Rubber Sissy Stories

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Family Chastity Story Ch. 03

by antares34 on Jul 30, 2019
BDSM

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. ***** My gimp son and I have settled into a routine. Permanent chastity with monthly releases. These releases occur on the first day of every month. I...

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...

Jack and Jill Pt. 02: Jean

by candyflosslover on Jul 13, 2020
Transgender & Crossdressers

It was two weeks later when Jean returned, it had been arranged that she would get there a couple of hours before Jill came home, to prepare him. He wasn't sure what to expect and he felt a mixture of excitement and anticipation. He followed her into the bathroom where she stripped him naked and shaved his entire body. He loved the smooth feel of his skin, e...

Sissy Pills Pt. 01

by Sissyhalo1 on Dec 23, 2019
Transgender & Crossdressers

Some say it was some sort of experiment gone wrong. But it hit the streets and it changed everything. A pill a drug that you took that made you sexually submissive and made you especially sexually submissive to men. Semen made it worse apparently. And there were addicts that ended up not just being gay or fags but entirely sissies and that was fastly bec...

A sissy visits the Headmistress

by maturesubmale_for_F on May 12, 2020
Transgender & Crossdressers

1. Miss Stern delivers both punishment and pleasure I knocked timidly on the heavy door and heard Miss Stern's voice from within, commanding me to enter. I slowly opened the door and walked into the presence of my Headmistress. She was in her mid-fifties and sat behind her massive oaken desk as I came in, studying a heavy file. I stood still just inside the...

Girl's Night Pt. 04

by DifferentBreed on Sep 14, 2017
Fetish

"You want to cum too, don't you bitch?" Sophie said. "But pleasure is only reserved for Mistresses and Dommes. Not sissy whores like you." Sophie looked down at him, grinning evilly, turned on by the lips descending her body and the sight of him kneeling there in sexual servitude and agony. She let her hand fall lightly on the back of Jenny's head as she fel...

Straight Guy Gets Some "Strange"

by nancyvasquez on Oct 15, 2017
Interracial Love

The Negro saw the bright lights across the street advertising the adult bookstore. He felt a stirring in his groin and he pushed down on his cock. He could use a jerk off session, he hadn't cum in a few days. It was a very warm night, and the rain had stopped, leaving the smell of wet asphalt in the air He went to the counter. "How much to go in the back?"...

The Prostate Exam Pt. 07

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

Please do not read on unless extreme sissification and forced gay and bi scenes, watersports and cum eating, really flick your switches. I don't want to offend anyone so thought this comment might help. ***** It'd all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his naturally submissive tendencies by pushing bac...

Loraine's Self Bondage Re-Creation

by loraineveritas on Mar 12, 2019
BDSM

The following is my re-creation of an event that happened a few years ago. I had been a sissy slave to Mistress Marie for over 2 decades during which I become a totally submissive slave to Her every desire. I think of Her often as She has passed now. While doing Self-Bondage activities shortly following Her passing my wild imagination conjures up the Mistres...

The Capture of Sweet Pussy Ch. 03

by SirStroker88 on Sep 17, 2017
BDSM

Chapter 3 – Donna's Story 'Damn Sid, you're right, she is a beautiful sight." Donna was looking down at Pam Martini, the bitch she knew from the office. What she saw now was a frightened young lady on all fours wearing nothing but a collar and a blindfold. She was leashed to a whipping post and quietly sobbing to herself. Donna knelt and stroked Pam Sweet...