Sissy Task Stories

44,281 results
Orientation
Length
Source
Infinite Scroll

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...

Sissy's Special Night

by mdw_dark_angel on Sep 17, 2017
BDSM

This girl was so excited as Master had agreed to a special surprise for sissy from angel. Master took sissy to work and came right away to fetch angel to return Home and ready things for angel's surprise..."Sissy's Special Night". Y/you see, this slave has belonged to Master... though one has not always retained one's physical collar... since Master first c...

Sissy Arlene's Soul Mate Ch. 02

by SissyArlene on Jul 10, 2019
Transgender & Crossdressers

Note to reader; This is part of the ongoing story of sissy Arlene. To get a full sense of this Saga, you need to read the 3 parts of "SIssy Wants Her Wife's Boyfriend," and then read "Sissy Arlene's Soul Mate." And now, "Sissy Arlene's Soul Mate chapter 2." ***** I awoke to the smell of coffee and bacon. My first thought was that my wife had slipped out...

Zoey's Basement Transformation Pt. 03

by SissyStoryTime on Sep 11, 2017
Transsexuals & Crossdressers

Zoey couldn't believe the cruelty of her Mistress. She shook her head desperately, feeling exhausted and sore everywhere from the waist down from already having so many awful things done to her. She didn't know if she could survive this fresh hell. Mia moved away from the tied girl, her helpless form bent over and restrained at waist height. "Aww, what's t...

Mistress Commands Me in the Office Pt. 02

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

Oh god, mistress, my dick is so hard in my panties now. At your command, in full view of the three vid-cams you made me install in my work cubicle, right here in the middle of my work day, with my associates working only feet away, on the other side of the cubical walls, you made me do it. Your commands, your training, your trigger words. My compliance. My s...

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:...

Domina Katarina Goes Shopping

by pbs444 on Sep 17, 2017
BDSM

Several days ago, there was an e-mail in my inbox. It was of course from my Domina, Katarina, because the e-mail account is for her exclusive use, when she wishes to communicate with me. Because I am her sissy slut, and from time to time she finds ways for me to prove my usefulness to her. The e-mail read: "Hello, sissy slut, I have decided I wish to go...

Developing Emma Ch. 04

by Sputnik57 on Sep 19, 2017
Transsexuals & Crossdressers

Emma took comfort in the shoes he'd bought her as the days passed, and as she slept she thought hard of the warm suitor's face and kissed her pillow; her anus tingling sweetly on the butt plug, imagining the beautiful sensation she'd experienced when he'd mastered her for the first time. She yearned for him and hoped he'd not just used her for a moment's ple...

Sissy Boy Secretary

by Hotenuf4u on Sep 19, 2017
Fetish

As I sit here in the outer office space of the company CO, I look like an ordinary male secretary. On the inside I'm wearing a pair of pink lace panties, at my bosses request. You see I'm really a sissy inside and my boss takes advantage of this at every possible opportunity. I've worked here for 2 years now and it wasn't always this way. My boss, Elaine, a...

Creating Ginger Ch. 09

by Ms_Allison on Aug 31, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into dominance and submission. If these are not topics you are interested in, then please move along. ~~~~~~~~~~~~~~~~~ To say ginger was in hell would be an understatement, although it would be more accur...