The Babysitter's Packing: She’s Transgender, He’s Transfixed

By Jessica Cockburn

Jack's life takes an unexpected turn when a babysitting arrangement leads him to explore his desires with his teenage trans babysitter, Milly.

• Language: English
• Publisher: Jessica Cockburn
• Release date: Sep 18, 2023
• ISBN: 9798201194895

Book preview

The Babysitter's Packing

She’s Transgender, He’s Transfixed

Copyright 2023 Jessica Cockburn

Published by Jessica Cockburn at Smashwords.com

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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.

Let me share with you the extraordinary events of a day that turned my ordinary life completely upside down. At that time, I believed I knew exactly who I was – Jack Smith, a respected educator, a devoted husband, and a loving father. I prided myself on being faithful to my wife, never deceiving a friend, and certainly never engaging in any inappropriate relationships. However, all of that changed within just a few hours. Surprisingly, I wouldn't change what unfolded for anything in the world.

Many years ago, I relocated to the quaint town of Heathford, Rhode Island to work as a biology and psychology teacher at Heathford High School. Back then, I was only twenty-seven years old. Seeking stability for my family, especially after the recent birth of our twins, Marty and Amber, I took the job. I had no idea just how much I would come to enjoy teaching. It quickly became my true calling and, besides my family, the greatest source of joy in my life for the past eight years.

I had settled in Heathford for a few years when I had the pleasure of meeting Milly Jacobs, the daughter of an old high school friend, Gale. Gale and I had