Sissie Training Stories Stories

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A Dream Come True Ch. 01

by severomi on Sep 18, 2017
Transsexuals & Crossdressers

This is a two part story. Part I is reality and true while part II is my Dom's dream. PART I - The truth I'm an American abroad, been in Europe most of my life, now 58 years old and have been married twice with little success. I decided to change what I'm looking for, after having reflected on my previous relationships, where I had also two TG/TS relatio...

The High School Principal Ch. 04

by JohnLaw1950 on Oct 7, 2019
Erotic Couplings

The Cruise© The school year finally ended. The Seniors graduated, which meant there would be a new batch starting in the fall. Lexi and Miranda both graduated and were off to college out of state. That meant I wouldn't be getting any more pussy from them. At least Lexi's mother, Marcie, was still available. Although she had started dating again, thanks to,...

Handsome Ch. 27

by Paris Waterman on Aug 31, 2017
Erotic Couplings

Chapter 27 The First Game I returned home from Hayley's, and made the first priority to find a decent hiding place for the $7500 she'd given me for the X-rated movies we'd made. I lay down on my bed and wondered where this thing with Hayley was going. I was young, and saw no reason why it couldn't continue unabated, for as long as we wanted it too. I reme...

Handsome Ch. 28

by Paris Waterman on Aug 31, 2017
Erotic Couplings

Chapter 28 This Time We Used a Script Later that night Noreen arrived at Hayley's, and we tested her as we had Sissie. Hayley thought her a natural for the camera, especially the way she masturbated while I was fucking her ass. We also learned that she was more than willing to go girl — girl, which pleased Hayley, who had an older woman who she could pai...

Nathalie's New World Ch. 02

by Cagivagurl on Mar 17, 2020
Transgender & Crossdressers

The night was a restless one for me. Mia on the other hand seemed completely at ease and slept the sleep of a totally sated contented kitten, her little snores breathlessly echoing in my ear. As the grey light of dawn filtered in I felt more agitated than when we went to bed. I lay there petrified, what to do, how to approach this unbelievable turn of even...

Nathalie's New World Ch. 03

by Cagivagurl on Jul 6, 2020
Transgender & Crossdressers

Wife... Mia Stephanie.... Girlfriend Terrence... Wife's lover Sasha ...... Salon Owner David.... Me My life was indeed changing. That day with Mia and Stephie was the point from which there could be no possible return. There could be no going back, but where it was going was anybody's guess. The next morning I woke early preparing to head into the offic...

Futopia

by Pflegeprofil on Apr 22, 2025

In the 1910s Futanari started being born. One tenth of all babies initially thought to be male turned out to be Futas instead. A Futa is a woman who possesses both male and female genitalia. Adult Futas are generally taller and better endowed than men. The adult Futa height average is 6 feet, and their average erect penis size is 7.0 inches. Of course, small...

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The High School Principal Ch. 05

by JohnLaw1950 on Oct 7, 2019
Erotic Couplings

A New Year Begins © The summer break was over, and a new school year was beginning. Over the summer break, I had gone on a cruise with several of the staff members. It turned out to be a sex cruise where everyone tossed away their inhibitions and had wild sex with each other. I was a little apprehensive about walking into school knowing I had fucked several...

Salty Liquids 1: Rachelle Ch. 01

by ChristopherMoon on Sep 12, 2017
Fetish

"So, Miss Kendall, everything is in perfect order. It just appears you have an unnaturally large bladder. In the tests we've ran, it turns out that it is capable of containing 2 liters. This is a very rare handicap: medical professionals estimate that only about a hundred people worldwide have this handicap." It went silent for a moment. "Can I answer any...

Nathalie's New World

by Cagivagurl on Feb 24, 2020
Transgender & Crossdressers

My heart was pounding out of my chest as the gorgeous assistant showed me to the chair. "OK Nathalie, just relax sweetie, lay back and Sasha will be with you directly, would you like a glass of wine?" "Yes please." I whispered in my most feminine voice. As I sat in the chair I glanced around at the salon, it was very trendy and chic, not up market but ver...