Cockblocked By Your Own Underwear!

Welcome to Great Moments in Drunken Hookup Failure, where we showcase four heartwarming true stories of drunken love gone horribly awry. Off we go.

Rip:

I'm getting ready to get picked up for a drive to New Hampshire to see some old buddies from college. As I'm rifling through my wardrobe I discover I'm fresh out of boxers. With my ride arriving outside blasting his horn like an asshole, I open a little used small musky drawer on the other side of my room and find a pair of Yankee pinstriped boxers I didn't remember having worn since freshman year of high school—about a decade earlier. I didn't even know I had them in my apartment; I brought the drawer with me when I moved out on my own, stuck it in the corner and hadn't really thought about it for the past two years. I thrown them on, put on my jeans, and I'm out the door.

Fast forward to the party. The boxers are way too tight for my no longer 15 year old self. In the front my dick is constantly poking through the boxer hole and into my jean zipper; in the back the boxers are constantly digging into my ass crack. I spend most of the evening "readjusting" myself as subtly as possible. As the night progresses I get reintroduced to a cute redhead friend of a friend I hadn't seen or talked to at all since graduation. I had always thought she was cute but I spent most of my college years in a long term relationship with my high school girlfriend. We spend the next hour or so talking about the old times, catching up on new developments-by the end of which she's sitting on my lap asking if we could go somewhere more private. Up the stairs we go.

We go at each other in my buddies guest room. She takes her top and bra off and starts unbuckling my jeans at the foot of the bed. She pulls my boxers down and starts to blow me. After about a minute of pleasure she goes down to work my balls. Suddenly, she pulls off and gets up off her knees. She starts coughing violently and trying to clear her throat like a cat hacking up a furball.

"What's wrong?' I ask.

I then look down at my junk; the entire underside of my ballsack is covered in musty smelling blue and white fuzzy lint. After about two minutes of loud, horrible hacking sounds, she spits out a quarter sized piece of ballsack lint. I ask her if she's OK. She says she feels a little better but tells me that she has to leave without ever looking me in the eye. I end up spending the next hour in my friends bathroom drinking a bottle of Captain while picking ball lint off my scroat with a pair of his tweezers. He doesn't know that.

THAT'S WHAT YOU GET FAHHH LIKING THE FACKIN' YANKEES!

Aaron:

I was a fifth year senior in college at a smallish school, and decided to stay in town and work over the summer. Most nights followed the same pattern: (1) get off work, (2) get food and beer, (3) meet up with co-workers who can actually tolerate, (4) get shitfaced, (5) wake up the next morning half clothed on your bathroom floor, (6) rinse and repeat.

A welcome break from the alcoholic monotony came when a buddy of mine invited me to hang out with him and some girls he knew one random night. Always intrigued by the possibility of getting some strange, I gladly accepted. We met up with said girls at their place and I immediately recognized the hot one from seeing her around campus (let's call her Brynn). I initiate some clumsy flirting, and shockingly, she shows interest.

After two or so hours of flirting and sexual innuendo, one of Brynn's friends pulls me into the bathroom and says, "I don't know what you are doing, but just so you know — Brynn will sleep with you. She broke up with her boyfriend a week ago, and this is the first time she has come out of her shell since. Just don't be a dick and screw her over." Elated, I floated back into the living room of their apartment and returned to my attempts to "throw game" which really entailed trying not to blow my chance with Brynn.

Fast forward another hour or so . . . my buddy has taken off for the night, leaving me alone with Brynn and her buddies. The buddies retire to their rooms and soon its just me and Brynn. At some point, I get up to grab myself another beer and see that these girls have a NERF hoop in their kitchen. I see a ball on the counter, and toss a shot towards the hoop . . . miss, and like Daryl Dawkins, grab my own board and thunderously dunk. I grab my beer and turn around to leave the kitchen, only to see Brynn right behind me.

She calls into question my NERF hoops skills, and I immediately offer to play her. She says that if I win, she has a special treat for me. Trying to be gentlemanly, I give her the ball first, and she immediately tries to back me down (this was probably just to encourage hand checking) and upon reaching the oven, tries some ill advised, drunken spin move towards the fridge to create space and get her shot off. Predictably, she falls and sprains her ankle. She tries to tough it out, but the game is clearly over and I feel like the window for me to get some has just been slammed shut.

She asked me to help her to her room, and I happily obliged - sensing a glimmer of hope that a hookup is still in my future. Once there, she closes and deadbolts (wtf?) the door, and clothes started coming off. Another 15 or so minutes of fooling around were interrupted when says how much her ankle hurts, and asks if I would get some ice for it. I get up, pull on some shorts and head back to the kitchen for ice They have none. I look for frozen peas, steak, freezer packs — nothing. I eventually settle on a half full bag of chicken strips and when I get back, she is completely passed out — and its clear that sexy time is over. Defeated, I throw a blanket on her, grab my clothes and head out.

