Sissy High School Stories

209,604 results
Orientation
Length
Source
Infinite Scroll

Revenge on Bully

by Johnthomas1969 on Sep 13, 2017
Exhibitionist & Voyeur

I won't bore you with the details of how I was bullied, suffice it to say it was bad and humiliating. When it got real bad one day, I made two promises to myself, one that I'd never be bullied again, and two that I'd get revenge on the main bully, Jeff. Fast forward a few years. I went to college as did Jeff. He became a teacher I became a businessman. Soon...

Karolina's Adventures Pt. 02: The Intern

by KarolinasAdventures on Oct 7, 2019
Loving Wives

Karolina sat in front of the computer typing, bored as can be. It had been a week since her adventure with Ben, and to say things had been rough at home was putting it lightly. Will had raged at her for hours the night after her adventure with Ben. Karolina was ashamed to admit to herself she didn't feel bad about it, but for the sake of her relationship, s...

Home Schooled

by BryanBiff on Sep 21, 2020
Exhibitionist & Voyeur

One of the perks in my otherwise dull job is that twice a year I get to see dozens of the local high school boys in their underwear. Spring and fall is physical exam time and I work as a nurse practitioner for Dr. Richard P. Thornberry, a much beloved elderly doctor in our small town. Dr. Thornberry gives the boys their physical exams so they can be cleared...

Scott's Story Pt. 01

by DeanaBard on May 12, 2020
Fetish

First Date, First Taste [Memories from a distant time. A time before VCR's, cell phones, and computerized everything.] The memories of that night are burned deeply into my brain. All it takes is a certain smell or taste to instantly transport me back in time; to my senior year of high school. To be more precise, the last six weeks of high school. When my...

Kim and her Son's Bully Ch. 02

by mrssanchez on May 27, 2019
Mature

DISCLAIMER: JAKE AND ANTHONY ARE IN HIGH SCHOOL BUT THEY'RE BOTH EIGHTEEN *** Slowly and heavily Kim's eyes open and came into focus on a wall of photos. Blinking rapidly, she saw the face of Jake in multiple pictures, in front of a beautiful beach, within an art exhibit, and in countless other places. The memory of her past two days came rushing back to...

Alpha and Omega Ch. 03 Pt. 01: The Double Trap

by DragonCobolt on Sep 16, 2017
NonHuman

Author's Note: This story is merely part one of two! Part two will be arriving once it is written. Enjoy~ ***** Bruce Robert Kinsey knew that today was going to be a weird day when he walked into shop class after school and found one of his classmates holding a raygun to her head. And that was saying something, considering that this week had been packed...

No Future Ch. 12

by bradley_stoke on Sep 15, 2017
Novels and Novellas

XII The Good Seed Molly & Mark 2071 There was no denying it. Molly had taken the death of her unborn child very badly. The shock of the loss sent her into a downward spiral of despondency and then depression. The inevitable result was that she lost her job. Her impressive academic qualifications notwithstanding, she was now no more useful to humanity than a...

First Time with Chris

by Sissyhalo on Mar 7, 2018
Transsexuals & Crossdressers

All characters are over 18 years of age. ***** High school sucked. Actually it didn't it was pretty dry sexually. I was gay, not even really gay but trans. I wasn't a guy but kinda stuck there. Short, chunky, uncomfortable in my skin and life and with people it all sucked. Getting out became as much as an obsession as changing. So my last two years o...

Bisexual Trickster's Adventure

by Samuelx on Sep 14, 2017
Erotic Couplings

The situations I get into simply continue to boggle the mind. Sometimes, I think I might be a magnet for trouble. Right now, I'm visiting my friend Robert Jean-Pierre's fine-looking, busty and big-booty mother Ashley. And man is she making my visit enjoyable! She once told me that she liked tall, burly brothers like myself but I never knew how much. Today I...

Carpe Diem

by panama trick on Sep 14, 2017
Erotic Couplings

Mr. Tantrick sticks his head into the classroom. "Maria?" She looks up from desk, a little nervous at the intrusion. "Yes sir?" "As soon as your class lets out please stop by my office, I'd like to talk to you about some of your recent schoolwork." "Yes Mr. Tantrick," Maria replies, swallowing. Oh my god, she thinks to herself, what did I do now? Class...