Sissy Anal Boipussy Stories

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The Bunny Way

by Lea1234 on Sep 16, 2017
Transsexuals & Crossdressers

I walk over, dressed in a black bunny suit, with fishnet pantyhose, black high heels and little bunny ears. I start rubbing my cock through the bunny suit as I stare at your pole. I start feeling the familiar feelings... I get weak in the knees... I start slowly kneeling, while staring at your hard cock, which is pointing at me. My knees touch the ground...

The Descent Ch. 03 - The Show

by pantywriter on Sep 28, 2020
Transgender & Crossdressers

She jarred me awake, destroying arguably the best slumber I had ever had. "Wh-what?" I managed. "Darling, you must get up, it's five AM and I have no wish for you to see me like this, yet," she softened her words. I blinked and rubbed my face with the palm of my hands. Sitting up still wearing incredibly sexy lingerie nearly made my clitty rise, but her...

A Sissy's New Daddy Ch. 05

by sissyneko on Sep 25, 2017
Transsexuals & Crossdressers

When the loud speaker blared that Billie had a visitor he was tied to a stool. Billie had become a plaything for a few of the more business savvy residents of Blofield State Penitentiary. When prisons became smoke free buildings cigarettes were no longer the illicit currency of choice. Stamps had come into fashion because they couldn't keep you from mailing...

Reminiscing on My Sissy Life

by Sjen451 on Nov 18, 2019
Transgender & Crossdressers

Things have gotten wild since my ex-wife mistress first took control. I've done everything she has requested of me. And with each accomplished task she only adds more challenges. I've never failed her yet, and yet she never ceases to ramp things up. In case you aren't caught up just yet, this all began one day when she stumbled across my secret fetish:...

Under Mommy's Direction Ch. 05

by MommysHypnoSissy on Apr 13, 2020
Transgender & Crossdressers

The rest of Jaime's day had been a whirlwind of tasks and chores to complete before his Mother got home. His online Sissy Trainer, who demanded that he refer to her as 'Mommy', had given him a myriad of tasks. First it was cleaning up his Mother's bed and sexy toys, putting everything back how he had found it. Then it was back to his room to dispose of his b...

A Sissy's New Daddy Ch. 04

by sissyneko on Sep 25, 2017
Transsexuals & Crossdressers

It was with great pleasure that I am finally able to upload chapter 4 of "A Sissy's New Daddy" I have spent the better part of a year working on this chapter. I was surprisingly hard to get down on paper. I want to thank all the readers that have taken a time to comment and rate the chapters of this story. It has meant a great deal to me and has at a few dar...

A Sissy's New Daddy Ch. 02

by sissyneko on Oct 8, 2019
Transgender & Crossdressers

I hope you enjoy this second installment of 'A Sissy's New Daddy'. I worked hard on it and hope that it brings all of you the same pleasure reading it that it has brought me writing it. There are some extreme moments in this chapter but also some very tender ones. There was a line in the first piece that gets expanded on at the end. I hope you enjoy what I h...

Sissy's Subservience to Wife Ch. 01

by JessicaSIssyGurl on Aug 1, 2018
Transsexuals & Crossdressers

Every Friday evening is my grooming ritual, shaving away every inch of body hair that has cropped up through the week, soaking myself in a bathtub to further soften my skin, red nail polish on my fingernails and toes and finally cocoa butter lathered all over before I sleep that is a thing I do every night though. But before sleeping I message my date for to...

A Sissy's New Daddy Ch. 06

by sissyneko on Sep 25, 2017
Transsexuals & Crossdressers

A loud crack of thunder broke the silence and Billie smiled in his bunk. Lights had been out for almost an hour and he couldn't sleep. The prison had gotten a new influx of prisoners. The first night was always the hardest and it was hard on Billie too, he could never sleep listening to the crying. Plus Billie had gotten a new cellmate in the process, a cell...

A Sissy's New Daddy Ch. 03

by sissyneko on Oct 8, 2019
Transgender & Crossdressers

I hope you enjoy this third chapter of "A Sissy's New Daddy" I hit a bit of a speed bump with this chapter, I wasn't sure where I wanted to go with it. I think I have that settled now. I am foreseeing this as a 9 chapter piece with the next three chapters jumping ahead a bit in time. I hope you enjoy this chapter, and if you haven't already please give the f...