Insult to injury . . . my buddy was gone, and her friends were long since passed out. Meaning, after all of this Florence Nightingale bullshit, not only was I not getting laid — I was going to have to walk 4 miles back to my house at 2am . . . with blue balls.

Fucking NERF.

Tom:

About a year and a half ago, a few buddies and I went out to a karaoke bar near the beach. It's about a 30 minute drive for us, but it was a cool spot and a bunch of the girls from one of the colleges out there would be there, so it was usually worth it. I had just finished up a particularly awful contract job, and was celebrating it's end by getting drunk off my ass. 5 Jack and Cokes in, I start talking to this Japanese lady who's there alone, and who's age I can't really figure out...partially because of the bad bar lighting, and partially because...Japanese. Anyway, we go from talking to drunkenly dancing to some dude's butchering of Sweet Child O Mine, and as the night wears on she's getting more and more frisky. By the time we start doing the whole sloppy bar make-out, it's getting near last call at the bar and I look up to see my buddies are all gone. I mention to her that it looks like they left, and she says "that's fine, I can take you home with me."

So we get into her car, and she (surprisingly sober at this point) starts driving. "How do I get there?" she asks. "I thought we were headed to your place," I say. "No, we can't do that," she says. "I have a kid." This isn't the first mother I've hooked up with, and probably will not be the last, so I brush this off as a very minor red flag and let the evening continue. We drive back to my place and stumble back to my room.

Four condoms later, we've had a pretty fun night. At this point, it still isn't quite a drunken hookup failure, aside from a brief bout with whiskey dick, and I fall asleep pretty happy. We decide, that morning, to wake each other up with a little morning-after sex. This is going pretty well until her phone rings. She looks over at it and sees that it's her daughter calling. She lets it go to voicemail. After we're finished, she takes her phone and, for some reason, decides to play the voicemail out loud. The message:

"Hey mom, it's me. I woke up and you weren't home...again. So, looks like I'll just have to take the bus to the orthodontist."

At this point, the situation becomes real to me. Her daughter is old enough not only to call her mom, but she has braces. I ask her how old the daughter is, so I can figure out the true age of the woman lying next to me (I still can't tell by looking at her because I'm a giant dumb ass apparently). She says her daughter is 17.

So, at minimum, we're looking at a woman at least 15 years my senior. And the comment "you weren't home...again." Also that.

I went home with a much older mother of (at least) one, who makes it a habit to pick up random bar guys, pretty often from the sound of it, and neglect her daughter. Fantastic.

We shared a long moment of awkward silence before I walked her to her car and out of my life forever. So many questions I didn't really want answers to still linger. Where's the dad? Are there other kids? And, most importantly, what did I really expect from a random bar hookup in Malibu?

ANOTHER PEARL CREAM VICTIM.

Daniel:

After we graduated from college my girlfriend needed a roommate. I paired her up with a Natalie Portman look-alike (seriously 97% Portman) female friend who I had known since Freshman year. Unfortunately, "Natalie" had the same scumbag boyfriend that entire time so I had never really had an opening.

A couple months later my girlfriend, "Natalie", and I all go out together. We have a pretty great time and so when it is closing I take a blind stab at suggesting they BOTH come back to my place to watch a movie (visions of angling for a 3-some foolishly dancing in my head). My girlfriend says she is tired. Natalie surprisingly says she would love to come over. I sheepishly ask my girlfriend if it is ok if just Natalie and I watch the movie. Since they are friends she has no recourse but to say "its fine".

So now I am back home with just Natalie and the movie watching is going well (she chose to sit next to me on the bed instead of in the chair). Soon there is some inappropriate message going on. Then wrestling/tickling. She suddenly goes to the bathroom and now I know it's down. When she moves to get back on the bed I grab her and we immediately start mauling each other and grinding away. I have been dying to bang this chick for 4 years and this is a delicate situation so I am taking my time with some make-out/dry-humping before going for the clothes removal. She is really enjoying herself. Really, really, enjoying herself. How could this go wrong?

I am just to make my move when she says "I am kind of embarrassed to say this, but I am done". I tell her that is fine with me, but she insists she is like a guy and doesn't like further stimulation after orgasm. My balls could not be bluer. She promises to go down on me, but at 9AM we are still going over what we are going to say when there is a knock on the door...it is my girlfriend....needless to say that did not go well. I will always remember that as the hottest and then most frustrating 15 minutes of my life.

A FEMALE premature orgasm? I feel like I've stumbled upon Loch Ness.