From Playboy to Plaything: Blossoming as a Corporate Sissy

By Jessica Cockburn

Follow Dan Morris as he embarks on a journey of self-discovery, surrendering herself to the world of femininity and pleasure.

• Language: English
• Publisher: Jessica Cockburn
• Release date: Sep 21, 2023
• ISBN: 9798215371992

Book preview

From Playboy to Plaything

Blossoming as a Corporate Sissy

Copyright 2023 Jessica Cockburn

Published by Jessica Cockburn at Smashwords.com

Smashwords.com Edition License Notes

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Table of Contents

Prologue

Chapter One

Chapter Two

Chapter Three

About the Author

Connect with Jessica Cockburn

Prologue

Author's note: All characters depicted in this work of fiction are 18 years of age or older.

As I recount the journey that led to my unexpected change of heart, a wave of conflicting emotions washes over me. It feels as though a lifetime has passed since I set my sights on a completely different path. Time has a way of altering one's perspective in ways you can never anticipate.

Freshly graduated with an MBA, I was brimming with a sense of purpose and determination. Armed with a prestigious degree from a renowned B school, I was eager to embark on a career that would define success. I couldn't help but feel a surge of confidence, as if my future could only bloom brighter.

The time had arrived for job interviews, and my confidence soared high. After all, I had sacrificed my social life, devoted countless hours to my studies, and invested a significant sum to reach this point. The world was my oyster, and I was determined to handpick the pearl of my choosing.

I refused to settle for a position as a mere associate at a big corporation. No, I would select a company where I would start at the top, propelling myself upwards and leaving a trail of broken hearts along the way. I envisioned myself as the CEO of a lucky firm, standing tall amidst a sea of conquests.

It's ironic how perspective can shift so dramatically in the face of reality.

My name is Daniele Michaels, and I currently serve as the personal assistant to Catherine Michaels, the CEO of Ladies' Dominion, LTD. This major corporation caters to women's fashion, cosmetics, lingerie, and all the delightful indulgences that we, as women, cherish. Catherine has tasked me with writing this story as part of my job, a role that represents the pinnacle of my career. It is a position that simultaneously fills me with fear and joy. As I sit here, dressed in my customary work attire – a form-fitting satin dress in a striking shade of red, complemented by sheer silk stockings and 4-inch stiletto heels – I am reminded of the dress code at Ladies' Dominion. We executive assistants are expected to embody the epitome of femininity, a visual representation of the brand's essence. And my relationship with Catherine is exceptional, for she is not just my boss; she is my Mistress, and I, her devoted wife. In truth, I am now a submissive transvestite slave to her will. You must be curious as to how I allowed myself to be swept away by this unconventional life. Allow me to share my tale...

During the initial rounds of job interviews, one particular opportunity caught my attention – Ladies' Dominion. The role they offered was that of executive