Disable your Ad Blocker! Thanks :)
Chapter 184
by
ArthurBalfour
Does Ian have any ideas?
Take my friend's virginity.
I had to admit, Elizabeth had a point. There was definitely a double standard in our relationship when I could fool around with Amy and the other girls on prom night and my girlfriend couldn't have other experiences also. But what sort of experience would she enjoy? The soft look in her eyes told me that she trusted me completely to give her a good memory. I wanted so badly to kiss her. Then I got an idea.
"Why don't you take Andy's virginity?"
Her eyebrows furrowed in thought.
Andy was one of my AV Club friends. He was a really good guy but painfully shy. Everyone knew that he hadn't done any dating and it had gotten around to me that he had a crush on Elizabeth that he'd kept hidden since freshman year. Since Elizabeth had come into her own, Andy more than anyone epitomized shyness to me. It was a perfect chance for my brunette beauty to take control of a sexual situation.
Elizabeth dropped her gaze as her face reddened. "You want me...to deflower your friend? To be his first?" She smiled. "Let's do it."
What followed was maybe the most surreal few human interactions that I've had. First, I had to arrange a date between my buddy Andy and my girlfriend. That conversation went something like:
"Hey, Andy, you know how you've been hoping to talk to more girls before college? Well, have I got news for you..." And then he collapsed into a puddle. He calmed down some and I told him that Elizabeth wanted to have coffee with him. He was understandably confused. I knew that if I got too explicit, he'd spook.
"Listen," I started, "you know that Elizabeth and I have a lot of... friends." He nodded. "And I have spent time with our... friends." He nodded. "Elizabeth would like to have you... as a friend." That last pause nearly killed him.
"A... friend?" Poor Andy.
"Well, maybe a little more than a friend." You could have knitted a sweater during the pause that followed. Andy's brain seemed to wander off and take a cold shower. He shuddered.
"You're... okay with that?" I smiled and nodded. Then he smiled back.
When it came to ironing out the actual details, we kept things euphemistic. Elizabeth was going to meet Andy at his house for coffee. It was the only way to get two full-on shy people to agree to a rendezvous but I also enjoyed the spy-novel secretive nature of it. Somehow the codes added to the heat building up around the situation.
On the appointed day, I picked Elizabeth up and drove her to Andy's house. She dressed to impress -- a thin, floral, halter-strap sundress accentuated her curves and lovely pale skin. The cut was a little daring, inviting attention toward her ample cleavage. Her legs were bare, too, and I wondered what she had on underneath. I wanted so badly to kiss every inch of bare skin but there would be time for that after.
We stopped in front of the long sidewalk leading up to Andy's front door. Elizabeth looked the picture of innocence, smiling sweetly with her eyes locked on mine. And here she was, hand delivered to take my friend's virginity.
Her pink lips met mine and soon we were exploring each other's mouths. I felt myself hardening just as she pulled away.
"I love you," we said. "See you in a few hours."
As I watched her heels click away up the sidewalk, she quickly turned up her skirt to flash her bare ass at me. She wasn't wearing panties! Elizabeth turned and winked before she headed inside.
Does the "coffee date" go as planned?
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
- 10,989,379 Views
- 4,827 Favorites
- 6,069 Bookmarks
- 754 Chapters
- 368 Chapters Deep
Comments moved below the chapter.
Jump to comments
Comments