Sissy Teacher Stories

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Just Another Story

by neoview on Oct 15, 2017
Transsexuals & Crossdressers

Once upon a time... "Wait, wait, wait! We're not actually starting the story like this, are we?" Said the short fat kid in his mid-twenties. "I'm neither short nor fat." He said while swallowing his stomach and lifting himself on his toes. "I'm not doing any of that. STOP GIVING THE READERS FALSE INFORMATION!!" The angry non-short, non-fat kid yelled. "H...

Yet Another Story

by neoview on Nov 26, 2017
Transsexuals & Crossdressers

You're back? I guess my previous story was a hit. The comments stroked my ego enough to write this bullshit. Before I begin, shout out to: Anonymous user, Anonymous user and xploring96 for the feedback. If it wasn't for you guys I probably wouldn't even bother to continue this... I guess I should make it a series... Naaahhhh. Too confusing. Super narrator p...

Miss Johnstone's Lesbian Sissy Slut

by maturesubmale_for_F on Apr 20, 2020
Transgender & Crossdressers

1. Becoming a lesbian sissy slut I was eighteen years old when I became a girl. Or rather: When I was turned into a submissive lesbian sissy slut by my High School teacher, Miss Johnstone. She was an imposing woman, in her late fifties, tall and with short cropped grey hair. She had piercing green eyes and a well-trained body that she kept in shape by regul...

Classroom suprise

by william125 on Mar 10, 2015
Transsexual

A recently qualified teacher, today is your first day at Tower sixth form college. You stand at 6' 2" and keep your self in good shape. On your way in this morning you saw a group of girls giggling and looking at you. Obviously talking about the new teacher. The bell rings and a little nervous you welcome in your 18 and 19 year old students. Note to r...

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I Love Men to wear my Satin Panties Pt. 01

by Manndee on Apr 25, 2018
Transsexuals & Crossdressers

I was a quiet unassuming lad from the East end of London; I was 22 years old when I left home, it followed a number of pure flukes that all happened back to back, because of this I had had an amazing start to my life in my first job as a City trader. Unfortunately, things at home with my girlfriend were getting difficult after me losing my job. It was now 4...

The Wedding Ch. 04

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

The Wedding (Patti Cake part 3) Chapter 4 -- Teaching, Teasing and Testimonials... I was a little stunned and leery after reading my version of this contract which wasn't all that different from Patti's... From changing my name to rescinding my rights to wear male clothing while in the employment of Darren and Carol -- or Ma'am and Sir, and also, not to f...

Mommy's Boy? Ch. 03

by yr_sissy_toy on Sep 13, 2017
Transsexuals & Crossdressers

I minced into the kitchen in a new dress, feeling terribly nervous. My small pink butt plug added somewhat to my wiggle, reminding me at every step that sissies need constant training. I brushed my hands against the skirt of my princess dress one more time, smoothing out again all the wrinkles that my imagination created, and again touched the hair of my wig...

The Locker Room Glory Hole

by Sissy_Sammi_ on May 30, 2018
Transsexuals & Crossdressers

*All characters are 18+ ***** The bell rang, rousing all of the students out of their seats. The students stuffed their books, binders, and pencils back into their bags before quickly rushing out the door to get to their next class. It was going into seventh period, the last period of the day for everyone without an after school class. Most students quickl...

Kinky Adele Mummy Fucker Ch. 02

by Sissy Adele Howells on Sep 17, 2017
Fetish

I had no idea what a dominant, perverted women Adele Howells could be. She wanted me to take her eighteen year old daughter's virginity, but at a price. Everything would be on her terms. She now had complete control over her husband Tony. I was made to sit naked on her bed, as I watched her put her lipstick and clothes on. My cock was as solid as a rock, as...

Teacher Made Me into Sissy

by johntamilandrea on Sep 13, 2017
Fetish

HI! I am Sissy Andrea. This is one my fantasies about my teachers. This story is about feminization, fantasy. If you don't like these topics Please don't read. ALL THE CHARACTERS IN THIS STORY ARE ABOVE 18 YEARS OF AGE. My special thanks to "mywifesslave" for helping me in editing this story. ***** The story happened when I was 19 years old I loved sho...