Mistress Sissy Stories

31,338 results
Orientation
Length
Source
Infinite Scroll

Mistress Chronicles Ch. 04

by MistressMtoyou on Sep 25, 2017
Fetish

Background: The next three stories involve my only long-term on-line subject who I have named Nancy. This subject passed all of the tests I described in story two ("A Few Good Subs"), but before we were able to arrange an in-person session, he was offered a job in a town a great distance away, precluding any in-person meets. We agreed to continue training...

Mistress Commands Me in the Office Pt. 03

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

First a little clarification, if you've been reading parts one and two (I hadn't kept this quite straight up to this point). Here are the correct character names: Bob, or Robert, or Dick (or whatever my mistress decides to call me): Me Rick: My boss Brad: An office co-worker Rod: Office co-worker in an adjacent cubical, very buff, quite manly Wilson: Of...

Sissy Life: Valentine's Day

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

This is a standalone story in the 'Sissy Life' universe. You don't need to have read any of the other stories to enjoy this one, but it does fit with those in terms of characters & themes. Consider it a 'Rogue One'. ***** 'Have you finished in the kitchen?' I had indeed. I'd cleared the pots and cleaned the surfaces. I couldn't talk with my ball gag in how...

Sissy Training Week 02: Obedience

by Peggylea on Mar 17, 2020
First Time

Week 2 Obedience I arrived at Mr Deal's my Master for the second week of the sissy course. Nervously I knocked on the backdoor to be greeted again by Mistress Rhea. She took my coat and led me straight to the changing room where I stripped naked as last week. Mistress R led me into the kitchen area and told to wait for my Master. Then assistant Toby came...

Transforming Brent Pt. 02

by sissymissyct on Jul 10, 2019
Loving Wives

Kept in Loving Wives to annoy the tiny dicked anonymous reviewers that love to trash everything they read (after they wank to it). *** I woke up Sunday morning with a painful erection in my chastity and the pumps still attached to my breasts. I reached down trying to find a way to ease the pain in my penis. Nothing seemed to help. Maybe Wendy will be up so...

My New Friend Amy Ch. 03

by DRobbie06 on Dec 23, 2019
Fetish

As I drove home that evening I had the replay of the days events running on a loop in my mind. I can't believe I paraded around in panties at lingerie store in front of strange women at the instruction of my new mistress. Hell, I signed a contract to obey her no matter what she says! Then I begged to jack off in front of her. I'm even a panty wearing sissy n...

Mistress In Control

by polishjoe on Sep 17, 2017
BDSM

Last Friday evening when I got home Mistress informed me that tonight was going to be a very hot night but I did not realize until later just how hot things were going to get. Mistress had dinner ready and she told me she wanted us to eat quickly so we could get straight to the "activities" she had planned. I thought it curious because Mistress usually did...

A Letter to Our Pantyhose-Sissy

by Sheermistress on Sep 19, 2017
Transsexuals & Crossdressers

I'm on my bed on my knees, my skirt pulled tight and just a little high, exposing my control-top pantyhose to your eager eye. My feet are dangling over the edge of the bed and you, my little pantyhose-slut, are standing behind me, dressed in your sexy schoolie outfit and mary-janes. Your face is made up in a prissy, sissy, teen-girl way and your hair is fini...

The Nemesess Ch. 02

by ProfessorPlums on Sep 15, 2017
Fetish

Correspondence from older (50-70), dominant ladies most welcome. * The next few weeks passed slowly for Chris. He was initially terrified of his new Mistress, - after the ordeal of his 'breaking in'! However, his new Mistress (Theresa) didn't want a simpering bundle of nerves to play with. Dominance for her was a varied and protracted feast; full of spice...

Stevie's Journey Ch. 03

by gbr2004 on Dec 2, 2019
Fetish

I get up and put on some of my regular clothes, workout shorts and a t-shirt and flip flops. Try to digest what happened yesterday and how everything just spiraled out of control and now I find myself in this impossible position. It's like all choices have been taken from me and this group of people took over my life. It was exciting but I can't be doing the...