Happy Maid Stories

160,291 results
Orientation
Length
Source
Infinite Scroll

Feliformia Ch. 11

by Tigerstretch on Sep 21, 2020
BDSM

"Master Mark! Aaah! You are hurting me!" "Just a bit longer, Syr, you can endure it for me, I'm sure. Both of us are going to be happy when this is done." "But, I'm bleeding. I'm not acting this time. You are too rough." "I'm not too rough. You are going to be fine!" "Be more gentle. AAaah! Not like this!" "Stop whining! You promised to do this for me."...

The Ant Woman Ch. 18

by DreamerByTheDiamonds on Oct 7, 2019
Sci-Fi & Fantasy

"Certainly you won't mind, Dear Wood Consort, if I play with your maid for some moments?" Empress Consort Miseo was in a playful mood this late morning. Wen couldn't help but smile. "I'll miss her once you take her away," Wen said from her seat in the reception room, "but I can rest well knowing she'll be cared for." She gestured towards Yuwei. Faintly s...

Magic Dress - Diana Pt. 01

by SlightlyRude on Apr 23, 2019
Transgender & Crossdressers

THE BEGINNING Shit! I thought. Oh fuck! Buggeration! Damn and fucking blast! Here was I a happily married man, standing in a dress. A real woman's dress. And I liked it. I really liked it. It was fucking wonderful! "Oh," I said. "What was that?" said my wife Gwen, just adjusting her moustache. "It's surprisingly comfortable," I answered weakly. "Hmn,"...

My Live-In Slave

by Martin Young on May 1, 2006
BDSM

It was Friday night and I was having a great time. I had been dating Sandra for almost a month and she was truly the girl of my dreams. She was beautiful, funny, smart and every time I was near her my heart started beating like an angry carpenter with a hammer. That specific night I had taken Sandra out to a fancy restaurant. The food was excellent and we we...

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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...

Meeting Leilani

by SandraMustard on Sep 12, 2017
Group Sex

[ This story was originally submitted in 2012 for a contest. I recently removed all my stories but I have been convinced to return them for the entertainment of readers. I am not playing any ratings game or wishing to plagiarize myself. Written by Sandra, the female half of a Literotica user-couple, in collaboration with and edited by Jack, her husband, thi...

The Profitable Wife Ch. 02

by Shadovin on Aug 21, 2018
Fetish

Chapter 2: Understanding the Game Last night was the first time that Izzy and I had truly had anal sex. The first time she had reluctantly tried and we had barely started before she played like it wasn't right and stopped everything. We didn't sleep together for over a month after that. After last night, though, I have begun to wonder what has really been g...

Welcome to the Party

by Sweetlisatv on Sep 14, 2017
Transsexuals & Crossdressers

Over the years I had dressed I had many experiences with guys, couples and dipped in and out of the Bdsm and fetish scene as I felt like but it wasn't until I was invited to a private interview I really got involved. It was a sunny Tuesday morning and as I awoke in my favourite purple satin baby doll and panties I felt the need to play so going online I sea...

The Princess Ch. 01

by Surprise1997 on Sep 13, 2017
Loving Wives

More than anything, Jessica had always wanted to be an English Princess. That had been her burning desire since childhood. Now, at age 23, she was Her Royal Highness Princess Alfred of Wilshire. A lifetime of social climbing and positioning had paid off. Her new husband, Prince Alfred, was a cousin of Her Majesty the Queen. A long time ago, he had been a hi...

From a Husband to a Dutiful Sissy Ch. 03

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Three: My sissy maid lifestyle becomes more set in reality. Morning comes and I carry on my new sissy morning ways, shower, shave, makeup and dress up in my maids dress, this morning a pink satin one over pink pantyhose and pink patent 5 inch spike heel pumps. I dutifully prepare breakfast for my Mistress Helen and get a bowl plain porridge for myse...