For me, being a crossdresser has always been incredibly confusing. A few years ago, starting to accept that I liked to wear women’s clothes, opened the floodgates for a lot of questions regarding my personality. First of all, I started wondering whether I wanted to go all the way and start dressing full-time. Perhaps I should even start looking into changing gender? After ruling this out – which took me over 2 years to accomplish – the question whether I was gay or not popped into mind. Surely heterosexual men don’t enjoy wearing dresses, right? Wrong. After many, many hours of pondering, I concluded that no part of me was gay, not even bisexual. After being able to rule out these things, my attention shifted to finding out what it is exactly that makes me want to dress in women’s clothes and how this will change my life.
What followed were several months of frantically looking for answers and getting increasingly frustrated by the fact I wasn’t finding any. My frustration levels peeked when I realised my search for answers had practically taken over my life without getting any results whatsoever and I sort of broke down and gave up crossdressing for several months.
During those months, the urge to crossdress never faded, which is why I decided to make a fresh start. I intended to start doing what felt good, without questioning why it felt good. I started experiencing more, tried different styles of clothing and some make-up techniques. I realised I wasn’t comfortable going out, so I focused my attention to dressing indoors. I bought some heels and learned how to walk on them. And, most importantly, I stopped following other crossdressers online and started to crossdress in my own way and not in the way the people I used to see as role models did.
All my little experiments ensured the way crossdressing fits in my day-to-day life now changed, compared to how it used to fit in. I abandoned the idea of ‘passing’ as I found out I was more comfortable being a guy wearing a dress than acting female as well. I gave up on planning how, when and where to go out dressed up for the first time, because I realised I simply didn’t feel comfortably doing it. I started doing the ‘guy stuff’ I used to do indoors (watching races and sports, gaming) whilst crossdressing, when I felt the urge to do so. As a result of this, crossdressing started to get entangled with my everyday life more and more, up to a point where I started accepting that crossdressing hasn’t changed my interests at all.