Sissy Training Stories

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Sissy Training Week 01: Induction

by Peggylea on Mar 17, 2020
First Time

Some years ago I was under the supervision of a Domme Mistress called Neve who organised for me to undertake a course in sissy training so I fully understood my role as a smalldick submissive. She found me a place on a 6 week sissy training course with a teacher called Mr Deal who was very experienced and had devised such a program. I was to meet Mr Deal a...

Domme Club Humiliation

by NancyPan on Sep 19, 2017
BDSM

I would never say that life was routine with Mistress Monica. She kept me on my toes—or, more literally, on my heels—at least around the house. On days when I got home from my law office before she got home from her corporate job, I would immediately take off my suit and tie and put on one of the frilly aprons Mistress preferred me to wear at home, and a pai...

Subliminal Obsessions Ch. 04

by Sissyhalo on Sep 14, 2017
Transsexuals & Crossdressers

*Before... I open my mouth and pump the last bits out of him and show him and Sarah's sort of become invisible as she recorded all of this. Alberta's standing and staring from the doorway and I show her too and her wide eyes widen more and then I swallow it. I rise up to standing and deeply kiss Leon. "That was perfect, worth all those years working for...

Anal Training Ch. 01

by Catchandrea2397 on Jan 20, 2020
Transgender & Crossdressers

This is the first in a series of sissy JOI training instructions. I want to provide real instructions that can be followed and enjoyed by anyone (well by any submissive sissy wanabee). Please only read this however if you are over 18. Feedback is welcome *** Day 1: Hello pet. Are you ready to have some fun? Are you ready to begin your training? Get...

From Her Ex-Boss to her Bitch Pt. 05

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

This story includes extreme themes of sissification, interracial domination, watersports, cock sucking, if any of these themes are not your thing, please don't read it. ***** "I think you should have tattoo on your back above your pussy cheeks and another above your little Sissy clit." "But I couldn't do that Master, my wife would see." Amber was almost b...

The Computerized Bed

by submissive~pet~ on Sep 14, 2017
Fetish

The year is 2020 all sorts of new inventions have been created. The time machine in which John Paul traveled was from the year 2002. He had no idea what was in store upon his arrival to the future. His machine carried him into a large bedroom. It was a very lovely room done in pinks and light blues. The bed was enormous in size, 4 times the size of any he...

The Dominatrix Order Pt. 02 Ch. 01 - Sissies

by Jwwsmith on Jan 22, 2019
Transgender & Crossdressers

THE DOMINATRIX ORDER: FEMDOM EROTICA 2 BOUND BY LAWS BY J.W. SMITH *** "All Women Are Created Equal" was inscribed on the bronze plated plaque on display in Representative Johanna Aletheia's office. It was the declaration put forth by The Founding Mothers of Femininus, of which Johanna's ancestor belonged to. Johanna was of the oldest lineage of Feminin...

Zoey's Basement Transformation Pt. 03

by SissyStoryTime on Sep 11, 2017
Transsexuals & Crossdressers

Zoey couldn't believe the cruelty of her Mistress. She shook her head desperately, feeling exhausted and sore everywhere from the waist down from already having so many awful things done to her. She didn't know if she could survive this fresh hell. Mia moved away from the tied girl, her helpless form bent over and restrained at waist height. "Aww, what's t...

Second Meeting with Master Gene

by sissysubTiffany on Jun 19, 2018
Transsexuals & Crossdressers

Friday evening comes finally as this was the slowest week of my life waiting for this day to get here as so looking forward to tonight even though I am still a little leery about becoming a sissy submissive of Master Gene's. I have shaved my entire body and sent pictures for proof as he demanded and now sitting in a pair of my pink with lavender lace bikini...

Holly's New Start

by Sissyhalo on Nov 26, 2017
Transsexuals & Crossdressers

I love Jamie so much it hurts. I mean there's a lot of things that would have people freaking out over this relationship of ours especially how I am and how we started. Jamie loves me despite my past. And like he really, really only has a sort of little picture of just how bad I was as Holt. Only he found reasons why Holt ended up so broken. No, no excu...