The Awakening: My First Public Transition into Female Clothing

It was around two decades ago, during my time in a rented apartment in a block of flats, that I first decided to venture into the world dressed as a woman. The experience was a mix of nerve-wracking and exhilarating.

Initial Nervousness and Small Steps

At that point, I was faced with the ordinary challenges of daily life, but in a much more pointed way. I didn't know many people in the area, which provided a sense of anonymity and helped me build the courage to take this step.

My first attempts to venture out were short-lived. I would step out of the apartment for a few seconds and then quickly retreat. I even went so far as to take the lift down and back up, and then do the same using the stairs while occasionally removing my heels in case someone would hear me and open the door to see me. It was quite ridiculous, but that’s how I felt at the time.

Gaining Confidence

After several months of these small steps, I finally gathered the courage one evening. This decision was partially influenced by the fact that it was a bank holiday and the city was nearly half-empty, making it less crowded and nerve-wracking. I also had a few glasses of wine, which helped me feel more liberated and horny.

The Perfect Outfit

For this outing, I aimed to look like I was going to the opera. Here's a detailed description of what I wore:

Bloody-red artificial nails on my hands Cuba-style skin-coloured stockings with a black seam in the back, strapping to a matching corset Fake cotton breasts underneath the corset, not too big to provide a different "view from above" Putting on a chastity cage with half-O-ring one size smaller than usual and inserting a brand new red heart-shaped diamond head plug A roughly knee-length, slightly see-through, long-sleeved, and very tight black-grey dress 10cm black high heels with a thin ankle strap to walk comfortably without any discomfort or pain

Before leaving, I spent a few minutes in the bathroom applying base-cover mascara, smooth-skin lipstick, deep-blue eyeshadow, and a little bit of black to my eyebrows. Looking at myself in the mirror, I was quite aroused as I looked sexy from head to toe, aside from my face.

The Nightly Walk

In addition to the necessary items like keys, my phone, pepper spray, cigarettes, and lighters, I even included condoms, even though the thought of having sex that night was more terrifying than exciting. I took a short stroll around the block, using the side walkway around the back of the buildings which was rarely frequented. I occasionally stopped in the shadows of street lamps to listen for any signs of people. Fortunately, I did not encounter anyone that evening, allowing me to complete the walk in solitude.

After returning to the apartment, I realized the significance of this experience. It was a mix of pride, satisfaction, arousal, and excitement, but not solely sexual. It truly transformed my perception of myself as a crossdressing individual. I believe that during that evening, I went beyond just being a closeted, self-loving crossdresser. This experience showed me how much dressing up meant to me emotionally and that it didn't have to be tied strictly to sex and masturbation. It was a realization that dressing up was a part of who I was.

It was an experience that truly changed my life, and one I hold in high regard. It's worth noting that I repeated these nighttime walks many times during my seven to eight years in that apartment, and I continue to do so now. However, this first time was particularly special and remains a vivid and cherished memory.