Sissy Maid Chastity Stories

25,197 results
Orientation
Length
Source
Infinite Scroll

Becoming a Sissy Maid & Slut Vol. 13

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twenty Two: Satin, Ruffles and Lace, Sissy Maids contracted out to Work. Monday morning and I arise as typical at 7:30am, enema, shower, shave do my makeup and put on a maids dress for the day. Today it's back into a black satin one. Master told me though to put on black back seem pantyhose for today which I dutifully do and make sure the seems are...

March Madness Ch. 09a

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

House of Kinks

by royal22erick on Dec 24, 2019
Fetish

The house of kinks is almost as old as the oldest profession in the history of mankind, its creation was founded upon three unrefutable principles. 1- There will always be a market for the pleasure of the flesh and the house of kink always need to be in touch with the populace needs. 2- No House of Kinks manager should seek power at the detriment of the hous...

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Mommy Adriana, I Will Obey You

by Gretatv on Sep 13, 2017
Transsexuals & Crossdressers

Dear Readers, since I am open to suggestions from now on I will start my stories with a recap of what has happened before. * Finally we were on our way home. Interestingly neither Mommy Adriana nor Mistress Andrea had cuffed or gagged me. So I just sat in the back of our car. During the short drive I had some time to think about what had happened in the p...

My Father, The Maid Ch. 03

by SissyOona on Dec 12, 2018
Transgender & Crossdressers

A Case Of The Mondays By Sissy Oona. Sleep came easy that night, I was frankly a bit worn out from the amazing sex we'd had. I was awoken by the door to the room opening and the click of heels on the wood floor. I cleared my weary eyes to see my father entering the room carrying the breakfast tray I had become accustomed to seeing in the morning. Noticing...

Mistress Monique Pt. 02

by bleedndkn on Sep 25, 2017
Fetish

This wasn't even my fantasy, I thought as I purchased the clamps, butt plug, heels and maid dress online with expedited shipping. The next day I brought the items in a backpack to Mistress Monique's apartment while she was at work. I put everything on then placed the butt plug in my ass and tightened the nipple clamps painfully so they wouldn't fall off, th...

Superstars Rise and Superstars Fall Ch. 01

by felicia_rene on Oct 6, 2020
Transgender & Crossdressers

Superstars rise and superstars fall 1 Part 1 of 4 By Felicia Rene This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy the story Synopsis: The underlying theme is transformation and sexual punishment of the main character for his anti-gay womanizing feelings. For his heinous actions initially making h...

Sorry Sissy You Lose Pt. 02

by LittleDickSissy on Jan 22, 2019
Fetish

Mistress enjoyed watching herself primp in the mirror. Music playing in the background, a glass of alcohol to sip from, and the knowledge she was going out on a date with George - the older gentleman she had been fantasizing about. As she slid her smooth legs into a pair of crotchless hose purchased by her sissy slave she looked at her trimmed bush. The si...

The Journey

by born2srvtv on Sep 19, 2017
Transsexuals & Crossdressers

Tom couldn't believe he was wearing a CB-6000 chastity device while driving to Knoxville to actually meet face to face with Jason. He and Jason had been chatting on a kink oriented website for the last few months. Jason had asked him to buy the CB6000 and Tom found himself incredibly eager to comply with Jasons' desire. Jason had asked him to wear it while t...

My Friday Night: Switch

by honey28 on Sep 5, 2017
Fetish

Driving home on Sunday night, my phone rang when I was stopped at the light waiting to turn onto my street. Seeing Nick's name, I put him on speaker phone. Before I could say anything, he very loudly declared, "I want to lick your pussy." Hearing that deep, sexy voice usually makes me melt, but I had to giggle. Note to self: never answer his call on speakerp...