School Sissy Stories

109,522 results
Orientation
Length
Source
Infinite Scroll

My Beloved

by quotidian01 on Aug 30, 2017
Fetish

"My Beloved, I am your dedicated lover and I will do anything for you. I thank you for letting me make this web site, where I can feel the whole world watching me. Everything I do here is for you, Beloved. And in pleasing you, I am pleased." My voice sounded a bit tinny in the cheap computer speakers. I knew I was displayed while the voice spoke: sometimes i...

HSPL - Trip to the Sorority

by sissydn on Aug 7, 2019
Transgender & Crossdressers

"After being left on the road by Meghan and Sophie, princess was caught by Cindy and her companions. Zoe, apparently the leader in the group, had informed sissy that she could get back to Sophie and Meghan if she pledged the sorority and joined with honor. If she chooses not to pledge, they would drive her to the other end of town and leave her there in her...

Black Cuckolding In Montreal

by Samuelx on Sep 11, 2017
Interracial Love

Never say never, I guess that's what the moral of the story is. When my husband Benjamin "Benny" LaCroix told me that he wanted me to cuckold him, I think my jaw hit the floor. Benny is six-foot-one, lean and muscular, with dark brown skin, curly Black hair and lime-green eyes. My darling husband is biracial, born in the City of Montreal to a French Canadian...

Planet Pretty Sissy

by Hayleykim on Aug 18, 2017
Fetish

Louise ordered her kinky slave to stand naked in front of her. He was in his late forties, about eight years older than the pretty blonde, who had him like putty in her hands. "Welcome to your ultimate fantasy. We don't take passengers on this parallel planet. Is that perfectly understood?" said Louise. "Yes of course, Louise," he replied in a stuttering w...

Bike Shed Rendezvous

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

You're hopelessly under her spell, captivated by her beauty, your little cocks been taken over. With no mind of your own you long to be put in her knickers and be her girl. Beg dog beg! She's got you by a psychological lead attached to your balls and is leading you to whatever and wherever she desires. 'Please, please!' you plead. 'Emasculate me.' Sound fa...

Maria's Sissy Boy

by blaud on Sep 11, 2017
BDSM

A princess housewife finds it useful in many ways to have a sissy house boy in her home. But the husband insists on a precautionary measure. Before Maria came into my life, I was just drifting. I was a West Texas slut boy, whose sole purpose in life was to find the next cock to suck. I'd seen her around the apartment complex, but had no interaction till tha...

Ensnared by a Corset

by spinder on Sep 16, 2017
Transsexuals & Crossdressers

Warning: This story is a work of fiction and contains descriptions of explicit sexual acts between women. If this type of content offends you or you are under the age of 18 do not read it. Author's Note: This story is the property of the author. It can be downloaded for personal reading pleasure or sending to a friend, but if you wish to re-post them at you...

The Making of Davina Ch. 02

by Timewarp10 on Nov 20, 2018
Transgender & Crossdressers

David put make up on, and looking in the mirror he liked what he saw. It was as if he saw himself for the first time; a person within being born. Davina came to life. "Oh God! It feels so right!" David remarked, seeing Davina smiling back with Davina's eyes, and not David's. He was looking through a portal into his own true soul, and he wanted to step into...

Pat's Panty Slave Ch. 03

by Sissyfreak on Sep 16, 2017
Transsexuals & Crossdressers

Having been humiliated for a second time, I thought things couldn't get any worse, how wrong could I be! I was sat at home one day, kids at school, Wife out shopping, when there was a knock at the front door. Jo was standing there with a carrier bag. She threw the bag to me and ordered me to put on the items within, then come to her house next door. I looked...

Dry Valley Ch. 11

by jushorny on Sep 12, 2017
Chain Stories

Mitch kissed his mom goodbye and drove off to his place to clean up, the oil change and fence repairs having covered his body dirt and sweat. On the way home he schemed ways to best to convince Jess to stay in Dry Valley. He knew it wouldn't be an easy, most likely taking the entire six day limit imposed on by Jess or possibly longer. Once home, he headed...