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Don't Leave A Rubber On All Night By Accident

Illustration for article titled Don't Leave A Rubber On All Night By Accident

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


It was May 2008, a year after my graduation, and I was conned into attending my fraternity's formal. You know how they "invite" the alums, hoping that they'd be generous enough to "support" the event? Whatever. Well, I was only one year out, and as a grad student, I was still very close to many of the guys in the chapter so I figured it would be a blast and an excuse to party and have some dirty fun.

I had been dating this girl-Kara-for a few months, and things were going great. She was still in school, so we were really excited to get away and have a good time. However, for some reason we decided to share a room with my little brother and his date. This made our plan of getting down and dirty a little more difficult than we expected, but we were persistent.

After a day at the resort, we managed to get roughly four minutes of alone time. The minute things started to go down my little brother barged in the room. With my dangles the size of grapefruits and throbbing worse than I had ever experienced before, I was forced to sit him down for a heart to heart before the big formal dinner. I explained that I needed a few hours after dinner to "file my TPS reports," and that he had to make himself scarce. He understood, and the plan was in motion.

To this day, I have never suffered through a longer dinner. It felt like an eternity; long winded speeches, annoying loud videos, and jokes that just didn't hit the mark. I felt like Charlie Brown when the teachers were talking: all I heard was, "Wah wahwahwah wahwah wahwahwahwah!" I was aching, and the whole time she was getting handsy under the table. By the time the dessert arrived, I was hard as a rock. I utilized the famous belt tuck and struggled through my tiramisu, all while painstakingly watching her lick the spoon. The minute she was done, I grabbed her by the waist, picked her up out of her chair and we ran to the elevator. It was on….

My suit was halfway off by the time we hit the door. I threw Kara on the bed and we started going at it. Clothes were strewn everywhere and it looked like a hurricane swept through the room. After a bit of fooling around, I put on a condom, and so it began. The first thrust was heaven; I was loving it. Not ten seconds later, though, the LOUDEST and most annoying sound that I have EVER endured pierced our ears and she pushed me off of her. The fire alarm was going off and she was freaking out, screaming and getting dressed. In the rush of things, I threw on a shirt, shorts and Sperrys (Ed note: Sperrys? Really?) and we ran out the door.

As we made it outside, we were joined by a crowd of several thousand people. She began to calm down and we thought that maybe it was a false alarm that we would be able to go back inside and finish what we started.

Little did we know that one of my genius fraternity brothers had thrown a lit cigarette off his balcony onto a t-shirt that another one had chucked off a lower balcony earlier that day. This epic miracle of hell led to the roof of the building catching fire, and while it was identified and squelched before major structural damage was done, we were forced to loiter outside until the "all clear" came at 4am.

Now is the point where I should inform you that, in the rush of our departure from our room, I did not have the time (or foresight) to remove the condom that I had on.

Finally, we got to return to our room. I was in bad shape; I needed to get this thing off ASAP. I ran to the bathroom and unzipped, and it wasn't pretty. My member looked like a snake shedding its skin, and I had to peel and pry off this shrunken glove. Think of it like ripping a Band-Aid off your dick. It was PAINFUL, and it left the poor little guy raw.

As you might have expected, we were obviously unable to finish the deed. What I thought was going to be a great, sex-filled weekend on the beach ended up leaving me with the worst blue balls of my life and a really raw deal.


Drew Magary writes for Deadspin and Gawker. He's also a correspondent for GQ. Follow him on Twitter @drewmagary and email him at


I'd been flirting with this cute girl, Sarah, who we shared a mutual friend with for quite a while and it became evident we would soon hookup. One night it all started well, pre-drinking at my place before heading out in the city. Many drinks were had and as the night was coming to a close the designated driver rounded us up took everyone back to my place, the central point for everyone. Well in the car me and Sarah are getting quite friendly in the back and Sarah's friend Sara who is smokin' hot starts getting handsy with my buddy up front. Naturally he doesn't mind and soon she's got his hands down her top and and it looks like I'm not the only one getting some tonight.

