Wear My Boobs

I dressed as a woman on the street: my first go out

What was it like with my first go out in a female version? How did I feel at that time and what emotions were in my head? In the following text I will try to present in detail that wonderful day.

I had resolved to only step outside presenting as female when I was completely content with my appearance, as I didn’t want to draw undue attention on the street. I spent time complimenting various outfits, learning to apply makeup with my fiancée’s help, searching the web, and reading about others’ experiences. Once I mastered concealing my beard shadow, I began to appreciate my reflection in the mirror. That’s when I wondered if it was time to step outside my comfort zone?

It began on a winter day when I felt particularly down. Envious of other women freely expressing themselves through fashion, I lamented my own concealment. Forbidden from heels, skirts, and makeup, I felt trapped and despondent. Despite my efforts to combat these feelings with stoic philosophy, acceptance was a distant goal, and the idea of stepping out en femme seemed like a boundary I was yet to cross.

The next day dawned brighter, and my previous night’s troubles seemed distant. Alone for the afternoon, as my fiancée attended a work training, I found myself in a familiar slump at work. However, an empowering thought took root – why not venture out en femme? It was harmless, merely an act. Resolved, I planned for Sonia to take her first stroll that day. Work couldn’t hold my focus; I was eager to start.

By 4 p.m., I was ready, donning a red blouse, navy blue skirt, and styled myself with makeup and a ginger red wig. The mirror reflected someone I was pleased to see.

I couldn’t wait until 8 p.m. and headed out at 7 p.m., dressed in a coat, scarf, and heeled boots against the cold. I liked my reflection – a lot. After snapping a few pictures and ensuring the coast was clear, I stepped out, heart pounding but less nervous than expected. Bypassing the pizza delivery person without incident, I ventured into the night, only to return briefly for an umbrella.

The neighborhood was dimly lit, but I relished every moment – the click of my heels, the breeze against my legs. I avoided people mostly and decided to drive around, momentarily worried when a neighbor spotted me, but figured he’d assume I was a relative. The freedom of being Sonia outside was exhilarating. I drove around the city, satisfied.

The rain continued, but I didn’t mind. I walked extensively, my confidence undimmed by the dark or passersby. Returning home felt surreal, with a heart full of joy and a head full of precious memories.

I had done it. The experience of going out en femme was gratifying, a dream realized. It wasn’t as frightening as I’d imagined. That evening, my spirits lifted, and the negative feelings dissipated. I had been authentic, and my home was no longer a constraint.