Shemale Sissy Stories

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Orientation
Length
Source
Infinite Scroll

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...

In My Dad's Panties

by britneyfan on Sep 11, 2017
Transsexuals & Crossdressers

I knew my parents hadn't been getting along at all well recently and I had even begun to fear that they may some day be getting a divorce, but still the discovery that my father could be having an affair came as both a shock and something really quite distressing. It was the first time I had to confront the truth that my parents' split was a very real possib...

Spicy Story

by TexanBelgianCutie on Jul 17, 2019
Transsexual

Family Kyle had wildly mixed feelings when he saw his mom walking towards him. He kept his feelings to himself however and forced a big smile to welcome her back from the SpringWood Adult Mental Hospice. He had not seen her since he was child, yet he was glad to see she looked healthy and happy. “Hey Sara”, he grimaced, “How are you? Sara had spent the last...

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Making Francesca Ch. 01

by Spango on Sep 12, 2017
Transsexuals & Crossdressers

Author's note: I originally posted this story on another site under the title "Kidnapped and Sissified" a few years ago. I have decided to pull it out, dust it off, do a little editing, slap on a new title that I like better and share it with you fine folks here. Enjoy. Frank was an ordinary guy in his mid-twenties; of average height and build, loved col...

The Bimbug

by Testytesterton on Jun 17, 2020
Science Fiction

The world changed overnight with the first cases of the Sexually Infected Subjects Spreading Infections Exponentially Syndrome, or SISSIES, became known. At first it sounded like some urban legend, men turning into hot, horny, hung shemales and spreading the infection to any man that came in them...or any man they came in. It was only after you saw video evi...

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The Society Ch. 02

by Barno on Sep 13, 2017
Transsexuals & Crossdressers

The French maid outfit was just a little loose. I was borrowing Corinna's dresses until I was fitted for my own uniforms and outfits. Actually Corinna and I were close to the same dress size yet our body types were different. I had a more feminine build with flared hips and hard round buttocks while Corinna's more muscular build created a deeper V shaped upp...

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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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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Birth of a New Sissy Ch. 01

by AltErik on Sep 18, 2017
Transsexuals & Crossdressers

Usual disclaimers, though if you are already browsing stories on this site, you must have an idea what you're getting into by now. ;-) This story contains male to male sex, Crossdressing and Dominant/Submissive themes, so if this is a problem . . . wave off! This story is fictional story based on a fantasy of mine. While it is fiction, I did use myself an...

Making Francesca Ch. 03

by Spango on Sep 12, 2017
Transsexuals & Crossdressers

As Frank lay there on the thin mattress, listening to Justin climb the stairs, he thought about all that had happened and what he feared was still to come. The dull ache in his ass told him that Mistress Celia was definitely not someone to trifle with. He also thought about the reaction his penis had shown to the various activities he had endured since arriv...