Chapter 37
by
BosomBuddies
Does he go through with it?
Yes, they make love
I nudged my tip inside her delicate folds. Stephanie let out a sudden gasp at the sensation. I could feel her heart beating wildly through her breast. I froze for a second, worried I’d hurt her, but then I felt her pelvis pushing forward to take up the slack, drawing me in deeper. I matched her speed, wanting to keep her first time as comfortable as possible, feeling every blissful millimeter of progress.
Our mouths found each other, kissing tenderly. Hands caressing faces. Sharing something extraordinary with each other. Then, far more easily than either of us expected, I was all the way inside. I’d heard so many urban legends and horror stories about the pain of a girl’s first time, but it simply wasn’t an issue for Stephanie. We both glanced down to see that I had bottomed out and she let out a huge sigh of relief.
“Oh, thank God! I was so scared it would hurt!”
“Me too!” I laughed and held her close, still disbelieving that I was really inside her. I kissed away the fresh tears on her cheeks and she looked me in the eyes, earnestly suggesting, “Let’s keep going.”
Stephanie’s hot, tight wetness squeezed around me, stimulating every cell of my penis as I slowly pulled out and then slid back home. I had come twice tonight, but that was hours ago, and I knew almost immediately that I wouldn’t be going for a world record here. This felt way too good.
She arched her back, rubbing her erect nipples up against my chest. Her eyes rolled back in a trance of pleasure and I knew we were both getting close. Soft, adorable meows of happiness came out of her with every quickening breath. God, she sounded sexy—
Stephanie sucked my finger into her mouth and that was all I could take. There was no holding back, so I just let myself go and emptied everything I had into her, grinding my pelvis against her clit as I came. Through the haze of my orgasm, I felt every muscle of my lover’s body tense around me, heard her breath catch in her throat, felt her fingers’ **** grip on my ass–
Then she relaxed beneath me, recovering from a very different orgasm than the “howling at the moon” one I had given her with my mouth a few hours ago. It was marvelous to witness: just as intense, but in a quiet, intimate way.
We collapsed together, recovering. I thought about what to say to her. What is a guy supposed to say in this situation? “Thank you?” A million possible phrases ran through my head. Cliches, things I’d heard in movies, read in books… None of it was real or right for the moment. Then I realized that the way I held her in my arms said all that I needed to, and I shut my mouth.
She rolled on top of me, her big breasts spilling out across my chest. That’s the last image I remember before we fell asleep.
What happens when he wakes back up?
Disable your Ad Blocker! Thanks :)
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.
- 35,288 Likes
- 10,987,103 Views
- 4,826 Favorites
- 6,069 Bookmarks
- 754 Chapters
- 368 Chapters Deep
Comments moved below the chapter.
Jump to comments
Comments