Sex With Sissy Maids Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

Life's Changes Ch. 14

by Scribler on Sep 19, 2017
Fetish

I awoke to a gentile kissing of my neck. It felt so good that it brought a smile to my lips. I was almost positive that it was Bill kissing me, but I couldn't sure. I enjoyed the feeling so much that I made believe I was still asleep so whoever it was would continue. I next felt my sides being touched then a hand on my tummy "I can see you smiling, you snea...

Sissy Shopping

by Candour on Sep 25, 2017
BDSM

My first story, finally edited and tidied up. I hope you enjoy it, I enjoyed writing it. --------- You were standing in your local department store in the make up section, looking for foundation. Not too sure what you are doing, and must have looked a little lost as one of the sales girls came up quietly behind you. She was a delightfully pretty 18 year ol...

Transforming Brent

by sissymissyct on Jul 9, 2019
Loving Wives

Katherine decides she wants to live with her lover Wendy. They come up with a plan to slowly change Wendy's husband, Brent, into their girly sissy maid full time. Will his resistance be broken? I put it in loving wives but it fits multiple categories. Will he will learn to love his new role in life? Yes, The narration switches between characters. If this bo...

A Sissy Saga Ch. 22

by Snurge on Sep 15, 2017
Novels and Novellas

By mid-afternoon Open Day for many was adjudged over, but while prospective clients and the purely curious were encouraged to depart the most valued of Miriam Hancock's supporters were skilfully spirited away elsewhere for tea and cakes. While the men went to the gymnasium, the ladies were assembled in one of the classrooms on the second floor where the desk...

The Slave Couple Ch. 03

by vvernbull on Dec 25, 2018
Fetish

Chapter 3- Gotcha and now you're mine. Dave Forsyth didn't know what the hell he was getting himself into. The fool practically walked into his own nightmare. He did this by being careless to the wrong person. A mistake that was to cost him very dearly. This is the story about a husband, his loving wife and dominant black man with a taste for sexual depravi...

Coffee, Tea or Chastity

by stateofdenial on Sep 14, 2017
Fetish

She jostled the beverage cart down the isle of the aircraft. She moved with a slow deliberate purpose. Her first goal was to do her job and tend to the passengers. Her second served her own. This was the first flight of her new route and she needed someone at her destination. She had a gift. One that she had honed to perfection since discovering it as a tee...

Fantasy Weekend

by DWornock on Sep 24, 2019
BDSM

MF, MM, MMF, FMF, Fetishes: sexual role-playing, cross-dressing, domination and submission, and pain. The youngest person in this story is a 19 year old receptionist. 4Play has given me permission to make modifications and additions to his story "Date Night." I changed the title to "Fantasy Weekend." I also added the first paragraph to chapter 1, deleted...

Life's Changes Ch. 08

by Scribler on Sep 16, 2017
Fetish

I awoke to the sense that something was different. I realized I wasn't in my own bedroom. The only light was coming from somewhere behind the wall. Then I smelled the scent of fresh brewed coffee close by. I felt a warm body next to mine that held me in its grasp. It was female. I could feel the swell of her warm breasts against my back. And the faint smell...

The Replacement

by ChristopherDB on Sep 17, 2017
BDSM

The Baroness would be home soon. She was a realtor so her working hours changed day by day. I'd taken to eavesdropping on her phone conversations and checking her agency's web site for her open house schedules in order to have a rough idea of when she might return. Starting with the second floor of the townhouse condominium, I double checked the bedrooms an...

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...