Sissy Bitch Stories

80,596 results
Orientation
Length
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Infinite Scroll

Black Cop's Stress Relief

by puzziboi on Jan 20, 2020
Transgender & Crossdressers

"We think you're doing a hell of a job, Corporal," the bronze-skinned police lieutenant explained. "But at this time we're going in a different direction." "Alright. Thanks for letting me know, Lew," replied Christopher Patterson with a fake smile. "Is the candidate internal or external?" "External," the supervisor revealed. "Alright. I'm kinda tired," Cp...

Another Submissive Slut Ch. 05

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

By the time Mr. Lennie had arrived I was once more primped and preened. She laughed meanly as She put me through my paces while awaiting His arrival. Harping at me mercilessly that Mr. Lennie would make me suffer painfully for my inadequacies. The sudden sharp knock at the door made my heart flutter and my knees tremble with anticipation. My dickette bell ti...

The Basement Ch. 04

by FiveDots on Feb 24, 2020
Transgender & Crossdressers

Please enjoy another chapter of this horrible situation. I have plans for the dark place this is going next, but please comment with ideas you would like to see explored! ***** The night where things became more violent had actually begun relatively mildly. Sure, there was an underlying current of violence in his every action as Ryan had blackmailed, shrun...

Stevie's Journey Ch. 03

by gbr2004 on Dec 2, 2019
Fetish

I get up and put on some of my regular clothes, workout shorts and a t-shirt and flip flops. Try to digest what happened yesterday and how everything just spiraled out of control and now I find myself in this impossible position. It's like all choices have been taken from me and this group of people took over my life. It was exciting but I can't be doing the...

Spanking Night Ch. 07

by Angelscuck on Sep 14, 2017
BDSM

The shower felt good against my freshly shaven skin. I was covered with cum, urine and pussy juice. I knew if I took too long, I would be punished by my wife and mistress so I cut it short. After towel drying, I put on a clean pair of my wife's panties and hurried down stairs. "Well, here's our little sissy bitch now. It took you long enough!" Mistress Sh...

Sissy's Decline into a Slut Pt. 02

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Three: Another Exciting Night as Sissy Slut Wannabe. Well about a week has gone by since I bought the dildo, wrist cuffs, ice lock and the lubricants at the adult sex shop. Dressing up as a sissy maid or a sissy slut everyday at home and learning how to use the dildo first with my mouth and trying out the flavoured lubes for added pleasure, but most...

A Sissy Girl Bitch, 'BEST IN SHOW'

by keptsissy on Mar 3, 2020
Fetish

** Author's note: All characters depicted in this story are fictional, well beyond age-of-consent, and are consenting adults. ********************************* He made a point of showing me off, displaying me. That was obviously his thing from the start. Many men at the clubs he'd take me to were allowed to not only look but touch me too. I never thought a...

Sister, Meet My Sissy

by satinmarabana on Sep 16, 2017
Transsexuals & Crossdressers

George was mincing around the bedroom on his new high heels, almost moaning in joy as his big cock slid around in the inside of his panties. I could see the thick buttplug in his ass through the thin panty material and I smiled. George was a lovely sissy with almost feminine body type and features but with that delicious big cock. He'd taught me as much abou...

Young Sissy Ch. 01

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series. * I don't know how long I was under...days, weeks....

Recruiting of a Sissy Maid Ch. 09

by Sissy_Chantel on Oct 31, 2017
Transsexuals & Crossdressers

Chapter Nine: Things Begin to Change for Chantel. Morning time, Chantel awakens and takes a moment to realize where she is and all that has happened. She sits up in the bed and looks over and sees Carl Luftgrin, her mind balances between the thoughts of a wonderful date last night with Carl and knowing this man as her Master owns her. Her mind battles these...