Sissy Teacher Stories

30,749 results
Orientation
Length
Source
Infinite Scroll

Trapped! Pt. 01

by TheEroticProspero on Jul 6, 2020
Transgender & Crossdressers

Trapped Part 1: A Trap Is Sprung As a teacher, I shouldn't admit this. But sometimes you have students you just hate. And for almost a year I had hated Jessica Dane. I was only 25, fresh out of university, straight into a job teaching English. For all my life I was poor, short, thin, and pale. My only saving grace appearance wise was my long, rocker...

The Wedding Ch. 02

by betamale08 on Mar 31, 2020
Transgender & Crossdressers

The Wedding (Patti Cake Part 3) Chapter 2 -- Party in Pink Purgatory... "Oh Wow Dale! You look fantastic! Very -- Very pretty... I can hardly tell that you're my boy anymore! Really sweetie I'm so impressed -- and Patti you look gorgeous too... I knew that dress would look stunning on you -- but Dale -- my pretty -- pretty -- son... That dress is perfect;...

Sissy Maid Son Pt. 03

by Robyn228 on Oct 21, 2019
Transgender & Crossdressers

Note: This story is entirely a work of fiction, and should only be viewed as a fantasy. Any similarities to actual events or people are entirely coincidental. All characters are over 18. ***** Peter stood there looking at the black stilettos, with so many questions on his mind. He wondered why his brother would ever own stilettos, much less why their mothe...

One of the Girls

by Erotictales4u on Sep 26, 2017
Transsexuals & Crossdressers

All characters in this story are over 21 years old. This is a fictional fantasy that contains elements of both femdom and the transsexual/cross-dressers niche. This is my first attempt at a story so go easy. ***** I couldn't believe my situation. I had signed up for porn, but I had not signed up for this. I was standing naked in the dressing room and the c...

My First... Turned Me Fabulous!

by BerkeleyJanine on Sep 16, 2017
First Time

I'm lying in the bed of a man who picked me up outside a gay bar a few hours ago, listening to the sounds of his gentle, contented sleep. Contented from my having given him delicious head, contented from having fucked me with my stockinged legs wrapped around his shoulders. I'm lying here, looking at the trail of clothing that marks our evening: my strap-y h...

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...

Chronicles of Heather Maureen Ch. 08

by HeatherMaureen on Sep 14, 2017
Transsexuals & Crossdressers

Schoolgirl Nights My paranoia about being seen or recognised going home was needless worry as I made it into my place without notice. Would anyone have cared even if they had seen me? Friends or family maybe but who else, my neighbors? I smiled ruefully as the thought crossed my mind that for the first time I'd just suffered thru the 'walk of shame'! I rus...

Panty Posers Ch. 04

by EROTICbearscribe on Sep 21, 2020
Transgender & Crossdressers

I must tell you of an experience Daphne and I had one Saturday night. I know, I know. You're dying to find out if I ever finally met Daddy. All good come things to those who wait. I really am a sissy tease. Aren't I? I think you'll enjoy this side trip though. *** It was a lazy Sunday morning. Daphne and I were sipping coffee and nibbling on some danis...

Panty Posers

by EROTICbearscribe on Jun 1, 2020
Transgender & Crossdressers

PRIVATE PANTY SESSIONS Ch. 01 "Wait! What? Say that again." Doug, my roommate of two years, closed his eyes and took a deep breath. Tension hung heavy in the air. I allowed him to take all the time he needed to explain even though my mind was racing the way it does when your entire world has been turned upside down. I could see he was struggling. It look...

The Dragon Ring Ch. 05

by Beatnic_jazzman on Sep 25, 2017
Sci-Fi & Fantasy

Councillor Cadwill was there already, having arrived minutes in front of us. "The talk is all of Prince Hallit being wrong footed. There are some that want to press forward, take him down a peg, but there are some that worry about reprisals; sabotage of their place men. It's turning into a kerfuffle large enough to attract the vultures of the café commentat...