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Chapter 215 by Twistinger
What's Ian's secret fantasy?
Watching the girls fool around with each other.
"You know Ian, if you're so embarrassed I could be the one to tell them," Amy smirked.
"No, it's fine." Biting my lip, I looked at our four friends. "You know how Amy and I roleplay? Sometimes we think about a threesome."
"That's not really scandalous, Ian," Stephanie pointed out. "It's just a sign that you're a healthy male."
"It's more than that," I admitted. "We started wondering what might happen if two of the girls ended up messing around with each other."
Four pairs of eyes grew large as saucers while Amy's smile practically stretched to the edge of her cheeks.
"Go on," urged Corrine.
"One time a few years back we decided that Amy would role-play as Elizabeth that night, and then she ended up asking her if I ever thought back to the time when the three of us began... experimenting with each other. You know, when Stephanie and I were still figuring things out," I continued. "Then we started talking about the pool party we had, and the time when - well - Talia came out as bi."
There was a brief moment of awkward silence as all eyes involuntarily turned to Talia, but she simply shrugged. "Okay, then what?"
"We remembered that Elizabeth and Stephanie admitted to playing with each other a few times during puberty. Then we started wondering what might have happened if the three of us had taken things even further. Like if Elizabeth got in on what Stephanie and I did at the time, or... if they were more than just best friends.
"The next thing I remember was eating Amy out while she, um, got into character. All of a sudden she moaned Stephanie's name," I went on. "Honestly, the two of us were pretty surprised. At least for a few moments. Then I dove back into her muff as she continued squealing for Stephanie. Our session that night ended up with me fingering and licking her all over while we fantasized that Stephanie and Elizabeth were... exploring."
I paused, partially unsure of how to continue but mostly uncertain of how the girls would take it if I did, but it became apparent that no one intended on interrupting the story. Stephanie's jaw dropped and the blank look in her eyes suggested that even an oncoming car wouldn't snap her out of it, while Elizabeth covered her mouth with her hand as if to contain the furious blush on her cheeks. Her other hand had drifted downwards, edged dangerously close to her pubes.
"Wow," Stephanie croaked weakly, in an attempt to break the silence.
"So basically," Corrine noted, "You two have fantasies about us screwing each other? And act them out regularly?"
"It's not like Ian puts on my clothes or anything, and we don't think about it that often - but in a nutshell, pretty much," Amy grinned. "I mean, let's face it. The five of us are so smoking hot Ian would have to be seven kinds of blind to have never thought about it, and frankly? I thought it was super-hot at the time. You're all goddesses!"
"Well, let me just say - " Leaning over, Talia planted a kiss on my cheek and finished by licking up my ear. "That I really like the way you think, Ian."
"But are we really - I mean - we - "
"What're you getting all shy for? It's not like we're strangers or anything. You were just kneading my tits like an hour ago," Amy nudged Corrine on the forehead, putting a stop to her babbling. "Nothing's going to change between us. We're all really good friends that really love each other, that's all. ...Besides, what else are you ladies going to do while waiting for your turns?"
I felt my brain start to overheat again. On one side Corrine was nervously edging away from Amy, unsure of how to respond to my wife looming closer towards her with a triumphantly predatory leer on her lips. The two best friends Stephanie and Elizabeth were exchanging glazed glances with each other, sporting matching blushes of uncertainty and hardened nipples under their costumes. Talia simply leaned closer, sandwiching her boobs around my arm and pulling my hand to her soaking quim. Her breath wafted into my ear, its warmth speaking of her desire far more melodiously than words could.
What happens next?
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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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