Sissy Task Stories

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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...

Robin and Jimmy Olsen - Sissies Ch. 05

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

Jamie Olsen hated Mondays, because on Monday morning she had to go back to being boring Jimmy Olsen after having spent all of the weekend as Jamie! Sunday evening had been disappointing. As usual she had been out on her street corner on the stroll. Last night she had chosen to look extra trampy, wearing torn stockings, her five inch heels, and her black lea...

Aztec Art - The Path to Submission Ch. 07

by Sputnik57 on Mar 20, 2018
BDSM

Lloyd had been treated to a gratuitous and well received whipping by Joyce, watched by Patti, Kay, and Maria, who noted the pleasing sign of a boning erection as his wife confirmed her new status as his owner, then was bundled into a walk-in wardrobe at Patti's house, trussed with his head down to await their further pleasure. He was not alone in the wardrob...

How I went from Domme to Slut Ch. 06

by Ms_Allison on Jun 26, 2018
BDSM

I would like to thank the darlin mymantoy999 for his editing and insight and in particular keeping my math and thought process straight while writing these! ***** As amber had suggested she and I settled into our new normal relatively quickly. Now on top of waitress duties every other week, house cleaning trips and the random frustration amber experienced...

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...

Sissy Surprise

by silkstockingslover on Jul 18, 2018
Interracial Love

Editor's note: this story contains scenes of gay male sexual content. Summary: Wife discovers her husband is a slut for BBC and... Note 1: This is a NUDE DAY 2018 Contest Story. Note 2: Thanks to Tex Beethoven, and MesaMan for editing this story. - SISSY SURPRISE My husband hadn't been the same since he returned from a six-month military tour. There w...

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...

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...

Miss Samantha's Guest

by Sissy_Desire on May 11, 2020
BDSM

After the last text from Miss Samantha, I've been waiting anxiously to see her again. After getting home that night a few weeks ago watching the video she sent and reading "See ya next time for some more fun, sweetie" I've been wondering what our next encounter has in store. A knock at the door snaps me out of my daydream. Opening the door I see a small bo...

Sorry Sissy You Lose Pt. 04

by LittleDickSissy on Apr 10, 2019
Fetish

Slave had been busy. Spending hours looking online for things for his Mistress. His little dick always swelling and throbbing as he went through pages of web sites, looking at heels, lingerie, hose, dresses, jewelry, etc. Mistress had tasked her slave. He was to purchase various outfits for her to wear on an upcoming trip. A work trip for his Mistress, but h...