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Clothing Optional:
A Trans Woman's
Erotic Memoir

Biography

Chapter 1 - The Cores of My Identity

Chapter 2 - Dating in the Before Times

Chapter 3 - Medical Montana

Chapter 4 - Pleasure and Pain in Portland

Chapter 5 - Face Value

Hedonism

Year 1 - Introduction

Year 1 - Night 1

Year 1 - Night 2

Year 1 - Night 3

Year 1 - Night 4

Year 1 - Night 5

Year 1 - Night 6

Year 1 - Night 7

Hedonism Year 2

Year 2 - Introduction

Year 2 - Night 1

Year 2 - Night 2

Year 2 - Night 3

Year 2 - Night 4

Year 2 - Night 5

Year 2 - Night 6

UPDATE: Beta copies are being shipped 7/15/25
 

At six years old, I learned that being different was dangerous. By thirty, I had perfected the art of hiding behind other people's expectations. By forty, I was at a nude resort in Jamaica finally understanding what authenticity actually costs.

 

This isn't your typical transgender memoir. Clothing Optional chronicles my journey from a masked overachiever to a woman who stopped hiding entirely, from herself and everyone else.

The story begins with a neurodivergent kid who built elaborate armor to survive public humiliation, then spent decades perfecting masculine performance while secretly dreaming of waking up as a girl. I excelled at everything: academics, athletics, corporate ladder-climbing, while dying inside from the exhaustion of being someone I wasn't. The pattern seeking that helped me master these performances also trapped me in increasingly toxic relationships, culminating in an abusive partnership that nearly broke me entirely.

 

At twenty-nine, living in the isolation of Montana, I finally found the words I'd been searching for: I'm transgender. What followed was a ten-year medical and legal odyssey involving hormone replacement therapy, multiple surgeries, and brutal insurance battles. I document the reality of medical transition with unflinching detail: the bureaucratic nightmares, the physical changes, the emotional rollercoaster of becoming yourself at thirty-something.

 

But the real transformation began when I emerged from my post-surgical recovery as a thirty-seven-year-old virgin, terrified of my own desires. Enter Hedonism II, a clothing-optional resort in Jamaica that became my finishing school in radical self-acceptance. Over two separate trips, I discovered that once you've already blown up your entire life to live authentically, accepting yourself is the most radical act of all.

 

This memoir tackles practical realities other trans narratives often gloss over: What does hormone therapy actually feel like? How do you navigate insurance companies that would rather let you die than pay for your care? What's it really like to have a neo-vagina? These unglamorous details matter because they're the reality of transition beyond the inspirational soundbites.

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©2021 by Lady Skye

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