Shemale Teacher Stories

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HypnoSissy: Educated to be Pegged

by silkstockingslover on Aug 13, 2019
Fetish

Summary: Cock sucker's training is advanced to hypno videos on anal sex. WARNING PLEASE READ: -This is a hypnosis story with potentially influential subliminal messages within it. -The story also contains hypnosis video scenes. -So if you begin behaving differently after reading this story and all your friends start pointing fingers, don't come crying to...

"A Shemale Submission": A Lust Story

by silkstockingslover on Dec 23, 2019
Illustrated

"A Shemale Submission": A Lust Story Summary: Author Jasmine falls for a hot new teacher with a big cock. Note: Thanks to hfernandez1983 for the many pictures used in this story. He spent weeks getting these perfect for the many different scenes I requested. If you like the pictures in this story, please feel free to read the multi-chaptered series Cheerle...

Revan fucks the Multiverse

by Revan on Nov 12, 2017
Miscellaneous

Revan's voyage to pussy Important Notice: On my vacation just now, I found out that I lost some of my fun at writing ever since posting what I created, because I always thought about what would be good for the readers. Something I never did in the years before. I wrote a story just as it came to my mind once again and can tell, that it does far more to rela...

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...

Sally: His Perfect Shemale Partner Ch. 1

by PunkFan on Sep 16, 2017
Fetish

I am in senior year of school and anyone who has been to school at 18 will know it is not a pleasant time to be working when your friends are all out drinking and enjoying themselves but I needed to go back to school to go the university I wanted to go to. I am a tall fairly muscular straight guy who has had a few sexual experiences before this chapter in my...

The Teachers

by DryLips on Mar 31, 2020
Group Sex

I'm lying in bed on a warm spring morning. The scent of cedar drifts in our open window, filling my soul with calmness. It's been a long cold winter, and this is the first warm spring morning we've had. The snow from a few weeks ago is just about gone, and the smell of damp pine needles that carpet the forest floor adds another layer of freshness to the morn...

A Shemale Shock: A MILF Falls

by silkstockingslover on Sep 25, 2017
Illustrated

Summary: Mom catches her daughter with a teenage shemale and.... Note 1: This is a Nude Day 2017 Contest Story so please vote. Note 2: Thanks to Tex Beethoven, Robert, and David for editing this story. I was having a bad day. I'd spilt coffee on myself on the drive to work. I'd gotten a rip in my nylons. And I'd forgotten my notes for tonight's intervi...

Jasmine Fantasies: Becoming a Bimbo

by silkstockingslover on Nov 25, 2017
Illustrated

Summary: Student turns teacher into cum addicted slut for the day. Note 1: This is a Halloween 2017 Contest Story so please vote. Note 2: Thanks to Tex Beethoven, thor_p, and Wayne for editing. I've always thoroughly enjoyed Halloween. My holiday begins at the high school where I love seeing the creativity of my students, although that creativity somet...

Just as I like it.

by Revan on Apr 18, 2017
Miscellaneous

Important Notice: On my vacation just now, I found out that I lost some of my fun at writing ever since posting what I created, because I always thought about what would be good for the readers. Something I never did in the years before. I wrote a story just as it came to my mind once again and can tell, that it does far more to relax me than what I did in t...

Omnipotence

by PervertedKatharina on Mar 18, 2020
Fantasy

Character description: Larry (18): Our main character. He still goes to school and has always been kind of an unpopular kid. He recently got together with a girl though. He's somewhat of a nerd and will soon be granted with godlike powers. Madison (49): Larry's mother. She's a very caring woman who raised 5 children after her husband died a few years after L...