Shemale Teacher Stories

25,923 results
Orientation
Length
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Infinite Scroll

A Son's Virginity: A Christmas Tale

by silkstockingslover on Dec 11, 2018
Illustrated

Summary: A mom gives her son the best Christmas present ever. Note 1: This is a 2018 Holiday Season Contest story so please vote. Note 2: Thanks to Tex Beethoven, Wayne and Robert for editing this story. 2018 had been a tough year for our family. First, a small fire in our house led to our losing almost all our family photos, among other less significa...

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...

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...

Pegged for Love

by silkstockingslover on Jan 31, 2018
Fetish

Summary: Straight guy is pegged by the girl of his dreams. This is a 2018 Valentine's Day story so please vote. Thanks to Tex Beethoven, thor_ph, Robert, and Wayne for editing. Pegged for Love It is probably the truest saying in the world: you can't just be friends with a girl of the opposite sex. I mean it may be possible when you're an adult or marri...

The Society Ch. 03

by Barno on Sep 13, 2017
Transsexuals & Crossdressers

Heidi's erect penis was sliding in and out more easily now. When she first mounted me being gentle wasn't her first priority. It was my first match and I had almost beaten her according to the wrestling judge. In fact many in the crowd of 60 or so spectators had disagreed and showed it by booing the decision, it had been that close a contest. This didn't sit...

mysterious secret

by Ssrd33 on May 21, 2019
Transsexual

It was the year 2055 the technology had reached a very surprising level, but even so, many things do not change. The protagonist of our story is a boy who attends university and is passionate about technoogy and virtual reality videogames. 24 hours before the event .... HAAAAAAAAAAAAAAAA !!!!! a yawn was heard ... Wake up Mark is late for school ... his moth...

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Shemale Devil in Disguise Pt. 03

by Chomedey on Mar 2, 2020
Transgender & Crossdressers

This story is the continuation of Shemale devil in disguise, part 02 Mid-July 2018: About two months have passed since I went back to my parents for work and almost a month since me and Joel decided to do some investigation about Rebecca. Okay, I'll admit, we didn't find too much. We both added her on Facebook but she never accepted the friend request. We d...

Danielle Ch. 04

by sexgundam666 on May 7, 2019
Sci-Fi & Fantasy

Her clothes were tighter yet again. Flesh squished against the cloth, bulging from the neckline as she struggled to keep her bra and shirt on. She sighed once the worst was over and worked on yanking her pants into place. They slid over her calves then staggered at her thighs. Fat squeezed over the waistband. Danielle scowled at the sight. Perhaps that was t...

Making Francesca Ch. 03

by Spango on Sep 12, 2017
Transsexuals & Crossdressers

As Frank lay there on the thin mattress, listening to Justin climb the stairs, he thought about all that had happened and what he feared was still to come. The dull ache in his ass told him that Mistress Celia was definitely not someone to trifle with. He also thought about the reaction his penis had shown to the various activities he had endured since arriv...

Shemale Surprise

by silkstockingslover on Oct 21, 2019
Transgender & Crossdressers

SUMMARY: A married man is seduced and taken by a friend of his wife's. EDITING THANKS: Thanks to Robert, goamz86 and MAB7991. NOTE: This story is dedicated to Robert who requested the fantasy...sorry but the story ended up a lot longer than originally planned. ***** "You can stay with Robert if you wish," Mary said on the phone. I looked up from my lapt...