Welcome to Great Moments in Drunken Hookup Failure, where we showcase four heartwarming true stories of drunken love gone horribly awry. Off we go.
So I finally get out of a terrible 1.5 year hell of a relationship with a girl, and I met a perky personal trainer. The Gods are smiling on me, I assume. After 2 or 3 blueball-inducing hookups, she finally relents and invites me to have sex. So I grab a condom as fast as possible, put it on, and slide in —- except I notice more friction than I remembered (hadn't worn a condom with the ex-gf for at least a year). I quickly notice that, in my drunken haste, I put the condom on inside-out. I think about plowing through it cause I am so revved up, but in a doomed moment of courtesy for her pleasure I announce said failure as such —- totally offhanded and kinda laughing at myself. Here is the convo:
Me: "Whoops, put it on inside-out, my bad. It's been a while."
Perky PT: "It's been a while since what?"
Me: "Since I wore a condom — I had a serious gf for a long time."
Perky PT: "When did you last sleep with her?"
Me: "I don't know, a couple months ago before we broke up."
Perky PT: "I'm not in the mood anymore. Get off me."
I never got anywhere close to sex with her again. The moral here —- never stop fucking anyone for anything. Especially if it's for an inside-out condom. Cause it feels pretty good on your unit anyways.
A vital lesson Jay teaches us here: talking more will only serve to fucking ruin you.
I stayed at college for the summer session one year early last decade — I think 2003, but I could be wrong — to take a couple of classes, keep a small part-time job, and just generally relax. In one of my classes, I was assigned to a group project with this very attractive, very nice girl ("Vanessa"). Things went well, we got the project done, and life moved on.
A few nights later, about 10:00 PM, I'm at a local bar when in walks Vanessa with a couple of friends. I'd had a couple drinks, but not many at this point. She comes over, we start talking, and I mention that I'm going to a party later that night. She says she'd be interested in going too, and we exchange numbers. But I never hear from her, and by 3 AM I've left the party and am home, drunk, falling asleep...when the phone rings.
It's my mother. Who wants to know why the hell this Vanessa person called and woke her up at 3 in the morning, when they're on vacation at a cabin in Wisconsin.
I apparently had given Vanessa the first three digits of my CELL number...and the last four of my HOME phone number...an XXX-YYYY combo that matched, exactly, my mother's cell phone number.
Vanessa and I didn't hook up. Oddly enough, we weren't paired up for any other group projects either.
Oof, that's a dagger. What are the odds Lone Dawg takes time out at least once a week to visualize that would-be hookup? 100%?
I had just graduated college and went back for a reunion weekend, and ran into a girl that I used to casually hook up with when in school. We drank all night and decided that even though we were both in serious relationships (she is now married to her guy) that it was worth it to go back to her dorm to hook up.
We go back to her room and I have to sit patiently as all her roommates berate me for hooking up with her even though she has a boyfriend. I sit through it and patience is rewarded and we start hooking up in her common room on the futon. We start to have plain old sex and it's okay. The futon is tight and we are both hammered, and somehow I end up on the side of her as she lays down on her stomach. I figure I'll just start fingering her to get her to roll back over so we can continue to have sex. She maneuvers it so I am now on top of her and I'm thinking okay I'll do her doggy style. But that doesn't happen. She speaks up and says, "Fuck me in the ass, fuck me in the ass."
Now I had been out of her for a minute and she is clearly not wet back there, but a man rarely hears these words, so without hesitation I just start to try to jam it in there. No dice. She tells me to go into the bathroom and grab some KY. I couldn't find it. I was so drunk it was probably right in front of me, but I somehow came out with some Herbal Essences shampoo. I get back to her and try to put some on her ass. I get some out, but she goes, "What is that?" I tell her and she says I can't use that and sends me back to the bathroom.
I go back to the bathroom and am frantically looking for anything. Finally, I see a bottle of St. Ives. I knew that was some kind of line of moisturizer, so I grabbed it. I get back to her and tell her that I have some lotion, and she agrees that we can use it. A little foreplay to get us going again and then I lube up. As I'm putting this St. Ives lotion on myself I'm wondering why the hell does it feel like there are little rocks in this stuff? I ignore it and put it on. I start to pump and after a few pumps the pain and discomfort is too noticeable. She asks that I stop, and asks what I was using. I told her St. Ives lotion and then she asked to see. I showed her and then she goes, "Oh my god I can't believe you EXFOLIATED MY ASS. You can't use exfoliant to do anal." We both pass out, wake up sober, and I try again in the morning only she says we can't have sex because she would feel to guilty about her boyfriend. The irony.
But think of how smooth the inside of that rectum will be from now on!
One evening my girlfriend and I were fooling around, and I, being the extra nice guy that I am, went below deck to dish out some oral pleasure. Things were going fine for a while, she seemed to be enjoying herself.
This quickly started to spiral out of control, however, as my girlfriend suddenly thought it would be a good idea to arch her back and begin thrusting her pelvis up and down in a violent motion. I don't know why she thought this was a good idea, but you can imagine how hard it was for me to stay in the zone in this situation. I was like a cat helplessly pursuing one of those fuzzy cat toys that's tied to a string. I struggled mightily as I tried to duck and dive with the sporadic movements of her pelvic region.
Right as I was about to stop and ask her to stay still, disaster struck. I zigged when she zagged and POW, she popped me right in the nose with her pubic bone. I mean she really walloped me. I had just been punched in the face by a vagina. And I'm not sure if you are aware of this or not, but a girl's pelvic bone is exceptionally hard. Check it out for yourself sometime. Instantly, blood came pouring out of both of my nostrils. I sat up immediately and saw through my watering eyes that her stomach and lady bits were now smeared with blood. We just sort of stared at each other for a few seconds, unsure of what our lives would be like after this moment, but aware that they would be irrevocably changed. I mean, at no point in my life had I imagined that one day I would get punched in the face by a vagina, as I am sure that she never imagined she would at one point in her life have to deal with cleaning nostril blood out of her vagina. It takes a while to process something like that.
Eventually we snapped out of our stupor, cleaned ourselves up, chuckled awkwardly about the whole situation and went to sleep. But to this day, I still get a little nervous every time I begin to make my way downtown and I see that pubic bone staring me menacingly in the face.