Sissy Maid Stories

19,946 results
Orientation
Length
Source
Infinite Scroll

My Father, The Maid

by SissyOona on Oct 16, 2018
Transgender & Crossdressers

I thought it was really weird when I received the random text from my step mother, even though I had known her for most of my adult life as my father's new wife we had never really been close. Hell, for that matter I had never really been close to my father either, he was always pulling long hours at the office when I was young, so he was never around. Nowad...

Sissy's Decline into a Slut Pt. 03

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Five: Oh, Oh, Things Look to Begin to Radically Change for Chantel. Well another week has passed by, it's Friday evening and tonight I have to go back to the rest area to hook up with Barry and Ralph as they instructed from last Friday after having me suck their cocks. They promised me that they will fuck me tonight and share me with even more men....

No Choice

by AZgirlMichelle on Sep 16, 2017
Transsexuals & Crossdressers

You act as if this is news to you. I'm surprised that you would even question the fact. This isn't a bedroom game. It never was. I have a plan and you WILL follow it. Choice? What choice? Whatever gave you the idea you had a choice? I told you that things would change if you wanted to live with me. I told you it was my way or the highway. And what did you s...

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...

Developing Emma Ch. 02

by Sputnik57 on Sep 19, 2017
Transsexuals & Crossdressers

She awoke to the sickly smell of a woman's perfume; the silky stockings were still there, but Emma was now naked apart from a chiffon negligee, her hands bound behind her back. The voice of the woman broke the silence. "Hello again 'Emma'; that's a very pretty name you've chosen for yourself, we shall soon have you worthy of being Emma, and you'll soon know...

Girl's Night Pt. 02

by DifferentBreed on Sep 14, 2017
Fetish

Fisher was upstairs, making the bed when he heard the front door opening, signaling Sophie's arrival home. He looked down at the list on her dresser, frowning. He had not completed four tasks. He reapplied his pink lipstick and kissed the paper above the words "make bed with gold satin sheets" as he was instructed. He then scurried downstairs, incomplete lis...

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...

Mistress Chronicles Ch. 01

by MistressMtoyou on Sep 25, 2017
Fetish

Subject and background. This is a recap of my first in-person session with a submissive. The subject passed the various pre-session requirements described in my second story "A few good subs" and after an extensive interview and evaluation process I offered him the opportunity to do an in-person session. I'll admit upfront that I was a novice at this point...

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 Maid Son Pt. 03

by Robyn228 on Oct 21, 2019
Transgender & Crossdressers

Note: This story is entirely a work of fiction, and should only be viewed as a fantasy. Any similarities to actual events or people are entirely coincidental. All characters are over 18. ***** Peter stood there looking at the black stilettos, with so many questions on his mind. He wondered why his brother would ever own stilettos, much less why their mothe...