When I was 16, my friends and I spent the summer at our friend Pete's ultra-wealthy, half-insane grandmother's house; a huge, multi-million dollar estate right on the rocks of York Beach, ME, where we partied almost every day, due in part to Pete's grandmother being away in Europe for the entire summer on vacation.
What was even cooler than Pete's mansion was Pete's crazy mom, who also lived at the estate. Being a responsible, conservative parent, she consistently made smart choices for her son and his friends; choices like buying us cases of Olde English 800, cartons of cigarettes and stacks of porn. She not only encouraged us to throw huge underage drinking parties, but also enjoyed laughing along as we blew up propane tanks and hairspray bottles on the private beach behind the estate. I specifically remember waking up at Pete's house to regularly find his mom enjoying her routine breakfast--a Marlboro Red and a glass of Johnny Walker Red Label on the rocks.
One fateful night that Pete's mom/enabler was away on business, we decided to throw a party to celebrate Pete and I successfully managing to jimmy open the unimaginably well-stocked wine cellar with a miniature crowbar the prior afternoon. Picture your typical underage drinking party, but substitute double fisted bottles of Mad Dog 20/20 and Natural Ice with magnums of Perrier Jolet and Krug Clos du Mesnil--the movie Kids and a rap video had a baby. It was a phenomenal waste of thousands upon thousands of dollars worth of investment wine, and our cat burglar tactics would actually be one of the deciding factors in getting Pete and his mother thrown out of the house upon his grandmother discovering it when she returned from her vacation.
Earlier that summer, Pete bought a Hi-8 camcorder, which we used to record all of our antics. Blowing up propane tanks, executing skateboard tricks, vomiting, the works. Every morning, we would groggily pry ourselves off of whatever swatch of carpet we had passed out on, congregate in Pete's room and review what we had recorded. The night of the party was no different, and the Hi-8 was being passed around the crowd, catching every minute of disjointed, drunken teenage flirtation and amateur hour alcohol intake management.
I was in the kitchen swilling the last half inch of Bollinger out of a bottle and popping some pizza rolls into the toaster oven when she walked into the room; a beautiful, sun-kissed 16 year-old girl with blond hair, sporting a tank top and flower print booty shorts. Her name was Rachel, and I got a socially devastating boner every time she was within fifty feet of me that summer. I offered her some of my pizza rolls, and we hung out in the kitchen and talked about high school, plans for college and anything else that kids that age talk about for an hour or so before she suddenly grabbed my hand, led me into one of the many guest bedrooms of the estate, and told me that she wanted me to be her first. I was thrilled, because I was also a virgin, and I couldn't even manage to ask this girl out on a date the entire summer, let alone tell her that I wanted to try and stick my teenage cock inside of her for 20 seconds. I wasn't sure how or why this was happening to me, and I didn't care. This was it; I was finally going to have sex.
Awkward kissing led to awkward groping, awkward groping led to awkward clothing removal, awkward clothing removal led to awkward, fumbling manual stimulation. I was nervous to the point that I had beads of sweat on my forehead, and so was she. We laid down on the guest bed and spent the next 15 minutes alternating between making out and trying to figure out how to put a condom on my pensive, harder than diamonds erection. I was so embarrassed; I so wanted to look like the cool, experienced guy, but there I was--playing Mr. Wizard's Experiment Hour with a three pack of Trojans and a girl who knew as much or less about the act of fucking than I did.
Once we managed to sheath my sword, I climbed on top of her and attempted penetration for the first time.
And the second time.
And the third time.
After the 15th time I tombstoned my dick into her taint, she finally grabbed me and guided me in. Well, she guided the head of my cock into her, because that was all that would fit. It was like trying to fuck a pair of vice grips. I spent the next 25 minutes gyrating my hips like I was trying to become the fifth member of Menudo after Ricky left, thinking that I could pry myself inside with a little finesse.
I looked at Rachel's face, hoping to see it frozen in boundless pleasure, but what I found was a facial expression that showed nothing but pure, unfiltered pain. I asked her if she was OK, and she grunted back, "Yeah, I'm OK. It kind of feels good. Keep going." So I did, until I finally managed to sink myself balls deep into her. It felt amazing. I did it! I finally did it! I looked down to see it, as that was the first time my penis was ever inside of a vagina, and I wanted to take a mental Polaroid. That's when I saw the blood. Lots and lots of blood. It looked like I had murdered a kitten with some bed sheets and a ball-peen hammer. I was just about to tell her that we should probably stop when all of a --
"YOOOOOOOO!!! LOOK AT MIKE HAVING SEX FOR THE FIRST TIME!!! HE'S A FUCKING STUD!!! WHOOOOO HOOOOOO!!!
The door to the guest room burst open, the lights came on and 25 people poured into the room, all led by Pete with his Hi-8 camcorder in front of him. I whipped the comforter over both Rachel and myself, and Rachel pulled some of the bedsheets over her head in some kind of hilariously futile attempt to mask her identity. I screamed and screamed for them to leave the room, but nobody budged. They just stood there, drinking champers and giggling at us. I started to laugh back; I was drunk and the ridiculousness of the situation was starting to sink in, but I was also figuring that they would start to feel bad after a while and take off, leaving Rachel and I to finish what we started. Pete zoomed in with his camera and caught the blood on his guest bed.
"Jesus Christ, Mike. What are you, fucking her with a table leg?! LOOK AT ALL THE BLOOD!!! HOLY SHIT!!! Guys, seriously, look at the blood!! This girl is going to need a transfusion!!! Ladies, get in line to fuck KungFu Mike. Apparently he's packing a cock the size of a baby's arm!"
That was it; the final nail in the coffin. Rachel started crying, my dick started to go limp, and I was sitting naked in a bed covered in blood, tears and broken dreams. The party guests left the room, Rachel threw her clothes on as fast as she could, and knowing that there was no way that I was going to be able to squirt any Fix-A-Flat into the flaccid tire that was my entrance into manhood, I walked into the kitchen to grab a drink--just in time for Pete to dump a bottle of Moet on my head as the rest of the party reviewed the new footage on a big screen TV in the piano room.
Posted by KungFu Mike at 9:03 PM