Sissy Bitch Stories

80,596 results
Orientation
Length
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Infinite Scroll

Mr Derrek

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

The room is filled with the sounds of sex emanating from the wide screen tv. On screen a sylph of a gurl is on display all fours on a small low table surrounded by a sea of men in various stages of undress. The slim smooth skinned gurl is dressed in a short flared skirt that frames her sweet ass beautifully in layers of ruffles and lace with her pretty match...

Another Submissive Slut Ch. 04

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

She was leading me unerringly to my place. How did She know where I lived, I wondered briefly before the effort of walking with such a large plug in sissy hole forced my attention else where. Panting more from nerves than the walk I quickly opened the door to the building to get us in and off the street. Almost immediately my landlady was upon us. I nearly s...

The Sissy Diaries Ch. 1

by colettegrrl on Aug 18, 2017
Fetish

This is a story about my new life, my new way of being. I wanted to share my story so I started to record my events. I figured the best place to start was, well the beginning. Here's how it all started. * * * * * I come home to find you sitting at the dining room table, laughing and drinking with a tall, dark, well-built and handsome black man. You introdu...

Card Shark

by Turned on Sep 14, 2017
Loving Wives

I returned to my hotel room from a poker tournament and realized I'd forgotten my key, so I knocked. After a few moments the door swung open and my pretty, young asian wife was waiting for me behind it. "Hi honey," she said, giving me a very strange look, "How did you do in your poker tournament?" "I did ok. Third place. I made a little money," I said, s...

Yeliza Awakens Pt. 02

by Yelizaveta on May 11, 2020
Transgender & Crossdressers

Part 2 of 2, hope you enjoy. Feel free to leave comments or thoughts. Or not, all good. Part four: The reveal Seeing him fully dressed, submissive, and made to look like a girl, her power was readily apparent. She reveled in it. He was patiently sitting on the bed, waiting for her direction. This power was becoming addictive. She enjoyed it more every ti...

My Girlfriend Made Me a Sissy Ch. 03

by libertinaXx on Sep 25, 2017
Transsexuals & Crossdressers

I lay on Jess' bed waiting for her and wondering what would happen for ages. She was in another room getting ready for her new lover, I was already dressed up. Pale blue, see through panties and matching bra, a short black skirt and a blue vest top. With my make up done to show off my pretty green eyes and my long brown hair styled wonderfully, I looked like...

My Beloved

by quotidian01 on Aug 30, 2017
Fetish

"My Beloved, I am your dedicated lover and I will do anything for you. I thank you for letting me make this web site, where I can feel the whole world watching me. Everything I do here is for you, Beloved. And in pleasing you, I am pleased." My voice sounded a bit tinny in the cheap computer speakers. I knew I was displayed while the voice spoke: sometimes i...

My Beloved Ch. 02

by quotidian01 on Sep 13, 2017
Fetish

"Start the camera." She was using The Voice and I had no choice. The camera was carefully set to include the bed and the wall behind it. We were making our second film for our website Sissy Slave. This film included both My Beloved and her lover Phineas. We stood in a line in front of the camera. Almost immediately, I heard the "ping" of new people entering...

Another Submissive Slut Ch. 02

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

I spent a tension filled week on edge. I was easily distracted from even the simplest of tasks as the memories of my adventures in the parking lot with Those People continued to haunt me. I fluctuated between arousal and disgust as visions of my performance played over in my dreams both waking and while a sleep. I had become nerve rattled, jumping at every s...

My Girlfriend Made Me a Sissy Ch. 02

by libertinaXx on Sep 25, 2017
Transsexuals & Crossdressers

Thank you to everyone who sent me messages about the last story, I've tried to include things people wanted to see in the sequel. Hope you enjoy ---------------------------------------- I woke up, stretched out and smiled as I felt the familiar sensation of my girlfriend's panties rubbing on my cock. The feeling instantly brought back memories of the night...