This may sound awfully clichéd, but I will never ever forget my first time. It happened on a warm, summer, Friday evening, which will forever go down as one of the most special moments of my life. I had been waiting for that moment for a long time, carefully preserving myself for the perfect time with the perfect partner. When it happened, it felt like a natural progression to a new level of my existence.
I still remember every little detail. In the beginning the anxiety of not knowing what to expect was crippling and my legs shook uncontrollably. Eventually, I started to relax and the discomfort subsided; overwhelming pleasure took its place inside me.
That night I did not lose my virginity – that is a vague memory. That night I finally grew balls, and for the very first time I wore an item of clothing traditionally designed for women. That night I took the first step to a journey of self-actualization. It began with a special pair of vintage, off-white, ‘Sissy Boy’ pants, with a high waist and black pinstripes.
Thanks to my accepting and unconditionally loving family, I’ve never had to keep my sexuality under wraps – which would have been an impossible mission considering my painfully effeminate nature. I am a proud cis gay man. I love being a man – so much so, that I love other men too. However, I have always struggled with gender roles and norms. Growing up I dreaded going to school because that is where gender roles were clearly defined. Boys this side and girls that side, pink for the girls and blue for the boys, soccer for the boys and netball for the girls. The entire system made me so uncomfortable; I withdrew from society and found comfort in my own company.
Overtime I became a happy recluse because I learnt how to escape the dull man-made principles of society by retreating to my imagination. I spent my days daydreaming about a world that would allow me to be myself – a man dressed in women’s clothing. Not a transvestite, not a drag queen, and not a transgender woman, or any of the labels that society sticks on people for its own convenience. I am simply a man, and I am most comfortable in women’s clothing.
For years, I suppressed the burning desire to walk into the ladies’ side of the shop and pick the most beautiful floral blouse. I continued dressing up in men’s clothing until I laid eyes on my special ‘Sissy Boy’ pants one Friday afternoon. They graced a window of a women’s clothing boutique, worn by a tall beautiful mannequin who looked so sure of herself. I wanted to be like her – to look so self-assured and bold, yet so feminine and striking. As I walked out of the shop I knew that night would be a life-defining moment. A moment I get to relive every day.