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From the Diary of a Colombo Crossdresser

19 December 2017 Posted by No Comment

I can’t remember exactly when I started to crossdress, but I can recall that I liked the sensation or silk and satin since I was a teenager. Back in the mid to late 90s, during my teen years, I had no idea this was a normal phenomenon. As I had no one to talk to or guide me, I embarked on this journey on my own and nearly 2 decades down the road, I decided to recount some of my experiences in the hope that it would help a budding crossdresser regardless of their situation.

The first real experience of crossdressing for me was during my school years. I went to a boys’ school and being rather small in stature and somewhat timid in nature, yet being good in spoken English, it was natural that I was chosen to play several female characters in school plays and ‘action’ songs during English Day celebrations at school.

I remember clearly the first dress I ever wore and while being totally embarrassed on the outside, how I loved I looked and how the dress, the shoes, the jewelry and the makeup felt. The dress was powder blue, long sleeved, ankle length, gathered at the waist, my makeup was done, I had two dainty tear drop earrings and a faux pearl necklace on. I cannot remember exactly which year this was, but I do know it was pre O/L, so no wigs were used on any of the boys who played girls in that song, but secretly it didn’t matter to me because I felt beautiful.

If I were to put my finger on the exact moment I knew I had a strong female presence in me, I would say that is the day. Once the song was over, I couldn’t wait to get out of the dress and into my school uniform. However, deep down I knew that was a charade and that I wanted to stay like that for as long as I could. But somewhere, somehow, one of my teachers may have noticed that I made a very passable girl. Or it could be that my command of English was the reason. But that lead to a performance in the Shakespeare play Macbeth as Lady Macbeth. I was 16 years old, and I now had the opportunity to play a full-fledged female role for the first time in my life. (Bit parts and several other songs and a few small dramas had gone in between) As soon as I heard I was chosen as Lady Macbeth, I began to fantasize about my costume. Nearly every day I envisioned myself dressed in a Victorian era ball gown made of satin, wearing a wig, flawless makeup, a pair of heels at least 2 inches tall, hair done up in an elegant do. My dreams were endless. I found myself looking forward to the dress rehearsals with great anticipation. Now all this fantasizing was done deep in my psyche as I realized if I showed even the slightest liking towards being a female avatar, my classmates would never let me hear the end of it.

The tension of wanting to dress up and yet not wanting to be ridiculed was quite tough to bear at times. Again, no one to talk to about my feelings and wanting to dress up meant I had to retreat to a world of my own. By this time the need for crossdressing in me was quite high, which scared me no end as well since I had no idea whether this was normal or not.

So came the day or the dress rehearsal. I was one of the several juniors in the drama club and as such was hazed every now and then. So when the lady teacher in charge put a bra in front of me, I was positive that this was another hazing. But it turned out that to complete the feminine figure, a bust is needed and the best and the easiest way is to wear a bra and stuff it with either socks or tissues. And the experience blew my mind. It was like a final puzzle piece falling into place. I now knew what I needed to become the female avatar that was growing inside my psyche. However, being a student and having no income, I resorted to the only options that were available to me. I decided to take a peek into my mother’s closet where I knew she kept clothes that she doesn’t wear anymore… Thus began the next chapter in my quest to become Anjali. More adventures in the next installment. Till then, stay beautiful girls.

– Anjali Gunawardana

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