Embracing Femininity: From Bullied Boy to Beautiful Woman

By Jessica Cockburn

A young man discovers his hidden desire for cross-dressing and finds solace and support in his best friend, Theresa. Their friendship deepens as they explore their own sexualities and help each other embrace their true identities. A night of passion at a party leads to new experiences and a hope for a future free of judgment.

• Language: English
• Publisher: Jessica Cockburn
• Release date: Sep 17, 2023
• ISBN: 9798215875070

Book preview

Embracing Femininity

From Bullied Boy to Beautiful Woman

Copyright 2023 Jessica Cockburn

Published by Jessica Cockburn at Smashwords.com

Smashwords.com Edition License Notes

This ebook is licensed for your personal enjoyment only. This ebook may not be re-sold or given away to other people. If you would like to share this book with another person, please purchase an additional copy for each recipient. If you’re reading this book and did not purchase it, or it was not purchased for your enjoyment only, then please return to Smashwords.com or your favorite retailer and purchase your own copy. Thank you for respecting the hard work of this author.

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.

Alright, Monica laughed. I can see you almost fainted. I won't look.

Glancing over my shoulder, I confirmed that she had indeed turned around. I placed the black panties on the bed and gingerly removed the boy shorts, carefully sliding them down over the stockings. Then, I examined the lacy black thong Monica had given me. There was no mistaking its provocative nature.

Doesn't leave much to the imagination, I grumbled, inspecting the underwear.

Imagination is all I have right now, Monica remarked, her voice echoing from behind. Hurry up, would ya?

Patience, I replied. I've never had to handle a piece of string before.

Monica erupted into laughter as I navigated the task of putting on the thong. First, I slipped my right foot through what seemed to be the correct opening, then did the same with my left foot. After pulling the panties up, I tried to discreetly arrange my erection to no avail. Once again, the head stubbornly peeked out above the waistband. Standing up, I glanced into the mirror and caught Monica's reflection. She wore a mischievous smile and burst into laughter at the expression on my face.

Saw the whole show, did you? I asked, unable to suppress a smile and finding it impossible to be angry at her.

Yep, she nodded.

Pervert.

Yep.

Might as well turn around then, I suggested, and she obliged.

You're looking quite attractive, Monica commented after inspecting me closely. Especially that little turtle head popping out of your panties!

We both erupted in laughter as I playfully swung a punch at her arm. I pursued her, laughing along, until we found ourselves cornered, where I cheekily swatted her behind a few times.

You truly are a perv, I remarked, taking a step back.

Guilty as charged, she confessed. I'd probably be behind bars if anyone found out about my proclivities.

Well, I know all about your perviness.

Coming from the boy dressed in girl's clothes, Monica continued laughing, her laughter music to my ears. I think you're the reigning champion of perviness.

I couldn't agree more, I nodded, a mischievous grin forming on my face. As unconventional as it may be, there was an undeniable thrill in embracing my more daring side.

It truly was an exhilarating experience. The feel of the stockings hugging my legs was surprisingly enjoyable, defying my initial expectations. The delicate thong, though I had anticipated discomfort, actually felt enticing against my skin, accentuating my every movement. And the lacy mesh, cradling my balls and teasing my cock, was an intoxicating sensation, coaxing pre-cum to emerge once again. I glanced up at Monica, curious to gauge her reaction, only to find her fixated on my aroused state. There was no need for words — her intentions were clear. Leaning forward, she sensually licked the pre-cum from the tip of my throbbing cock, sending an electric shock through my body.

Once I was cleaned, Monica stood up, a contemplative expression on her face.

I sometimes wish you were a girl, she confessed, her voice slightly husky.

Right now, I sincerely wish you were a boy! I playfully retorted.

Our shared laughter punctuated the moment, dissipating any lingering tension. Monica helped me readjust my bra before disappearing into her closet. Meanwhile, I obediently slipped back into the dress, successfully managing to do so without her assistance. When she returned, bearing a striking pair of sky-high heels, her gaze froze as she took in the sight before her. Meeting her wide-eyed stare, I couldn't help but question her reaction.

What's the matter? I quizzed.

You look absolutely stunning, she breathed, her voice tinged with genuine admiration.

Thank you, I responded, a newfound confidence coursing through me. I must admit, I feel incredibly seductive.

You truly look sexy, Monica confessed, her tone filled with awe. Even more alluring than I ever did in that dress.

Absolutely not, I retorted, but deep down I couldn't help but feel a surge of delight.

Monica passed me the footwear - a pair of sleek black four-inch stilettos.

These will be the death of me if I attempt to walk in them, I chuckled, holding them up for inspection.

Sit on the bed, Monica commanded.

Complying, I settled onto the mattress