From the Diary of a Colombo Crossdresser Part III

So once I bought the dress, I had to figure out a way to stash it and I could not risk shoving it in with the old clothes I had discovered earlier, especially since my mother would frequently root inside that cupboard for old cloth.

So I decided I was going to stash the dress in a suitcase that used to conveniently sit under my bed (yeah, real convenient :D). So one day I managed to do just that. Now this suitcase is also full of old used clothes and hardly ever gets opened. So I knew it wasn’t a big risk. By this time I had developed a habit of staying up really late and dressing up in my room after my folks went to bed. Unfortunately though, since both of them were light sleepers, I had to really channel my inner ninja to make sure I was stealthy enough to not make a racket when I pulled out the suitcase and opened it. Slowly but surely I got good at it and soon I was dolling up late night several times a week, albeit, without make up as the makeup was in my mother’s dresser.

So I continued like this to get in some girlie time whenever I can until I began my A/Levels. With the pressure mounting on to get studying, crossdressing took a back seat for a while. I will fast forward through this time as there wasn’t really much happening to Anjali until after A/Level exams were over. Once the exams were over, I enrolled in a private university in Colombo and went to stay with my uncle and aunt as they offered to take me in.

Now the interesting thing is, my aunt is an amazing costume designer and a lot of elite schools in Colombo used to come to her to get costumes made. So there was an abundance of ballet outfits, leotards, flared dresses and the works around all the time and I was in heaven. Instead of planning what to do to settle down (now this place was home away from home to me) my head was running at a hundred miles an hour trying to figure out how to dress up. So lo and behold I get the room on my cousin sister used to use and inside the wardrobe in the room I find an assortment of sarees and dresses and once particular satin dance costume. And so I began to plan and once again I decided to doll up in the dead of the night as that is the easiest and most discrete thing to do. Since the costume came with a headdress, I decided it was time to at least wear some lipstick. So once I started that I was utterly hooked on looking as feminine as humanely possible.

It was around this time that I discovered what a treasure trove the internet is for a budding crossdresser. Pretty soon I was the subscriber of several ezines and youtube channels that dealt exclusively with content regarding crossdressers ranging from how to walk in heels, how to do make up, how to choosing lingerie to even how to ‘tuck’ to make sure any ungainly bulges disappear to spoil the feminine illusion.

Then I began to branch out. I wanted to explore other outfits and that’s when I started to check out saree draping tutorials on Youtube. Now anyone who has tried this knows how difficult it is to drape a saree on your own for the first time. Even a cotton saree. The saree I tried was a smooth silky charmeuse one and the first attempt ended up being a total freak show. But that was the catalyst for me to start to learn more and more and soon I thought I did an ok job. By this time though I had become online friends (this was pre Facebook, back in the hi5 days) with several other “crossdressers”. Now I use the inverted commas because most of them were actually not. It took me a long time to learn how to identify the genuine crossdressers from the pretend ones, but back then I had no idea how dangerous the internet could be.

That was until I came across my first true crossdresser friend. Her name was Erandhi and in my opinion she was the most beautiful CD I had ever come across. And that meeting and friendship would lead me to my very next adventure and a life changing moment on which I look back now with utter happiness because that was what truly freed Anjali to be who she is today. That’s all for today my lovelies. I will catch you next time with my next adventure. Till then, stay safe and dress fabulous!!! xoxoxoxox

– Anjali Gunawardana

Read Part I here and Part II here 

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