Femdom Sissy Cuckold Stories

14,168 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Sissy Cuckolded by Girlfriend Ch. 01

by SaraRurik on Sep 16, 2017
Transsexuals & Crossdressers

My name is Josh and I'm a 19 year old white guy with a beautiful girlfriend. Her name is Angel and she is the best thing that has ever happened to me. I love her with a passion and intensity that is hard to describe, she is everything a man could ever ask for and more. She is caring, sexy, understanding, kind, intelligent, and totally a bad bitch. We have...

Easy and Hardy

by Tiberius_Daniel on Aug 6, 2019
Loving Wives

Don't miss this modern fable. It's a fictional story, has nothing in common with reality. Please don't suppose anything; I give you only original stories. For local flavor, I used English and London words and phrases. (Example bare means a lot, fag= cigarette.) ***** First chapter For today we have two couples who lived in Chiswick, where rents are high...

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....

The Cuckold's Babysitter

by yumacd on Sep 26, 2017
Loving Wives

Hi, I haven't written in a while. The set-up for the sex is probably too long. I'm thinking of continuing the story. Hope you enjoy it. YumaCD === My wife, Tami, has been cucking me for a couple of years now. Most of you Literotica readers have heard the story before... - It started when I revealed my fantasy of watching her with another man one night...

A Perverse Plan

by Candyboi on Sep 25, 2017
Transsexuals & Crossdressers

It started off with little things, small suggestions, that quickly snowballed into perversion. My wife Carla, who for the first decade of our marriage displayed little interest in kinky sex games became a hot wife virtually overnight with total control over me... Carla is 44, has a very curvaceous ass, 34DD tits, and works as a doctor at the local hospital....

Femdom Cocksucking Contest

by reddbunnz on Sep 14, 2017
BDSM

Chapter 1: The End of Slavery It had been two months since Debbie had been sold into sexual slavery with Beth, and she was becoming very depressed. She had thought that she wanted to be a full time sexual slave to a dominant woman. And, she now is serving as a pussy eating, sexual slave to her friend, Beth. And, her best friend, Marion, was also serving sim...

Training Bi Males

by MistressDelia on Sep 11, 2017
How To

I have written some of my thoughts on training my own bi slave husband in the past and thought that perhaps a primer on bringing new bi slaves into the fold would be helpful. I have been the Domme to my bi submissive slave husband for 15 years. We have been married for 20 years, are in our early 50's, and it was obviously a journey to get where we are and a...

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 Bradfords Ch. 01

by Erotictales4u on Oct 13, 2017
Transsexuals & Crossdressers

All characters in this story are over 21 years old. This is a fictional fantasy that contains elements of both femdom and transsexual/cross-dressers niche, it is focused on humiliation. This is the first of a new series. I would love your feedback. ***** "What the fuck is the meaning of this Tim!" screamed Tim's wife Jane as she ran her hand through her lo...

Adult Trip Pt. 02

by cuckcpl4play on Jul 3, 2018
Interracial Love

The trip back to the room was embarrassing given I was coated with the cum of my new Master. I rushed back and within seconds of arriving, my phone went off. The text read, Dearest white slut, please provide an inventory of the sex toys that were brought with you. It is now 4:00 and I expect you and your small dicked cuckold husband to join us on the beach...