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Chapter 5
by
BosomBuddies
How does Ian answer?
Taunt her back: "Why do you like teasing me so much?"
“I don’t know,” I sighed, raising my gaze to her eyes. “Why do you like teasing me so much?”
Corrine opened her mouth to say something smartass, but the seriousness in my tone of voice must have changed her mind. Instead, she lowered her voice to a whisper and answered, “I don’t know. I guess because I’m not really good at anything else. I’m not good at art, I’m not good at sports, and my GPA’s such a joke I might not even graduate.”
Corrine was usually the most confident person I knew. Even that small show of vulnerability couldn’t have been easy for her. I brushed a hair from her eye and pulled her close for a hug, saying, “You’re good at tons of stuff, Corrine. You’re funny, you’re friendly, and you’re really easy to get along with. And yeah, you’re excruciatingly hot. Look, don’t worry about graduating! School is the one thing that I’m really good at, and I’m not gonna let you flunk out.”
Corrine hugged me back as tight as she could, letting out a deep sigh. “Sorry I got all serious like that.”
“Anytime, Corrine, you’re my friend.”
“Is it cool if I keep teasing you?”
“Yes, Corrine, it’s very cool.”
She grinned, wicked as ever. “Good, then you can finish my back rub!”
With that, she laid down on her stomach and hiked her shirt all the way up to her neck, revealing a slender back and a pair of magnificent breasts splashed out to the sides of her body.
I believe I actually groaned at the sight.
As the school year progressed, I made a real effort to prove myself wrong about my presumed zero percent chance with the opposite sex. I asked other girls in my class out on dates, and a few of them even said yes. That’s when I started experiencing some of the downsides of hanging out with the hottest babes in school.
My handful of relationships never lasted more than a couple weeks. It was always the same story: no matter how much I liked a girl, she just couldn’t get over feeling intimidated by my bevy of gorgeous friends. Girls always got weird about my social circle before I could even get past second base with them. One truly awful girl broke things off with me on New Year’s Eve, leaving me dateless when midnight rolled around. It may sound silly, but I had never had a chance to ring in the New Year with a kiss and I had been really looking forward to that milestone. My five beautiful friends all tried to cheer me up by kissing me after they had kissed their own dates, but it wasn’t the same. I wanted to be somebody’s first choice, not a charity case.
The situation pissed me off, but deep down I could understand. On some level, that girl was right to be jealous. Even though I wasn’t romantically interested in any of my five friends, I hardly ever fantasized about anyone else. It didn’t matter if I was dating another pretty girl, or if I had just bought pornography—whenever I was in the mood, I would inevitably picture myself with one or more of my friends, pounding away while they wrapped their supple legs around me—or better yet—squeezed their massive tits around my cock and tit-fucked me into oblivion.
I felt schizophrenic. One second we’d be happily bitching about homework or whatever, and the next second I was trying to hide the erection that sprang up whenever one of my girls stretched out and yawned. It was humiliating.
The fact that I mainly hung out with girls also got a rumor started that I was gay, which made it even more difficult to convince other chicks I wanted to date them.
By the time Valentine’s Day rolled around, I didn’t even bother finding a date.
What happens on Valentine's Day?
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Bosom Buddies
A coming of age story: a nerd befriends the five hottest girls in school
What happens when the best friends you’ve ever had are also objects of your every carnal desire? You choose the names for the unlikely hero and his lovely young friends. He was just another shy, nerdy high school senior—before a chance encounter led him to befriend five of the hottest girls in his class. But “friends” is all they’ll ever be, because these ladies are way out of his league. Or are they? As the his relationship with the girls goes from purely platonic to mind-blowingly erotic, the possibility for true love enters the picture. With Graduation Day fast approaching, will he and his “bosom buddies” be able to sort things out before their high school experience comes crashing to an end? And can their friendship—or whatever it’s become—survive? Author's Note: I originally published several of my stories on Literotica.com, and am re-posting them here at the request of some readers. For now, I'm posting the stories with only one path, but there are multiple points where the story can branch off if other writers are interested in participating.
Updated on Oct 1, 2025
by BosomBuddies
Created on Dec 5, 2015
by BosomBuddies
You can customize this story. Simply enter the following details about the main characters.
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