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Chapter 185
by
BosomBuddies
That's quite an invitation. Does he make a move on her?
He's still too torn up about Elizabeth
But for some reason, I choked.
Here she was, actually trying to seduce ME, and I couldn’t bring myself to go for it. It was like my body had forgotten how to respond to a woman who wasn’t Elizabeth. I sought out that vodka bottle for an emergency swallow.
For her part, Jessica seemed a bit confused by the fact that I hadn’t already pounced on her like some horny, slobbering Labrador. Guess she figured I was playing hard-to-get.
Still holding her breasts, Jessica snuggled into my arms. I felt the bare skin of her back beneath my fingers. Felt the heat of her lips pressing softly into the crook of my neck. I grew painfully hard within the constraints of my jeans.
“I’m still in love with her,” I sighed. Jessica quietly broke away, meeting my eyes with her own.
“Does that mean you don’t want to do this?”
My eyes drifted south, to the soft, delectable pillows of flesh ballooning out around her fingers.
“Of course I do, I just—I don’t want to be unfair to you. I’m kind of a mess on the inside, right now.”
Jessica mulled over what I’d said, then flashed me a sweet smile. She shifted her body so that she was covering both breasts with one arm, and used her free hand to ruffle my hair.
“Kind of a mess on the outside, too,” she teased. “But at least you’re honest. And the mood I’m in right now, the most ‘unfair’ thing you could do would be to leave me alone and unsatisfied.”
She let her fingers slowly trace their way down from my hair, caressing my cheek, grazing her nails across my chest…
We both lowered our gaze to watch intently as those fingers of hers reached my jeans and began stroking the shape of my cock.
“Oh Jesus.”
“It’s okay,” she cooed. “You’ve had a rough year. Why don’t you just let me take care of you for a little while?”
It was the first time since prom night—almost a year now—that someone other than Elizabeth had touched me like that. I felt wrong and guilty, and so-goddam-fucking-horny I thought I was going to pass out.
Jessica was gentle; sweet and affectionate. Her touch reminded me of how I had behaved the first time I’d caressed Elizabeth’s breasts, her body literally shaking with desire at my touch—
Goddammit! Why can’t I go five minutes without thinking of Elizabeth?
Jessica squeezed me through my jeans, wrenching my thoughts back to reality. Elizabeth and I were on a break, after all. And the point of that break was so that we could enjoy moments like this.
Wasn't it?
Does Ian finally give in and enjoy himself?
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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