Black Owned Sissy Stories

198,936 results
Orientation
Length
Source
Infinite Scroll

The Sexy Cuckold Couple Pt. 10b

by cuckcpl4play on Sep 19, 2017
Fetish

Precursor: This is part 10b of the series and it is about the fantasy we have as a cuckold couple. We have engaged in many acts of cuckoldry, but the story itself is fiction. If you are offended by this type of lifestyle than please don't read. It amazes me that we continue to get such negative comments to this series from people claiming that we are uneduca...

The Unsuspecting Candidate Ch. 03

by missvicky53 on Sep 11, 2017
Fetish

I awoke at 6:00 A.M. and set about preparing for my sissy's surprise. I opened the door to see him there on the bed, his ankles and wrists still cuffed to the four corners of the bed. His head was still encased in the bondage hood and he lifted it as I shut the door and approached the bed. "I trust my sissy slept well," I cooed as I began to release him fr...

The Man That Owns Me Ch. 04

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

"Don't be shy. Pull your panties down, baby boy. Show the man that cute little thing." He laughs, smiles at me. He's seated on the couch next to a man I've never seen before. When they entered my house I expected only him. I hurry to do as told. It's something that is part of me now. I never hesitate to do as he orders, dominant of otherwise. He owns me com...

My New Friend Amy Ch. 03

by DRobbie06 on Dec 23, 2019
Fetish

As I drove home that evening I had the replay of the days events running on a loop in my mind. I can't believe I paraded around in panties at lingerie store in front of strange women at the instruction of my new mistress. Hell, I signed a contract to obey her no matter what she says! Then I begged to jack off in front of her. I'm even a panty wearing sissy n...

Never Cum Again

by Sion Sierra on Sep 17, 2017
BDSM

Her name is not important however I dream about being her bitch. I am writing this to her and about her to explain to her my sick perverted desires. Although she already knows them, she does nothing. I masturbate thinking about her degrading me, taking me and making me a whore. I jerk off to the thought of dressing up in lingerie while she straps on a big pl...

Humiliated Stable Sissy Pt. 02

by SissyTwinkleToes on Oct 5, 2020
Transgender & Crossdressers

I woke up exhausted at the crack of dawn to Fairy Godmother obnoxiously clicking her fingers next to my ear. I minced downstairs, still locked into my ultra prissy outfit (where was the key?) and my totally exposed diaper, already damp from last night. I shuddered as Fairy Godmother ordered me out into the back garden, where I stood and curtsied to the risin...

A Natural Sissy Ch. 07

by harv069 on Sep 15, 2017
Transsexuals & Crossdressers

Author's note: This is a story about a young woman turning an older man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you don't like this kind of story, but read it anyway, please don't bomb me. I warned you to go away. If you like the idea, read on, and don't forget to vote and leave a comment. More will...

Miss Danver's Crime Prevention Ch. 03

by VeryCuriousIan on Jul 14, 2020
Fetish

William lay wide awake in his bed knowing this was to be his final day with Miss Danvers. The sheer thought of her majestic presence sent his cock hard and he closed his eyes and dreamt of her. Her perfume seemed to be permanently in his nostrils and it sent his senses swirling. She had changed his world upside down and made him into a subservient cocksucke...

Toni's First Night Out

by the_apocalypse on Sep 13, 2017
Transsexuals & Crossdressers

I stared at the woman in front of me, she was an absolute stunner. Her legs were, slim, long, smooth just like her arms. She had slightly tanned skin, long flowing black hair, pert but fake 36c tits and a perfectly rounded ass. Standing before him in just a white corset with lace trim, matching thong and stockings with black stiletto shoes she looked like...

A Weekend Visit to the Office

by Marty Fisher on Jun 4, 2019
Transgender & Crossdressers

I usually work from home as I have a very private place with a wonderful view and Lord knows I've put in more than my fair share of office hours over the years. But I do occasionally elect to make visits to the office both during normal office hours and off-hours to make copies, restock my home supplies and have a cup of coffee with a long-term friend or two...