Bosom Buddies

(This story was originally published as a single, continuous narrative -- but I figured people might have fun playing around with other outcomes for the characters. Please feel free to contribute, thanks!)

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I turned eighteen a month into my senior year of high school. Skinny, shy, good at math; I was last pick for the basketball team and last pick for the opposite sex. But by Christmas, I had gone from being terrified of girls to living the cliché as the official “sexually non-threatening platonic guy friend” of the five hottest chicks in school.

As nice as it was to have popular friends and beautiful women to look at all day long, I was also anguishing in a special circle of Hell, where my penis and I were at a constant state of war with each other. The argument went something like this:

MY PENIS: “Fuck her! She’s hot!”

THE REST OF ME: “No, we’re friends, it’d be weird…”

PENIS: “But… tits!”

Needless to say, it was a confusing time for me.

It all started with Corrine, a bodacious blonde who was clearly destined for the Playboy centerfold. For a late-blooming nerd like me, she was also the most intimidating person on the planet. Every detail about her seemed specifically designed to twist my tongue into knots. First off, she was the tallest girl in school. I was 5’11” and she had maybe half an inch on me (Corrine liked to joke that this was due to her “Viking ancestry”). She also had a dazzling smile that belied an impish, teasing spirit, and a natural hourglass figure. But what really made my head spin were her tits. Her absolutely gigantic tits. The day those things had grown in, every guy in school promptly forgot his name. Seriously, her tits could stop traffic.

She and I became friends when I sheepishly asked her to be in an amateur horror movie I was directing with some buddies. Asking had not been an easy task for a guy like me — Corrine had always been a merciless tease. But nonetheless, as soon as the class bell rang, I stumbled over to her desk, feeling mortified but knowing that all the other AV club guys were counting on me to succeed for the sake of our film. I tried to play it cool, but my cheeks went crimson and my voice sounded like it was coming from inside a box:

“Hey Corrine, I’m making this horror movie and we kind of need someone to play the, like, buxom bombshell in distress. I was just wondering if you might think that was fun… or something.”

She raised an eyebrow and grinned wickedly, leaning so far forward it took all my willpower to keep my eyes away from her pendulous breasts. “Sure, Ian,” she said simply, “What do you want me to wear?”

It turned out my nervousness had been completely unfounded. While Corrine was definitely a tease, she was also really easy to get along with. She and I hit it off the first day of filming. We made each other laugh, hit an easy rhythm of conversation, and she even made fun of her own intoxicating hotness—happily donning the increasingly skimpy outfits I asked her to wear. She totally got the movie’s trashy sense of humor, too, and would throw an extra bounce into each step as she fled from a lifeguard-turned-werewolf (Yeah, the movie was crap).

Even after we finished the film, Corrine still called me every day after school, just to chat. We had almost nothing in common besides our sense of humor, but that made our talks all the more interesting. I would keep her on the phone as long as I could, inwardly glowing at the thought of such a gorgeous creature enjoying my company.

I wasn’t deluding myself that it was love—I certainly wasn’t in “love” with her—but a part of me hoped that against all odds she had started finding the scrawny nerd kid mysteriously attractive. That was all dashed to pieces four weeks into our friendship, when I finally got up the guts to ask her out.

It was at a party Corrine had invited me to. I threw down a couple beers and headed through the dim lights, finally finding my girl in a dark corner, speaking quietly with her equally hot friend, Talia. They didn’t see me in the dark, and I was just about to speak up when I overheard Talia say: “You and Ian seem to be getting pretty tight, would you ever think of going out with him?”