Slutty Sissy Maid Stories

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Becoming a Sissy Maid & Slut Vol. 07

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Thirteen: Work, Work, Work, Around the House, At the Adult Store and as a Slut at Night. Monday, morning and back to my sissy maid services. Promptly I wake up at 7:30am. As per usual my morning routine of an enema, showering and dressing. Today I did have to reapply depilatory cream to keep my body smooth and hairless. It takes an extra 10 minutes...

Sissy's Decline into a Slut Pt. 06

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Eight: Moving Along with my Sissy Maid Life and lots of Sissy Slutty Sex too. [Beep, beep, beep] My alarm clock goes off and a struggle to wake up. It is 7:00am and I come around to realize I'm in my sissy bedroom in my Master's house. I get up quickly now, in my white satin bra and panty with white satin full slip, this is my sleeping lingerie. I t...

Becoming a Sissy Maid & Slut Vol. 05

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Prefix: A continuation of my sissy maid and slut journey. I hope you all do enjoy my unfolding story here. I am writing further chapters with hopes to give you all a semblance of some of my sissy ideas and thoughts so that these may excite you as the reader. I will try hard to keep each chapter on an exciting flow of what I feel may be life of a full time si...

Becoming a Sissy Maid & Slut Vol. 09

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Prefix: I will be fast forwarding a few days in my sissy maid, sissy slut lifestyle story here. From the last chapter ending on a Tuesday night going into my second week as Master George's full time sissy maid and slut to that of me getting ready for the following Saturday night of slut service. I feel the story's journey no longer has to follow a linear da...

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...

Becoming a Sissy Maid & Slut Vol. 10

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Seventeen: It's time that Chantel Earned Her Keep. Well it's the morning of a Saturday, to where by night time I will soon be doing some true sissy slut street walking and now truly begin to earn my keep and begin to earn some serious money for my Master. I awake like all other mornings at 7:30am and follow my morning routine, enema, shower, shave...

From a Husband to a Dutiful Sissy Ch. 05

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Five: I'm going to be more than just a sissy maid. Waking up Sunday morning, I sit in my bed and think about my slut duties last night at the rest area. I get into the shower and it all floods back to me as I shower, then dry off, moisturize and get back to my maids quarters and do my makeup, put on my bra, panty and maids outfit, black one today wi...

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...

Futanari Academy Ch. 14

by TheOrcKing on Jun 10, 2019
Transgender & Crossdressers

(All characters participating in sexual activity are age 18 or over.) This chapter is a repost, it has been edited and has undergone very minor rewrites for style and flow. Nothing in the story has been changed. Halloween Special, 2018 Danielle walked up the steps to her friend Maddie's house, still wearing her Westbrook school uniform which now consisted...

Sissy's Decline into a Slut Pt. 05

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Seven: I've been taken, Made into a Maid, Turned out as a Slut. Two days have passed by, it's Thursday morning. Today Master Gage and Master Martin are to arrive by 10:00am. I awake by 8:00am and my stomach is turning. I get up sit on the edge of my bed wearing my sleeping lingerie today it's a white satin full slip, white lace bra and satiny panty....