Sissy Game Stories

87,858 results
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Black Mistress 4 Black Male Sissy

by Samuelx on Aug 18, 2017
Fetish

Sitting in my chair completely naked, I stroked my strap-on dildo as I watched my Black male slut parade in front of me. My name is Veronique Marceau and I am a Dominatrix. Standing five feet eleven inches tall, wiry and muscular with a thick booty, I look damn hot and I know it. My skin is dark brown, shined to perfection with lotion for tonight's performan...

Young Master Ch. 05

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

I was running through the mansion, being chased by something so horrifying that I didn't dare to turn around and see what it was. I tried to find my room, but the once familiar hallways were now disjointed and strange, as if the building had be rearranged and some pieces had been replaced with imitations that had a sinisterly artificial look to them. My purs...

Mistress's Party Entertainment

by sissyapril on Sep 15, 2017
Transsexuals & Crossdressers

My Mistress was entertaining her sister Lady Brandi and her friend Lady Alexis in the living room and watching a Mistress dominate and humiliate a couple of her sissy slut males on DVD. The ladies were drinking wine as I was attending to the dishes after serving them dinner. I was wearing a French maid's uniform with black patent leather pumps and fishnet st...

Sissy Slut Ch. 02

by Scribler on Sep 13, 2017
Transsexuals & Crossdressers

At first I was a little pissed she just discarded me like that so easily, but I quickly got over it, as I was now free. Thankfully there were no other houses nearby that I had to worry about being seen in all my naked glory. It took me a few minutes before I was able to drive away, as I had to get dressed first. I kept looking back at the house, as I wanted...

Young Sissy Ch. 02

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

I was walking in a field, the cool grass crushed softly between my toes, the sun warm on my skin, the smells of spring were in the air and every deep breath I took filled my lungs with the promise of a fresh start and new hope. The sky was a flawless blue and looked clear enough to take a swim in. Everywhere I turned, all I could see was endless rows of roll...

Simon Sissy Slave Ch. 04

by Timewarp10 on Aug 20, 2019
BDSM

Simon staggered in for work the day after the slave auction, his body stiff and sore. Mr Berne and the others in the post room were shocked to see the sissy's bruised and lacerated buttocks. Barry's stiff cock betrayed his feelings; whipping and torture excited him. His sadistic nature relished the thought of thrashing Sissy senseless. Sissy was his fuck t...

A Shell of A Man

by uppishcarrot on Sep 13, 2017
Transsexuals & Crossdressers

Six years ago, I was doing well enough to finally afford my dream apartment. It was a studio apartment on the upper side of town. So, I had the job, the apartment, the money... but I was lonely. Very lonely and very horny. Not only would I get all hot and bothered from looking at all of the pretty women at work, but there were also plenty of hot women who li...

Sarah Goes to College Ch. 05

by Sarahcheer on Sep 19, 2017
BDSM

Chapter 5: Sarah and Brian's First Game Sarah and Brian had been kept in separate kennels and had practiced at different times with the cheerleaders. Both were learning that their routine was going to be somewhat based on being chased, but neither could figure out exactly what or who was going to be chasing them. For Sarah, the ordeal seemed to be easier, a...

The Seven Dressing Sins: Vanity

by purekink on Jul 15, 2020
Transgender & Crossdressers

"To recreate this scene, you will need..." John tightened his calf muscles as he watched the young woman on the TV present an untidy scrap of cloth. "One white fishnet dress." He thought he knew her, somehow - something in her voice perhaps. He didn't know anybody with a crimson streak through her long blonde hair. And he certainly didn't know anybody who...

Panty Potion

by JBfrankenstein on Sep 14, 2017
Transsexuals & Crossdressers

Dylan rushed home from school as fast as he could. He'd wanted to play the new Gears of War game all day and could finally get home and relax. He burst in through the door and ran over to his Xbox. The game was nowhere to be found. He searched around for about 10 minutes before he noticed the note his mom left him on the table. "No videogames until you do...