Lost Bet, Gained Daddy: Poolside Crossdressing with Friend’s Dad

By Jessica Cockburn

Dani and his best friend's father, Jack, find themselves in a steamy encounter filled with passion, secrets, and a mix of pleasure and apprehension. As their desires ignite, they navigate the boundaries of their friendship and explore a forbidden love that they never anticipated.

• Language: English
• Publisher: Jessica Cockburn
• Release date: Sep 15, 2023
• ISBN: 9798215060209

Book preview

Lost Bet, Gained Daddy

Poolside Crossdressing with Friend’s Dad

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.

My buddy and I were chilling at his dad's place, indulging in the typical activities of unemployed graduates: lounging around, being lazy, and smoking pot. We had just gotten our hands on a bag of weed and a massive six-foot bong, getting ready for our first smoke session with it.

Neither of us had any clue what to expect from the bong, so my friend Mark jokingly threw a challenge my way. Dani, if you can't handle the whole bong, you're a pussy and you'll have to rock a bikini by the pool all day.

I laughed and fired back, Alright, but if you can't handle it, you're an even bigger pussy and you'll have to strut into the gas station wearing a dress to get us smokes.

With our little bet settled, we packed the bong and Mark volunteered to go first. As the smoke filled up the bong, I couldn't believe we actually thought we could finish it. But Mark surprised me and cleared the entire thing effortlessly, even though I did my best to distract him and make him fail.

Now it was my turn, and seeing Mark conquer it so easily, I figured I should have no problem as well. I took my first hit, but halfway through, it became overwhelming. The coughing fit took over, and I had to give up. Right when I stopped, Mark burst into laughter and declared, I'll find you a bikini!

At first, I didn't think he was serious and went ahead to finish the remaining part of the bong without much thought.

Now, I was soaring high, and Mark looked at me with a mischievous grin, asking, Do you have any preference for the bikini I should get you?

I chuckled and responded, Like hell I'm wearing a bikini, and besides, you don't even have one.

Mark locked eyes with me and said, dead serious, You made the bet that I would wear a damn dress, so you're damn sure gonna wear that bikini. My dad has a bunch of stuff from his ex, and we'll find one for you.

Perhaps it was the intense high that dulled my resistance, or maybe I just didn't feel like arguing anymore. I surrendered and followed Mark into his