Sissy Task Stories

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Sissy Chantel, New Reality Ch. 02

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Two: If One was Fun, Two will be Better. Late night I get a call and I look to see that it is my new Master. I answer, "Hello Master Camron, how may I help you?" "Bitch ass sissy, I am gonna need you here tomorrow morning, by 10:00am." he excitedly replies. I reply, "Oh, ok I guess I can make it to your home tomorrow morning Master." "You God Dam...

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...

James Explores Ch. 02: Daddy's Girl

by ShyBiSub on Sep 24, 2019
Transgender & Crossdressers

All Characters are over 18. The first part got wayy more views than I ever imagined so I decided to continue ;) Thank you *.*.*.*.*.*.*.*.*.*.*.*.*.*.*.*.*.*.*.*. Memories from Part 1 "Good girl. See you again next week, same time" He squeezed James' bottom in his hand. "Yes Daddy" The Crush James couldn't stop thinking of what happened that d...

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 Little Twist Over the Road

by mdw_dark_angel on Sep 17, 2017
BDSM

Master is an OTR driver for a national corporation. That could make things very difficult for O/our relationship as W/we would not be able to see Him very often, for very long at a time, except that - sissy, affectionately known as pet, and angel, referring to this girl - are His relief drivers. W/we travel with Him everywhere so it makes life a bit more exc...

My Dom's Decisions

by davesubboi on Oct 12, 2017
BDSM

The thought of being submissive and letting another superior being guide, direct and change me has become one of my driving desires. Over the past 15 years I have realized I am much better at pleasing others and have determined based on numerous online doms/master/mentors that I really should not care about my own pleasure if I can serve another and give the...

The Neighbours Situation Ch. 03

by Missclo on Oct 8, 2019
Transgender & Crossdressers

I tugged at the bow and it fell lightly to either side of the large box. I slowly removed the lid, terrified of the contents, which felt ridiculous but based on previous events I knew I wouldn't be keen on whatever was inside. There were multiple bags with pink numbers written on them. I opened number one and found a note which I grabbed and began to read....

The Descent Ch. 02 - A Slow Glide

by pantywriter on Sep 28, 2020
Transgender & Crossdressers

I sat up, the dried remnants of last night's orgasm sticking uncomfortably to my body. I looked down at my...clitty, I reminded myself. My clitty. To something akin to horror I felt the familiar lurch in the organ, and the equally familiar sensation of tightening in my balls. My clitty rose, slowly at first, but soon to its fullest extent. It began to pulse,...

A Week End with Mistress Pt. 02

by gasissynora on Oct 30, 2018
Transgender & Crossdressers

Dear readers this is my first story and I hope you enjoy it. Your comments and suggests will be most helpful. I am planning on continuing the story if the feedback is positive. This story is based in part on facts and part on fiction. I will leave it to the reader to decide which is which. ***** I arrive at Mistress Nikki''s a couple of minutes before 2:0...

Sissy Training Week 01: Induction

by Peggylea on Mar 17, 2020
First Time

Some years ago I was under the supervision of a Domme Mistress called Neve who organised for me to undertake a course in sissy training so I fully understood my role as a smalldick submissive. She found me a place on a 6 week sissy training course with a teacher called Mr Deal who was very experienced and had devised such a program. I was to meet Mr Deal a...