So, with the urge to dress up starting to increase with each passing day, I was wracking my brain trying to figure out how to pull this off without anyone catching on. As with most crossdressers, I had only one option. Since I had no sisters my only option was to try on some of my mother’s old clothes.

Then it became a waiting game to find a time window where I was home alone. Lo and behold that day came and after checking, double checking and triple checking my parents were really gone for a while, I started to root around the wardrobes that were there in the house.

That was when I came across a bag full of my mom’s old clothes. Most of them were in the 70’s style and I realized that most fit me. But as fate would have it, just as I was done with my search my parents returned and I had to hastily shove everything back to where they were and scoot out of the room. But overall, my mission was a success since I found what I was looking for. It was a real jackpot because I even found some old bras and as fate would have it, they were the front closure style which meant I did not have to throw my shoulders out of joint to clasp the hooks.

By this time, even though I was physically active and leading a rough and tumble life, I still recall how a well dressed woman or a girl would distract me from whatever I was doing. While I was attracted to girls and much as any teenager would be, I was different in the sense that I was also attracted to what they wore and found myself constantly wondering how I would look in that saree or a dress or skirt and top ensemble.

So once again, it was a matter of waiting till my parents weren’t home. But since some of their visits were short I needed to wait till they left town to try on some of the clothes I found. While the wait was excruciating in its duration, I also knew that the reward for waiting was going to be worth it, so I knuckled down and waited and finally I got my chance.

So when they left, I quickly went to the wardrobe and picked out a dress. It was a multi-color, swinging sixties type mini dress. When I slipped it on, it was as if it was made for me. Of course, with my natural hair being curly, I tried my best to style it in a way that was feminine, and I have to admit, it didn’t turn out too bad. At least in my eyes… Of course at this point of time, I wasn’t aware of the intricacies of makeup, and had to resort to a dash of magenta lipstick. I was thrilled with the result and I remember spending almost one hour like that before I decided to change back and stash the dress and bra away.

This became a regular thing for me to do and eventually I even dared to try on a saree, although it turned out to be a disaster. Back then we had no internet, hence no access to youtube, which meant I had no access to any of the tutorial videos that would eventually shape Anjali into the woman she became.

This was when I started to save as much pocket money as I can in order to buy a pink satin maxi dress which I saw in a shop in town. It was a party dress that teenage girls would wear for weddings and such and I was immediately drawn to it. Of course for a kid getting Rs. 50 of pocket money every school day, saving 1500 rupees was a long long long haul, but I was determined to do it, since I had to have that dress. However, I have to admit, I was terrified when I walked into the shop after school, dressed in my school uniform of all things and spoke to the lady behind the counter asking her the price of the dress. Before I knew it, I was spinning a yarn about being involved in a drama and so on and so forth and even figured out whether the dress fit me or not.

But in the back of my head I also knew if I waited too long, chances were I’d outgrow the dress, so I decided to sell a sticker collection I had (this was back when collecting edna cricket stickers to get a bat and other prices were the rage) to augment my finances and low and behold, I suddenly realized that I had the money. Now it was a matter of smuggling the dress into the house. Little did I realize that, smuggling the dress in was the easy part. I never gave thought of where to stash the dress after use. This was when panic started to grow. I knew if the dress was discovered, I had no answer to give and since I am an only child, I knew the first in line for questioning would be me…

And on that note, comes the end to this edition of my chronicles. Stay tuned for the next chapter where I explore my femininity further and experiment with various looks, discovering the internet and of course how I came up with a foolproof (also hair brained) idea to stash the dress I just bought. Till then, stay gorgeous boys and girls. xoxoxoxox

– Anjali Gunawardana

Read Part I here