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Chapter 99
by
BosomBuddies
Who does Ian get?
Stephanie! Awkward...
I gave the bottle a spin, and it came to a stop pointing directly at Stephanie’s crotch. Our eyes met, and I suddenly felt very anxious about what we were supposed to do. Excepting Rachel, I had been intimate with every single girl in that room—yet with Stephanie I still felt like things were weird. I wished I could just kiss the girl and enjoy it for what it was. Why did things have to be weird?!
And then, all of a sudden, it dawned on me: they didn’t. It was all in my head. Stephanie was an unbelievably gorgeous woman, and a fun-loving, loyal friend. And that was all she needed to be. There was no reason at all why we shouldn’t both enjoy this kiss.
And I knew exactly how I wanted her to enjoy it.
“Hey Stephanie, I’m gonna kiss you the same way Rachel just kissed me, cool?”
I think she must have sense the casual ease in my voice, because Stephanie visibly relaxed when I said that. As I crawled across the circle towards the stunning blonde, she smiled in anticipation, and reclined on her elbows to grant me easier access to her smooth bare midriff.
Ever so slowly, I lowered my mouth to her stomach and teased her with my tongue. I kissed around her bellybutton, then breathed a gentle gust of hot air across her skin, causing her to tremble ever so slightly. I glanced up a few inches, at the enormous pink breasts bulging out around the cups of her borrowed black bra.
I fought back the urge to reach up and squeeze them.
Stephanie’s hips began to writhe beneath me, and I forcefully held them still with my hands as I continued licking her beautiful belly. My licking became harder and hungrier, turning me on as much as it did her—
But I kept myself in check. Just as she was really getting into the sensation, I dialed down the intensity. I pulled my mouth off of her body and crawled a few more inches, glancing briefly down at her huge tits as they passed beneath my chin, until our faces were level with each other. I gave Stephanie a friendly kiss on the lips and smiled.
She smiled back. At that moment, as the two of us looked each other in the eye, we both silently acknowledged that we were cool again. It was like a ten thousand pound weight had been lifted off our shoulders.
Stephanie spun the bottle and got:
Who does Stephanie kiss?
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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
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