I was at a friend's house for her birthday party, mainly because a girl I had been flirty with was her best friend, and would be there too. When I was there however, she largely ignored me and spent time with her friends. As such, I started being a bit of an ass with the people I knew there, I guess to get attention or something. Anyway, we were tossing around bits of wrapping paper. For some reason I threw one at the girl and said "Think fast!".
It hit her square in the eye. The eye turned vivid red and she was in discomfort for the rest of the night. She pretty much went back to ignoring me for the rest of the night, though she ended up driving me home. The conversation was understandably tense and short the entire time.
It turns out she was too nervous to talk to me for most of the night and she spent the time with her friends trying to figure out a way to do so. The ride home was largely tense because she wanted me to ask her out.
I got drunk at a party with this girl, things were going well and we went back to my place. We get naked and one thing leads to another and it's time to get laid!
The day before I had bought a 25-pack of assorted Durex condoms. They were color coded by the wrapper, but they didn't have any legend as to what each color meant. I said fuck it, dumped them all in my nightstand so that all the different types were mixed together and threw away the box.
Back to the night in question: The lights are out, and I reach for a condom. Condom goes on and I'm going strong. Ten minutes in, and I kind of just start to lose interest or something. My erection begins to lose steam and I figure it's because I'm not intensely attracted to the girl and condoms suck.
I'm pretty embarrassed at this point. I think she probably felt pretty lame too. We awkwardly stop, I blame it on the alcohol.
Reach in for another condom, put it on and I'm back in action!
... for about 5 minutes and I lose it. AWK-WARD. For the record we tried once more after that but my dick wasn't even up to the task by that point. I went to sleep horribly embarrassed.
The next morning I we sheepishly drove to her house so I could drop her off. I said goodbye vowing to call her but knowing full well I never would. I drove back home and found the condom wrapper on the floor.
"Huh! What a coincidence... They're all the same color."
As I turn to throw the condom away, I finally notice (in very fine print) a label on the back of the wrapper: [5% Benzocaine]
That's when the horrific realization set in that I had the night before applied THREE of these fucking things in rapid succession and fully numbed my dick. No wonder I couldn't seal the deal. Just to recap, the probability of this happening to me that night exactly like that was one 1 in 230.
I have never lived this down, but it doesn't even compare to the time I accidentally mashed chewing gum into a girl's s pubic hair while performing cunnilingus.
I had this big ol' crush on this guy in my Spanish class in high school, and, horror of horrors, he seemed marginally interested in me, as well. One day he's passing me in the halls, and he gives me that snap-into-pointed-finger thing (you know, like the Fonz does) and says, "What's up?" I mean to say something clever, and even have it all picked out in my mind, and am about to do it when something in my mind trips over itself. Instead of saying something charming, I stop dead in my tracks, arms akimbo, and open my mouth:
Somehow, between my brain and my mouth, my fabulously witty response turned into the noise a sleepy retard makes. He gives me a weird look, and just keeps walking down the hall.
I went to a dance club with a bunch of friends. We all got dressed up really nicely, which immediately set us apart from the crowd (typical fashion around here is t-shirts or polos and jeans). The DJ they had on had a string of maybe 5 songs that were just absolutely fun to dance to, and he ends his run on "Billie Jean." I looked over and noticed this really tall lady (6'0" I think, and I'm 5'10") trying to get her boyfriend to dance. Some guys just have lead feet or something and can not get into the rhythm.
As soon as he went to the bathroom I moved in and took her by the hand and moonwalked her back onto the dance floor. We were really groovin' and getting along nicely. Then she started talking to me, which is GREAT because I have shitty hearing and the speakers are so loud that there's some mild distortion going on. Through the loud club, her drunken speaking, and my drunken hearing, "Do you want to come over tonight" became "You look like a girl tonight."
I don't remember what I said in reply, but I DO remember that she looked really disappointed and stormed off the dance floor.
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