Shemale Mistress Stories

27,874 results
Orientation
Length
Source
Infinite Scroll

Futanari World

by styxmaster on Apr 16, 2016
Fetish

You wake up this morning to the sight of your younger sister Sarah pulling your covers off of you. "Get up Doug, you don't want to be late for school." You get dressed for school after Sarah leaves your room. you never mind school that much, you mostly get B's and A's in your classes but given the opportunity you would like to just stay home and wa...

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Small Cock Frustration Pt. 02

by jamtby on Oct 7, 2019
Transgender & Crossdressers

Despite the relatively short distance to my home from Mistress Alexa's club, it seemed like it took hours to get home. The bulge in my pants demanded release but remained restrained in my new panties. It felt strange but all I wanted to do was get out of my clothes. Finally, after what seemed like hours, I arrived home. Once inside I stripped off everything...

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...

T's First Escort

by HORNYWRITERTS on Sep 26, 2017
Transsexuals & Crossdressers

I'd been waiting for about twenty minutes before the doorbell rang. Earlier that evening I decided I would finally take the plunge. I went online to Craigslist and, under the Casual Encounters Section, I found the list for Men Seeking Transsexuals and another list for Transsexuals Seeking Men. Of course, pretty much all of the ads were for escorts. A few ye...

Bdsm adventures

by Sgtwolf on Dec 7, 2017
BDSM

This story is for a compilation of many different bdsm adventures. It was formerly known as latex adventures, but as chapters developed they dealt more and more with different aspects of bdsm, and less consistently with latex. Latex still exists as a strong element in many of the chapters, namely because I like to write about characters wearing it. I created...

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Somali Femdom: New Convert

by Samuelx on Sep 14, 2017
Transsexuals & Crossdressers

Mistress Fatuma Suleiman, Supreme Matriarch of the world-fastest growing religion, the Fatumanism Faith, looked down at her latest supplicant, Ahmed Dawit. The six-foot-tall, burly and broad-shouldered, bronze-skinned and brown-eyed, hairy Egyptian male grimaced as Fatuma's cohort, Lady Karma, thrust her cock into his asshole. Mistress Fatuma Suleiman smiled...

The Pantysissy Diaries Ch. 02

by JPantyboyVSL on Jun 5, 2018
Transsexuals & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapter 1 before reading chapter 2. *** The Amtrak train Jaymie was onboard with his new Mistress, Sydney had just pulled into NYC. Jaymie had to get...

Mommy Adriana, I Will Obey You

by Gretatv on Sep 13, 2017
Transsexuals & Crossdressers

Dear Readers, since I am open to suggestions from now on I will start my stories with a recap of what has happened before. * Finally we were on our way home. Interestingly neither Mommy Adriana nor Mistress Andrea had cuffed or gagged me. So I just sat in the back of our car. During the short drive I had some time to think about what had happened in the p...

Cuckold's Descent

by syncbush on Mar 27, 2020
Cheating Spouses

Thank you to those of you who have liked or taken the time to comment/message me. I really appreciate the feedback. Feel free to add additional chapters, suggest ideas or leave comments. It is great to get ffedback and encourages writers to continue developing the stories. And special thanks to the Admins for making this story of the week! Really appreciated...

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Reason? Nah.

by curdles on Nov 8, 2020
Bisexual

"Oh, fuck!" she gasped as soon as my cock had slid out of her throat. She had held it there for almost a full minute, massaging my balls with her tongue all the while. We hadn't seen each other for almost a week, so our appetites rivaled those of Erysichthon of Thessaly. "I'm almost there," I said, stroking my shaft. "Open up,"...

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