Male Maid Stories

87,121 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 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...

Becoming a Sissy Maid & Slut Vol. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Title: How I became a Sissy Maid and Slut for a Dominant Master. Preface: I would like to begin by thanking all who will read my story here. This is a sissy story based on many thoughts I have imagined, many times throughout my life. These erotic thoughts have been enjoyed for a long while in my life. Like many sissy girls, stories like the one I will wri...

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...

From a Husband to a Dutiful Sissy Ch. 02

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Two: My reveal, a true reveal for the sissy in me. I reach to the bottom of the stairs and at the front doorway entrance, Helen and Jenny are standing and looking at me in my black maids dress, white tights, black velvet 5 inch spike heel pumps, wig and makeup. The look on their faces seeing me dressed as such is priceless. This is the first time He...

At Her Disposal Ch. 07

by Sputnik57 on Sep 17, 2017
BDSM

Fiona Brown slipped a finger through the slick wetness of her cunt, as her masked pet was choked back on the leash as he masturbated on his knees. She stood in regal triumph in the comfort of her room at the Palace, the East End publication presented to her by the astute women slavers, open at the picture which confirmed the extent of her dominance so graphi...

Recruiting of a Sissy Maid Ch. 11

by Sissy_Chantel on Nov 23, 2017
Transsexuals & Crossdressers

Chapter Eleven: People Moving into New Roles and More. Chantel has made her way back to her club dorm room, enjoying the corrective measures of being a Domme over Biff and Marty. She is certain they will be much more mature and even though they still hold powers over the sissy girls like all other male minder/staff, they will better respect what these sissy...

New Girl Ch. 02

by tiffanymanners on Sep 16, 2017
Transsexuals & Crossdressers

Olivia's hands shook as she read the note, a look of stunned disbelief on her face. She had to hold on to the bar for fear of falling over. The note shook her to her core. 'Olivia, Tim agreed to leave with me. I am in the process of moving. Please come to my new address in two months time, at 7 p.m. 4744 Patrick Road. No point coming to this address until t...

Freedom and the Widow Ch. 19

by Sputnik57 on Sep 14, 2017
BDSM

Victoria silently slid the bolt on the rear gate to open, before pausing and waiting a moment. She smiled as she imagined the scenario had she not bolted the gate and her staid friend had arrived just five minutes earlier; she'd have seen just how merry a widow she had become, and one the gardener was prepared to show his humblest respects for. The thought o...

From a Husband to a Dutiful Sissy Ch. 07

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Seven will also advance the time of my story here a bit. To move my story along into a lifestyle changing story I will have this chapter set seven months after Phil was outed as crossdressing sissy named Chantel. Over the last seven months, life for Chantel has become entrenched as a sissy maid and slut. The sex video productions put up online have...

She Male Maid Ch. 01

by Anal Slave on Sep 12, 2017
Transsexuals & Crossdressers

My wife has a real good job and she has made lots of money this year. She has been working long hours and she decided to hire a live in maid. Someone to clean the house and cook meals. I wanted a butler but she insisted on a maid. I was away on a trip when she hired a maid named Rosey. All my wife Pam would say on the phone is that I will be surprised when...