The Crimson Circle
Copyright© 2025 by jamesbreitbart
Chapter 14
Coming of Age Sex Story: Chapter 14 - The story of Nolan Pierce, a freshman at a prestigious boarding school with an influential network of secret societies and a number of storied traditions - many of which involve nudity.
Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft mt/Fa mt Mult Teenagers Blackmail NonConsensual Gay Heterosexual School Alternate History Humiliation Group Sex Orgy Polygamy/Polyamory Interracial Anal Sex Exhibitionism First Masturbation Oral Sex Voyeurism Foot Fetish Public Sex Nudism Politics
Jordie Shriver
I’d spent most of my evening with a Wilson School student directory and google, finding out which of the students had famous parents. Around 10:00, I got a message from Dylan on AIM.
Check out the live feed!
He had set up a live feed of the video cameras Haley had installed in her dorm, so we could watch the prep school kids do whatever it was they did behind closed doors. Right now, it looked like a bunch of them were coming back from some event buck naked. I scanned the faces for one I recognized and found Finn Callahan, younger son of the Governor of Washington.
“Hey Dylan,” I typed “can we zoom in on an individual camera?”
“Yeah, just double click and it will pull up audio, too.”
I watched Callahan enter one of the dorm rooms with another boy and two girls. One of the girls had a tattoo on her ass, but the resolution wasn’t quite clear enough to make out what it said. Maybe the boy was his roommate and they were each going to fuck one of the girls.
The girl with the tattoo turned around and I realized that she was Sloane Kensington, daughter of the director Graham Kensington and an actress who’d been nominated for an Oscar a couple of years ago. The audience for a sex tape of her would be massive.
I put in my earbuds, eager to hear what she was saying.
“I always say if a guy’s not willing to take it up the ass, he’s not any good in bed.”
“Well, I can definitely take it,” Callahan said confidently.
“All of it?” the other girl giggled.
Callahan and the other boy were both hard, and the other boy was hung like a horse, was Callahan really...?
He was. They started kissing and stroking each other’s cocks. The other boy took a bottle of lotion and squirted some onto his finger, which he stuck up Callahan’s ass. We were officially into the territory where if this got out, it would make front page news. Come to think of it, what was Jas Whitfield up to? I toggled through screens showing boys doing various things they weren’t supposed to – smoking pot, jacking off, jacking each other off – until I found Jasper Whitfield, sitting on his bed in his pajamas (and socks – I thought anyone who wore socks to bed had to be a serial killer in waiting) and reading a book with headphones on – boring.
I toggled back to Callahan. By this point he had straddled the other boy and seemed to be gradually lowering himself onto his horse-dick. The camera was placed in a ceiling tile right over the bed, so I was looking directly at Callahan’s face, watching it contort as the other boy impaled him. I was starting to get hard, totally from imagining what Sloane Kesington and her friend were doing just offscreen, and definitely not from Finn Callahan. There was no way I was gay for that preppy motherfucker.
Unfortunately, there was no way to move the camera, so I couldn’t see what Kensington and the other girl were doing.
“Are you guys seeing this?” I messaged the group chat.
“Pierce?” Haley messaged me back
“No, fuck Pierce!”
“That’s what Owen Fitzgerald is doing,” Kendra said.
“They’re both nobodies. Look at Finn Callahan.” At the moment, Finn Callahan was looking straight at the camera and shouting:
“Oh, yeah! Fuck me harder Dylan!” He clearly wasn’t worried about being overheard.
“What, do you have a crush on him?” Kendra messaged.
“No!” The tent in my pants was totally because of the girls. I decided that we needed to get some of these cameras in the girls’ dorms ASAP.
“Sounds he has a crush on Dylan,” Ty messaged, “LOL.”
“Dylan Reed is his roommate,” Haley explained.
“Dylan, are we recording these?” I asked.
“Yes, but we can’t do anything with them until we get video from other dorms, remember?”
“The first home football game is tomorrow,” Haley messaged
“Great,” Dylan responded, “Everyone meet in the computer lab at lunch tomorrow.”
We assembled in the computer lab the next day, and Dylan gave us instructions, whispering so as not to be overheard by the teacher.
“Here’s the plan. After school, everyone go home and change into the preppiest clothes you own, then we meet Haley at the entrance to the school. Haley, your mom has a master key, right?”
“Yeah.”
“We’re going to need to borrow it. We act like students, follow kids into dorms, and hide out in the bathrooms until all the students leave for the football game. Then, we use the master key to get into their rooms and put the cameras in their ceilings.”
“Do you know which room Conor Callahan is in?” I asked.
Haley rolled her eyes, “What is he, your boyfriend?”
“He’s a governor’s son.”
“You mentioned that.”
“You don’t understand. If a sex tape of him leaks, it’ll be the biggest sex scandal since Gary Condit!”
“Who?”
“Never mind.”
“We need to focus on freshman dorms for now,” Dylan insisted, “the upperclassmen won’t all be at the football games. Once we start getting some money coming in, we can buy fancier cameras. They make ones we can install in the light fixtures in the showers. I’ll bet that’s where the real action is.”
I went home after school and put on the preppiest clothes I could find – khakis, a blue button-down shirt, and dress shoes. We all met Haley at the front entrance to the school right at 5:00, and went back to her apartment to fill our backpacks with webcams.
“Is there anywhere we can go between now and kickoff time?” Kendra asked. “I’m getting nervous.”
“I want to check out the library,” I announced.
“I really doubt we’re going to catch anyone fucking in the library,” Dylan objected.
“No, but I bet that’s where the secret societies meet, and we need to restock on cameras anyway.”
Haley rolled her eyes. “Fine.”
When we got to the library, we headed for the basement where the tech desk was. Haley removed some of the webcams from a box put them in her backpack, while Dylan geeked out over the school’s technology.
“Dude! They’ve got the Mac G5s!”
“Shh!!” we snuck out of the tech room and walked around the basement, but the rest of it looked like it was just offices and microfilm rooms. We took the elevator up to the second floor, which was mostly deserted, and I tried doors until I came to one that was locked.
“Hey, Haley, come open this!”