Male Maids Stories

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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...

Days of the Raj Ch. 01

by aaronburr on Sep 17, 2017
Exhibitionist & Voyeur

(Let me lead you through the sepia-toned, historic setting for this tale - colonial India - where you will experience some of the most delicious Clothed Female Naked Male fun you have ever come across. On the banks of the Ganges the senior boys' college was filled with aristocratic 18 year olds, thrillingly subject to the discipline of female English teacher...

Recruiting of a Sissy Maid Ch. 10

by Sissy_Chantel on Nov 23, 2017
Transsexuals & Crossdressers

Chapter Ten: Changes Continue for Chantel as Her Relationship with Carl Grows. Awake and having a great breakfast superbly made by Carl, Chantel enjoys her morning with him. He has her in one of his robes as they talk about things and their future together. After breakfast Carl says, "Put on a pair of my jeans with your white satin blouse, you can wear yo...

Eleanor of Penkhull Ch. 03

by Sputnik57 on Jul 13, 2020
BDSM

Despite having to duck low to avoid the swirling cloud of sooty smoke from the huge Bottle kiln below which she stood, Elaine Stringer's cunt bulged lusciously, on the confirmation of her prior thoughts that the urchin at her feet was a submissive. He may have been in need of some less worn clothing, but his slight yet robust masculine shape would please wom...

At Her Disposal Ch. 06

by Sputnik57 on Sep 14, 2017
BDSM

The mule was flanked by the two victorious horsewomen, and the hanged male's journey to meet his purchaser began, his cock erect and rubbing at the silken bondage with the movement of the mule as he squirmed, his anus tingling at his divine sense of helplessness as it clenched and dilated on the stimulating plug as the two women whipped mule and enslaved ars...

Freedom and the Widow Ch. 15

by Sputnik57 on Sep 14, 2017
BDSM

In the hot morning sun beside the pool, Eric was put to good use by his mistress. As she, Wanda and Cherie basked naked, Eric was pleased to be of service to the three women; he was told to remain naked too and the women enjoyed noting his unhidden excitement as he oiled their shimmering bodies in the warmth of the sun. The women took great delight in allowi...

Recruiting of a Sissy Maid Ch. 04

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Four: Chantel, Fitting Into Her New Lifestyle. Master Holt says, as the two of them walk out from the elevator on the 2nd floor, "This will be the floor that you will begin your life in servitude to us Chantel. Lets go find your head maid Penny and then get you to your room." Chantel grows more and more resigned to this new life as she see's a very...

Sissy Chantel, New Reality Ch. 10

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Ten: My First Saturday and Sunday as They are Special Days For Us. "Wake up girls." as sissy Traci calls out to us. We all rise from our sleep and another day in our sissy maids, sissy sluts lives begins. Just like in the previous days starts we spend our time with a morning enema, shower, shave and makeup. We get dressed but not in any maids out...

A Maid for Timon

by TarnishedPenny on Aug 28, 2018
Sci-Fi & Fantasy

This is my entry for the Summer Lovin' contest. Thanks for your interest! + "Have you decided on your mating gift yet, Timon?" The young man looked at Ranin, his cousin and best friend. "I have been thinking of my grandfather's knife," he said, stepping around a puddle in their path. "Will your father permit it? The knife has been in your family for ge...

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...