Sissy Maid Spank Stories

37,458 results
Orientation
Length
Source
Infinite Scroll

The Writer's Secret Ch. 09-10

by AnnMichelle on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 9: Laura's Mall Odyssey Loren was sweating bullets by the time Stephanie finally parked the car. He expected they would go home. They hadn't. Instead, they were parked outside Raycine's, a department store at one end of the Valleyview Mall. The mall was only five miles from their house and they shopped here occasionally. "I can't go in there." "Yo...

New Job, New Life as as Sissy Slut

by sdbottomslut on Sep 25, 2017
Transsexuals & Crossdressers

I was nearing my thirtieth birthday and times were getting tough financially. I had gotten laid off from my job and was collecting unemployment and doing some part-time work helping out friends with odd jobs. One of them suggested that I look into cleaning houses. I've always been very neat and people often thought I was gay. I had dated many women, but neve...

Sissy Maids & Sex Slaves Ch. 01

by RickyRooster on Sep 13, 2017
Fetish

Reader Notes This is a fantasy story patched together from a series of e-mails I have sent to a very sexy lady. She loves bisexual men and she loves men who wear panties. She is dominant but in a very genteel way, if that is possible. It's told and written in a different style than I usually employ. I feel this style is rather staccato, telling her what w...

The Writer's Secret Ch. 07-08

by AnnMichelle on Sep 16, 2017
Transsexuals & Crossdressers

Synopsis: Loren had no idea what he was getting into when his agent suggested he write transvestite fiction. Nor did he realize how eagerly his wife Stephanie would embrace the idea of feminizing her husband. How far would they go? Chapter 7: Laura Buys Shoes. . . Lots of Shoes Loren rolled out of bed the following morning. He yawned. Despite having sex w...

Creating Ginger Ch. 06

by Ms_Allison on Jun 9, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into dominance and submission. If these are not topics you are interested in, then please move along. In the below story I refer to the male character several ways but try to maintain a consistent in referr...

Creating Ginger Ch. 09

by Ms_Allison on Aug 31, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into dominance and submission. If these are not topics you are interested in, then please move along. ~~~~~~~~~~~~~~~~~ To say ginger was in hell would be an understatement, although it would be more accur...

Slave to My Indian Maid Ch. 05

by spankedboy on Sep 19, 2017
BDSM

My older maid involves the younger maid in my punishments – Tarek Zia. It was 11 pm on a Thursday night, and everyone in our house was in bed, fast asleep. Well, almost everyone. I was in the servants' quarters, in my maid Rashida's room. She was sitting on the bed, and I was lying naked across her knees on her lap, while she, my maid servant, was spanking...

Slave to My Indian Maid Ch. 10

by spankedboy on Oct 12, 2017
BDSM

My maids make me their personal maid and chore slave (continued) - Tarek I would like to thank Ms. AT Khan for reviewing some of the story with me. - Tarek ***** Let me start once again from the events of the following morning. I had just woken up with a sore bum - the result of last night's spankings. I was just about to head to my washroom when I rem...

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...