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The Worst Lost Virginity Story Ever

Illustration for article titled The Worst Lost Virginity Story Ever

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

We've had a lot of pathetic stories here at DHF. This one might be the most brutal:


This is the story of how I lost my virginity. Thankfully, most - but not all - of my sexual exploits in the decade since have ended better.

In high school, my friend Charlie, as a 17 year old, lived in a tiny one-bedroom house next to his parent's home and his Mom was fine with us drinking, so long as no one drove. The house was little more than a kitchen/living room, a bedroom and a bathroom; an average classroom has more square footage. Our weekend routine all senior year was to (a) score some booze from a 21 year old and then (b) invite girls over to drink it in the hopes that (c) we'd gain entrance to that holiest of holy holes, the mystical vagina. This particular weekend was no different.

Both Kevin, our 21-year-old friend, and Rob, Charlie's asshole of an uncle (by marriage - Rob is only a few years old than us) graced us with a few delectable 30s of High Life, so we set about calling girls. Rob, being a dick, went to go fool around with his girlfriend and refused to ask her to bring friends. But we hit the phones anyway, calling every girl foolish enough to give us her number. Soon enough, Charlie had managed to convince Aimee to come over with a friend, which is still amazes me a bit because Charlie and Aimee had never actually met. You see, this was in the glorious age of AOL Instant Messenger: Aimee was a friend of a friend's girlfriend and wanted to go to our winter formal, so our friend forwarded along her AIM screen name. So she decided to go over to a next-to-complete stranger's house and drink: we took this as a promising sign.

Aimee showed up with a friend (who drove) and the two of us hit it off immediately. A little while later, we were making out on the couch. Her friend decided to go, but Aimee decided to stay. Charlie, already a seasoned man in the art of getting laid, pulled me aside.

"Listen, man, you are IN! I'm tired of everyone banging on my sheets, but I'm going to put a comforter and some pillows on the ground - fuck her on that." He went into his room, made the arrangements and emerged. Aimee and I shuffled awkwardly towards the door and hesitated for a bit before Charlie pushed us in, hit the lights and shut the door.

I proceeded to start ripping her clothes off, throwing them all about the room with reckless abandon, while she politely and neatly removed my shirt and pants (I think she might have somehow even folded them). For the first and last time ever, I managed to suavely remove her bra with one hand, before tossing it over my shoulder. Soon enough, her panties were off, my boxers were gone and I was fumbling around like a thisrty blind man in search of well. Finally, she took the matter into her own hands, and the sweet gloriousness of my every masturbatory fantasy had finally arrived! Oh, God, yes, FINALLY! THIS. IS. IT!

Or so I thought. Just as I had entered Aimee, Rob had entered the house. I heard him bellow, "Jim's doing WHAT?!?! Oh, I gotta see this!" I heard Charlie yell in vain "Rob, NO, don't!" and then BOOM, Rob barges through the door. I jump off Aimee, and Rob screams, "HOLY SHIT! LOOK AT THAT BUSH! I COULD GO DEER HUNTING IN THAT FOREST!" Charlie grabbed Rob and shut the door.

To this day I don't know how, but I somehow convinced Aimee to continue where we left off. Once again, I started to thrust away. And that's when I heard Charlie yell at Rob again. BOOM, Rob kicks down the door again, this time holding a hunting bow, laughing maniacally and screaming "I'MMA GONNA GET ME A 10 POINTER!" Charlie once again drags him away, only this time I cannot work my magic again. Aimee wants to go. NOW. We gathered up half of her clothes (we later found her panties and one sock) and I, hammered, drove her home. When I got back to Charlie's, it was decided after long debate and deliberation that the total of 30 seconds I was in her counted as losing my virginity - if it had been one uninterrupted session, that's probably how long I would have lasted anyway. If I was lucky.

Aimee didn't speak to me again until we ran into each other at a Christmas Party in 2009. This is my go-to story to tell at parties, complete with recreations of certain key scenes and lots of yelling. She still doesn't find it funny. And Rob is still a colossal dick.


God, what a dick! This Rob is the face of evil.


I was out drinking heavily one Friday night in college and my friend and I manage to strike up conversation with 2 fine young ladies at a bar. These 2 (no idea their names) are clearly interested in us (also drunk), so some playful banter ensues and we manage to bring the 2 girls back to my apartment for some late night beer pong. I lived in a 2 bedroom on campus apartment that year with three of my friends, so I shared a room with one of them. My roommate was with us at the bar and saw what was transpiring and told me he would take the couch to allow me to work my magic. After a few games of beer pong, one of the girls and I retire to my bedroom to seal the deal.

