Adult Anal Cd Tranny Gangbang Stories Stories

118,399 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

A New Adventure...

by johnjinglez1 on May 16, 2018
Transsexuals & Crossdressers

I saw someone begin a "diary" of their experiences as a sissy on here recently and it inspired me to give it a shot myself. The following will be true stories from my past starting from the first time I ever hooked up with a Tranny / Cross dresser / Sissy. First things first, I consider myself to be a straight male; despite having had sex with all of the a...

A New Adventure... Ch. 04

by johnjinglez1 on Nov 19, 2018
Transgender & Crossdressers

This is the fourth installment of my "Sex Diary." For the better part of a year and a half I decided to try some new things in the world of CD / TS / Sissy boys. All stories are 100% real. After my last encounter with Mia things really started to cool down on the TS/CD front for me; I'd met a couple of girls who really interested me and were satisfying my s...

The Hentai Simulation

by FootLicker8 on Apr 29, 2025

(Cover image by Kairunoburogu) This story is public and I would greatly appreciate if you considered writing your own branch for it to give some more options to the readers. Anything allowed by the Chyoa rules is allowed here as long as it fits the premise of course. Please read the writer guidelines to help you fit your branch with the overarching lore befo...

Open in Reader

Joel Gets Caught by His Wife

by Downforeverything on Sep 18, 2017
Transsexuals & Crossdressers

This is a fictional story written for a fan about their sex life. If anyone else has a story they'd like written for them about fact or fictional events feel free to message me. As always please leave comments or constructive criticism so I can make your pleasure better! * It was Monday afternoon. Joel had taken the day as an opportunity to work from home...

A College Sissy Ch. 03

by nat_rose on Sep 26, 2017
Transsexuals & Crossdressers

There was the time I was playing hide and seek at my friend's house. I was hiding. I ran upstairs, looking for some place to sneak into so I wouldn't be found. I felt my time slipping, but before it was too late, my friend's sister caught onto the game we were playing and waved me into her room. Her name was Stephanie. I was a shy kid, and my face turned r...

The Virgin Tranny & the Bride Ch. 08

by yano on Sep 25, 2017
Transsexuals & Crossdressers

My transvestite friend Roberta writes to tell me that recent surrender of her boy pussy to her Master was, sadly, not for love but as a means of gaining embarrassing video footage to use as sexual blackmail. Master John is now teasing Roberta and she is about to embark on a new career as a call girl and prostitute. She writes: With the lining removed and m...

A Few Notes from Mindy

by mindyrose on Sep 17, 2017
Non-Erotic

Dear Literotica Readers: Some random thoughts, in no particular order, about my story that don't seem to fit into my narrative but should help you know me better, which should help you understand the themes of my transition stories... Thank you to all of the people that have left me positive comments. I haven't been writing the stories for public approval;...

Mistress Chantel, Tranny Dominatrix Ch. 12-13

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twelve: Another Play Day Work Day at Our Studio. I arrive at my studio dressed for another day of fun and exciting dominatrix work. I park my "Plum Crazy Girl." step out in my red leather thigh high boots over my black sheer pantyhose. On my feminine looking body is a red leather form fitted mini dress with loose pleated, A-line skirt barely coverin...

Recruiting of a Sissy Maid Ch. 15

by Sissy_Chantel on Dec 22, 2017
Transsexuals & Crossdressers

Chapter Fifteen: Life Changes but Normalizes Monday morning, Carl and Chantel are up and at it, breakfast in the hotel restaurant and then a shopping excursion to an are Jewelry store for Carl to buy Chantel her engagement ring. Dressed sharply but casually Carl in a white button down shirt, Khakis and black walking shoes. Chantel a white turtle neck, black...

When Desire Boils Over! "SWALLOW"

by 7yearsitched on Sep 14, 2017
Fetish

My experiences accrued between my two marriages. I had watched straight porn through my teenage and early adulthood even though I had girlfriends that I was happily and regularly engaging in sex with. I generally watched straight porn. I enjoyed like most, girl on girl for a couple of reasons, for one they were all pretty hot and there seemed to be a few...