Girls Night: Crossdressing with the Wait-Babes

By Jessica Cockburn

Ten years working at a bar has left this lonely barman longing for more than just drinks. A birthday celebration turns into a night of steamy encounters, secrets, and unexpected desires. Follow along as they navigate the complex relationships and erotic experiences that unfold in the world of waitresses after work.

• Language: English
• Publisher: Jessica Cockburn
• Release date: Sep 17, 2023
• ISBN: 9798215243794

Book preview

Girls Night

Crossdressing with the Wait-Babes

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

Working at the bar feels like time has flown by. It's been ten years since I started here, but it feels like just yesterday when I walked in, desperate for a job after losing my previous career due to the economic downturn and a sexual harassment accusation. Back then, I saw this job as temporary, a means to get back on my feet. Little did I know the impact it would have on my life.

The local pub, where I used to be a regular before getting hired, had transformed itself into more of a sports bar to keep up with the trends. My previous experience bartending in the Army helped me adapt quickly and become successful from the start. I kept telling myself it was only a temporary situation, that I would soon return to my old line of work. However, the money was good and the tips were even better. I couldn't deny that the bar was becoming more than just a stepping stone for me.

The real stars of the bar, though, were the waitresses. They were the reason why I used to frequent this place before becoming an employee. It was a sight to behold - beautiful women in a charming uniform that showed just the right amount of skin. The waitresses were the heart and soul of the bar, attracting customers with their looks and charming personalities. Behind the scenes, however, their lives were far from perfect.

Flirting was a constant part of their job, but it came with a price. The constant attention and temptation often led to drama, grudges, and catfights. Emotional instability was the norm, and most of the girls didn't last more than a year or two. It was easy to see that getting involved with them was a mistake.

Despite being older and not particularly good-looking, I managed to catch the attention of Sandra, a sassy redhead with a troubled past. We had a short-lived affair, but her emotional baggage and the toxic environment at work eventually led her to leave town without even saying goodbye.

Another waitress, Jessica, had more potential. She was intelligent, stunning, and we connected on an intellectual level. We even had a brief relationship, but she moved on and started a family shortly after graduating. It was the last time I saw her, and it left me feeling empty.

Since then, I've steered clear of any involvement with the waitresses. Part of it is due to seeing beyond their looks and understanding the complexities of their lives. But mostly, it's because of the stark difference in age and appearance. If any of them were interested, I wouldn't hesitate, but it seems unlikely.

Working at the bar consumed most of my time, leaving little room for a social life of my own. Weekends