Chapter 4
by
BosomBuddies
Are any of these beautiful girls romantically interested in Ian?
Just friends... for now
To my great surprise, I learned that, of my beautiful new friends, only Amy and Talia had any serious sexual experience. Even professional cock-tease Corrine had never gone further than letting a guy feel her up, and Elizabeth had never even done that. My adolescent assumptions about these gorgeous women with their wild, wanton sex lives evaporated when I got to know them all as a group of regular, cool people with the same frustrations and anxieties about sex as every teenager.
Pretty early into our friendship, Amy took it upon herself to get me into shape, and I must say she made the typically miserable task of exercising a lot of fun. Running laps around the park actually became a treat when I was running behind her, watching that impossibly fine ass stretching her tight little shorts. Over time, my body filled out with some nice, lean muscle definition.
I asked all five girls to take me shopping so I could replace my wardrobe. Instead of dropping the money from my summer job on video games, I saved up for some decent clothes. After some female advice and a few trips to the mall, I started to look like a grown man.
As the only male in our group, the babes teased me incessantly. But it was always good-natured and no sane man would complain. Occasionally, however, the line between platonic friendship and sexual curiosity would blur ever so slightly. Somehow, the stars had aligned to make all five girls single during those early months of our friendship, so when I’d be hanging out alone with one of them there seemed no harm in us snuggling up on the sofa to watch a movie, our hands gently roaming each other’s bodies, always careful to avoid direct contact with the naughty bits. It was pleasantly arousing, but never overt enough that things felt weird between me and the girls afterwards.
One time, this innocent snuggling led to me giving Corrine a prolonged massage. I worked my hands up her back until she asked, “Could you undo my bra? It would feel better.”
I swallowed, throat tight. My hands were actually shaking a little bit as I blindly reached beneath her shirt and fumbled with the hooks. My awkward fumbling must have been pretty obvious, because Corrine sat up wearing a Cheshire grin.
“Have you never taken a girl’s bra off before?” she asked. I shrugged, wishing it could be anyone else in the world having this conversation with me. Corrine turned away, helpfully lifting up the back of her tank top to reveal the heavy-duty strap beneath her shoulder blades.
“Here, let me show you.” She demonstrated the clasp for me a few times, then said, “Now you try.”
My mouth turned to cotton while I imitated what she had done, unclasping the garment from her back. Suddenly unsupported, her substantial breasts dropped to their natural slope, and my eyes dropped with them. Corrine cast aside the enormous bra and turned to me, her tits swaying braless, hidden beneath her tank top. I wanted her so bad it hurt.
“There, now you’re an expert.”
My eyes were glued to the fabric tugging across her curves. Corrine glanced down at her boobs, cocking her head to the side. “Ian?” she asked coyly, “Why do you like my boobs so much?”
How 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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