Erotic Crossdressing Stories 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

Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

Mando & Lek

by Purple_Raihne on Sep 16, 2017
Romance

(I was writing this story when I was involved with two people. The three of us were the character basis. But they ended up committing to each other and forgetting I even exist, so I have no desire to bother trying to finish this story in the slightest. No names need to be changed as I already changed their names and Marie is my own middle name. To whomever d...

My Life as Isaac Newton

by Prizmatic on Sep 16, 2017
Romance

This character has nothing to do with the Isaac in Midnight Plush (q.v.). The idea for this story came in a dream, and that was his name in the dream, so I didn't change it. This is the closest thing to a traditional short story I've submitted, and I would really like solid critique on it. Especially, did I do a good job of writing from a man's point of view...

Just a Girl

by katie_risita on Sep 18, 2017
Loving Wives

My name is Frank. OK, it WAS Frank, until recently, when things...changed. Now, more often than not, I answer to Katie. I know, I know. Yes, I am a guy, technically, but, well...to explain, it's gonna take a story, a loooong story...but not a boring one, I promise! I am a 33-year-old guy from Long Island. I have always been overweight, not great-looking, s...

Diary of First Time

by hubbyofprincess on Sep 11, 2017
Loving Wives

This is the journal of my life and the evolution of my sexual awakening over the past four years. My name is Nina and I am a 40 year old Caucasian woman who is happily married with four wonderful children, a devoted husband, and a good job. I am your average neighbor who lives right down the street, or you see rounding up the kids at school, and you would mo...

Literotica

by komrad1156 on Sep 13, 2017
Mature

"Dear RomanticGuy05, I'm not sure why I feel the need to apologize for writing you, but if you knew me, you'd understand. That's just me. I suppose it's because sending you an email makes me feel like I'm intruding into your personal life, and since you don't know me, I'm sure you see me as some stranger butting in without an invitation. So I hope you'll fo...

Roomers Ch. 02

by grgy56 on Jun 18, 2018
Erotic Couplings

While separated from my wife and needing a place to stay, my friend Rick allowed me to stay in Harry his son's room temporarily. Rick was now divorced and living with his current, Tina. Tina was a very tall, very skinny Taiwanese with small tits and a nice shaped bum. She was a licensed RMT so when I injured my back lifting some heavy crap, she offered me a...

A Couple's Journey Into Depravity

by johncockenfurs on Sep 17, 2017
Loving Wives

I'd been slowly easing my wife Lisa into my fantasies for awhile now. We're in our early 40's and have been married almost 20 years, so we had to find ways to mix things up a bit. It started with her wearing leather and pvc clothing for me, allowing me to shoot photos of her and fucking. She's so fucking hot, even though she's in her 40's, she has the body o...

Bed and Breakfast Hotwife

by donaldelliott11 on Mar 9, 2020
Loving Wives

[Note: The hotwife in this story is, well, a wife, right? That means she has a husband. When she gets hot, he becomes a cuckold. You following this, Annony? Get over it, or read a different story. Oh, yeah, one more thing -- BTB is a fetish and has no place in Loving Wives.] *** Tracy and Don Elliott, empty-nesters in their late 40s, supplement their incom...

Loving Wives

by NemosFolly on Sep 14, 2017
Reviews & Essays

First of all, it must be noted that I am not a writer of erotica. I find it much more fun, and erotic, reading stories where I'm not sure exactly what's going to happen (even if it's pretty clear from the direction of the story so far) than writing ones where I have such absolute control. But I am an avid reader, and I have read many stories in each of the c...