I have a tolerate-hate relationship with Deadspin (as I do with most Gawker sites), but I am not above pilfering one of their series' for use here. Every week, they showcase stories of people failing to get it on; with a population as sexually vibrant and unfailingly awkward as ours, I bet we can come up with something interesting too. Focus: Post about your hookups gone haywire.
Failed Threesome. I used to travel frequently from LA to San Francisco on business. At some point I struck up an on-again/off again thing with a very attractive Norwegian art student about 15 years my junior (i.e., when she was dating someone it was off). One trip I joined her, and some of her fellow students for drinks to celebrate my friend's birthday. Among the group was a fit, attractive woman of about 40 (much closer to my age) who had taken up art late in life. I ended up hitting it off with this lady. After drinks, I take my friend and the older art student to dinner at one of my favorite SF eateries (quick plug, "Bix" -- its down an alleyway, is a spectacular room, and the food is very good.) We have more drinks before dinner, and when I look at the menu I notice I am having trouble focusing. Of course I press on, and order some great wine to celebrate the birthday. We then hit several bars for more drinks, which included some very provocative dancing amongst the three of us. We decide to head to my hotel. Eventually we end up in my hotel room, the three of us on my bed. After some fumbling around I say, "I'm gonna lay back for a second." I awake, several hours later, not having participated in a threesome, but rather to the sound of the older art student leaving through the door to catch the morning train back across the bay. She gave me a rueful smile and wave as she left.
A little back story: For the first year I went away for college, this guy lived in the apartment below me. We were in the same major, and we had the majority of our classes together. Throughout that first year, it slowly became obvious that he has a thing for me. He sat next to me in all my classes, came to every party we threw, and would randomly knock on my door when he was drunk to see what I was up to. For that whole year, I blew him off because my roommates didn't think he was attractive and I cared too much about what they thought. ( I've told stories on this board about my college roommates before, so you might know how stupid my caring about what they thought of men was.) Fast forward to the next year. He moved to a bigger apartment, and I stayed in the one I had. We still had a bunch of classes together, but he wasn't knocking on my door as much. We had a mutual friend and I got invited to a party at his place. It had been awhile since I had sex, and I had a little too much to drink. I'm not sure how much I had had before i decided i would sleep with him, but it wasn't much. As the party is winding down, I see him slip away to his bedroom, and I decide to make my move. I don't remember everything that happened, but these are the highlights: [*]Got into his bed with my pants and bra off [*]Fell asleep [*]Woke up some time later and ask if he wants to have sex. He doesn't have any condoms (For some reason I forgot I was on birth control at this point) [*]Fell back to sleep [*]Gave what was later called "the Saddest Handjob in the History of the World". Sad because I fell asleep before he was even hard [*]Get woken up a little while later because he sobered up and remembered he had a girlfriend. He asks me to leave [*]Left his apartment at 5 am with my bra in my hand and walked back to my apartment (about a block away). I had to sit next to him in all 5 of my classes for the rest of the school year (This happened in September.)
In the early90's before everyone had cell phones random girls my roommate and I knew from the country night club we hung out at would sometimes show up at 2 or 3 in the morning, as luck would have it one night this girl who liked my roommate showed up with her larger friend (5-2 190ish) and while my roommate was otherwise occupied I consumated my relationship of 10 minutes with the larger girl by having drunken 3am sex with her which she apparently enjoyed, she was mad that I would not kiss her but she got over it. I grabbed a beer from the fridge and put some fresh dip in and went to sleep. Since lightning strikes twice on occasion a week later same girls show up but my roommate is out of town, I had forgotten both of the girls names but welcomed them in, the larger girl was quickly told by the other girl to "Hurry up, we drove here so you could have sex with him." Since tequila had been a large portion of my intake that day I had a problem finishing, so after what seemed like an hour, but was probably 5 minutes I got bored and asked her if she would go get her friend, who was waiting patiently, to join us. She was not amused but still wanted some more so I went about stabbing her guts some more, a few minutes later I asked her again to get her friend to join us, again she objected but I insisted. She finally agreed and got out of bed (and stealthfully grabs her clothes) and went to ask her friend. I laid and waited will being very pleased with myself about how awesome I was, a few minutes later I hear some cursing and my front door slams and a car leaves. So ended my free sex with larger girl.
