Sissy Task Stories

44,281 results
Orientation
Length
Source
Infinite Scroll

Miss Johnstone's Lesbian Sissy Slut

by maturesubmale_for_F on Apr 20, 2020
Transgender & Crossdressers

1. Becoming a lesbian sissy slut I was eighteen years old when I became a girl. Or rather: When I was turned into a submissive lesbian sissy slut by my High School teacher, Miss Johnstone. She was an imposing woman, in her late fifties, tall and with short cropped grey hair. She had piercing green eyes and a well-trained body that she kept in shape by regul...

Creating Ginger Ch. 03

by Ms_Allison on Jun 1, 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, cuckoldry, dominance and submission. If these are not topics you are interested in, then please move along. In the below story I refer to the male character several ways but try to maintain a consiste...

Loraine's Self Bondage Re-Creation

by loraineveritas on Mar 12, 2019
BDSM

The following is my re-creation of an event that happened a few years ago. I had been a sissy slave to Mistress Marie for over 2 decades during which I become a totally submissive slave to Her every desire. I think of Her often as She has passed now. While doing Self-Bondage activities shortly following Her passing my wild imagination conjures up the Mistres...

Owned by my Mother-in-Law Ch. 08

by Sputnik57 on Sep 13, 2017
BDSM

Eventually, my tongue a little worse for wear, only Arabella, Miranda, and Agnes and her sissy remained as the fat ginger woman said her goodbyes. Though chubby, she was just as attractive as any of the other women, just as dominant. I had thoroughly enjoyed delving into her soft folds when punished, and had been closed to coming when she took her turn with...

Anonymous

by hyperpress on Aug 30, 2017
Fetish

I'm on my knees, staring up at a beautifully round, fleshy, tanned ass. It's spherical shape so perfect, and because the woman who belonged to it was bending slightly forward and bending at the knees as if she's about to sit down directly onto my open mouth I was infatuated and driven to fanatical heights thinking about it, looking at it, admiring it...it be...

The Awakening of a Sissy Pt. 06

by sissyjolie4u on Mar 2, 2020
Transgender & Crossdressers

While still admiring myself in the mirror, I received a text from Mistress, that read: I am so happy to hear that you are embracing and accepting that you are and were always meant to be sissy Jolie. Let me assure you, I will assist you and help you blossom into the ultimate sissy that you are meant to be. In time Joe will be completely stripped away. You ha...

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...

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 Stretching for Princess T Pt. 02

by Subboi23 on May 12, 2020
Fetish

Once I get home, I practically run to my room. Sitting in the car has pressed my plug deep into my ass and now my running causes it to wiggle around while still deep inside me. "Home Princess," I text as soon as I close and lock the door to my room. I quickly peel all my clothes off except for my panties and get on my knees. My toy is retrieved from a draw...

Robin and Jimmy Olsen - Sissies Ch. 04

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

The Date Continues (finally) ***** Just as Ollie and John began to wonder what was keeping their dates, they spotted the delectable pair of sissies returning from the rest room. When they reached the table, both men stood. Their politeness was rewarded by a brief kisses from the pretty lads. Each girlyboy also managed to run her hands across the crotch of...