Sissy Chyoa Stories

27,236 results
Orientation
Length
Source
Infinite Scroll

To create the perfect Sissy World

by Heinrich12345 on Apr 29, 2025

In this story unexpected souls find objects of power, these have the power to change the world and its inhabitants, even reality itself can be changed with them. However, these objects have only one purpose and that is to create a perfect sissy world. Even if these objects have godlike abilities, they will only change the world if a better sissy world is cre...

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PR Sissy is back!

by PR Sissy on Apr 22, 2025

So after three years of the COVID Pandemic I can't wait to become the whore I have always been. For safety reasons I didn't fuck around with no one (fuck that was hard!) It's a good thing that I have all kinds of sex toys and cucumbers, zucchini's and eggplants filled the void of Coach Moore's huge ebony pole and all the people he ordered me to fuck. I took...

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First time Sissy

by PR Sissy on Sep 29, 2019
Transsexual

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any s...

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Sissy Starlet

by Queen_Diana on Nov 18, 2020
Fetish

First Sissy tell me. Who are you? Jenn- A tall long and blonde sissy. Platinum blonde locks that go all the way down to her back, glossy pink lipstick, long manicured nails, a model face, and killer ass and legs. One of the favorites for this year. Racheal - A brunette Sissy, with wonderful perky titties and plush ass, dark skin and luscious lips. Kim - An A...

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Sissy Suite

by Titlecardpink on Apr 22, 2025

Here you are. The Sissy Suite. You've been waiting your entire life for this moment, saving every penny, every dime, and every dollar you could come across. You've always felt like a girl, always wanted to dress like one, and you always wanted to be treated like one. Your name doesn't matter, it'll be void once you step through that pink threshold. You're 18...

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My Sissy Cuckold Life

by SissyCuckMike on Jan 2, 2021
Fetish

Hello everyone, my name is Mike and i am now a sissy cuckold. If you don't know what a sissy or a cuckold is i will explain, a sissy is like a cross-dresser but usually dresses up in pink frilly women's clothing and cuckolding is similar to a hotwifing where she goes out on dates and fucks other men without her husband/boyfriend around but with cuckolding it...

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Alphabetical Sissy journey

by Thrawn34t on Apr 22, 2025

Note for readers. This story is centered around characters becoming sissies following the ABCs. I know not very original, however the limitations placed by the 24 letters of the English language makes storytelling that much more interesting. Each chapter must start with the letter following the last, either by the letter alone which needs to bw incorporated...

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My sissy sister

by Alana-S on Jun 9, 2020
Transsexual

Did I really want this? That question had haunted me for weeks now. For years sissy porn had been my main masturbation fodder, and two months ago I had decided it could be more. That I could be more. I always wanted to be pretty like girls were, and had been openly bisexual for years. Why not try this? Why not be a sissy? I signed up to an online feminizatio...

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Sissy Nursery

by CandyAce on Apr 22, 2025

"Hey, get up", you feel some light tapping on the side of your face, "Wake up!" she calls out louder. You wake up with a start, where were you, and why were you restrained like that? Arms in handcuffs and legs cuffed in straps. You don't even have any clothes on as the A/C blasts your cold skin. You try to get a word out, but your mouth i...

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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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