Sissy Teacher Stories

30,749 results
Orientation
Length
Source
Infinite Scroll

Wishful Thinking

by Artican on Dec 20, 2001
Fantasy

The day is bright and sunny. You are on your way to school, taking your time to appreciate the sights of the bustling people moving around to get to where they might need to be. Upon passing an alleyway, you are alerted by a muffled scream of distress. You move in to investigate. You discover a girl. Her clothes are shredded and there is a large thug looking...

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A Sissy Saga Ch. 17

by Snurge on Sep 15, 2017
Novels and Novellas

Titled people were a weakness with Miriam Hancock. She frequently spoke of them with harsh condescension, but the snob in her heart secretly rated them higher than wealthy businessmen, and so it was with some delight she agreed to the visit of the ennobled Marchioness of Wiggleswick. The delight had doubled when she discovered that in both Debrett's Distingu...

Chinese - Watercolor - Lesson

by JRFreddy on Sep 14, 2020
Erotic Couplings

I was teaching watercolor at the local craft store. Most of my students were ladies between forty and eighty. I was twenty-six, tall and thin, and a walking erection. Not an obnoxious erection, but a conservative one, I hadn't been with anyone in over a year. And every patch of lady flesh was like soft butter smeared across hot bread. I hated my job, the art...

Someday Scores Settled? Ch. 03

by eymach on Apr 9, 2019
Erotic Couplings

Someday Scores Settled? Chapter 3 More Abuse Ryan got a call from Ricki one day after school and from the emotion in her voice he could tell something was wrong. As he walked over to Ricki's, it was clear to him that the elite high school group had derived some type of cruel satisfaction at her expense. Even after his accident, they had never shown any c...

Jamie's Descent Pt. 01

by nikkiesilk on Sep 18, 2017
Transsexuals & Crossdressers

Chapter 1 What did we do before social media? How did we manage to get through the day without that endless stream of dirty jokes, funny photographs, gossip and links to dodgy websites that now fill our lives? Yeah, yeah, I can hear you grumble. Get on with it, I can hear you say. Well, dear reader, it was one of those links that started me down the road to...

Generation Z Pt. 02

by contactsteph77 on Sep 24, 2019
Transgender & Crossdressers

Hi Guys This is the second part of my Generation Z story. This story follows a young transvestite, this particular chapter is more world building, developing the character. There is a little dressing, and some male on male smut. Hopefully it is worth it in the end. * Chapter 3 - Market Day James A new world had opened up for James. It wasn’t long befor...

Cumming of Age

by Ewriter111 on Jul 3, 2018
Interracial Love

At the end of my senior year of high school, I had just turned 18 and was looking to have some fun with all the upcoming parties. I had just quit my part time job after I paid off my car and had plenty of time to spare. Because I was young looking, it was not until my senior year that I got invited to parties. Even now I was told that I looked only 15 or 16....

The Sexy Cuckold Couple Pt. 07

by cuckcpl4play on Sep 19, 2017
Loving Wives

The Day of the Ceremony is Finally Here Part 7 As I drove home from work, I could not stop thinking about how our lives as slave and slut had escalated so quickly. What felt like days ago, I was a powerful executive about to obtain my new and even more respected position, but instead I was driving home soaked in my colleagues urine as the new office demoral...

A Sissy Saga Ch. 07

by Snurge on Sep 15, 2017
Novels and Novellas

The following morning Sammy was in Mrs Pardoe's class sewing a plain white collar onto a skimpy black dress. It was a compulsory project. During their first term all sissies had to produce their own parlour maid outfit, and it had to be done by hand because Mrs Pardoe claimed exclusive use of the only sewing-machine in the house. Sewing was one thing he hate...

The Sexy Cuckold Couple Pt. 08

by cuckcpl4play on Sep 19, 2017
Fetish

As I drove home from work, I could not stop thinking about how our lives as slave and slut had escalated so quickly. What felt like days ago, I was a powerful executive about to obtain my new and even more respected position, but instead I was driving home soaked in my colleagues urine as the new office demoralized submissive. My wife, who was the love of...