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Chapter 36
by
BosomBuddies
What happens when Ian wakes up?
Stephanie has disappeared from bed...
I woke up in the middle of the night with a raging hard-on and a naked goddess on my arm. Faint moonlight shone through my window blinds, warping stripes of illumination around Elizabeth’s every voluptuous curve.
I discreetly slipped off the bed, grabbed a pair of boxers, then headed downstairs to get a glass of water and see where Stephanie had disappeared to. I found her sitting on my couch, in the dark, all by herself. She jumped a bit at the sound of my footsteps on the stairs.
“Hey, it’s just me,” I whispered. Stephanie was dressed in one of my T-shirts, but with her being a scant three inches shorter than me it barely covered her up. The braless breasts beneath swung nicely when she turned towards me.
“Sorry,” she said, “I woke up and couldn’t go back to sleep. Too much on my mind. Tonight was amazing, but it’s kind of a lot to take in. And I don’t just mean what happened with you, I mean everything with Elizabeth, too. She was always so innocent! I took it upon myself to shelter her from things like this. Now that’s all over. I just can’t wrap my head around the fact that we… well, that we basically had a threesome with you.”
As I got a bit closer, I could see that her eyes were watering up. “Elizabeth will be fine,” I assured her. “I think she did exactly what she wanted to.” I sat down on the couch beside her and pulled her into a big, safe hug.
“I know, it’s not that. I’m happy for her. For all of us. It’s just a really big, really sudden change to how I thought things were.”
“Nothing’s changing,” I promised, “We were all great friends before tonight, and we’ll all be great friends in the morning. The only thing that’s changed is how a bunch of this sex stuff—these things that were freaking us all out because we’d never tried them before—suddenly they don’t have to be scary anymore. Like for example, before I went down on you tonight, I had no idea whether I would even like that. How it would taste, whether I’d be any good at it, all kinds of stuff. Now I’m not nervous about it anymore. I know what it’s like, and I know I want more.”
She lifted her eyes to meet mine and I kissed her. As her soft face pressed against mine, I felt her tears on my cheeks. “I’m not scared of it anymore,” she panted, taking a moment to wipe away the moisture beneath her eyes. “I’m not scared of any of it when I’m with you.”
We kept kissing in the moonlight for what felt like hours. I loved the feel of her warm body in my arms, the caress of her lips against mine. It felt reassuring; reminded me I was really there. She climbed onto my lap, her palms caressing my chest as she settled her bare pussy down onto me, the thin cotton of my boxers all that stood between us.
I could feel her warm wetness seeping through the material as we kissed, our pelvises involuntarily rocking against each other. With each slow, agonizing movement, my erection slid further and further out of my fly, the shaft rubbing directly against the her slippery outer lips. Skin on skin.
Stephanie moaned into my mouth as we slowly ground out genitals together. Her body penned my dick down to my pelvis, meaning I couldn’t penetrate her. But that hot, sopping wet pussy felt incredible as it glided up and down my rigid length. I rolled my hips forward, grinding my swollen cockhead against her clit. My arousal was unbearable, but it was unbearable in the best way possible.
Then she said the magic words: “I want—I want you inside me.” The sentence a guy spends his whole adolescence waiting to hear. “It’s okay,” she hurriedly added, “I’m on the pill.” Good thing too, because I’m not sure either of us would have been able to stop at that point anyway.
Without further ado, I grabbed the T-shirt she had stolen from me and pulled it over her head, drinking in the sight of her naked breasts in the moonlight. I rolled our bodies down to the couch cushions, her lying comfortably on her back, me on top. Stephanie’s hands impatiently reached up and pulled my boxers down around my knees, letting my cock spring free mere inches above her nubile young body.
We waited one final moment, looking deeply into each other’s eyes for confirmation...
Does he go through with it?
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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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