Fiction Sissy Maid Books Stories

71,161 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

The Valentine Surprise

by rogkw99 on Sep 16, 2017
Transsexuals & Crossdressers

(This is not fiction or fantasy. It is a true accounting of what happened to me last Valentines Day. Even if you think it is fiction, I think you will enjoy it. I would enjoy it if it were about someone else and not me!) I can't help but think of Valentine's Day last year, a day that forever changed my life. In the weeks leading up to that day my wife Ama...

Pinky the Sissy Maid

by Pinkytoes66 on Sep 16, 2017
Transsexuals & Crossdressers

Disclaimer: All my stories are pure fiction, unless otherwise noted. Any similar events that may have occurred are purely coincidental. ;) This is part 2 of my current series. Part 1 was "Pinky's First Shopping Assignment". I've yet to decide on a title of the series and am open for ideas. Thank you. *********************** A few days after I completed...

Sissy Maid Son Pt. 01

by Robyn228 on Jul 16, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** 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 walked into his house, feeling excitement clenching in his stomach. He's been pa...

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...

Sissy Auction

by davine on Sep 26, 2017
Transsexuals & Crossdressers

Authors note: this story is a fill in while I get over a block with the fifty shades part three. I also need to revise part two of sissy downfall as Literotica rightly pulled it due to excessive violence. I wish this story was autobiographical. It's not but has some elements of truth in it. I hope you enjoy reading it. I love feedback; even negative. All cha...

Forced To Get Dumped

by footcucknerd on Sep 16, 2017
Transsexuals & Crossdressers

James looked at himself in the mirror and shuddered, wiping another tear from his eye. He had to refrain from crying today, it would only make everything worse. Crying would ruin his make up and earn him a stern punishment before bed. Not to mention, his Mother would probably make good on her threats if he didn't perform perfectly today, and there was no way...

Sarah Applied to be a French Maid

by SarahCD on Feb 26, 2019
Transgender & Crossdressers

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences my writing skills have improved a little. While I cannot change what actually happened to me, I have added some more detail and corrected some g...

Steve's Maid

by Mixedwritings1993 on Sep 13, 2017
Fetish

Steve always had a thing for maids. He doesn't know what actually turns him on, their uniform or really the person inside the dress, but when there is a maid around; Steve can never keep his eyes away from her. Back at states when he was with his parents, he had an older lady as their house maid around her late thirties. Steve can't even count the number of...

Sissy Life: 50 Days in Chastity

by sissymark79 on Sep 15, 2017
Transsexuals & Crossdressers

This is a standalone story in the 'Sissy Life' universe. You don't need to have read any of the other stories to enjoy this one, but it does fit with those in terms of characters & themes. Consider it a 'Rogue One'. ***** 'Congratulations! You've managed 50 whole days of proper service. I'm very proud of you. I knew re-focussing you by putting you in that...

Sissy Maid Son Pt. 02

by Robyn228 on Jul 18, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** 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 wept on his mother's bed feeling violated and abused. The maid uniform still on...