Anal Stretching Sissy Stories

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Wife in Control Ch. 07

by wifetoy on Sep 25, 2017
Fetish

This is the seventh chapter of my wife's fulfillment of the punishment poem I submitted suggesting ways to atone for my inability to control my orgasm. Please read the earlier chapters for the full poem and the humiliations I have been forced to endure because of my failure. I am grateful that my wife loves me enough to exercise the total control over me tha...

Wife in Control Ch. 03

by wifetoy on Sep 25, 2017
Fetish

This is the third chapter in the story of my submission to my wife for punishment for failure to control my orgasm. My full offer of punishment for my transgression is fully set out in the first chapter for your reference. Each part of this story is true and is told as it actually occurred. As with the previous chapters, my wife told me to let the readers kn...

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...

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...

Caught in Panties & Dominated

by Tracy69 on Sep 12, 2017
Transsexuals & Crossdressers

I love to wear sissy clothes, and I fantasize about being controlled by a dominating mistress, who forces me to wear her clothes, to take her boyfriend's cock into my virgin mouth, make love to his big stiff cock, deep throating it until he comes into my mouth, filling up my mouth until his hot cum drools out of the corners of my mouth, around the sides of h...

Zoey's Basement Transformation Pt. 02

by SissyStoryTime on Sep 11, 2017
Transsexuals & Crossdressers

"Stand up," the whip crack of Mia's voice caused Zoey to flinch, but she didn't move from where she kneeled. With a sigh, Mia grabbed the leash attached to her chastity cage and started to give it a firm pull. Zoey quickly found her motivation, legs scrambling beneath her to find purchase. In her haste she slipped, almost falling back down. "Slower," Mia sa...

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...

Jack and Jill Pt. 06: Jean

by candyflosslover on Jul 13, 2020
Transgender & Crossdressers

They had been trying for a baby for some time and had come to the sad realisation that it wasn't going to happen without some intervention. The doctors wanted them to use donated sperm and have insemination, but it seemed so clinical. Jean had told them about a breeding club that she had worked in and they both liked the sound of it, but as she was walking t...

Dinner Date with Mommy Pt. 04

by SissyStoryTime on Dec 3, 2018
Transgender & Crossdressers

Disclaimer - This story includes the following themes: Femdom, sissification, feminization, forced-bi, forced cum-eating, butt plugs, anal play, strap-ons, spanking, humiliation, CBT, chastity, and domestic servitude. If these themes do not interest you, then this story isn't for you, sweetheart. For everyone else... This is it. What you've waited for. Th...

My Sissy Cuckold Life

by SissyCuckMike on Jan 2, 2021
Fetish

Hello everyone, my name is Mike and i am now a sissy cuckold. If you don't know what a sissy or a cuckold is i will explain, a sissy is like a cross-dresser but usually dresses up in pink frilly women's clothing and cuckolding is similar to a hotwifing where she goes out on dates and fucks other men without her husband/boyfriend around but with cuckolding it...

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