Sissy Schoolgirl Stories

13,642 results
Orientation
Length
Source
Infinite Scroll

A Sissy Saga Ch. 04

by Snurge on Sep 15, 2017
Novels and Novellas

The highly polished writing table was uncluttered, the only item encroaching its pristine surface being the letter of application Miriam Hancock had received from Emma Twist, the young woman who now sat stiff backed in the chair facing her. Miss Hancock folded her hands over the pieces of paper and gave the impression of ignoring them as she assessed the ca...

Cheap Sissy Whore To Call Girl

by HardSoft on Sep 15, 2017
Transsexuals & Crossdressers

I looked at the throbbing red cock within inches of my face, split seconds before I was to be showered with thick musty spunk on the back alley streets while I thought back to what had happened 24 hours ago when I was a normal 22 year old male living a normal heterosexual life. It all started when my girl friend of the time, Doreen, had filmed us having sex...

A Sissy Saga Ch. 11

by Snurge on Sep 15, 2017
Novels and Novellas

"Your financial accounting is abysmal, Miss Hancock." said the man from the Department of Inland Revenue. "Some of the necessary records are incomplete and others are totally missing. How can you hope to complete a Tax Return for your business without appropriate qualifying evidence?" Miriam Hancock eyed him with some malevolence as he poked the documents i...

Sissy Pantyhose Twins Ch. 01

by Sheermistress on Sep 12, 2017
Transsexuals & Crossdressers

Twice The Fun... Part One... My Slut had received her orders in the envelope which was always left on the kitchen counter before I left for work. She was to perform whatever was mentioned in this envelope, each day, without question -- either during the day if so asked, or to be ready for me when I get home. Whether it was a new outfit, a specific outfit,...

Luke's Field Trip

by LucyAnn51 on Sep 16, 2017
Transsexuals & Crossdressers

All characters in this story are over 18 years old. This is a work of fiction and any similarity to other works or real people is simply coincidental. Hope you enjoy, love you dolls! Xoxo ------------------------------------------------- Luke was a sissy. The kids at school called him mean names and threw things at him. They played keepaway with his book...

For His Mistress's Pleasure Ch. 02

by femmepen on Sep 12, 2017
BDSM

I heard a car coming up the alley and moved to the left a little to be hidden from sight, though with all the shrubbery I knew I was out of view. Her silver BMW drove right past the patio into the spacious garage as I looked down afraid to meet her sunglassed glance. The engine was turned off as the solid sound of the door opening sent shivers up my spine. T...

Master and Four Subs

by totk6432 on Apr 17, 2018
Fetish

This is a fantasy written by myself for fun. It contains spanking, humiliation and fetish; if this bothers you please seek other authors. All characters are 25 years old or older. ======= The rule is simple: I ring the doorbell and let myself into Master Daddy's house. Susan, my 25 year old personal assistant, is with me. She is in charge of me at work. Sh...

Story of Sissy Submission

by Sissy_Kimmie on Sep 25, 2018
Transsexuals & Crossdressers

He had taught how to suck cock. He had shared my mouth with others at the adult bookstore. He had taught me to dress like a sissy. We had been meeting on and off for years. Sometimes we would go a year without meeting and then I would get the urge again to be his slut. Over the past couple of months, I had met him at the local ABS to suck his cock. But I jus...

Daddy at the Truckstop Pt. 01

by StaceyDeprave on Sep 15, 2017
Transsexuals & Crossdressers

This was an encounter that almost happened with a Daddy a while back. We talked about doing this for a first meet to make up for other times that didn't work out, and while talking about it with him was undeniably hot, it ended up not happening for a few reasons, chief among them safety. I think about how hot it would have been to smash a lot of my boundarie...

Carol, Candy & the Ex Pt. 02

by corduroysissy on Mar 26, 2019
Transgender & Crossdressers

(Will Candy make a good cuck?) Davie was standing at Carol's front door dressed in a pair of copper brown wide-wale corduroy dress trousers, and a beige polo shirt. Oddly enough, he felt more nervous than he did the night before when he was in full drag, and he attributed it to the ex-factor. Last night Davie as "Debbie" was there to meet Robbie as "Candy"...