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


You want an awful hookup story? Here's your awful hookup story. During college, I was drunkenly hooking up with a lady-friend, as collegians are known to do. This particular relationship was a Texas Chainsaw Nightmare, but this one instance stands out. As the lady and I were having intercourse I felt a bit of a pinch, but sometimes it hurts so good, so I ignored it. When I looked down a minute later, I got an eyeful of bloody dick. Red Flag. I thought she'd gotten her period or something, but it turns out the blood was on the inside of the condom. I'd torn my frenulum, (wikipedia it). Now any kind of genital tear is excruciating, but when all your blood is in one particular location, and it springs a leak, there's a LOT of blood. If I'd had the wisdom I have now, I would have put on another condom and gotten out of there, but instead I bled all over this girl's bed, desk, chair, clothes and floor, eventually jury rigging a paper-towel dick-sheath with inferior absorption capabilities, and hobbled into the night full of shame, confusion, and heavily oxygenated erectile blood.

Wiki says, "The word frenulum on its own is often used for the frenulum of prepuce of penis or frenulum preputii penis, which is an elastic band of tissue under the glans penis that connects to the prepuce, or foreskin to the vernal mucosa, and helps contract the prepuce over the glans." I didn't understand any of that, yet I remain horrified.


High school was a time filled with either awkward backseat hookups, using your friend's little brothers room, or the joyous occasion that either his or her parents were out of town. Aged 17, the girl at the time calls me up on Saturday afternoon, begging me to make the 20 minute trek across town. I'm 17, what the hell else was I going to do? Hell yeah, I'll be there! So I arrive at the house and comfortably find the driveway and garage empty.

When I get inside the house, she was already in her "easy access" no bra and t-shirt, accompanied with sweatpants that I would later find out were not hiding underwear. Another cool thing about the parents being out of town at this age was it was considered a free invitation to raid dad's liquor cabinet and that we did. Naturally, being the male, I go straight for the scotch...and winced with each sip. Of course she goes straight for the vodka, standard procedure for girls.

Some where along the way, I inquire about our amazing situation and come to find out that Dad is out of town on business and won't be home until Sunday night, and Mom has the little sister at a soccer tournament the next town away and won't be home till that night. Hell, it's 3:30 Saturday afternoon, I'm already kinda drunk, and there's nothing close to a threat of getting caught until sundown.

Having been in the living room this entire time, we begin making out right there on the couch. I'm immediately thinking boobs in my complex teenager mind and go for her shirt, only to find her moving my hands away. What the hell? Why would I drive all the way over here on Saturday if I wasn't going to AT LEAST see some boobs? However, she has a change of heart and begins to take my shirt of. I'm thinking, awesome right here on her parents couch...but she decides she wants to go into her bedroom. So we get up, and I'm shirtless, and head down the hall to her room...Of course we couldn't make it there without me realizing that we forgot our drinks so she undoes my belt in the hall and goes and gets the drinks.

Meanwhile, I'm trying to make myself comfortable in the bedroom and already have my pants on the floor...down to just boxers and socks...she heads back in with the drinks, already fumbling a little bit....we continue making out in her bed and slowly but surely I get her completely naked. Not really sure what would happen next, I open the flap in my boxers, giving her the signal that I was ready for a full hardcore "through the boxer-hole" blow job...I'm not sure why I was all about the boxer-hole BJ, I think I thought this was what the hole was for, because honestly I was more of an "over-the-gate" type when I went to the pisser...

Anyways she's doing her thing and I'm sitting up leaning back on the pillows with my eyes closed (for concentration purposes), and my right arm fondling away when all of the sudden I open my eyes and Dad walks in the doorway...I'm not sure what my first reaction was but whatever it was it made her realize something was up and she pulls off of me (having to wipe the side of her mouth away right in front of Pops). I thought the man was going to castrate me on the spot...."GET THE HELL OUT!" he yelled at me as his daughter put her clothes back on and I scrambled to find all my articles of clothing that were sprawled around the house...a few deadly minutes later I somehow have it all in my drunken state and proceeded to drive home and struggle to keep it in between the mustard and mayonnaise...

I make it home and think I'm in the clear about the situation but the guy calls my Sunday school teaching mother and tells her the entire story...even worse, my mom proceeds to make me call him up and apologize. I think I struggled with this so much that I asked my mom what to say, she told me, and I immediately went to my room and tried to write it down word for word and recite it in the phone message...

From that day on I never spoke to her again...we didn't go to the same school or really have the same group of friends so it was easy...we ended up going to the same college and of course during the first few months of school I walked into the "freshman bar" and saw her drunk dancing on the bar half naked with her friends (classy...but God Bless College at the same time...)...

