Bondage Cross Dressing Stories Stories

121,386 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Tags.

by RicoLouis on Apr 19, 2017
Miscellaneous

As seen below their are many names for the large variety of sexual topics and no real agreed upon list of Tags so I am making a list as best I can to help readers find the stories that interest them. I will be using the most common named tags to make it easier for the readers to find what they like. Below we have an example. Name Stories Blowjob 34...

Open in Reader

Story Tags and Searches

by wishfulthinking on Sep 18, 2017
How To

I read this really great story a couple of months ago, but I can't find it now. I'm sure it had black/blue and/or orchid in the user name, and it was about a girl and her boyfriend at her boyfriend's place for a party, and she ends up sleeping with his cute dad. (If any one knows the story I'm talking about, please PM me! Seriously) I've searched: boyfriend...

You Can Always Say No Ch. 01

by AngelCherysse on Sep 25, 2017
Fetish

I have always considered myself a liberated woman. Rising through the business ranks to become a Vice-President at a major media consulting agency was just one of many goals I set, then met. I don't see any conflict between that and being a 'girly-girl'. I'm not ashamed to admit; I have used my raven-haired beauty and generous natural charms to advance my ca...

Friday the 13th Pt. 01

by Slave_Georgina on Sep 14, 2017
Transsexuals & Crossdressers

This is my first attempt at fiction. Part 1 is to set up the following parts and act as a foundation for the story. Please bear with me and I hope you will find the completed story enjoyable. My thanks go to SlaveGirl70 for her editing skills and to LunarSirius for his review and ideas. ***** Ha! I should have known that if my life was going to take a ba...

Lisa, A Story From A Male Admirer

by RubberBudcus on Sep 16, 2017
Transsexuals & Crossdressers

This story is based on the truth and real people. It all started in a routine sort of a way. Well, routine in a Literotica sort of way really! Let me explain. I am a lifetime fetishist. Male, 63, heavy build and hairy to gorilla standard. I experimented at an early age with wet clothing and kept at that converting to female attire through two marriages, tw...

The Last Graphic Fantasy Pt. 02

by RalphKing on Mar 16, 2020
Romance

Again, with thanks to DawnJ for her invaluable help with the editing The next evening, the party in the shop went well. I had a chance to meet all the volunteers and staff and as the drinks flowed, the atmosphere was great. When the time came for us to hit the local bars, Nicola asked Trudie to stay behind whilst she changed. I and the others went off to th...

Model Slave Ch. 01

by Oupa99 on Sep 26, 2017
Exhibitionist & Voyeur

This is basically an erotic love story and of course all characters are over 21. It will definitely not start out as a love story, but it will get there. Please vote often (fives are most welcome) and of course please leave constructive comments. PS -- If you have fantasies, ideas, etc for new stories please let me know, that includes twists on existing sto...

And When I Return Ch. 01

by sublocked on Sep 25, 2017
Transsexuals & Crossdressers

The first of many chapters to come. This may not appeal to many, but I hope that those that like it, like it a lot. Smiles to all those cross dressers, fetishists, and sissies out there. * Jason had been dreaming of this for years, planning it for months, and as he lay in bed, sleepless beside his wife Jenna, he had some last minute pangs of guilt. The tw...

Something Had To Change

by sublocked on Sep 16, 2017
Transsexuals & Crossdressers

This was not going the way Diane had thought it would or should. Basically nothing, and yet everything, had changed in their marriage in the last six months. She watched him now, sitting on the sofa, drinking a beer, unshaven, and between picking his nose and scratching his ass, she wasn't sure what his biggest pleasure was. At least he was fit. There was...

My Biography

by spknannie on Sep 14, 2017
BDSM

My name is Annie; my nickname is Spankin Annie, we will be described this nickname as my story continues. I am an attractive buxom, quite curvaceous single woman in my early 30's. I have big long red curly hair, dark skin, plump cheeks and deep sexy blue eyes. I'm a white, 5'7" tall woman with a DD breast size, my measurements are 46-34-38 and I weigh roughl...