Sissy Task Stories

44,281 results
Orientation
Length
Source
Infinite Scroll

Sissy Life: Valentine's Day

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

This is a standalone story in the 'Sissy Life' universe. You don't need to have read any of the other stories to enjoy this one, but it does fit with those in terms of characters & themes. Consider it a 'Rogue One'. ***** 'Have you finished in the kitchen?' I had indeed. I'd cleared the pots and cleaned the surfaces. I couldn't talk with my ball gag in how...

Goddess Monica's Beta Bitches h. 01

by DonGarciaWallaceIII on Sep 12, 2017
BDSM

Meeting Gustavo Monica Garza's austere, coprolite-like walls, covered with aquarelles of men in tutus and women's swimwear, are sound-proof, and Gustavo must intuit or presume this since, once inside, his voice climbs in pitch in a way it wouldn't in any other of her condo's rooms. In the little kitchen, for instance, he nearly whispered. The tutu- and wome...

High School Dilemma Ch. 05

by LaurenWestley on Sep 15, 2017
Fetish

(Authoress's note: of course all disclaimers are still in place regarding characters etc. PLEASE DON'T READ THIS IS YOU HAVE AN AVERSION TO PEE SCENES AND EXTREME HUMILIATION. This is only a fantasy story XXX+. I only wish there is enough here to make each of you happy. To those who have given me constructive criticisms as well as those with praise thanks. L...

April Fool Office Sissy

by lululuvsblack on Apr 10, 2018
Transsexuals & Crossdressers

"Dear Colleagues This week, in order to help with our efforts to raise money for charitable causes, we have decided to mix up our usual policy of dress down Fridays. This Friday we are instead instigating a "dress up Friday" in which staff are strongly encouraged to come to the office dressed in the office attire of the opposite gender (that's suits and tie...

Jacki's Journey into Sissyhood Pt. 03

by jacki697 on Sep 18, 2017
Transsexuals & Crossdressers

This is the 3rd installment of the Jacki's Journey series. I'd like to thank those who were nice enough to add comments and feedback on the proceeding stories. I'll try and keep them cumming. ***** I had a couple days to evaluate Steve and Laura's offer and I was no closer to a decision than I had been. I went back and forth on the verdict. How was I goin...

From Her Ex-Boss to her Bitch Pt. 04

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

This story contains extreme fantasies of Fem Domme, watersports, cock sucking, forced bi, if these aspects are likely to upset you please do not read on. ***** Pete had been taken in by Rachel his ex-employee, encouraged along the way, with a little titillation, a lot of flirting and confessions of her bisexuality. She'd used her submissive Claire to help...

The Educator Ch. 01

by wesleyann on Sep 16, 2017
Novels and Novellas

It was the biggest, nicest, room that Madeline had ever seen. She almost burst out laughing but checked herself when she remembered that Sissy, one of the kitchen girls, was standing behind her carrying her small bag. She took a breath and composed herself. "Lay the bag on the window seat and you can go." "I'm sorry miss, I was told to get you dressed for...

Online Fantasy Leads to Real

by puzziboi on Jan 20, 2020
Transgender & Crossdressers

Gabrielle McBeth had a good life. She and her husband, Antonio, were 28 years old and had been married for six years. They had an eight year-old son named Aiden Antonio and a five year-old daughter named Ava Gabrielle. Her husband was an industrious fellow who flipped houses for a living earning just over six figures a year. She was able to be a stay-at-home...

Behavior Modification Institute Ch. 11

by NancyPan on Sep 12, 2017
Fetish

Thanks to all who have recently encouraged me to continue this story. I very much enjoy getting feedback and appreciate your positive votes. If you do not enjoy FemDom, or sexual humiliation, please do not bother to read this story. ***** "Now, Tom, we must do something about those wet panties. Nurse Pyre did the right thing to douse your little pleasure s...

Legally Binding

by MistressMtoyou on Aug 31, 2017
Fetish

As I explained in my first story (My first submissive), I'm fortunate to have a high paying job at a large well known firm. While my employer is equal opportunity and all of that, even the most open minded employer wouldn't react well if they learned they had an amateur dominatrix on their senior staff. Accordingly, before going much farther with my little h...