Leotard Crossdress Stories Stories

60,278 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

A New Direction Ch. 01

by MyUncensoredSelf on Sep 15, 2017
Transsexuals & Crossdressers

I was nervous when I texted my wife that morning. She'd gone to the shops and I asked her to buy me some nylons. She knew I liked to crossdress and we'd even fooled around once while dating with me in a leopard print stretch leotard and my breast forms. She'd loved it that time and it was one of the horniest weekends we had together. But since then things ha...

Halloween Party Aftermath

by Sabnock on Oct 19, 2020
Transgender & Crossdressers

Oh my GOD I'm so hungover. I creak my eyes creak open, and immediately regret doing so. Everything hurts. My head is pounding. My mouth tastes like something died in it. I try to sit up, pause, flop back onto the couch. At least I've got blanket. Wait... I'm not in my bed. Where the fuck am I? I rub the back of my hand over my eyes, feeling a weird, heavy...

Forced Crossdressing Stories

by Dayeandknight on Feb 1, 2018
Transsexual

All of these stories share a central theme of Crossdressing. Rather than add yet another story for one of my ideas, new ones will now go here. I'm making the call, out loud, for additional authors to add their own threads and work with me. I would love anyone interested in any of these stories or my previous ones to add their own threads. If writing isn't yo...

Open in Reader

Grab Bag Transvestite Story

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

I am a part time transvestite, who, if I do say so myself, looks quite attractive when dressed as a woman. It has taken me years to become adept at makeup and being capable of selecting sexy clothing that is in my size and that suits me. I have also had a number of lovely encounters with other TVs and male admirers. You can read my True Stories on this site....

Fulfilling all My Fantasies Ch. 01

by classmate1119 on Apr 23, 2019
Transgender & Crossdressers

"Last chance to change your mind, Cristi," Jalen said. "It's probably the most outrageous one so far! Not that I'm worried, of course, but you never know what else might happen... " I reapplied my lipstick in the reflection of the club's glass entrance. "Hey, we spent too much time preparing for this. Don't back out on me now, Jalen!" I threw him a coy smi...

ENF to ENM

by Jhal00 on Apr 22, 2025

ENF Stories from the internet converted to ENM stories. There simply aren't enough ENM stories compared to ENF stories, the goal of this project is to convert ENF stories to work with an ENM situation instead. No need for the stories to be specifically about males, just that the protagonist has a penis and balls. They can be non-binary or anything. Remember...

Open in Reader

My Sexual Fantasies

by Submissive Timmy on Sep 16, 2017
Letters & Transcripts

My Sexual Fantasies (OD Repost) I wrote this in November 2002 for my online journal on Open Diary. I'm posting this simply to have something posted. I do intend to actually write eventually. ***** I have a penis. Isn't that amazing? I also have two testicles. The flu had a stranglehold on them and killed my sex drive. But, I've since driven the flu off wi...

Adventure for Sue Ch. 04

by Tansy15 on Sep 13, 2017
Loving Wives

In this installment there are two short stories, I had started doing some amateur glamour modelling as well as the kissograms. I was still working as a hairdresser in a salon and the extra money I was getting was helping us with our first house. If anyone wants to know what I look like there are a couple of pictures on my profile page. ***** The agency I u...

Nude Beach Waifus

by andymoo on Aug 12, 2020
Exhibitionist & Voyeur

In a world far off from ours existing between fictional realities, there exists a nude beach visited solely by females looking to unwind by taking it all off called ワイフビーチ (Japanese for Waifu Beach). These beautiful babes can be found on this beach either catching rays, playing in the water, having a game of volleyball and other seaside activities you'd find...

Open in Reader

Confiding in My Hairdresser

by Leighharding on Dec 19, 2018
Transgender & Crossdressers

I've always had a great relationship with my hairdresser, Mary. She'd been cutting my hair for years and we probably shared a few more details than we should about sex, she made me laugh at some of the naughty stuff she'd been up to! On occasion around a year ago, she came to the new house that I'd just moved into with my girlfriend to cut my hair. The cha...