Welcome to Great Moments in Drunken Hookup Failure, where we showcase three heartwarming true stories of drunken love gone horribly awry. Off we go.
Senior year of college, the last day before Spring break fell on St. Patty's Day. It was also the first day of the NCAA tournament. No, I didn't go to class that day. Turned in a couple papers that morning and then went to a friend's house to smoke before buying beer and heading to a party. We arrived at the party just before tip-off (10:55 central time) and raged through the first two games. From there, we made the rounds, went to four or five other places, the whole time getting beyond shitty thanks to overflowing Jameson and March Madness adrenalin. The night rolls on, and at the end of the second round of games, browning out pretty hard but able to function thanks to the 60 extra pounds of beer-sopping weight I carried at this point, I walk this girl that I'd sort of been talking to home for the night. We kiss a little bit, nothing crazy, and say goodnight. I stop by a greasy spoon on the way home and afterward decide to check out what's going on at the big mid-campus bar, since I could still see and the restaurant was next door.
A couple of my buds are there, and we talk nonsense for a while until, in the back corner of the bar, I see this chick that I'd been friendly with for a few years. Nothing had ever happened between us, but she was cute, she liked to party, and she lived across the street. Drunk as I was, inhibitions sufficiently obliterated, I had no problem heading back to where she was and saying what's up. She responded well to my entreaty and we got along like best buds. By night's end, I'd forgotten about both the girl I walked home earlier and the fact that I'd been drinking and smoking for well over twelve consecutive hours. She was down, I was in, and so on I marched. We actually made it all the way to closing time (2:30 in these parts), having a good time and keeping the party going. Finally she turned to me and said, "You want to walk me home?"
It didn't take long after getting back to her place for the two of us to start tearing into each other. After tossing each other around the kitchen for a while, we make our way back to her room. Everything is exactly as sloppy and rough as you'd imagine it would be. From the outside, I bet it looked like two blind people dancing with each other to different songs playing in separate headphones. Anyway, we make it over to the bed, and we take turns going down on each other. I go first, and enjoy my time down south, which lingered on a little too long, for reasons which should be obvious. She tells me that she's good, that it's my turn, so I flip over. She seems eager, so I lay back and put my hands behind my head, totally relaxed and feeling awesome. So relaxed and awesome, in fact, that I pass out not long after she puts her mouth on my penis.
Next thing I know, I wake up at 10 AM in an empty, unfamiliar, incredibly bright bedroom. Thankfully, the house is also empty. It's take a minute to process the way everything went down, to remember any details, and even so I'm still not entirely willing to admit I fell asleep during a blowjob. In what I later figured was an attempt to hide my shame from myself, I leave her a "Let's do this again sometime" note that read something like, "Nice running into you last night. If you want to hang out again, here's my number," below which I put my digits. She never called. In fact, I saw her plenty over the rest of that year, and she would barely look at me. I found out later that her friends had put the note up on the fridge in their place, meaning lots and lots of people I knew or lived around saw it at some point, though none of them ever told me about it, and I never received any prank calls.
Did I tell my friends that we had sex that night? Yes. Yes I did. Did any confidence I may have had concerning women at the time die a bit every time I did? Yes. Yes it did.
My freshman year of College, I hung out almost exclusively with the guys on my floor, almost all of whom were on the football team. As a result, I ended up frequenting the football team's bars and meeting most of the team. Through this, I met "Kevin," a senior, a captain of the team, and the president of the football fraternity. My dude friends assured me that he was a great guy, and I progressively started hanging out with him more throughout first semester. Though we had come close countless times, we still hadn't hooked up.
Over break, he invited me to come up to New York for a weekend. By the time I bought my ticket, he had already made plans to leave the city that weekend. To make up for our missed connection, he promised to take me out on a date when I returned to school. My dreams of becoming the First Lady were in motion. We decided to see Up in the Air. Because we smuggled a bottle of SoCo into the theatre in truly romantic college fashion, and talked throughout the movie (yeah, we were those people...I apologize), I didn't realize it was an absolutely terrible date movie until I watched it a second time. We got a little handsy on the subway en route to the football bar.
We drank some more at the bar then headed back to his place. Once we got to his room, we immediately started macking and were quickly on his bed sans clothing. He started to go for the gold, but I was on my period and said we couldn't. The gentleman he his, he suggested that we put a towel down and proceed, something I had absolutely no desire to do. So we started cuddling, which was problematic for a few reasons: he's 6'5" while I'm 5'3", he had a raging boner, and the size of his penis (inhumanely large) scared the shit out of me. The cuddling turned slowly turned into him thrusting into my backside and, eventually, titty-fucking my buttcheeks. I didn't know how to respond to this spontaneous "hotdogging," as my friends affectionately call it, so I just pretended to be asleep. The hotdogging stopped and he fell asleep, and I tried to extract myself from his ninja grip on my body. I soon realized that I couldn't get free without waking him and risking more hotdogging, so I was forced to spend the night. My desire to be first lady was so strong, though, that we continued hooking up for a couple months. Still, we never fucked because it proved physically impossible, even with gallons of lube, to fit his monster cock into my body. Fittingly, he now works on Wall Street.
Spring Break 2012, we head to Nashville. Drinking some beers and a self-made rum and coke, 2 female friends with me yell my name and ask "How old are you? 28?" I turn around and there's a moderately attractive blonde with massive tits. I respond that I'm 26, and they introduce me to the blonde whose name went in one ear and out the other. My friends tell me that Blondie is 32, and a mother of 2. So of course, I'm suddenly an old 26, almost 27. Start chatting her up, telling her that her friend, who is my age, is the one who looks 32 and the normal hitting on conversation, while staring at the tits, and it all seems to be working well.
Blondie and her friend are also chatting up my friends, becoming facebook friends with one of them, drunkenly planning on come to visit us in for a party coming up in a couple months. Blondie at one point exchanges email addresses with me, at which point I laugh out loud at the 32 year old's AOL email address. Nevertheless, Blondie wants to continue the party, so she's ready to come back to drink more rum. Flirting is getting heavy, and we're waiting on the cab on the street.
Out of nowhere comes "Hans," a friendly German fellow. "Hans" is chatting us up, and I have doubts as to the authenticity of his German-ness, and he seems to be getting too touchy-feely with Blondie. Naturally I call into question his German-ness, and he insists its real. By now, the cab has pulled up, but I'm too fixated on discrediting "Hans." I'm arguing with "Hans" to the point that he pulls out his "passport," a laminated index card with his pic and some German words on it. I then call him out on the authenticity of the passport, to which he admits its all fake, he's a local Nashvilian. Finally, mission accomplished! Time to bang the 32 year old and finally see the rest of the tits. But its too late, Blondie is now smitten with "Hans." I try to get her to come in the cab and now she's having second thoughts, about leaving her friend and "Hans." I go to get in the cab, and my friends suggest I try one last time. Giving it my all, I literally grab Blondie and start pulling her to the cab, but alas, "Hans" won. I was cockblocked by a dude with a fucking fake German accent.
Who fakes being a German? That makes no sense.