First Shemale 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

Jabba's Shemale Slave Pt. 02

by mkh78 on Oct 8, 2019
Celebrities & Fan Fiction

This story is from the imagination of the writer and inspired by Return of the Jedi. I have used Huttese words in some parts. These are not of my own. *** 1:30 am. Tarno and the Twi'lek shemale prostitute he found and subsequently bought from the brothel's owner, were now quickly speeding across the Tatooine desert. He considered spending the night at a...

"A Shemale Submission": A Lust Story

by silkstockingslover on Dec 23, 2019
Illustrated

"A Shemale Submission": A Lust Story Summary: Author Jasmine falls for a hot new teacher with a big cock. Note: Thanks to hfernandez1983 for the many pictures used in this story. He spent weeks getting these perfect for the many different scenes I requested. If you like the pictures in this story, please feel free to read the multi-chaptered series Cheerle...

Showing Off For My Wife's Pleasure

by HotJennieh on Sep 19, 2017
Fetish

A first time effort based on real events. * There I was lying on my back, on the floor of a cheap adult bookstore. All I was wearing were 5" heels, black thighhighs, and a nipple chain. In one hand, I was jerking my throbbing shaved shaft while I was using my other hand to fuck my ass with a double headed dong. Cum was glistening on my face and chest and r...

Lust and Love with Leona

by cbachtland on Sep 17, 2017
Celebrities & Fan Fiction

This is a work of fiction. * The days after I fucked with Leona I spent alone. She has told me that she was going for shoot in the Bahamas for a week. I was a man who had everything in terms of material comforts, and there was not a girl I couldn't pull in a bar. But I found that I could not stop thinking of Leona and that I stayed at home fretting and loo...

The Resort Ch. 03

by chinookwind on Sep 19, 2017
Erotic Couplings

03.01 Megan and Jamie, Introduction: 03.02 Jamie, Fantasy Center, Preparation: 03.03 Jamie, Fantasy Center, Entity: 03.04 Megan, Fantasy Center, Plant Lover: * 03.01 Megan and Jamie, Introduction: Jamie was an impulsive boy as he was growing up and wouldn't think twice about trying out something new, no matter what the consequences might be. When he tu...

Leona

by cbachtland on Sep 13, 2017
Celebrities & Fan Fiction

This is a work of fiction. * I think of myself as resolutely straight. I look at a lot of porn although I have plenty of girls to fuck. Steven, an old college buddy, dropped by and proposed that we go to a shemale bar that night. I was shocked and refused. But Steven retorted that if I was sure about my sexuality, I should have no problems being there. I c...

Boy Brides Ch. 2

by yano on Sep 14, 2017
Fetish

Chapter 2: A Shock from Victoria Darren continues his story of his introduction to the KBG. "On Saturday evening I arrived at the shop in time to meet the two men with Mandy and Victoria. This time Victoria had on a bright pink dress which looked no more than a multi layered petticoat. "Once into the fitting rooms I was ordered to strip by Mandy and then...

Twenty Questions

by silkstockingslover on Jan 7, 2018
Reviews & Essays

Summary: Jasmine responds to most common questions asked by readers. Thanks to: Tex Beethoven, thor_ph, Robert, and Wayne for editing. 20 Questions I get asked a lot of questions about myself and my writing. There was even an article by Bob_Aganoush called Literotica Authors 02: silkstockingslover. This makes me think I should go into more detail. So her...

My First Bottom Experience

by NoLongerCurious on Jun 4, 2019
First Time

I never thought of being with a man until I was 45. It was the internet that sparked my curiosity. I first discovered shemales on the internet and was very aroused by men sucking shemale cock. I realized that cock was really hot and I wondered if it might be fun to suck one. That lead to a nervous craigslist encounter with a very nice guy who lead me patie...

A Shemale Shock: A MILF Falls

by silkstockingslover on Sep 25, 2017
Illustrated

Summary: Mom catches her daughter with a teenage shemale and.... Note 1: This is a Nude Day 2017 Contest Story so please vote. Note 2: Thanks to Tex Beethoven, Robert, and David for editing this story. I was having a bad day. I'd spilt coffee on myself on the drive to work. I'd gotten a rip in my nylons. And I'd forgotten my notes for tonight's intervi...