Embracing the Risk Element: My Journey in Cross-Dressing

From my teenage years onwards, the thrill of stepping out in something unconventional has always brought me immense joy. This unique risk element has been a part of my life, allowing me to explore my identity and embrace my true self.

Early Nighttime Escapes

Back in the days when I could only wear my own version of sweats over a slutty outfit at night, the trails near my home were my escape route. I found solace and freedom in the quiet solitude, walking the dead of night and reveling in the anonymity that came with it.

The Drive to Wear What I Love

The allure of driving to visit my girlfriend in college was a perfect opportunity to express myself. I would meticulously plan the drive, selecting a skirt and panties that would make the journey feel worth it. Even in the car, getting dressed in the final layers was a moment of sheer excitement, which I would enjoy with the window down, the wind in my hair, and the sun on my face.

Transition to contemporary dressing

Now, my dressing up rituals have evolved. I plan an entire day, making multiple stops in different towns, each designed to enrich my experience. I often leave the house already dressed or in a state of near-completion. The first thing I do is put on makeup, and then I set off in search of the perfect piece at a hot dress barn or Hanes outlet. Thrift stores have now become my go-to, offering a treasure trove of unique and affordable options.

Masked Freedom and Beyond

The world is changing, and with the implementation of mask policies, I've found myself even more passable. Today, I wear minimal makeup, just a fashionable face mask and sunglasses. My legs are shaved, and I'm always in pantyhose and flats, which, by the way, are surprisingly hard to find in larger sizes. This outfit allows me to walk around without much fear of recognition.

A Day at the Mall

One dare challenge I couldn't resist was going to the mall. It was a thrilling experience as I faced various situations with people treating me with surprise and acceptance. At a restaurant, I was addressed as m'am, and the feelings of being myself were absolutely joyous. The mall and its varied experiences are a testament to the expanding acceptance of gender expression.

These adventures have taught me that embracing my true self, even with the risk of stares and questions, is incredibly rewarding. Each step forward in my journey is a celebration of my courage and happiness.