Sissy Training Stories

41,670 results
Orientation
Length
Source
Infinite Scroll

Sissy Boy Secretary Ch. 06

by Hotenuf4u on Sep 19, 2017
Fetish

When we got to the car Elaine said, "This won't do, you are missing something Sissy Boy. Kneel down here," as she pointed to a place just behind her car. I immediately knelt down, hoping no one would see. "Lisa my little Slut, remove your stockings and garter belt," it wasn't a question. As Lisa was getting done removing the items, smiling at Elaine as she...

Training of Mistress' New Sub Day 01

by naughtyboy082 on Sep 19, 2017
BDSM

As Mistress Sharon has requested, a written story... THE FIRST MEETING MISTRESS SHARON sends out a late night text that her new submissive has been waiting for anxiously all week long as he sought to prove his obedience and worthiness. "Congratulations, sub! You have successfully completed your probationary period...official training begins in the morning...

Foxfire Stables

by centaur mare on Sep 16, 2017
BDSM

I was silently fuming as Marina worked the kinks from my lower back. Her oil slick palms and roughly digging fingertips worked the tension out slowly. The room was scented a deeply, rich with lavender and dragons breath from the incense burner cradled on a low bench in front of the massage table. I expelled a short “ugh” as Marina continued deeply stroking m...

Becoming Marc's Sissy

by grizzley123 on Jun 19, 2018
Transsexuals & Crossdressers

This is a story with themes some may not like. If that is you, read it, don't read it, your call. But if you are going to comment, keep in mind that no one required you to read it, and no one requires you to like the themes. Writing nasty comments only makes you look foolish. For others, I would love to hear your comments. And I hope you enjoy the story....

The Journey Ch. 02

by born2srvtv on Sep 19, 2017
Transsexuals & Crossdressers

(You may want to read The Journey before reading this so you will know the background of Tom/Tonya and Jason. These stories are a combination of real life and fiction. Thanks for sharing your comments.) Tonya was content as she stretched across Jason's lap. She had given Jason a long slow blow job and now Jason was rubbing his sissy slut's smooth ass a...

Trapped and Trained Ch. 02

by SissyIndy on Sep 25, 2017
Transsexuals & Crossdressers

I drifted in and out of consciousness over the next hour, periodically snapped back into reality when the dildo assaulting my mouth would pause deep in my throat and eject a fresh deposit of cum into my bowels. Looking up at the television display of my abuse I would normally have been turned on by the sight of this brunette in a pink corset and black stocki...

The Pantysissy Diaries Ch. 03

by JPantyboyVSL on Apr 23, 2019
Transgender & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapters 1 and 2 before reading chapter 3. ***** It was nighttime in NYC, and Jaymie and her 6 Mistresses had just left their apartment to head to Vic...

The Unsuspecting Candidate Ch. 02

by missvicky53 on Sep 11, 2017
Fetish

Part 2 Helen continues Mike's training, this time in a French Maid's uniform The aftershocks of his climax were still coursing through his body as I teased him. "Did you have a nice cum, sissy?" I cooed at his still bound form. "Do you want me to release you now?" "Yes, please," he replied. "I'd like to get dressed now." "And get dressed you shall," I tea...

The Awakening of a Sissy Pt. 06

by sissyjolie4u on Mar 2, 2020
Transgender & Crossdressers

While still admiring myself in the mirror, I received a text from Mistress, that read: I am so happy to hear that you are embracing and accepting that you are and were always meant to be sissy Jolie. Let me assure you, I will assist you and help you blossom into the ultimate sissy that you are meant to be. In time Joe will be completely stripped away. You ha...

Mistress Chronicles Ch. 01

by MistressMtoyou on Sep 25, 2017
Fetish

Subject and background. This is a recap of my first in-person session with a submissive. The subject passed the various pre-session requirements described in my second story "A few good subs" and after an extensive interview and evaluation process I offered him the opportunity to do an in-person session. I'll admit upfront that I was a novice at this point...