Sissy Task Stories

44,281 results
Orientation
Length
Source
Infinite Scroll

The Dominatrix Order Pt. 02 Ch. 03 - Romance

by Jwwsmith on Feb 12, 2019
Transgender & Crossdressers

The next afternoon, Johanna invited many of the Goddesses of the Council over for lunch. Much to everyone's surprise, Representative Pencalia arrived as an uninvited guest. Pomona prepared a fine meal as the Goddesses deliberated over various issues. Pomona was very accommodating to the guests, serving them tea and salad and shrimp. She even placed cloth nap...

A Very Public Sissy Adventure

by DivinaTellsAll on Jun 4, 2019
BDSM

At Madame Vega's instruction I had spent the last hour edging myself. This is not always an easy task for a sissy who is not allowed to stroke her clitty. The edging was primarily accomplished by the use of a vibrating wand inserted in my fuck hole, and an Hitachi wand that I could rub my clitty on, as I teased my fuck hole deep inside. I had been banned fro...

Service Day 01: Sissy's Breakfast

by SissyHubbyD on Aug 7, 2019
Transgender & Crossdressers

His alarm goes off at 6 AM that Saturday. On any other Saturday he would ignore the alarm and sleep in until 10 or 11, but not today. Today is Service Day, and he couldn't be happier about it. He gets out of bed quietly, careful not to wake his wife as he does so, and tiptoes out of the room and down the hall to the empty guest room. His outfit for the day...

Being a Sissy for Viv Ch. 05

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

Mistress Viv wondered around the bed, filled with the most feminine and sissy items from my wardrobe. Her fingers stroking and examining various items in turn. The first things she picked up were some nylon panties. They were one of my earlier eBay purchases. A double layer of nylon ensured they always gave that nylon sliding on nylon feel even when worn on...

Another Submissive Slut Ch. 11

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

My land lady's knowing look held me transfixed. Quietly Mrs. Lehrer purred, "What are you?" A spasm of trembling shook my body before I could mew out, "I am a sub sissy slut, Mrs. Lehrer." "Hemmmmm," She hummed, "And what else are you slut?" Her voice was quiet, soothing, inquiring. "I am a wanton cum whore, Mrs. Lehrer," I admitted, blushing at such an a...

A Tale of Two Bitches

by Lordheed on Sep 12, 2017
BDSM

"Game Over", a deep voice pronounced from the television. Johnny threw down the controller in frustration. 'Can't even win at video games, let alone anything else', he thought to himself in disgust, 'What a way to start winter break'. He'd been home now for 3 days; already missed campus, his dorm room, and the constant business of schoolwork that could keep...

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...

A New Life

by sissycinnamonswirl on Sep 18, 2017
Transsexuals & Crossdressers

It was nearly 7 o'clock PM, and I was running late. I had gotten held up at work, and there was no way I could tell them exactly why I had to be home by a certain time. How could I begin to tell them that my Mistress would be expecting me home at exactly seven in order to receive my night's instructions? Not only would I sound pathetic, but I would be disgra...

The Slave and the Sissy Ch. 05

by Sputnik57 on Sep 12, 2017
Transsexuals & Crossdressers

Ayesha was not to be denied; slave was rampant after witnessing the erotic antics of the maids, and was anxious to please Ayesha quickly, so that he may watch over Pepper; she was so soft and vulnerable. Slave's cock rose quickly as he sniffed at the gloriously rich scent of the dusky beauty's thong. She smiled with a sense of admiration as he licked and lap...

The Wedding Ch. 05

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

(Patti Cake part 3) Chapter 5 -- Femdom, Fucking and Femininity... At the end of our time spent with Ms. Walsh, I was left with a lot of questions and I wasn't sure how to deal or cope with any of it... But one thing was for certain, I was starting to see more of the old Patti bubbling back to the surface, being direct and without compromise... The whole d...