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 was a senior in high school back in 2006 and this girl I've been seeing/dating and I decided we would skip class and head on over to her place since nobody was home. For these purposes we will name her Michelle. Michelle was one of those girls with a set time limit that had to go by before she would let me get some of her. We park my truck on the street about 3 blocks down and the minute we walk in the house we start making out like the two high school kids we were. We head to the nearest couch available and start messing around. She decides that I've hung out with her enough that we could finally have sex, which was perfect with nobody home. I swore I heard a car door slam outside but it didn't fucking matter because I was about to bang Michelle after all my efforts and because nobody could be home from work this early. Michelle requests that I do her doggy and just as I put it in her I heard the old "exaggerated cough". There is her 83 year old grandpa and he is PISSED. He came over to repair the dishwasher. I pull out, scramble for my keys and wallet and he is in the hallway blocking the only exit out of the room. I didn't have time to put clothes on or even take off the rubber for that matter. I had to do give him my best Barry Sanders move to get around him to get outside. I'm 100% naked and my truck is blocks away. Clearly I couldn't ask for a ride so I streak through the back yards of numerous people's homes to my truck. I never did get to get more of Michelle. Thanks gramps.
Right after college graduation, one of my friend's parents (both are doctors) bought him and his brother an apartment; in a high rise building in Downtown Long Beach that overlooked the ocean. Needless to say, this instantly became our party spot and we took full advantage of all the perks that came with it. The brothers knew a girl from school who lived there with her parents and invited her out with us that weekend. She agreed and asked if her older sister and cousin (who lived in San Pedro) could come along, of course it was a yes....
Fast forward to Friday night and the brothers, myself, and our two other buddies, Adam and Mike are pre-gaming a bit, the girls come up, made the introductions, and after about 5 minutes I knew I was going to hook up with the cousin whose name was "Stacey." We go to the club and Stacey and I are pretty much all over each other the second we get in. After a while, the girls go to the bathroom and Adam and I run into a couple girls that were friends with Mark's GF. I had been trying to get Mark's GF to put in a good word for me with one of them, whose name was "Lauren," since the beginning of Senior year, but Mark's GF wasn't a big fan of me, to say the least.
We start talking with them, agree that we should go take shots, not wanting to blow it with Stacey, but definitely wanting to try my luck with Lauren I suggest we go to the bar on the other side of the dance floor because, "I knew the bartender." I tell one of the brothers where we are going and to keep the other girls occupied, and that we will be back. After 4 shots of Patron we decide to hit the dance floor, Lauren and I start making out instantly, while this is going on she is telling me that "She's wanted to fuck me since last year," and a few other wonderful things that a guy wants to hear on a Friday night. Next thing you know, her friend that Adam is with pukes all over the place, in the process gets it on Adam and about 3 other people. Her friend gets kicked out, but Lauren gives me her phone to put my number in, and says to hit her up tomorrow if I would like to do something tomorrow night.
They leave and I realize the brothers are entertaining Stacey and the other girls on the other side of the club. We come back and after some smooth talking Stacey is back to being all over me.
About that time, everyone decides to take the party back to the brother's apartment. Stacey and I jump in a cab and start going at it, when we get up to the apartment everyone is in the front room getting high, so we run out to the balcony that happens to have an outside couch and a chair. After some furniture maneuvering, she is on her back and her boobs are out and I'm all over those things (large B to small C cup in my estimation). At this point I move her thong to the side and start fingering her, after a few minutes I'm taking my pants off with one arm, while my other arm is balancing me over her while we make out.
Just as I'm getting in my shoulder dislocates (my shoulder is pretty much shot from getting sacked and landing on it during football and pitching during baseball), I fall on her, hit my head on her nose, which of course starts bleeding immediately. I roll over, put my pants on with one arm, go inside, throw my shoulder back in, go to the room where everyone is still getting high and say "Stacey has a bloody nose," then walk straight into the next room and pass out on the bed. Needless to say they never hung out with us again, but we did see them at the pool time to time which was quite awkward.
And for Lauren for the next night, Mark like an idiot told his GF what happened, who obviously told Lauren immediately, who gave me a nice "I should have listened about you, Fuck off," when I texted her the next day.
It is summer in Chicago and my sister had made the trip down to the city to visit me for a Friday night out with some friends. We are pretty close in age, so she comes down pretty regularly to crash on the couch and hit the bar scene. This particular Friday was nothing special, a few bars here and a few bars there. It is around 2 am and the bars are closing up, but our group of friends didn't want the party to end, so we invited everyone back to my apartment.
I tossed them the keys to the apartment, while my sister and I went into the 7/11 near my place to grab a bottle of wine and some beer for the group. If anyone is from the near north side of Chicago, they will know the 7/11 I'm talking about, as there is a guy that works behind the counter who is commonly referred to as "Daddio". He kind of resembles Snoop Dogg, in both tone and appearance, and always greets his customers with a "What's happenin' Daddio?" "What can I get for you Daddio?" "Credit Card machine is right over there Daddio."
The common response to this greeting is to usually respond with "Thanks, Daddio" or some kind of awkward exchange in which the 7/11 guy actually gets called Daddio as well. He is actually usually a cool guy, always really friendly, remembers who you are and good for a few laughs when you are getting a nightcap hammered.
My sister and I purchase the wine / beer from Daddio, exchange a few "daddio's" and head on our way. Everything is perfectly normal. Fast forward to Saturday night, and my sister has gone back to her own home city. I'm out with a few buddies of mine at one of our favorite bars, and of course, quite the bit of drinking ensues. The night continues on, and eventually I meet this girl Katie, who is this beautiful blond girl, not only charming and very successful, but also someone who has been hitting the sauce hard all night, and thus, into me.
I execute the plan perfectly, say goodbye to my friends, grab Katie and begin to head back to my place for a "night cap" The only problem, is that the night before my sister and our friends drank me out of booze, which isn't quite a problem being that I live so close to that 7/11. Katie and I stop at the 7/11 for a bottle of wine on my way home, and I'm counting my blessings that a girl this out of my league is still OK to go home with me after buying her $7.00 yellow tail at 2 am.
We head up to the register, which is yet again being patrolled by "Daddio" to pay for the wine. Daddio takes a second to look at the Katie, then looks at me, and the first thing out of his mouth is "Dadddiiiooo... two girls in one weekend, that's what I'm talkin' bout" Katie, horrified, and thinking she is 2 of 2, hits me in the arm and runs out of the 7/11 to hail a cab. I chase after her with the desperation that only can come after watching your dream girl be chased away by Snoop Daddio the 7/11 attendant. The thing is, you could tell on "Daddio's" face the minute he let it slip that he was trying to reel his words back into his mouth, but just couldn't do it in time.