Sissy Crossdresser Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

Glory Hole

by GateKeeper_A on Jun 11, 2014
Group Sex

Last month, you had discovered that your local adult novelty store had a glory hole. Since that day, that glory hole has been all you can think about. Every time you close your eyes, you picture a cock sliding through a hole towards you. Every time you masturbate, your mind is filled with fantasies of strange men's cocks. You shudder with a mixture of trepid...

Promotion/Demotion Slips

by pikapache on Apr 29, 2025

The promotion/demotion slip is one of the strangest types of magical item throughout the multiverse. They are A5 sheets of paper with four bits. At the top of the page was a bit to put the name of the person that is being affected, different people with the same name are not affected as only the person the writer of the slip is thinking about is affected and...

My Metaphor

by hyperpress on Dec 24, 2018
Fetish

The audience drops into a continuing story written in first person POV (mostly). The following based on a true story. Given enough time, any question that occurs to the reader shall be answered, eventually. * I woke the next day, showered, put on a comfortable chemise, a microfiber and nylon blend thong and open toed sandals, made some coffee and sat down...

First Time Blowjob

by MyWhoreWife on Dec 10, 2019
First Time

I'm a man and I love crossdressing. I love the feeling of nylons on my legs and wearing strappy high heel shoes. While wearing them I would wonder what it would be like to suck a COCK in them. Kneeling between a man's legs and sucking his hard and meaty COCK. I started to go to adult cinema's in the downtown area after accidentally discovering their existen...

Basketball Crossdresser

by Cute Little Thing on Sep 14, 2017
Fetish

This story is about an athletic but small man who has fantasized about cross dressing from an early age. When his wife finds a strange number on the phone bill, she calls the number and has a conversation with his phone mistress. What follows contains blackmail, humiliation and of course - sex. If sex and crossdressing offend you, or if you are underage, ple...

Crossdresser's Rassling Dreams

by footqueen99 on Sep 17, 2017
Fetish

The following is an email chain between two crossdresser's who enjoy wrestling. All persons depicted in this writing are well over 18 years old. ***** I wish i could have been there! I would love to see a few pics if u can share. I love pro style fantasy matches. I love all the holds, drama, trash talking and victory poses where u pose with your stocking...

A Latex Crossdresser's Dream Pt. 05

by shinyglove on Nov 18, 2019
Fetish

Please read A Crossdressers Dream parts 1-2-3& 4 before moving on to this story. *** The party was certainly in full swing as we had all seen some sort of action. The room smelled entirely of sex and latex, I was very happy with this as the aroma of rubber turned me on. Every time I opened the bag where I kept my latex collection the smell coming from it w...

My sissy boss.

by mally01 on Apr 22, 2025

Craig was in his office at Lingerie International watching the wall clock his left drifting under his shirt stroking his soft hairless skin. He was waiting for five thirty knock-off time to come. His secretary Charlotte came in and asked if he needed anything else, and he gruffly replied that she could leave for the day. After he had witnessed Chantelle get...

Teaching Assistants CH. 02

by Eli is Coming on Sep 12, 2017
BDSM

[Chapter one is located in the Transsexual/Crossdressers category.] ANNA The following afternoon as was custom Xander and Anna met for coffee before their Latin America class. Both were punctual to a virtue but this time she was early, giving her the pleasure to find him walking through the door. Well, walking was not the proper word for it, more like hobb...

A Mistress, a Sissy, and a Slave Ch. 01

by thejm4n on Sep 15, 2017
Fetish

Clad in a skintight, black latex dress, and tall, 4 inch platform black heels, Jessica was a stunning figure as she looked down at her two slaves, on their knees. "Up" she said to Hailey. "Yes Mistress Jessica." Hailey stood, naked, save for the black collar around her neck. "Now" Jessica said, looking at the other slave, "it's time for a little fun with...