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Chapter 152 by criscotwister
Who does Ian see?
Stephanie - it's beyond complicated
I frowned while keeping my eyes closed. I couldn't possibly tell the truth. It was so fucked. Why the fuck was I still having these thoughts? These pathetic fucking feelings. I thought I had truly made peace with the fact that Stephanie had moved on and we were back to just being two of six best friends. But images of her dressed in a ruffled skirt, shimmering beading across her top, and a baby blue gown to match her bright blue eyes came unbidden into my mind. The sexy way the skirt accentuated her hips and ass. Her top pulled tight across her chest. Just enough makeup to bring out all of her natural beauty without going overboard and making her look "whorish." Her beautiful blonde curls framed her face perfectly.
The Stephanie in my mind was so gorgeous I was almost disappointed when I felt the table jostle in front of me as the real Stephanie grew impatient with my continued silence and slapped her hand on the table to break me out of my stupor and answer her question. But when I opened my eyes I realized the real Stephanie was far more beautiful because she was right there in front of me.
"Earth to Ian. Well? Who is it?" she asked as she took a sip of her milkshake.
I sighed, flustered, "Umm well... it's beyond complicated."
"Ian, we're all best friends here. None of the three of them are going to be heartbroken you didn't choose them. The other two will have no problem finding dates on their own once you let them know. Simple as that."
But it wasn't. It was so complicated, I couldn't even fathom a higher math problem to compare it with. Dealing with my feelings for Stephanie was a million times harder than any calculus exam. I couldn't tell her. I needed a way to deflect intelligently while revealing just enough to get her off my back. Maybe a half-answer would work.
"Are you familiar with that Heller novel about WWII? Catch -22?"
"Not particularly. I believe I've heard the 'catch-22' phrase before though. Isn't it like an unsolvable problem?" She was noticeably slightly irritated that I tried to change the subject.
"Yeah, well basically the plot is how the fictional U.S. Air **** had a guideline that mentally unfit airmen didn't have to fly missions but couldn't actually get out of doing so because voicing this concern on one's own behalf meant the airman was showing rational concern for his and his fellow airmen's safety."
Stephanie narrowed her eyes at me, "Well, that's all very interesting and all Ian but you know I'm not going to just forget why I sat down with you in the first place."
At this point I wasn't sure if I could keep steering the conversation away so I chose to stay with it but maybe twist it in some odd way. An idea struck me. "I know, and that's what I'm getting at... To me, it's a damned if I do, damned if I don't situation. I can absolutely promise no one will like my decision."
Stephanie let out a derisive guffaw. "What are you talking about? Do you really think that Corrine, Elizabeth, or Amy can't handle themselves if you're not there for them during prom in some way? You know we'll all be going as a group anyway. I seriously don't follow what you're trying to say."
Okay, good. I was at least spinning my sentences in weird circles and slightly throwing her off. I would rather had her think I was being over-protective than tell her the truth. The look we shared at the cabin signaled that she felt comfortable now and that I wasn't really in the picture anymore. Just friends. And I couldn't deny how horny I was when I watched her blow Simon as much as I wished it had been me and not him. That was our position. Stephanie and I had done it first. And he can never take that away. I could feel a slow roiling rage in my gut just thinking about Simon. It wasn't so much that I hated him specifically. We probably could have been good friends if we had met before all of this mess - the guy knows his video games. I hated myself for not being able to let go. I hated how I let sex ruin my feelings for Stephanie. I hated that I agreed to our "friends with benefits" plan without realizing what might happen. I hated myself for falling for her. I was Stephanie's first lover as she was mine. That meant something. Talia had said as much. When I was distracted by Elizabeth and Amy at the cabin, the nagging feeling inside me was pushed aside long enough that it didn't hurt. But now we were back at school and every day my thoughts were brought back to Stephanie and how much I wanted to somehow politely remove Simon from the equation.
"What the fuck?! Where was this **** flash of jealousy coming from?" I thought. "Who am I kidding, I know exactly where it's coming from. Ugh, be cool Ian. You said you were okay with it, remember? You only want her to be happy. Don't fuck this up."
After gathering my thoughts while Stephanie talked about not following my conversation I spoke up. "Look, Stephanie. I don't even know either. I need another day or so to decide."
"Well, you better make up your mind quick if you want to go," Stephanie sighed. "I doubt the girls are going to wait much longer. They can only stall other guys for so long. I really don't understand what your problem is... Wait! You said no one would like your decision. That means you do know, you're just stalling for some reason!"
Was she able to coax it out of him?
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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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