Shemale Mature Stories

30,071 results
Orientation
Length
Source
Infinite Scroll

The Powers

by Mr.M on Jan 2, 2020
Mature

You have just gotten back from a long day at school and are ready to start your weekend. As you near your house you see a ring in the grass, so you go to it, pick it up and put it on. Once you put it on, it phrases into your finger. You suddenly feel different and look at your hands to see that you are a ghost. You are about to freak out when suddenly you tu...

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Hogwarts School of Witchdom and Fuckery

by Kazza on Feb 3, 2019
Fan Fiction

[Thanks for choosing HSOWAF! I have started introducing conditional chapters into the story, so please hit that 'start game' button on the right of your screen for the best reading experience. Also, feel free to leave a like or comment on any chapters that tickle you along the way. Enjoy!] Harry Potter was back at the newly rebuilt Hogwarts to complete his w...

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First Time Sissy Maid

by bart2077 on Sep 13, 2017
Transsexuals & Crossdressers

I had been fantasizing for many years about serving a dominant Mistress, watching lots of movies online, and generally lusting over the doms I saw posting ads. At the age of 28 I finally found the courage to answer a rather intriguing post by an older woman and her trans partner who were looking for a sissy maid for ongoing service. I answered the ad, includ...

Shemale First Time

by Canine51 on Sep 13, 2017
Transsexuals & Crossdressers

First time Sex with a shemale. Intro. I have read several stories of first time sex with Transexuals and none relate to my experience. So for those who are truly curious about how to go about it and what it is like this is my tale. I have always been a straight guy as far as I know. Married for over 15 years and never strayed once. Early in my life I was...

Pam's Shemale Experience Ch. 10

by majicman21 on Dec 2, 2019
Transgender & Crossdressers

Pam woke up, and as she remembered what day it was, a smile crept across her lips. Earlier in the week, her owner had decreed that she would not fuck Pam until Wednesday. That had been Sunday night, and now, with Monday and Tuesday past, today would be the first time in a long time she would feel that magnificent cock opening her up. It's been too long.....

Pam's Shemale Experience Ch. 08

by majicman21 on Mar 11, 2019
Transgender & Crossdressers

Content warning: one scene with a golden shower... Pam woke with a start. It took her a few seconds to hear her alarm ringing. Next to her, Tanya was still asleep, and further down on the bed, Alex was as well, her head resting on Tanya's thigh. Pam reached over to the bedside table and quickly turned off the alarm. Neither of the other women stirred....

Gemini Triad Ch. 02

by JordonLynn on Sep 13, 2017
Transsexuals & Crossdressers

Author's explanation of a minor editorial glitch: 3 places in the last chapter (Chapter 1) you will see something like this 1. Please ignore the number and consider what is written inside the brackets to be in italics. Chapter 2 Except for the wide staircases leading up to her apartment and Domino's rooms on the third floor, Solitaire had the second floor...

Pam's Shemale Experience Ch. 11

by majicman21 on Jun 1, 2020
Transgender & Crossdressers

Content warning: one scene with a golden shower. "Ah, what a way to start the day," Tanya sighed, letting her cock slip from Alex's pussy. The shemale had just filled it with a load of cum, dribbles of that gift already leaking out. Pam smiled from next to them, at the possessive yet affectionate way Tanya slapped her cock onto one of Alex's thighs and...

Shemale Utopia

by Lewd_Ruby on Jun 15, 2016
Transsexual

*De-De-De-De-Deep* *De-De-De-De-Deep* *Click* I gently pressed the large red button atop my alarm clock to stop the annoying racket of those high pitched beeps. Sitting up I began to take a look around at my surroundings, Beige wallpaper spread across the walls, the odd video game poster stuck on lazily with some blu-tack. Letting out a small sigh I swung my...

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The Gym Ch. 4

by Kip Carson on Sep 14, 2017
Group Sex

John arrived at Kate's house at 6:50 pm. She answered the door in a very tight fitting short dress. "Damn, you look good" John told her. "Sorry I'm so early, but I was so excited about tonight" he added. "That's fine, I'm always ready early" she said. "And you look pretty damn good, too" she added. She eyed him up and down. He was wearing black dockers, a ni...