We get back to my place, and we are a mess. I head off with Sarah to my room, everyone else crashes in the lounge, but as soon as we close the door in to my room, it swings open. It's Sara. No longer wants part of my buddy, wants to join in with us. Well first I'm quite excited at this prospect, and Sara comes over and pins me down and starts making out with me. Now I look for Sarah, and I don't know if she knew what was going on, she was pretty hammered, we all were, but i was still unsure if she approved of Sara joining or not. To play it safe, I stop making out with Sara (it hurt me to stop, but I didn't want to mess up a sure thing and be potentially left with nothing) and tell Sarah "SARAH! Sara is making out with me!". Now I'm pretty disappointed I put a stop to this as I wasn't sure if Sarah knew what was going on fully and I didn't want to ruin my chances with her (It seemed like we were heading for a pretty regular thing) if she wasn't in to it. So Sara stops and looks kinda pissed I stopped making out and started yelling, she storms out and slams the door. However Sarah doesn't seem to have minded or at least grasped what was going on because she picks up where Sara left off and we start going at it, it feels like she would have been okay with Sara staying after all, but whatever I'm not too upset. A little manual stimulation and she was really in to. So I drop my pants and get down to business.

A few thrusts in and "STOP, stop stop stop", I ask what's wrong. She starts to cry and tells me she has a boyfriend. Well they're on a break or something and she feels terrible. I spend the next hour unsure what to do, do I comfort her or should I leave her alone? I really had no idea. I comforted in the end and she ended up falling asleep on my arm, as I lay there still with my pants around my ankles and some severe blue balls. I had gone from a Sarah/Sara threesome to nothing in what seemed the blink of an eye. Adding further insult to this, I had to be up early in the morning to attend a family lunch, a two hour drive away. Naturally, I overslept leaving no time to shower, just changing my t-shirt and emptying a can of deodorant on myself hoping no one would notice the smell of failed sex and last night's booze.


It's the 4th of July 2010, I am a new resident of Philadelphia, going to grad school. I had just broken up with my girlfriend of two years at graduation in May, so you can imagine the state that I'm in.

Goo Goo Dolls and The Roots are playing the big concert by the Art Museum in Philly. A friend and I go to the concert, bring a few beers and try to stand as close to the stage as possible. After some boring warm-up acts, it gets dark and our buzz begins to die down. Luckily, near the end of the Roots set (yes, the Roots were opening for the Goo Goo Dolls, which is like eating your cake before you sing the silly birthday song), three girls ended up in our section. They had beer in their backpacks, which they forced us to pay them a dollar each for, but we happily complied. A few beers in and suddenly I'm grinding with a cute, short brown-haired girl while singing "I JUST WAAANT YOU TO KNOWWWW WHO I AM."

Soon, we're doing the I-know-this-is-gross-but-I'm-doing-it-anyway public makeout. At the end of the set, my friend is not having the same luck as me, so he leaves, while I'm invited back by my new friend Julie to her place nearby. We hold hands and walk back to her place, over the bridge and watching the fireworks, to some Drexel student housing.
We make-out outside of her apartment and drink some more with her friends. She is sloppy drunk while I'm merely drunk. Everyone pretty much leaves, but for some reason she doesn't want to go back to her room, she wants to sit out on her front porch. We makeout more and at some point, I go from merely groping her to full-on finger-blasting her under her shorts on her front porch next to the street. This goes on quite some time. She's making noises and everything.

Eventually we move to her room where clothes come off. I do not have a condom, and due to my recent relationship ending, I don't feel like banging this random chick either. But, I am looking forward to getting some sort of penis-touching action. She's set up doggy-style while I'm finger-banging her from behind and she's saying dirty things like "DON'T YOU WISH YOU HAD A CONDOM FOR THAT BIG COCK OF YOURS." This chick was sloppy drunk and, my impression was, not unfamiliar with sex with random dudes.

Finally she starts to slowly tease me and begins to go down on me. Things are just getting good, and I'm starting to get into it. I'm on my back and as she goes down, I place my hands lightly on her head to encourage her to keep going further. She does not like this. She immediately stops and says that I'm being "Disrespectful to her" and "disrespectful of women." She refuses to continue and pouts for awhile, while I'm in full-on damage control mode trying to get some sort of action out of this. But to no avail.

We make out more and I'm trying to get her back in the mood, even for just a hand job, but she just passes out and I am left with the bluest of blue balls.

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