Sissy Schoolgirl Stories

13,642 results
Orientation
Length
Source
Infinite Scroll

The Path to Happiness Pt. 03

by brendachaplin2000 on Sep 23, 2019
Transgender & Crossdressers

I woke from a blissful slumber to the smell of coffee. I was grateful for the sofa that acted as my bed in my squat, but this bed was so comfortable I did not want to get up. As my senses returned to me, I noticed my arse was a little sore, Becky's cock cage would need more lube than a little spit if it was to go back in me. I slipped reluctantly out of the...

A Sissy Saga Ch. 25

by Snurge on Sep 13, 2017
Novels and Novellas

Emma Twist didn't attend the champagne reception after Poppy's wedding. After helping take most of the students back to the Grange she left them in the capable hand of Margaret Pardoe and climbed into her little second-hand Fiat. It was her preference that day to make a visit to a certain Lavender Cottage on the periphery of Peasmarsh. The windows were ope...

My Correction in Phoenix Day 02

by Bobby4you on Sep 19, 2017
BDSM

My sleep of rest ended abruptly as cold water was thrown on me. Ma'am slapped me and told me I had a busy day and I needed to attended to her needs. She began by sitting on my face and making me lick her ass before she changed positions to straddle my face so I could eat her pussy until she had an orgasm. As she got up she slapped my face hard and called me...

The Slave and the Sissy

by Sputnik57 on Sep 12, 2017
Transsexuals & Crossdressers

She had always been very rough with him, the big woman, but this morning was exceptional, and different. She had come home late from her usual soiree with other local mistresses and had whipped him mercilessly for no apparent reason; she had woken him during the early hours several times, tormented him and had her arse licked while she applied her dildo or h...

Mom's Big Black Hobby Ch. 06

by MiddleKoala on Jul 13, 2020
Transgender & Crossdressers

This story has with incestuous and homoerotic themes as well as non-consensual sex. If you are offended by such, do not read. This level of depravity is not to be taken lightly and the deeper down the rabbit hole you go the more you will find that may offend you. You have been warned! All characters in this story are over the age of 18. The entire story is...

Happy Endings Ch. 02

by desireethtttv on Sep 13, 2017
Transsexuals & Crossdressers

"So Desiree how did you like your first night at Happy Endings Massage Parlor?" queried Judy as daybreak shown through the open doors she was now bolting shut. Speaking with slight hesitation, I told her that I think I could become accustomed to the lifestyle quite easily. "You liked being in control of the men I had you pleasure tonight, didn't you Desir...

Explore the Inner Woman In You

by Tomsparty on Sep 14, 2017
Transsexuals & Crossdressers

I fancied the arse off a girl at school called Sharon. The problem was most of my year did. She was beautiful with long blonde hair, willowy legs, a butt to die for and stunning pert tits. She was way out of my league but quite amazingly we did get on and began to make slow but steady headway. My dizzy ambition was to ask her to the end of year college dance...

Katelyn's New Sissy Pt. 01

by bluesbirds on Dec 25, 2018
Transgender & Crossdressers

I remember she made me try the Sissy Peni-Pacifier in the store. It was a humiliating day outing, meant as "my" Christmas gift. Dressed up in a tiny bright red sexy elf costume with marabou trim around the edges that ended at my sissy clit, black fishnet stockings and 4" black heels, with a ridiculously large shiny red bow in my hair, surrounded by mirrors a...

How I Became A Girly Slut Ch. 03

by richfun71 on Sep 13, 2017
Transsexuals & Crossdressers

Copyright 2008 [email protected] To make sense, I recommend reading parts 1 and 2 first.... Samantha, moaned as I lay on the floor underneath her in my school uniform, licking the cum from her freshly fucked arse as she ground herself onto my face, rubbing her clit through her skirt. It seemed to go on forever as she kept orgasming and telling me...

My Mistress

by Kandy5647 on Sep 12, 2017
BDSM

Hey there! How's it going? My name is Andrew Scott Nelson or Drew for short and I am a sissy white slut to the most amazingly drop dead gorgeous Chocolate Mistress ever! Here let me give you a little background on myself and my mistress before I really get into this story. I'll start with my background. I am 36yrold 6'1 130lbs green eyed submissive bisex...