Book Sissy Maid Stories

67,072 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Appointment by Card Only Ch. 02

by Sputnik57 on Sep 17, 2017
BDSM

Madam Ruth was more than pleased with her days work as she descended to the bed and stroked the soft white body of the helpless sissy, Poppy mustering a whimper as the dominant Madam. Cupped the soft pink scrotum and gently worked the dainty cock to an erection; she was scared but the surreal situation along with the gentle warmth of the two females, combine...

Sissy Auction

by davine on Sep 26, 2017
Transsexuals & Crossdressers

Authors note: this story is a fill in while I get over a block with the fifty shades part three. I also need to revise part two of sissy downfall as Literotica rightly pulled it due to excessive violence. I wish this story was autobiographical. It's not but has some elements of truth in it. I hope you enjoy reading it. I love feedback; even negative. All cha...

Recruiting of a Sissy Maid Ch. 01

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

[Welcome to my next story. This story has become a little different in how I planned to write it as compared to my previous stories. It has been fully written up already, as of this first uploaded chapter. Doing it this way allows me to better proof read and adjust for future chapters before uploading each. I will submit uploads on a regular basis for my rea...

The Writer's Secret Ch. 07-08

by AnnMichelle on Sep 16, 2017
Transsexuals & Crossdressers

Synopsis: Loren had no idea what he was getting into when his agent suggested he write transvestite fiction. Nor did he realize how eagerly his wife Stephanie would embrace the idea of feminizing her husband. How far would they go? Chapter 7: Laura Buys Shoes. . . Lots of Shoes Loren rolled out of bed the following morning. He yawned. Despite having sex w...

Steve's Maid

by Mixedwritings1993 on Sep 13, 2017
Fetish

Steve always had a thing for maids. He doesn't know what actually turns him on, their uniform or really the person inside the dress, but when there is a maid around; Steve can never keep his eyes away from her. Back at states when he was with his parents, he had an older lady as their house maid around her late thirties. Steve can't even count the number of...

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...

Mistress Chantel, Tranny Dominatrix Ch. 02

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Two: A Day in the Life of Tranny Dominatrix Chantel Waking up into another morning where this transvestite dominatrix gets to dress up and enjoy her life of toying with sub men and sissies/crossdressers. Working hard to get my femme look down over the last couple of years prior to operating this Dominatrix business, I enter my very lady-like powder...

Heiress MMM gets Her Cuckold

by mmms_ricki on Sep 19, 2017
Loving Wives

Mary had recently inherited a rather large family fortune and become a multi-millionaire. As a result She was feeling extremely Independent and Powerful. Now that she was independently wealthy she had the urge to release Her Female Supremacy and Female Dominance side. She especially looked forward to showing off the Power She had over Her sissy submissive hu...

Angel Learns My Secret

by Angelscuck on Sep 16, 2017
Loving Wives

My wrists strained at the ropes that bound me to the chair. The vibrator taped to my cock was driving me mad while I watched my leather clad bride mount her lover's huge black cock. Angel smiled at me teasingly, knowing the pleasure and pain I was experiencing.... Suddenly I heard her key in the door I quickly turn off the magic wand, put it in the desk dra...

Sissy Chantel, New Reality Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

A new story of a sissy's fantasy becoming her reality. But a reality, much more than she ever thought. This will be a multi chapter sissy maid and sissy slut story around Sissy Chantel finding reality of sissy maid and slut life can be more than she bargained for, enjoy. ***** Chapter One: The Journey Starts. Well another night and here I sit dressed in m...