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Chapter 53
by
BosomBuddies
What does Ian think of Simon?
He's a good guy, and he treats the girls well
Though I admit this grudgingly, I could see why Stephanie liked him so much.
Simon had a sweet-natured, soft-spoken personality, almost like a male version of Elizabeth (which maybe explained why he was such a good fit for Stephanie). He had a swimmer’s build, with impressive muscle tone I was a bit jealous of, and that triangular shaped torso you only get from a lifetime in the water.
More than once, I overheard the girls giggling about how much they were looking forward to Spring Break, and getting to see a lot more of Simon in his speedo.
Much as I resented Simon for infringing upon the perfect little social utopia I had with my girls, I just couldn’t dislike the guy. He was one of those rare people who is genuinely nice to everyone. The fact that he and I had pretty much the exact same taste in video games didn’t exactly hurt his cause, either.
In the months I had known them, my girls had dated plenty of guys; some were assholes, some were awesome, but nobody before Simon had clicked with the rest of us. Our group of six became a group of seven. I watched with a mixture of jealousy and pity as shy, sweet Simon tried to survive the same gauntlet of flirting and teasing I had endured during the early months of my friendship with the girls. Stephanie protectively kept some of her friends’ more overt behavior at bay, but there was nothing she could do to keep her man’s eyes from wandering to Corrine’s expansive, swaying bosom every time the stacked Nordic babe so much as leaned over.
One time, when we were all hanging out at Stephanie’s, Corrine showed up dressed in a little pink knit vest meant for a much shorter woman. At nearly six feet tall and wearing literally nothing else on her chest, Corrine looked positively ridiculous. The garment pulled so tightly around her breasts that the knit stretched loose, hinting at the luscious skin and pink nipples beneath. Corrine’s height also essentially transformed it into a belly shirt, and its plunging scoop neck revealed an obscene amount of mouthwatering cleavage.
Amy burst out laughing at the sight. “Oh my God, Corrine, that’s hilarious! Whose is that?”
“Mine,” Corrine answered, grinning naughtily at our combined reactions. “From about six years ago. I found it in the attic.”
I could think of nothing I wanted to do more than to rip that vest off with my bare hands and ravage Corrine’s impossibly fine body, smothering my face with her huge tits.
Stephanie teasingly prodded her utterly stunned boyfriend, “What do you think of Corrine’s outfit, honey?”
“Uh!” Simon jumped a bit, fumbling to respond, “I think it looks…”
He just trailed off, unable to tear his eyes away from her rack. We all cracked up at Simon’s non-response, and the guy turned a deep scarlet, profusely apologizing to both Corrine and Stephanie. Old pro that I was, I took him aside a bit later and assured him, man-to-man, that this kind of thing was just a form of hazing for any guy that wanted to be friends with these girls.
“It will be both the best, and the worst thing in your life.”
Simon just nodded, still embarrassed.
Elizabeth came over to me after Simon had rejoined the others. Ever since the night of our first threesome with Stephanie, Elizabeth had started dressing a lot less modestly. Today she was wearing a sparkling purple top with spaghetti straps and a plunging neckline. Her cleavage looked fantastic.
“Giving the new guy some pointers on how to survive all the teasing?” she asked.
“Yeah, though I think he’ll have an easier time of it than I did, what with Stephanie to take out his frustrations on.”
Elizabeth gave me a funny look, then pressed: “Has Stephanie not told you?”
“Told me what?”
What has Stephanie not told Ian?
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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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