Welcome to Great Moments in Drunken Hookup Failure, where we showcase four heartwarming true stories of drunken love gone horribly awry. Off we go.
Before we get to this week's stories, a quick announcement: I will not be doing a Funbag or a Jamboroo next week. Fear not, they're in good hands. But I have to spend next week working something seeeecret with Mr. AJ. I'll be back right after. If you have a Funbag submission, a Jamboroo contribution, or a DHF story in the meantime, send it to the tips line.
I'd been dating Terri for a few months. I met her early on in college. We weren't really serious, we basically fooled around from time to time. Great deal, you'd figure. I was still a virgin, technically. And that's the reason for my hookup failure, and how I failed to lose my virginity to her.
We drove the two hours to my hometown for Halloween weekend. My folks were gonna let her stay at our house on the condition that she and I sleep in the living room. Late that Saturday night, long after my folks went to bed, we were still up. Terri and I get to talking and decide that TONIGHT's THE NIGHT. But it's not safe in the living room. Not with the potential for Mom or Dad to walk in mid-stroke. No, that wouldn't do. I get the great idea to take her out in the field behind the house in my Jeep. Cue angels singing, this is going to happen.
Cut to the jeep way out in the field, far from the house. Cows grazing in the distance. Our clothes come off. There's the titty-sucking, and there's the dick-sucking, and there's the pussy-eating. Now it's go time. She's on her back with her legs braced on the wall, and she asks if I have a condom. Fortunately, I do and get that sucker on. And she says, "Take me." Yes, she actually said "Take me."
Now I have to climb on top of her, which means I have to get up from beside her. For a brief moment, my butt is going to be sticking out of the Jeep. But I'm ready to go. Dark of the night, no one around. Angels singing.
And then I go to get on top of Terri and as my butt pokes out of the Jeep window, I feel a giant wet, warm SHLUURP all the way up my crack. It is unexpected and disgusting. My cock shrivels up and I turn around to see a cow outside our window looking in. I'm disgusted and flaccid, Terri is laughing, the mood is ruined. I can't recover from this. I've just had my salad tossed by Bossy.
I never did lose my virginity to that girl. Not after that. I wasn't even blue-balled after that. A cow's tongue in the ass will do that to you.
/throws away tongue sandwich I made for lunch
About a year ago, there was a this girl that I had been casually dating for about a month, but hadn't done anything with yet. Actually, we had barely kissed, which was fine because I was going out with others girls also. Anyway, one night we went out to a bar and grill for what I assumed would just be a few drinks. She only drank the hard stuff and didn't drink often so she ended up getting drunk fairly quickly. We ended up at another shadier bar that you only go to when you're already drunk and then, finally, at the shadiest of shady bars that you only go to at the end of the night when you're really drunk and everything else is closed. We meet another random couple there and after my girl's failed attempt to bring the other girl back for a threesome we get to my apartment and she tells them, "he's about to find out how wild I am." As we get inside she comments on how loud she is and how thin my walls are and proceeds to start undressing herself.
She then says she hasn't had sex in three years and literally starts jumping up and down on my bed screaming, "We're gonna have sex"! So I get my clothes off and she says come here. Honestly, I'm a little taken aback, because I'm not used to a girl being so giddy and forward about having sex, but she's hot and I hadn't been with her yet, so I was still pretty pumped about it. So we start going at it and I realize that three years without sex apparently makes a girl extremely tight. So she tells me to stop because it hurts so much and to use my hand. Even this is too painful for her so she asks me if I have any lube or whatever. I don't, so in my drunkeness, the only thing I can think of to get is this shower gel for your face that someone had given me. Needless to say, it's intended purpose was not lubrication, so about 15 seconds after I put it on her and we try again, it starts burning both of us uncontrollably.
So we run into the bathroom and wash it off as quickly as possible. Unfortunately, her private area hurt way too much to even think about trying again. She ended up falling asleep next to me crying as she poured out her life story to me, including how she had a child as a teenager. I still got to see her naked so, ya know, could've been worse.
Indeed. A cow could have stormed in and tongued your starfish.
