Sissy+school Stories

109,522 results
Orientation
Length
Source
Infinite Scroll

Ms. Marca Ch. 42

by Ms. Marca on Sep 15, 2017
Fetish

Many of you have ask me to tell about my sexual actives when I was at home and doing it with the different men in the neighborhood that I lived in when I graduated from high school. My last year of high school I was 18 years old and had that grown up look and could pass for a woman 25 or more. Today I'm 33 and I stand 5' 10" 140# with a 40DD 23X38 figure and...

Yes, Sir

by HardAlyx on Nov 5, 2018
Erotic Couplings

A/N: This is a true story about one of my friends. All the names have been changed. If anything is similar to another story, again this is true and not fiction. Beta Reader: HeyAllStories ~~~~~ The warm September heat beats down on her suntanned shoulders as Alison continues the slow incline walk up toward the local high school, Lake Valley High. The tw...

Detention Pt. 03

by Croony on Sep 15, 2017
Mature

Toby Johnson had a fitful sleep recalling all the things that had happened that afternoon. How he'd been seduced, sucked and fucked by Mr Gayson, his music teacher, while his mother had been used and abused by his headmaster, Adam Jones and Mrs Smith, the school secretary who when Mr Grayson left came to the bedroom he was in and sucked and fucked him for t...

Sexting Pt. 02

by pbon44 on Sep 19, 2017
Erotic Couplings

Four weeks after Jennifer and the Major got together they had a few encounters. He even took her to dinner. The semester ended and the Major took a group of his cadets on summer camp. There were emails but not like the series of text messages that ended with a night of wild sex. Jennifer enrolled in a summer legal clinic program helping low-income people wit...

GTO - The Beginning Pt. 04

by GTO_Racer on Apr 3, 2018
BDSM

All characters are over 18 years old. This story is about how Gail became the seductress she is. I really encourage you to read my first story "GTO" to understand fully who Gail is as I spent much more time on her background there. This story takes place at the beginning of summer between her Junior and Senior year of high school. As you read this, please...

The Humper Game Pt. 02 Ch. 19

by WilCox49 on Jun 19, 2018
Romance

Author's note: This is, in all its seven parts and their many chapters, one very, very long story. If long stories bother you, I suggest you read something else. No part of this story is written so as to stand on its own. I strongly suggest that you start with the beginning of Part 1 and read sequentially—giving up at any point you choose, of course....

Ripe Fruit

by peterpecker on Sep 13, 2017
First Time

It was the summer vacation and my parents were at work. I was sunbathing in the backyard, laying semi-prone on a lounger by the pool and wearing just my shorts. The wooden deck on my side of the pool was not overlooked by any other house. On three sides of the pool a high concrete wall on the boundary encloses it, with our house doing the same on the fourt...

A Life She Learned Ch. 02

by adventurous_ on Sep 14, 2017
Erotic Couplings

Behind her bedroom doors, Lora arched and moaned as the hand between her legs rubbed her clit furiously. This time however, she was not alone. With Brett as a driving force behind her, hand on her ass, gripping her tightly, slamming his cock deep inside of her, she panted and groaned as her legs quivered, and she came all over Brett's cock. He followed her l...

Making My Fantasy Real

by mdiver on Sep 14, 2017
Loving Wives

Author's note: This is a story based on a conversation with a couple who live in Colorado. The names have been changed and it is written in "Cindy's" voice. ***** I looked at the words I had just written in my journal, "It finally happened," simple words yet quite a history in the making. I took a sip of wine and sat back and reflected on how today, this...

A Handyman's Memoir Ch. 44

by riverboy on Sep 15, 2017
Mature

"Hey man, how's it goin'?" Ron said. It was my usual late afternoon phone call from him to set up the next days work. "It's goin' good, buddy," I said. "Just finished up that kitchen faucet job for the Hendricks." "Good," he said. "Hey, I got a call requesting you tomorrow. A Mrs. Millbanks? She said you'd know who she was." "Wow. I had a teacher in high...