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Chapter 152
by
Duskford
Who does Ian see?
It's always been Corrine
The answer was obvious, even if I tried to hide behind all the casual sex the girls and I started having. The one with whom everything started, the one I had a crush on in the first place and introduced me to the other girls who ended up becoming the best friends I could ever ask for. It's always been Corrine.
"Hello? Ian?" I shook my head to see Stephanie waving her hand in front of my face.
"Oh, sorry, I was distracted."
"Well, who did you see?" she asked impatiently.
I looked down at my forgotten burger before sighing. "Corrine."
Stephanie grinned. "That's awesome, everyone knew you always liked her," she said. "And it's a fact she has a soft spot for you too, I mean, the way she always teases you must mean something."
I groaned. "That's the problem, how can I know the teasing isn't just that, a way to have some fun?" I inquired. "Sure, we had sex, but for all I know she wants to keep it casual without any strings attached, like the other girls."
"Well..."
"I won't be able to see her as just someone to take to prom, I really like her, and I don't think I can take being rejected by Corrine, Stephanie," I interrupted her. "Not her. It would destroy our friendship, and I prefer to have her in my life even if it means we're never gonna be more than friends or fuck buddies."
I looked down again and then felt Stephanie's hand squeezing mine. "Ian, you can't live with that inside you," she said. "Sometimes you have to risk it and see what happens."
I lifted my chin to face my friend, losing two brief seconds to ogle her amazing boobs once more and then shook my head negatively. "Not this, Stephanie, the risk is too big."
I dropped my burger and left, feeling my friend's eyes staring at my back the whole way. I spent the rest of the day and most of the next one deep in thought. The whole casual sex thing wasn't working, I was only getting a taste of what was like being with Corrine and the other girls without actually having a shot with them. That is, except for Elizabeth, I couldn't deny there was a connection between us, but now I realized I couldn't keep stringing her along if my heart and soul were set on Corrine.
Is that what I'll always be to Corrine? A friend? I wondered. I saw no way that scenario could improve, even if somehow my stacked friend had the same feelings for me, she would stay in town once Summer came to an end, while I would leave for college. I would never be able to be away from her if we were together. At every angle I analyzed the situation, I got more numb and depressed.
At afternoon, I wasn't feeling up to my usual run with Amy, so I decided to go and buy a Playboy issue. Getting home, I jerked myself off violently to the centerfold, which made me even sadder after I realized the girl had some resemblance to Corrine. Why I ended up falling for the hottest girl in the entire school?
I gave up after that and just lied down in my room. Around eleven o'clock at night, I was roused from sleep by someone knocking on the front door. I went to answer it and came face to face with Corrine and Stephanie, looking beautiful as always. My heart skipped a beat at the sight of Corrine after I thought about her for most of the past couple of days. I managed a smile before Corrine stepped forward and enveloped me in a fierce hug, her magnificent chest squashing between our bodies and stirring the beginnings of an erection at my crotch.
"Ian," she said once we broke off the embrace. "You look like shit."
I chuckled at her sincere, yet playful statement before Stephanie smiled and placed a hand on my shoulder, giving me a very pointed look as she managed to motion at our tall friend with only her eyes. "Ian, you really need to ask someone to prom."
What does Ian answer?
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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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