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 Jolene Cana  


When did I first start Crossdressing?

I remember my sister dressing me up when I was quite young but it wasn't something I instigated. However when I was 9 years old, I remember seeing a pair of my mother's shoes and trying them on. The feeling was electric! After that I was totally hooked!!

My early experiences dressing as a child -

I would wait for an opportunity to be alone at home and then I would raid my sisters and mother's closets! I experimented a little with makeup but wasn't very good at it.

In my later teen years and university years I dressed very little, more because of lack of opportunity than anything. I always had thought I could give it up or quit but I always came back to it.

When I was about 30 I bought my first wig and makeup. I stored most of my stuff in a locked trunk. It was such a thrill to actually see my self in a wig and looking like a girl for the first time!

How did i learn to apply makeup?

I actually took a few lessons from an amazing makeup artist in Toronto - Dorota Buczel. On a whim I decided I wanted to take lessons and found her on google. I emailed her to see if she was open to teaching a crossdresser and she was more than happy to do so! She has given me several lessons and done my makeup for going out several times! It is still a big learning process for me and I want to get better!

What was your first experience going out as a girl?

About 5 years ago I went out for the first time as a girl. It was just for lunch at a little place in Toronto on Zelda's. I was very nervous but it was so much fun!

Since then I get out a couple of times a year. Usually to dinner with friends. This last year I was lucky enough to get our for Halloween. I wore a Dirndl, it was so much fun!

How often do you get to spend time as Jolene?

I dress about 2-3 times a month but only really get out about 4 times a year.

Do you feel like you want to transition or take this further?

I have no real plan or desire to transition. I have been doing some laser and electrolysis to make myself more passable or at least less hairy! But no plans to go any further than that.

What is your favorite style of clothing to wear?

Well, my favorite has to be wedding dresses or ball dresses. However, those are not exactly practical for day to day wear. I try to look as natural as I can but I do prefer a skirt or dress to pants!

I just want to thank Rachel for the opportunity to be a cover girl! I am so incredibly flattered!

Thanks so much!

Click on Penny’s portrait below to go to her Facebook page.