Sissy Maid Chastity Stories

25,197 results
Orientation
Length
Source
Infinite Scroll

Submission Contract

by Anniekneels on May 2, 2018
BDSM

Submission Contract I, Annie, promise to obey and serve Mischelle in any and all ways she deems appropriate and necessary. This commitment includes the following stipulations. At any time Mischelle has the right to add to this list and Annie cannot reject new demands without voiding the contract. The only way Annie can void this contract is if new stipulati...

Carol's Gifts

by Belongs2Beth on Sep 16, 2017
BDSM

Authors note: This is the third story featuring characters introduced in "Carol's Christmas." In this installment Carol give's Jack his Christmas gift one night late with the help of Irena, "Marcia" and several well hung younger men. The sex action in this story is unrestrained, and since the tags are at the bottom of the page, I will issue the following mil...

Allyson's First Blowjob

by sissymaidallyson on Sep 16, 2017
Transsexuals & Crossdressers

I have been a closet cross dresser for many years. A few people knew but it wasn't well known and that is how I liked it. I enjoyed dressing up and prancing around my flat in ladies clothing but I always had fantasies about going further. I kept stopping myself from doing anything further but there was that burning desire to be truly slutty inside of me. On...

My Teasing Hotwife Ch. 03

by footslave85 on Mar 25, 2019
Fetish

Part three - the dreaded choice My wife and Mistress is now dressed beautifully and ready for a fancy meal and a few cocktails at a rather expensive restaurant and bar. I met my wife in our spare bedroom where I immediately see what has been laid out on the bed. There are two outfits, one is my nicest blue suit with a new shirt and tie that my wife has obv...

The Teamviewer Mature Files

by jothesmo on Apr 23, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. * The computer screen shone light upon my plain-white panties and bra, making them glow obscenely atop my peachy white skin. Since the divorce, I'd become brave in private and crossdressed on occasion. That sometimes ended up all day. The webcam was on, but I wasn't in any kind o...

The Locksmith

by cdbrittany4bbc on Jul 18, 2018
Transsexuals & Crossdressers

I wish to thank thewinedarksea for editing this beast. Summary: Fantasy night goes awry. Let me start off by saying my wife Amy and I have been married eight years now. I must admit our love life has been waning, and sex — when and if we have it — is plain vanilla. Our anniversary weekend was coming up. I told her we needed to do something to reignite our...

Service Day 01: Sissy's Breakfast

by SissyHubbyD on Aug 7, 2019
Transgender & Crossdressers

His alarm goes off at 6 AM that Saturday. On any other Saturday he would ignore the alarm and sleep in until 10 or 11, but not today. Today is Service Day, and he couldn't be happier about it. He gets out of bed quietly, careful not to wake his wife as he does so, and tiptoes out of the room and down the hall to the empty guest room. His outfit for the day...

Behavior Modification Institute Ch. 04

by NancyPan on Sep 12, 2017
Fetish

I received some very negative and very aggressive comments about previous chapter postings. If you are not aroused by FemDom, Humiliation, and Forced Fem please do not bother to read this. These stories are for the benefit of those who enjoy this form of erotica. ***** I lost all concept of time as I fell into a rhythm of incredible stimulation to my penis...

Chaste (A One Week Chronicles Story) Pt. 02

by Louise69 on Oct 14, 2017
Transsexuals & Crossdressers

Dear Reader, thank you for clicking on this story and reading it. I hope that you enjoy it, but know that it will be my most divisive story! Hopefully, by the end, you will see why the story was told...each story I tell has a part of me in it and helps prepare me for my other writing, but some of my stories have more of me in them that others. The One Week...

The Wedding Ch. 06

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

The Wedding (Patti Cake part 3) Chapter 6 -- Haberdashery, Hedonism and Highlights... We were into Patti's second week being overseas with Dean -- where by day they were supposedly riding around in expensive luxury cars yet by night? I had to figure, or it was safe to assume that is was more like Patti was riding Dean on their shared hotel room bed, stra...