Sissy+school Stories

109,522 results
Orientation
Length
Source
Infinite Scroll

Marine Girl Ch. 02

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 2 - Bikini Girl The walk from the changing room to the outside pool meant a lonely exposed trek across the cold wet tiled floors. In front of the whole wide eyed class who all laugh like crazed hyenas. Sir was joined by Miss the girls tutor who looks at me sympathetically. 'Have you met our new girl?' Sir says briefly explaining the situation to...

Made Over Ch. 03

by gbr2004 on Sep 15, 2017
Fetish

This story involves forced cross dressing, gay sex and bdsm scenes. Don't read if not into these scenes. * I had met a man in my apartment building and he had invited me to join him at a club he goes to in LA. I was a naive boy from Kansas attending USC and I had no idea what I was getting into. The club ended up being a gay leather bar and before the nigh...

A Letter to Our Pantyhose-Sissy

by Sheermistress on Sep 19, 2017
Transsexuals & Crossdressers

I'm on my bed on my knees, my skirt pulled tight and just a little high, exposing my control-top pantyhose to your eager eye. My feet are dangling over the edge of the bed and you, my little pantyhose-slut, are standing behind me, dressed in your sexy schoolie outfit and mary-janes. Your face is made up in a prissy, sissy, teen-girl way and your hair is fini...

Karate Girls Ch. 2

by jabberwok on Sep 17, 2017
BDSM

My life in school after that was much different. I was shunned by everyone. No one would eat lunch with me. Word had gotten out obviously to the whole school. My day was filled with howling laughter at every turn, and snickering behind my back. Even the chess club dropped me for fear of something happening to them. I was on my own. I would go home and disro...

Panty Posers Ch. 03

by EROTICbearscribe on Sep 14, 2020
Transgender & Crossdressers

It was early on Sunday morning. I awoke needing to pee and slipped out of bed, doing my best not to wake Daphne. I could hear him breathing deeply next to me most of the covers on his side as usual. My roomie was lying on his stomach, his head under his pillow. He looked so sexy lying there. I felt the warm rays of the sun on my back as I breathed in his cu...

Brianna Spends Time with Daddy

by Sissy_Sammi_ on Dec 31, 2017
Transsexuals & Crossdressers

It was Tuesday now, as Brian woke up in his bed at seven in the morning to the sound of his ringing alarm clock. It was time for him to go to school. As he rolled out of his bed and began to do his regular morning routine in preparation for school, he couldn't get his mind off of yesterday. As he passed the mirror in his bathroom he saw back to Brianna stand...

The Babysitter Takes Over

by sissysherry2 on Mar 13, 2018
BDSM

"I know your secret." These were the words that I had both dreaded and longed to hear from my babysitter. Let me start at the beginning. I am single and have a couple of kids at home who aren't quite old enough to be on their own when I have business obligations. I share custody with my ex, who left me to be with another man, who happened to be black. I ge...

A Shell of A Man

by uppishcarrot on Sep 13, 2017
Transsexuals & Crossdressers

Six years ago, I was doing well enough to finally afford my dream apartment. It was a studio apartment on the upper side of town. So, I had the job, the apartment, the money... but I was lonely. Very lonely and very horny. Not only would I get all hot and bothered from looking at all of the pretty women at work, but there were also plenty of hot women who li...

Sissy and Missy

by ChristopherDB on Feb 12, 2019
BDSM

Copyright 2019 Christopher D.B. * The central vacuum system made barely a sound as I made my way through the apartment. It was spacious and occupied the entire third floor. Although fully furnished and containing some of Countess Tori's personal items, she only stayed here a few nights a week. My feet were hurting, as the toe box on my pumps fit a little...

Sissy for the Family

by sissyboi4daddy on Aug 21, 2018
Transsexuals & Crossdressers

Hi, my name is Isaac. I'm 21 years old, Asian and a child of divorce. My father decided he wanted nothing to do with me the moment I was born, and my mother held 2 jobs to raise me. When I was 18, she decided she had enough of the hard life and remarried. She remarried Jack. Jack was a white, bordering on obese man, who was 12 years older than my 42-year-o...