Mistress Sissy Stories

31,338 results
Orientation
Length
Source
Infinite Scroll

Halloween Pool Party Pt. 08

by sissymissyct on Sep 14, 2017
Fetish

Friday morning cam and I was awakened with an electric shock that ran from my tits to my clit. My eyes flew open to see Miss Maddy and her girlfriend each with one of my nipples in their mouth. Pulling at the rings with their tongue, my high pitched squeal announced I was awake. My clitty tried to get hard but had no place to go. I reached to touch it and co...

A Mistress to Obey Ch. 05

by gbr2004 on Sep 12, 2017
BDSM

Continuation of this story that involves forced fem, forced bi, discipline, humiliation and submission. Not your thing, move on to another story. * We got back to her house and she opened the car door and let me out. I followed her into the house and she went and set down in her chair and I just stood there in front of her. 'Present sissy boy.' I droppe...

Suddenly Sarah, A Different Tale

by grizzley123 on Sep 14, 2020
Fetish

Suddenly Sarah, A Different Tale ************************** This is an alternative Chapter 2 to the Suddenly Sarah story I wrote recently. It takes day number two with Sarah in a whole different direction. It likely helps to read the first story. The themes of this story are not for everyone, but for those that like submission I hope you enjoy. As always,...

The Training of Sissy Paula Ch. 2

by submissive~pet~ on Sep 14, 2017
Fetish

Mistress carolyn patted me on the head and said i did good. Then she sent me home. The chastity belt still on me, and the cucumber still in my bottom. I logged on line yet no e-mails from Mistress carolyn. It was 4 days before she sent me another e-mail. Hello my pet i bet you thought i had forgot about you. i replied with a yes Mistress i was be...

Yeliza Awakens Pt. 02

by Yelizaveta on May 11, 2020
Transgender & Crossdressers

Part 2 of 2, hope you enjoy. Feel free to leave comments or thoughts. Or not, all good. Part four: The reveal Seeing him fully dressed, submissive, and made to look like a girl, her power was readily apparent. She reveled in it. He was patiently sitting on the bed, waiting for her direction. This power was becoming addictive. She enjoyed it more every ti...

The Office Ch. 04

by EasilyConfused on Jan 23, 2018
Transsexuals & Crossdressers

There were six screens in total, one for each of those being monitored. Their heart rate, blood pressure and neural receptors all key indicators. The technician made gentle adjustments to the controls in response to certain measurements that she noticed on each of the screens before her. Behind her a woman in a business suit watched on. Paula Hamilton was sk...

The Awakening of a Sissy Pt. 09

by sissyjolie4u on Apr 13, 2020
Transgender & Crossdressers

Mistress Di pulled her car into her garage and instructed me that I was to immediately go prepare myself for the evening. "Remember to douche extra well for your evening time with Tim," she added. "Who knows what Tim might have planned for you tonight Jolie." She said that while winking at me. My mind was full of thoughts as I made my way to the bedroom. W...

Halloween Pool Party Pt. 04

by sissymissyct on Sep 14, 2017
Fetish

Monday morning I was awakened early by Miss Annie releasing the air from my plug and swiftly pulling it from my bottom. I cried out from being so crudely awakened from my slumber and that got me a quick but hard smack on my already bruised bottom. "Good morning Brenda, time to shower and get ready for a big day", she informed me. "Thank you Mistress" I answ...

Transforming Brent Pt. 05

by sissymissyct on Dec 2, 2019
Fetish

I awoke early, partially due to the pressure of morning wood in the chastity. Once I settled down, I showered and slipped on a robe and quietly made my way to the kitchen. I quickly familiarized myself with the layout and, finding what I needed, started cooking a nice breakfast for my mistresses and myself. Ham and cheese omelet, OJ, toast and sausage, along...

Sissy Girl Forever Pt. 02

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

No going back now. Mistress was going to be certain that there would be no turning back for me. Over the next few weeks she made certain that I used my hormone cream daily. No my breasts haven't started to grow yet but I could notice some slow down in hair growth. My male wardrobe seemed to be dwindling, with more camis, blouses, soft pullovers and ladies p...