Later in college, when her hotter little sister was an 18 year old high school senior, she decides to come up and visit big sis. Somehow she had my number and begins to text me about coming over, which of course I was OK with...being dangerous makes it that much more fun...she borrows her older sisters car to "go visit a friend" and heads over to my apartment for some fun (sans boxers this time)...nobody ever found out about this, including her older sister and Dad, who will most definitely kill me...

Note to self: Do not have a Daughter. EVER.

Too late!


So I was a sophomore in college (20 years old) when my female friend's cousin came to visit for a weekend. Her very hot cousin. She introduced me as I was on my way to the gym for a 3-on-3 basketball game. The cousin asked if she could come and watch. After, she went to dinner with me (the caf!) and we went to a party that night. We ended up back at my dorm room and we got talking and making out. She kept stopping to talk. Then she mentions a boy in her home room.

Wait, what?

"Oh, shit," she says. I asked her how old she was, and she said 16. I couldn't go through with it. It was so difficult to turn her away. My friend who introduced us just laughed. She didn't think it would be a big deal.

What do you think?

I think you probably did the right thing, even if every fiber in your body said otherwise.



I have an interesting story, because although I was not responsible for the failure, to this day I still live with the ensuing frustration.

It was first year, and we were having a party in my residence. Pretty standard night. Lisa, a girl from a neighbouring rez I had hooked up with a couple times, calls me to say she's coming over. This was good news, not only because it meant I was probably gonna score, but also because she was bringing along her incredibly hot friend, Cammy. Cammy was notoriously hot. She was well-known around campus as "Barbie." Needless to say, her presence alone was going to make this party in my lame residence a thousand times sexier. Which is always nice.

When the girls arrived around midnight, they were incredibly drunk. Again, pretty standard night. Although this time they were a little too drunk, especially Lisa. Having not been at the party more than 20 minutes, Lisa tells me she needs to lie down. I offer her my bed, figuring I'll probably join her in there at the end of the night. She lies down and passes out almost immediately. When we check on her a little later, we discover she has puked all over the bed and the wall. It smelled horrible, but she was still managing to sleep through it somehow. Cammy and I clean up what we can, and leave Lisa in there for the night. Cammy goes home, and I go upstairs to sleep in a (male) friend's room.

The next day, after she'd gone home and I'd finished digging out the puke from between my bed and the wall, Lisa calls me:

"I'm really sorry about last night," she said.

"Ahh, don't worry about it," I replied, "these things happen".

"Yeah," Lisa continued, "but you don't understand. Do you know why Cammy and I came over last night?"

"To party?"

"Well, yes, but also, we were planning on having a threesome with you."


Nothing like that ever came close to happening again. Cammy is now a fitness model. There are hundreds of hot pictures of her online, and they haunt me to this day. I cannot hear her name without recalling the agonizing stench of the threesome that was puked away.


Oh, that just SUCKS. Much better to be foiled by your own drunkeness than someone else's.

And why did the girl even tell you that afterwards? She just knows that'll haunt you until the end of time. EVIL GIRL.


My story dates back to my sophomore year of college, circa 2005. I had recently started to hook up with my cousin's roommate. My cousin's roommate was very cute and had recently broken up with her high school boyfriend. We had various make out/ finger blasting encounters, but had yet to seal the deal. During thanksgiving break, she invited me to come to her parent's house because she was having a big party (her parents were out of town). So I immediately jumped out that chance because she only lived an hour away from my parents house.

All night I was relatively nervous because 1) didn't know any of her high school friends at the party 2) was getting the vibe from my lady friend that she might allow me in her pleasure box for the first time. So to deal with both issues, I decided to get blacked out. Getting hammered helped me socialize with her friends, and would help me perform better later. But I took it a little too far because the next thing I remember was waking up in her bed, both of us butt-ass naked.

I took recon on the area to figure out what might have happened and found two used condoms on the floor. I was very proud of myself, but also in a drunken stupor. I also realized I had to piss or my bladder was going to explode. I stumbled throughout her house looking for the closest bathroom, still naked. I finally found a toilet in her parents' room and immediately began to relieve myself. We all the know that feeling of ecstasy when you release a long overdue piss. But something was different about this particular piss. Even though I could feel the urine exiting my dick, there was no accompanying splash in the toilet bowl.

Baffled for a few moments as to what was going on, I finally looked down at my dick to see another condom hanging off the end of my dick, now filled with piss. The 7 seconds from when I started pissing to when I noticed the condom on my dick were by far the most confusing of my life. I pulled the condom off my dick, only to drop a bomb off piss onto the bathroom floor. Being that I was still fucked up, and didn't care, I finished my piss, flushed the condom and left the piss on the floor. She later told me that someone had pissed all over her parents' bathroom, and I replied with the obvious answer, "What an asshole!"


And you were right!