Sissy Prince Stories

14,095 results
Orientation
Length
Source
Infinite Scroll

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...

Eve Quest Pt. 03

by JJ Neal on Sep 19, 2017
Transsexuals & Crossdressers

Sometime during the night I was released. That exquisite pain at the point my limbs were release must have dulled my recollection of the events. I'm reasonably sure I was given the Toilet command and I hope I did a good job. In any event, I was still on the bathroom floor when I heard my mistresses stirring around the next morning. I got up, crawled under th...

Eve Quest

by JJ Neal on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 1 My name is, or maybe we better make that was, Andy Moore. Until recently my personal identification was in the name of Jamie Jo Moore and everyone I knew called me Sissy. My parents died in an automobile accident when I was twenty-four years old leaving me an estate of around $3,000,000.00 and an eighteen percent interest in an insurance company...

Butterflies

by marybethsanford on Sep 15, 2017
Transsexuals & Crossdressers

There were a lot of good reasons to be out this early, but none as wonderful as seeing this first Giant Swallowtail awakening, and John smiled as it moved. Magnificent, he whispered, in awe of this giant as it slowly unfurled it's Forewings against the sun's morning warmth. It was, as they always were at this time of day, lethargic and calm. "Papilio Cresph...

Chrysalis of Kirsten Ch. 03

by kirstensubts on May 7, 2019
Transgender & Crossdressers

My name is Steven aka Kirsten. This story is about how I went from a closet cross dresser to becoming a full time transgender slave. This story is mostly true, based on my journals with dramatic license to make it more exciting and readable. Names have been changed. This is who I am. A special thanks to Shy Girl Whore for her help with polishing this story!...

AliExpress and Sissy Downfall Pt. 06

by His_fag_wife on Mar 6, 2018
Transsexuals & Crossdressers

"Ok, now you've been fed, back in the chair and Candice will get your make up done, so that you are as pretty as you can be when you return to your Mistress and Master." "Get all that mess cleaned off her face please Candice and start making her up to look pretty." "Yes Miss Bell." Charlie got back in the chair and Candice prepared to make her look as pre...

A Sissy Saga Ch. 11

by Snurge on Sep 15, 2017
Novels and Novellas

"Your financial accounting is abysmal, Miss Hancock." said the man from the Department of Inland Revenue. "Some of the necessary records are incomplete and others are totally missing. How can you hope to complete a Tax Return for your business without appropriate qualifying evidence?" Miriam Hancock eyed him with some malevolence as he poked the documents i...

Letter From Hobson Bend

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: I've enjoyed the letters I've read, and I wanted to tell you of my unique relationship with my dominant wife, Beatrix, "Trix" for short. I am Doctor Lionel Lithgow, author of 20 books... University professor of physics... And president of the biggest quantum physics research facility in the Western Hemisphere... But at home I'm just a...

Letter from Lythgoe Heights

by justincbenedict on Mar 7, 2018
Transsexuals & Crossdressers

Dear Shoeblossom: I want to tell you about my male master, Emil. He is Austrian, and although I am, I think a heterosexual male, not really bisexual, or maybe a bit now... But Emil is a find! Just this morning I was being tutored in how to edge without cumming. When I got close, kneeling in front of Emil, he reached down and tweaked the mousetrap on my ri...

The Club Pt. 01

by Paulateevee on Jul 13, 2020
Transgender & Crossdressers

This is a continuation of 'The Trap'. It would be best to read that story (5 parts) first before reading this one although I will try to make this story as stand alone as I can. Background - Paul has been outed as a cock sucking sissy to his friends, family and work. He's lost his job, his wife and friends. Louise offers him a way out. Usual disclaimer. An...