We said hookup failures, not successes. FOCUS: My favorite happened my last year of college. I was running game on a cute girl I knew from an extracurricular group. She was wearing one of those slinky dresses that were sort of loose and flowing, but hugged a great ass perfectly. Well after drinks and her begging me to play her some slow jams on my guitar, she was ready to get after it. Well as we had been drunkenly making out around my house and outside, another friend of mine passed out in my room on my bed. So I began to contemplate other hookup locales. Then I got a brilliant idea. My house had a pretty flat roof with an area that was almost a cove of sorts. The only issue was that it was tricky to get up and you had to climb up off of a bench on the deck. I should have noticed the omen as we climbed the steps up the deck, she tripped and scraped her knee a bit. Unfazed, she kissed me wickedly and grabbed my groin. So we stand on the bench and I hoist myself onto the roof like the chivalrous gentleman I was. I reach down to pull her up, glancing greedily down her dress as I did. However, as she took a wobbly step up, she slipped and I caught and managed to pull her halfway up. But she was wasted and my drunk strength was lacking, she lost her balance and slipped away from me. I tried to hold, but we both had palms sweaty with sexual anticipation, so she fell from my grasp. I was tempted to snarl "Long live the king!" as she fell, but I resisted as she banged onto the deck and fell off the side into a teary mess in the grass. I dropped down to help in a mixture of confusion, anger, and worry. So instead of ending the night with a fantastic outdoor bang session, I settled for applying neosporin and confusing a crying girl that she didn't dislocate her hip and a hospital visit was unnecessary.
I'll proffer a relatively tame one with little payoff. I was hanging out at a friend's college, at some fraternity house. Not usually my thing, but a third friend was the head of the chapter, and it provided a convenient place to get drunk. Whatever. We're all smashed into the room of one of the more introverted guys. Good guy, and more important for this story, an excellent amateur bartender with (by college standards) and impressively stocked bar. He offered to make the group whatever drink we suggested, and eventually, it was decided that that drink would be Sex on the Beaches. You can mock me as much as you like, but I'm speaking without hyperbole when I say that that particular drink was the best mixed drink I'd ever had. It was obviously full of sugar, but the bitter tang of the alcohol actually played off of it wonderfully. I have never ordered a Sex on the Beach in a bar (because I am not a 34 year old tourist in 2003), but rest assured that this was one delicious drink. And strong. So strong, in fact, that the girl sitting next to me basically jumped me as she finished the last of her beverage. As is the case when this happens, the room cleared out fairly quickly, leaving me with this amorous young lady. What she may have lacked in attractiveness, she made up for in being right next to me-ness, and it was on. I actually recall her being moderately attractive, but that might be hindsight; in any event, I would have done it either way. I unzip her hoodie to find that she is impressively endowed AND not wearing a shirt. Great. It's at this point that my bladder deal comes back to bite me -- the deal, simply, is that I don't require too much of my bladder, and it doesn't require too much of me. It works, but it also means that I have to get up and go pee. I do so, and I'm washed and back in a couple minutes. As I get back, she springs up, zips her hoodie and wails, "you're totally hot, but I can't do this to Mark!" and flounces out of the room. I am left, drunk and confused, in the bedroom of some guy I just met. If you thought reading this story ended abruptly and without a satisfying resolution, imagine living it.
My freshmen year of college I had yet to lose my virginity. At one rather slamming house party one of my friend's from my floor decided he'd help change that. It was probably one of my favorite house parties of all of college. They had some seriously strong Hairy Buff, it can't not be powerful with everclear, and one of the longest continuous flip cup tournaments I had ever been in. All of the good friends I had made up to that point where there letting off that glorious college aged steam. Towards the end of the night I was seeing doubles, something I rarely do, either Im not drunk or Im black out wasted. But I go to the back yard after the flip cup game had finally ended. I was shooting the shit with some people when my friend came up to me with a girl he had been chatting up. With out giving my prior notice he had been telling her I was a virgin and telling her she should be the one to take it. It was enough for her and I guess the thought of being my first intrigued her since "everyone remembers their first." I had been kind of pissed at my friend for not warning me but I was down for it as she was cute and I was beyond wasted. I think she was a hellavu lot less wasted than I was at this point. She took me back to her dorm room to get condoms. The last thing I remember was her introducing me to her roommate and telling her straight out she was going to take my virginity. As she searched for her condoms, I managed to pass out against the door and fell to the ground. She eventually had to find my buddy to help drag me back to my room.* I woke up a while later and found her hanging outside our dorms with my friend, she let me know the deal was off. I finally lost it a few months later after I had moved into my own apartment. * a funny side not is that earlier in the year another buddy and I had randomly had to carry this same girl back to her room when she passed out in front of our dorm's elevators and pissed her pants. I miss college so fucking much.