Chastity Training Stories

41,592 results
Orientation
Length
Source
Infinite Scroll

Mandy's Reward

by sissymaidrose on Sep 12, 2017
Transsexuals & Crossdressers

There was a sharp, heavy rap at the door. Mandy scrambled out of bed as Mistress Charlotte pushed the door open, hastily smoothing the tiny, soft, pink and green nightdress that barely went past her hips and surreptitiously tugged the matching knickers down from where they had ridden up into her bottom. As Mistress sashayed past to the throne like chair in t...

Sissy School

by zeta515 on Jun 19, 2018
Novels and Novellas

Copyright 2018 by Zeta All rights reserved This story may be freely distributed in electronic form but must include this copyright. Sissy School is a work for pure fiction and all locales, names, characters, places, and incidents are the products of the author's imagination. Any resemblance to actual events, locales, or living persons is entirely coincide...

The Office Boy Ch. 04

by Aussie Worm on Sep 25, 2017
BDSM

Here I was, back in the city, well an hours drive away in the suburbs, I had managed to find a small two bedroom house to rent for a while until I get things sorted out. I had managed to buy the basics, a little furniture, television, computer and other things, but in reality I had accomplished next to nothing in the two months since I had be asked to leave...

Pussy In Boots Ch. 6

by Natalya on Sep 15, 2017
Fetish

I woke the following morning to find that Helena had already left. There was a note on the bedside table saying that she had left early to go home and change before going to work. I laid awake in bed for a while taking in the events of the previous day and a wetness crept through my pussy. I wondered if Phil, as he lay asleep beside me, was dreaming about th...

Trapped and Trained Ch. 05

by SissyIndy on Sep 25, 2017
Transsexuals & Crossdressers

There I was, Saturday morning, back in the driveway of my quote/unquote "Master", as he liked to call himself. I turned off the key to the ignition of my car and prepared to step out. He had sent me an email the previous night telling me to show up in the outfit that I had left in during our last session. I looked down at myself and shivered as I saw the s...

Mistresses Anne and Kait

by ahbedeah on Aug 20, 2018
BDSM

1 Mistress Anne and her pet Autumn had been at the party for an hour. Anne was wearing a leather bustier that served to exaggerate the already impressive smallness of her waist and large, attentiveness of her breasts. She was wearing a very short cotton skirt that did nothing to hide her long, flaccid cock. There was no reason for her to hide it; she had en...

The Prisoner Pt. 02

by Jamie77917 on Mar 3, 2020
BDSM

After awakening in a room and being forced to undress by a mysterious woman known only as 'Warden', Martin is about to be searched. But first he is given the opportunity to ask one question. "What did I do to be here, Warden?" Martin asked. The Warden stepped back away from Martin, composed herself, and then answered his question. "You were nominated, Ma...

Learning to Dance

by grizzley123 on Oct 19, 2020
BDSM

Dance Lessons It was a set up from the beginning. I had signed my daughter up for dance lessons for two reasons. First, she seemed to want to, and second, Erin, the studio owner was very direct in her approach, practically telling me to do so. Throw in the fact that the instructor was a hot young coed student of mine and the fact that Erin herself was damn...

Star Wars Imperial Prostitute 2 Ch. 00

by HandcuffGirl on Mar 13, 2019
Celebrities & Fan Fiction

Authoress's notes: This is an update on the status of some of the characters from Imperial Prostitute SX-51472, and a few more people you might have wondered about. A couple have short stories, and the rest are just summaries of what has happened to them so far. I'd also like to point out a few things that I haven't discussed. First, the ProCorps training...

Duncan Gets Engaged

by justincbenedict on Sep 12, 2018
BDSM

Duncan Lipscomb looked at Wren Johnson sadly. He really wanted her to marry him one day, but he kept pissing her off. And she looked very annoyed now. Wren was reclining on the bed, gazing fixedly at her Ipad. "Wren, please." Duncan begged. Wren looked over at Duncan, cocking her head. God she looked so cute in that body stocking. It was worth every penny...