Femdom Sissy Maid Stories

21,516 results
Orientation
Length
Source
Infinite Scroll

Black Femdom For Black Sissy

by Samuelx on Sep 11, 2017
Fetish

Sitting comfortably in her basement/dungeon, Ottawa's premier dominatrix Madame Whitley looked at her submissive, Shane Johnson, as the big and tall, formerly masculine Black dude stepped out. Clad in a pink Tutu, blonde wig, crimson pantyhose and high heels, the brother was finally letting out his inner slut. For years, Madame Whitley struggled to help Shan...

Miss A's New Play Thing

by Pornenthusiest on Oct 8, 2019
BDSM

Chapter 1: Sexual Awakening Alex's morning ritual had changed lately. Typically he would start his day by slamming his alarm clock, getting out of bed, brewing coffee and taking a shower. But now, Alex was generally restless, always waking before his alarm could rouse him. He would rush to his computer immediately checking his messages, today was no differe...

Cuckold's Descent

by syncbush on Mar 27, 2020
Cheating Spouses

Thank you to those of you who have liked or taken the time to comment/message me. I really appreciate the feedback. Feel free to add additional chapters, suggest ideas or leave comments. It is great to get ffedback and encourages writers to continue developing the stories. And special thanks to the Admins for making this story of the week! Really appreciated...

Open in Reader

Sissy Manners Classes Ch. 01

by fridaysissy on Sep 12, 2018
Transsexuals & Crossdressers

It was late night, I am 10 km away from my room waiting for sharing cab or auto service to reach my room at last I joined a sharing auto service with two members including me. The other passengers stop came early, and I remain alone in auto waiting for my stop to come. Driver said he is stopping the service and returning to his home and asked me to get down....

My Stroll outside the Car

by triffle64 on Sep 12, 2017
Transsexuals & Crossdressers

It was a beautiful evening in the spring of 1982. My wife and I were taking a drive up the coast of California for an evening stroll. She was driving. We had been married for about 5 years. She was 27, and I was 30. My wife is feminine, but she grew up as a tom boy. I had no idea that she would take so well to my submissive desires to be her sissy husband. T...

The Women in My Life Cuck Me Ch. 02

by Philyssis on Mar 18, 2020
Fetish

Continued from part 1, right in the middle of a sex club... I was relieved when my wife grinned. Then I was a bit concerned as it turned into an evil grin. "Wow Phil" my wife said to me. "I knew you had a dirty mind, but I didn't know you had THIS in you!" Amy, my wife's little sister, leaned over and kissed me on the cheek, then looked at Tara, "I'm s...

The Massage Away Ch. 01 Pt. 01-02

by formyqueenspleasure on Aug 20, 2018
Fetish

Fair Warning 1 - I am a first time writer Fair Warning 2 - this story involves Femdom, a wife, cross dressing, sissy husband, interracial, group sex and obviously may not be everyone's cup of tea (but I hope it is appealing to some comfortable fetishists!) The first chapter is tame. Fair Warning #3 - stupid ignorant comments will be ignored. If you don't l...

Whore for Succubus Ch. 02

by Mixedwritings1993 on Sep 13, 2017
Sci-Fi & Fantasy

David woke up at around 8 o' clock in the morning. He was feeling really numb and half dead to begin with. He wondered what dream-like state he was in as he tried to differentiate between his trance and reality. Both of them seemed identical, except for the presence of a specter-like, bizarre woman. His hands were holding his penis lightly and he felt the od...

The Wedding Ch. 05

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

(Patti Cake part 3) Chapter 5 -- Femdom, Fucking and Femininity... At the end of our time spent with Ms. Walsh, I was left with a lot of questions and I wasn't sure how to deal or cope with any of it... But one thing was for certain, I was starting to see more of the old Patti bubbling back to the surface, being direct and without compromise... The whole d...

A Big Surprise!

by rj1774 on Jul 6, 2020
Transgender & Crossdressers

As a man's sexual desires come to light this story features, femdom, pegging, crossdressing, and dating a TS woman. Please share any constructive criticism or where to take a next chapter. I hope you enjoy! **************** My sweet, caring, brilliant girlfriend, Stephanie, and I have been dating for a few months and we decided to plan a long weekend get a...