I walk outside to meet my friends and one of them yells at me, "Come take a picture with our new friend Megan!" I walk up to this girl, we take a picture and my buddy yells, "Now kiss in this one, make it good." So we do. I don't know how this worked, but I'm in the game. Now me, my three buddies, and this girl get in a taxi-van. We're planning on going to the new casino across town. Someone ends up dropping some ash in the van (from the black and milds I thought would be a good idea to purchase) and we get kicked out. Megan doesn't want to go to the casino anymore. She asks me, "Do you want to go back to my room?"
I'm in. I tell the guys I'll see them back at the hotel later and we start walking. Now, mind you, there are bridges everywhere in Pittsburgh and this girl now wants me to carry her across a bridge. I'm in decent shape, but I only get halfway before I'm done with that idea. We get to the other side and I'm exhausted... now she informs me we have to walk up these stairs to get to her "room." These are outdoor stairs... and they're about 10 stories high. We get up after about what seems like 30 minutes. This is when she informs me that she needs to "get me an ID." I question this. She reveals to me that she is 20 years old (I'm 28) and lives in a dorm room of a college there. You have got to be shitting me. I say whatever and try to sneak in behind her. The door woman asks for my ID, I pretend to look in my wallet and give the "I can't find it." "What's your name?" I make something up. "What room number?" I stare blankly at her. "You need to leave right now or I'm calling the cops."
So, now my friends are at the casino (they actually made a killing that night) and I am walking as quickly away from this college as I can. The girl is repeatedly calling me, but I'm just over it. I get lost in what I come to find out is not the best area of Pittsburgh. I walk around for about 2 hours before I finally figure out where I am and make it back to the hotel. I immediately walk into the room and crush the mini-bar and fall asleep, but not before I go stand in the shower and vomit for about 15 minutes.
DAMN YOU STAIRS!!!
A few weeks after a break-up with my long-term girlfriend, I went and visited my younger brother in a large Northeastern city where he went to school. I basically just inserted myself into his group of college drinking buddies and I was making a good impression on everybody, a fact that was made very apparent when one of the girls in the group started brushing her hand against my thigh in the most obvious way possible. I'm not gross-looking, but I don't get hit on this aggressively very often, and this was exciting. One things gave me pause, however: I knew that she was basically in love with my brother, and the two of them and another girl were in a drama-filled love triangle. My brother had slept with her once, which he told me was "huge mistake."
So I'd be getting my own brother's sloppy seconds, and also she might be just trying to make him jealous. But I have been really plowing through the drinks (we all have), so I think this is maybe a good idea. I whisper to my brother, "Uh, dude, this girl is really, really coming on to me. Would it be weird if I banged her?"
My brother: "Uh, sure dude. Go ahead. Whatever."
So I go and make out with her in the bathroom, then we leave together, which makes it obvious to everyone that we're going to hook up. I don't care, because I don't know anyone and I want to hook up with someone so I can say I've been with someone since my break-up. She has a bike she has to get home, so she tells me to take a cab with this other guy who lives nearby and meet her there. This barely makes sense, and I'm so drunk I forget where she lives, but I finally get to her place and we start making out and before I know it I'm sucking on her breasts. Then she says, "Hey, want to do some blow?"
I say sure, and she invites her cokehead stock-trader neighbor over, and we all do coke and smoke cigarettes and talk about whatever you talk about when you're coked out. My shirt is off for this entire time, and so is his, for some reason. Finally, at like 3 a.m., he leaves us alone and we go back to her bed. She's into it, but whether it's the coke or the drinks or my general apathy towards her body, I can't get it up. So we go down on each other until I'm hard, and I get it in her at last (no condom, because I'm a moron), and...I come early. I don't pull out in time. Shit.
Long story short, the next morning I borrow her roommates' bike and we cycle over to the Planned Parenthood, where protestors wave nasty signs in our face and I have to fork over thirty bucks for the morning after pill. So I'm paying for birth control for a chick who was in love with my brother. Great.
Thirty bucks? To avoid children? My friend, that is the bargain of a fucking lifetime.