to avoid any actual conversation with family and find a group of girls I had met earlier in the evening.
I notice a cute girl from the group was looking at me. She was Jewish and no conversation was had. I found my brother, drank and then waited for the first set to begin, at which point I found the Jewish girl again and in short order were doing the white person variant of dancing the whole time. On break I buy her a drink and separate again to find my father and brother. They were in awe of the place, I was not paying attention to the casual racism coming out of their mouths and my brother is making plans for after we leave the bar.
I mention that he is going back with our father. The second set begins, and I go find the girl on the floor again. We started full on making out on the dance floor only to break to mention that my family and her friends were watching. We start talking about getting back to her place. She said she needs to find her roommate and for me to tell my family the plan. I go back to formerly meet the roommate and get told the rules for coming over schedules, and trading phone #'s with both of them. Out of the corner of my eye I notice my father leaves out the front door and my brother walks towards us. I was confused and then he tried to do a silent aside to me but instead uttered to me drunkenly and loudly:
"Are you gonna show me around the city or you gonna go home with the girl with the Shylock nose?"
Needless to say both the girl and her roommate heard him say this and I was on the defensive but far too drunk to think how to get myself out of it and still get laid.
It was a disaster. They were both pissed, calling him a racist yet he just walked off to the bar to get another Bud Light. I got complained to for another 30 seconds and then asked if I could call her later. Her roommate told me where I could stick my request so I went and found my brother at the bar for more whiskey. He said "that Shylock girl's friend was a real bitch." I was so confused, drunk, and almost expectant that I wasn't even pissed. I then showed my little brother around NOLA drinking the whole time for another 6 hours. That next day hurt a bit. I tried calling her on the Thursday but found out all her friends from school had taken pictures of us making out on the dance floor.
She was not impressed.
I never saw her again.
Prior to my third year of college, I transferred to UW-Madison. I grew up in Wisconsin and had gone to a small school up north for two years. I didn't want to be just like everyone else in my graduating class and head straight for Madison, for some hipster-like reason. Anyway, I found an apartment right on Fraternity/Sorority Row.
One night in early fall my roommate and I had some friends over for a dinner and drinks. We're almost 21 now, sophisticated and shit. I made Manicotti and we drank wine coolers and Old Mil. Many of the people that came over that night went to high school with us. This one girl, Kim, I knew since about 1st grade. Blond hair, round ass, nice tits. And a smile that would light up the room. She was gorgeous. I flirted with her most of the night but seemed to be getting nowhere. She had a boyfriend at a different state school she talked about every time I mention us getting together.
She's happy to talk about the lack of sex since he's nowhere near Mad town and I offer to fill in for him, half jokingly, but not joking at all. The night was winding down and she and the other 8-10 people there all left about the same time. My roommate and I sat down to play Sega Genesis (this was a while ago) and about 10 minutes later there's a knock at the door. It's Kim. She says she just had to kiss me good night. She proceeds to wrap her arms around me and push me to the couch. We fall back over the arm into my roommate. She gets up and without missing a beat tells me we should go to my room.
She leads me to my bedroom and I lock the door behind us. We fall onto my double bed and start making out and rubbing all over each other like the sex deprived students we are. "This is Awesome!" I tell myself. It's like a dream, I always wanted her back in the day. I take my shirt off and start to pull her pants down when she says wait. "Oh no, do not do this to me." I'm thinking, probably out loud. She looks into my eyes and says, "Do you have rubbers?"
I sit up and start to rack my brain, where the hell am I going to find a ..wait! I remember visiting my step brother a few months prior and using his gym bag to bring some stuff back home. There was one solo condom in there. Now if I can just remember what I did with that bag. "Hold on!" I shouted, "I'll be right back." I bust out of my bedroom and run into the living room where my roommate is still playing video games.
I found the bag in the top of the dusty hall closet and took it with me back to my darkened bedroom. Now I'm nervous and sweating. I'm this close to banging one of the hottest girls I grew up with. Sitting on the edge of the bed I pull out one lone, crumpled, but unopened packet. I crack it open, literally. This thing was old, I mean origins of the prophylactic old. "God damn it!" I screamed inside my head. It looked as much like a packet of alka seltzer plus as it did a condom. Still, it was whole and semi solid and I needed it to work.
"Please, Jesus, if you are as holy and Divine as they say, make this motherfucker fit." Again, in my head. She's leaning against me, running her fingers down my back. I am about to burst with anticipation. I'm trying to roll the condom on and it's a no go. It's too small or too old, whatever it is it doesn't fit. In fact I think it got torn and started to disintegrate as I tried to maneuver it. "What's wrong?" Kim asks. "Umm, nothing, nothing." I say unconvincingly. I'm thinking perhaps I'll just fake it.
She sits up, "It doesn't fit?" she says somewhat concerned. I turned and showed her the lack of progress and my throbbing manhood. "Yeah, it won't fit." With that she stands up. Clearly she's drawn her own conclusions about the situation. "I should go." She says. "No, wait." I pleaded. "No, really, I gotta go." She said as she gathered up her clothes. She didn't even wait to get dressed. She took her clothes and went out the backdoor. I think she got dressed in the hallway. I didn't go back out to the living room. I wanted my roommate to think perhaps I got lucky. He didn't. I saw Kim once more that year, second semester actually. I tried to get close to her and told her the situation wouldn't end like that again. She agreed as her boyfriend had transferred in at winter break.
When I was a freshman in college, I roomed with a high school buddy of mine, Mitch. About a month into the semester, he hooked up with this girl Karen from another school nearby. They kept in touch and decided it would be a good idea if she invited her friends from school and we invited our friends from high school up for a weekend. We lived in a crappy freshman dorm, so we could only promise floor space for our friends to crash on. In order to maximize that floor space, we rearranged our beds as bunk beds (with mine on top).
After everyone showed up, we made our way to a few parties. Eventually, everyone was pretty wasted and we all headed back to the dorm together. My roommate and his girlfriend passed out in his bed, and I offered my bed up to one of my buddies, Jack. He gladly accepted, leaving 4 of us (2 guys and 2 girls) to sleep on the floor. After a few minutes, one of the girls decided that she couldn't sleep on the floor anymore - she'd like to sleep on the top bunk with my buddy Jack. But don't worry, she said, nothing was going to happen because she had a boyfriend.
Well, a few minutes later and she was blowing Jack as we're cheering them on from the floor. After a couple minutes of fellatio, the girl went to throw back her hair. Unfortunately for her, our concrete ceiling was less than 3 feet above the top bunk and she cracked the back of her skull directly on it. In fact, she hit her head so hard that she passed out right on top of him. After a few minutes of deliberation about whether a trip to the hospital was necessary, she woke up and instinctively started sucking again! But the effects of the concussion would soon take hold, and she passed out for good this time - unable to finish the deed.