Things start off going as planned, as she is topless in a matter of minutes. I then make the not so smooth transition to removing her pants where I am confronted by a worthy challenger. She is wearing some extremely skin-tight pants that are held up by a drawstring.

In my drunken state, I manage to twist the string into the Gregorian knot, and I quickly realize there is no way I am getting this knot undone without Alexander the Great's sword. She makes an attempt at it, but is also unsuccessful. She then tries to wiggle out of the pants, but these things were so tight that there was no way we were getting these things off without the jaws of life.

After another minute of some dejected making out, it becomes obvious this isn't going to happen and the hook upends abruptly.

When I awake the next morning, there is no sign of the girl, so I saunter out to the living room to alert my roommate he is free to return to the bedroom. A minute later, I hear him yell, "What the hell is that?" I run back to the room and about 2/3 of the way down his bed is a big, wet puddle. Upon further inspection, there was no doubt that the girl had pissed his bed. So while I was unsuccessful in finishing matters night before, at least I didn't have her piss my bed.



Shortly after arriving at college to start my freshman year in August '05, Hurricane Katrina forced us to flee. I ended up evacuating with some upperclassmen guys I had met the day before, crammed in a minivan with a keg and dozens of firearms. Hours on the road, booze, partial nudity and the excitement of escaping death and destruction caused me to fall deeply in lust with one of my fellow evacuees, Mitch. After a week or so of hooking up without sex (I was pretty innocent at the time and the despair for our city didn't help) we had to face reality and find schools to go to for the semester.

Fast forward to Spring semester when we can all go back to school in New Orleans. Mitch calls me the day we get back to hit the bars with him and we get hammered reminiscing about that fateful evacuation. Ready to take things to the next level, we head back to his place and start undressing. Just as I'm telling him I want to sleep with him we hear frantic banging on the front door. Asshole must have forgotten to tell me about his girlfriend, who is there, demanding to be let in. Mitch makes me hide in the bathroom while he tries to get rid of her. After about 20 minutes, my drunken anger boils over and I decide to climb out the bathroom window in my bra and panties and his shorts and shoes. I get completely lost trying to find my way back to the dorm and if drunkenly wandering the post-Katrina, National Guard-patrolled streets practically naked wasn't bad enough, I had to convince the jerk at the dorm front desk that I was not drug-addled prostitute, but in fact a student who lived there, because I left my wallet, ID, clothes—everything at Mitch's house.

Two years later he tells me, in front of my then-boyfriend, that he made a huge mistake and should have ended it that night with her and tried things with me. They are still together to this day. (I will never understand men.)


Hey, we're not all morons like that guy. I think.


In the early 90s, I moved to Los Angeles, days after graduating from the king of party schools, Arizona. I was crashing in the kitchen of a friend's studio apartment in Beverly Hills. He had landed a "glamorous" job as a personal assistant to a prominent movie producer; I was a pool boy at a well-known luxury hotel nearby.

One night, we were at a club in Beverly Hills that was perhaps best known for the weekly performances of Harry Dean Stanton's band, which were so bad they were good. We did nothing halfway, and I was completely obliterated within a half hour of arrival. Suddenly, a very attractive brunette, presumably much older (the term cougar did not exist) came up to me and introduced herself, with some very flattering comments. Ten minutes later we're obnoxiously making out, and by the time the bar was closing, we were probably offending everybody in sight. She told me she had an errand to run (drugs), and that she would like me to wait for her at her place. She even gave me her key and wrote down her address, telling me she'd be there in a half hour. I was certain a happy ending was in store.

It didn't occur to me that getting cross-eyed drunk and doing blow with a stranger was a bad idea considering I had to work the next morning at 8 a.m. But I cabbed it over there, and was surprised that the key actually worked, though her apartment was a barren shithole. However, I had never been more confident in my odds, so I made myself comfortable, and waited, and waited, and waited. I was awakened by cruel direct sunlight at 7:45, fully clothed, still sitting in the same chair, with the girl nowhere in sight. I barely made it to work on time in a taxi (summoned via landline), but still had to explain to my boss that in spite of reeking like alcohol, being un-showered and unshaven, and sporting a decent case of bed head, I didn't get laid…


You should have pooped on her couch! That's the classy move.

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