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Chapter 187
by
ArthurBalfour
Do they try anything else?
How about a double date?
On the second to last night before my flight East, Elizabeth and I decided to invite Stephanie and Simon out on a double date. We chose a nice restaurant, one of the best in town, but our impending separation hung in the air. We talked excitedly about future plans, swore up and down to keep in touch, and generally tried to forget that soon none of us would so much as share a zip code. It didn't take long before the conversation turned personal.
"Listen, having kissed them both, Simon has him beat. No offense, Ian."
"None taken."
"You know what, this is ridiculous," Elizabeth sighed, "I'm going to have to give him a proper try."
Simon's eyes were big as saucers. I knew that he'd been nursing a polygamous crush on my girlfriend since before prom, but we all thought that was a one-off, outlier event. As if they'd coordinated this in advance, the girls were now making arrangements for a nightcap back at Stephanie's house.
Our two cars rolled up and the four of us headed down to her finished basement. It was a little chilly, but her parents didn't keep a lock on the liquor cabinet. Soon we were buzzing and giggling about old times, our troubles forgotten. Us boys were dressed casually, t-shirts and jeans, the standard uniform. The girls, of course, had dressed to impress. Elizabeth stunned in a casual red dress that scooped into her cleavage and stopped mid-thigh, and Stephanie had herself on full display in Daisy Dukes and a black spaghetti-strap tank top.
Finally, Simon dropped "What about that kiss, huh?" and let it sit there. Elizabeth dutifully got up and planted a deep kiss on his lips that left him completely starry eyed.
Stephanie watched this with a sly grin and turned her blond curls toward me. "You don't mind?"
"Not if she rules in my favor. What do you say, honey?"
Elizabeth shook her head. "It's Ian, for sure. No contest."
"Bullshit!" Stephanie cried. "This is stupid. Kissing's dumb anyway." She took a sip of her drink, something brown that made her cringe. "We should be comparing their REAL talents."
I asked, "What does that mean?"
"Simon gives really good head."
All three of us nearly spat our drinks. Simon blurted, "What the fuck?"
Stephanie dug in her heels. "It's true! He gets me that way, every time, in no time."
"It's not a race," Elizabeth sounded, prim and proper. "Besides, Ian's extremely effective when he's... you know."
The blonde grinned maliciously. "There's an idea! We should have a race."
What do you say to that?
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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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