Sissy Brother Stories

49,708 results
Orientation
Length
Source
Infinite Scroll

Recruiting of a Sissy Maid Ch. 02

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Two: Onto Her Training and Breaking Down. The feeling of fear and dread falls over Chantel as she sits on the flimsy bed in what is for now her prison cell. Totally alone and isolated except for the fact that Mitch and Nate Burrows will lord over her as they orientate, train and ultimately break Chantel from a fantasy sissy to what will be a living...

Cucky Trained by CD DOM Pt. 02

by sndycd on Sep 15, 2017
Transsexuals & Crossdressers

Your alarm went off promptly at 6:00am. The dildo in your ass made you squirm as you got out of bed. There was a wet spot on your panties. Your face felt tight and you remembered the cum that was on you had dried. On your night stand was a note. "Slut...Go into the bathroom. You may relieve yourself in the bottle, not the toilet. You may remove the dildo f...

Sissy Slut Boy

by SissyBoiToi1 on Jan 2, 2017
Fetish

You wake up in your bed, in your attic bedroom. You sigh, not wanting to get out of bed. But then, you realize 2 things--one, your alarm clock didn't go off, you overslept! You have 5 minutes to get to the bus! And two--your bed is soaked in warm, smelly liquid. Did you wet yourself? (Just a note: The "catch the bus" route leads to diaper-related c...

Open in Reader

The Wish of a Submissive Older Brother

by SubmissiveJosh on Dec 20, 2018
Fetish

Hello people, this is my first story, I am not a native English speaker, so the first chapters might have some mistakes. This was already posted up to chapter 14 in other sites so I am just porting the story over to the Chyoa format. I would like as much feedback as possible. Don't be afraid to lay hard on me what you think and how bad my writing is! I would...

Open in Reader

Merry ChristmASS, Bitch Boy!

by humbleslave on Sep 16, 2017
Celebrities & Fan Fiction

The holidays were upon us. I had spent the last three months of my life as the personal sex slave of Brittany Andrews and Chantz Fortune. By now I was used to the chores, and the beatings, and constantly servicing and being fucked by their various strapon dildos. However, I never got used to the humiliating situations that they placed me in on a daily basis....

Jamie's Descent Pt. 01

by nikkiesilk on Sep 18, 2017
Transsexuals & Crossdressers

Chapter 1 What did we do before social media? How did we manage to get through the day without that endless stream of dirty jokes, funny photographs, gossip and links to dodgy websites that now fill our lives? Yeah, yeah, I can hear you grumble. Get on with it, I can hear you say. Well, dear reader, it was one of those links that started me down the road to...

Wendy The Haitian Sadist

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

Salutations, dear readers. It has most definitely been a while, hasn't it? The name is Wendy Stefania Polydor, and I'm a young Haitian-American woman living in the City of Boston, Massachusetts. Mother of two, divorcee, college graduate and nurse, I am all of these things and more. I have been delving into the world of BDSM, and more fun things like swinging...

TS Princess Ch. 01: Fucked by My Warden

by TSPRINCESS on Sep 16, 2017
Transsexuals & Crossdressers

It had been several weeks since I left home with my cousin brother for my breast-enhancement surgery. All our family knew was that I was going to some cram-school to get coaching for Pre-Medical Exam (AIPMT). My cousin brother had been supportive of me not only since he cared for me; it was due to his own advantage of having a full-formed girl at his disposa...

The Dragon Ring Ch. 03

by Beatnic_jazzman on Sep 25, 2017
Sci-Fi & Fantasy

Three Fool me once shame on me, fool you twice...? I awoke in the early dawn. The sun yet to broach the horizon, but casting its rosy glow high into the cloud speckled sky. Sissy was lying across me; her head nestled into my shoulder, her arm curled around my neck, her hips across mine and her foot wedged twixt my knees. I reached over and smoothed her...

The Truth is Known

by desireethtttv on Sep 16, 2017
Transsexuals & Crossdressers

While my wife of 16 years has known of my fancy for cross dressing, she really didn't realize how far I delved into the realm of womanhood. That is until yesterday, when I forgot to lock my office door. It all came to a head, in more ways than one, when she burst into my office and found Desiree, "The Hot to Trot Transvestite" busy with one cock in her ass a...