Latex Sissy Maid Stories

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The Sissy Trap

by Slavedogg on Apr 29, 2025

As you struggle hopelessly your black leather restraints locked shut tightly making escape impossible. You have to wonder what you did to wrong to end up in this situation. Yes you wanted to be a sissy maid to a Dominant couple, yes you wanted them to use and humiliate you. You was the one to search and suggest this to your captors but now they are talking a...

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Futanari Academy Ch. 14

by TheOrcKing on Jun 10, 2019
Transgender & Crossdressers

(All characters participating in sexual activity are age 18 or over.) This chapter is a repost, it has been edited and has undergone very minor rewrites for style and flow. Nothing in the story has been changed. Halloween Special, 2018 Danielle walked up the steps to her friend Maddie's house, still wearing her Westbrook school uniform which now consisted...

Owned by my Mother-in-Law Ch. 04

by Sputnik57 on Sep 13, 2017
BDSM

The area by the window had a padded surface; no doubt Blanche's departed husband and many other enslaved men had been made to kneel for hours at this window, whilst they contemplated their fate on just such an evening as this. The padding would not be for their comfort, it would be there to ensure that their knees functioned when the time came to entertain....

The Holiday Pt. 01

by mandiejune on May 16, 2018
Transsexuals & Crossdressers

My name use to be Frank its now Helen sissyslut and I was surfing web looking at crossdressing sites on my computer when this holiday competition came up. For some reason may be my wife had left me after finding me dressed up like a hooker! I decided to enter the competition not really expecting to winner a free 4 weeks holiday in South of France. Two weeks...

The Fantasy Twist Ch. 02

by oneguy4fun on Sep 18, 2017
Transsexuals & Crossdressers

Sunday morning was a morning for sleeping in. Dan spooned Lisa's naked body. This was not typical of Dan, as he usually preferred to sleep facing away from Melissa. Melissa was happy with this change. She enjoyed the warmth of his body. She stirred under the covers, snuggling even closer to Dan. Dan broke the morning silence, whispering into Melissa ear, "L...

Trixie's Chastity 01

by trixie47cd on Sep 19, 2017
Transsexuals & Crossdressers

Part 2: Trixie learns his new role. Since my wife came home early and caught me masturbating in women's frilly lace 2 month ago, so much has changed. She has taken control of my life since I begged her not to spread the story and pictures of my humiliation around town. After I made the choice of submitting to her feminization training, there really was no...

Balls On The Line In City Trading Ch. 02

by gomorrah on Sep 16, 2017
Transsexuals & Crossdressers

So with much apprehension, I turned the handle on the blue door. Stepping through, I struggled to adjust my eyes to the brilliantly white light streaming out of the other side. I raised my hand to try and filter the glare, and heard the door click shut behind me, and then double-click again. Instinctively, I tried for the handle on my side, but there was no...

Being a Sissy for Viv Ch. 04

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

With great care I slowly pulled the 10 denier black nylon stocking up my leg. I had other pairs, but these were my best and today it was important to have the best. Cautiously I rolled up the second one and with the same deliberation pulled it onto my other leg. The feeling, of soft nylon sliding over my naked skin exquisite and exciting as always, but today...

Caitlin and Mistress Vicky

by Jemina004 on Sep 19, 2017
Transsexuals & Crossdressers

*Clack* *Clack* *Clack* The sound of my heels on the kitchen tile was distracting me right when I needed to focus. My wife, or Mistress Vicky as I'm to call her from now on, had left me quite a bit of chores to do today. I had just finished dusting and was getting ready to polish the kitchen floor when the doorbell rang. *ring ring* Swallowing nervously,...

Darling Nikki

by Latexsissy69 on Sep 25, 2017
Transsexuals & Crossdressers

Chapter 1 - The Setup "I'm going to catch him!" Samantha thought to herself as she looked at her disheveled panty drawer. She now had proof that her roommate, Nick, had been wearing her clothes, but had to catch him in the act. She did a search online for ideas on how to catch him. She looked at cameras, tape recorders, etc... but she knew it wouldn't hold...