Sissy Maid Stories

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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...

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...

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. 06

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Six: On My Way to My New Life at The Agency. Well the day has come for my transition in my life to becoming another sissy maid and sissy slut (aka: comfort girl) to 'The Agency'. Over the last two hard and humiliating weeks Master Camron and Sir Gage now as paid agents to my joining the team at 'The Agency' have helped me sell, give away or toss o...

Sissy Chantel, New Reality Ch. 02

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Two: If One was Fun, Two will be Better. Late night I get a call and I look to see that it is my new Master. I answer, "Hello Master Camron, how may I help you?" "Bitch ass sissy, I am gonna need you here tomorrow morning, by 10:00am." he excitedly replies. I reply, "Oh, ok I guess I can make it to your home tomorrow morning Master." "You God Dam...

Sissy Chantel, New Reality Ch. 05

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Five: Oh, Oh, My Surprise. "Ohh, Ahhh...Wha...what." I say as I wake up and am lost with where I am and what is going on. "What the... What the Hell? Where am I and what is this? Huh, what the Hell? Why am I chained and padlocked around my waist?" I'm groggy and very confused as I look at the room, dimly lit with a single hanging light bulb, I'm on...

From a Husband to a Dutiful Sissy Ch. 06

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Six will compress time a bit more forward in moving the story through time. It will be set two months forward from the original start date of the story in Chapter One, when Helen found out her husband Phil enjoyed crossdressing and fantasized about being sissy maid and a sissy slut. It all picks up with bit of recollecting from Phil who is now Chante...

Sissy Maid to Be... Ch. 03

by missjennymaid on Apr 8, 2019
Transgender & Crossdressers

I would recommend reading the first chapters to get to up to speed on the story, but if you want to start in the middle... Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife. Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves. Jere...

Sissy's Decline into a Slut Pt. 04

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Six: Chantel's Decline is Achieved, Owned by a Black Master as his Sissy Maid and Slut. I cannot believe at what is happening to me here. Master named Gage is about to purchase me and place me into slavery as his sissy maid and sissy slut. I am near in panic, I want to run away, get into my car and drive for the safety of my home. But I know this wi...