Sissy Story Hentai Stories

142,530 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Ms. Tanaka Fixes Me Ch. 02

by chenwanli on May 4, 2020
BDSM

Chapter 2- Ms. Tanaka Takes Charge Ms. Tanaka stood up, straightened her sheath dress and bowed to her daughter Hiroki to say goodbye. They exchanged a few final words in Japanese that I didn't understand, gesturing at me and smiling then Ms. Tanaka laughed throatily and demanded the rest of my clothes. I took my pants off from around my ankles and gave her...

My Bestfriend's Girlfriend

by Shauna_Wood on Jul 9, 2019
Transgender & Crossdressers

When I was in my early 20's I used to play a lot of online video games. First person shooters, mostly. The Battlefield series, especially. I had started playing games online with a guy named Chris who had gone to high school with my ex-fiancé. He and I had met through her and had really hit it off. We had remained close even after she and I split. He lived u...

Ms. Tanaka Fixes Me Ch. 01

by chenwanli on Apr 27, 2020
BDSM

Chapter 1: Meeting my Future Wife and her Mother I met my wife Hiroki in my mid-20's when I was living in Osaka. I'd been living in Japan for a few years leading the bachelor life and dating some gorgeous women but the majority were stereotypically Japanese: expecting to be subservient and deferential to the man, which I found boring in anything longer than...

X-Change

by Noah_Peal on May 15, 2015
Miscellaneous

Pills Pink pills change males to females. Blue pills change females to males. Purple pills (X-Trans) change males or females into transgenders, can be combined with pink or blue. X-Change (Formula subject to change) Acquired from unlicensed "street" vendors. Changed (defective/in testing) formula. Cheapest. High pregnancy risk. Can lead to mental a...

Open in Reader

Slow Descent into Sissy-Hood... Ch. 01

by Slipperylock on Oct 31, 2018
Transgender & Crossdressers

Beta boy beginnings. It started when I was online, lonely and drunk. I'd been at University for maybe three months at that point, struggling along with a Masters degree in Economics. Unlike my undergraduate years, I had decided to live alone in a one bedroom flat - I thought that with more privacy would come more focus. What I hadn't counted on was that wi...

Sissy Pantyhose Twins Ch. 01

by Sheermistress on Sep 12, 2017
Transsexuals & Crossdressers

Twice The Fun... Part One... My Slut had received her orders in the envelope which was always left on the kitchen counter before I left for work. She was to perform whatever was mentioned in this envelope, each day, without question -- either during the day if so asked, or to be ready for me when I get home. Whether it was a new outfit, a specific outfit,...

Our Vision

by MrLightningStar on May 13, 2020
Reviews & Essays

If we reeeally take a look at the history of the world... Erotica has always been at the forefront of art's beginnings in every culture's rise. From Bawdy folk songs, Egyptian erotic poetry, Ancient Greek sculptures, to Renaissance paintings, to Japanese woodblock canvases - it's even in the Bible! Go read Songs of Solomon! Today, we have the biggest and...

Subliminal Obsessions Ch. 03

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

*Before... She shows me our profits and stuff...and stuff meaning gifts with cash transfers and e-notes sent for who. I'm floored, literally floored I've never had this much money in my life. I'm not rich but holy fuck...I can...I just sit and stare and look at the screen. "What are you going to buy first Nikki?" "Bills, bills and some savings but the r...

The Hentai Simulation

by FootLicker8 on Apr 29, 2025

(Cover image by Kairunoburogu) This story is public and I would greatly appreciate if you considered writing your own branch for it to give some more options to the readers. Anything allowed by the Chyoa rules is allowed here as long as it fits the premise of course. Please read the writer guidelines to help you fit your branch with the overarching lore befo...

Open in Reader

Hentai World Ch. 01

by PrevertOne on Sep 19, 2017
Sci-Fi & Fantasy

Thanks to Jon B 1969 for the edit. The story was old, so old only naughty children at bedtime believed it. The story of Scott Hansen, multitrillionaire media mogul; the richest human ever to have lived during the Second Age of Human Space Exploration. How he laid claim to an obscure planet, conveniently located along the most popular trade route. How he bui...