Second place winner of our Kittens Category from our 2016 Glamour Girl Photo Contest

“Is it so wrong to want to grow up to be a smart, beautiful, sexy woman?

It’s something I have always wanted to be,ever since I was a little, well, boy. Jill, has been a part of me for as long as I can remember. I was lucky enough to have a slightly younger sister who wore roughly the same size as me. I remember sneaking into her room when no one was around to try on her clothes and let Jill out. I wished all her dresses, cheerleading uniforms, and dance recital costumes were mine. I just loved the Holidays. Every Christmas and Easter she would always get these beautiful new dresses with matching tights and shoes. I was so jealous, I could not wait until I had the chance to wear them. Then of course was the handful of times she was asked to be a Flower Girl. What I would have given to trade places just once, to attend the bridal shower with all the other girls to get my hair, nails, and makeup done for the big day.

As puberty hit, I was extremely confused. I was totally attracted to girls, but still had this desire to dress as one. When my sister entered high school, I was finally able to try makeup; what a disaster. LOL! The hardest time was always the spring, when prom season rolled around. I always had girlfriends in high school and I always envied them around this time. Instead of renting plain old tuxes, I wished I was the one that got to go dress shopping or getting a pretty updo at the hair salon, or slipping on some heels just to seem like a princess for the day.

The addition of roommates and the absence of my sister’s closet, throughout college and my late twenties, created what I called “Jill’s hibernation period”. It lasted quite a long time, I might add. It was during this time that I met and married my wonderful wife (who does not know about Jill). It wasn’t until a few years later that Jill came back into my mind. Me (now armed with a tool I didn’t have as a kid, the internet), I was able to buy some of my own things, and gain access to lots of useful tips. I also found photos of amazing looking woman. Although, I didn’t think I could ever look as good as any of them, I wanted to try. After mup any trials and tribulations with makeup and clothing sizes, I finally purchased a wig in late 2014. When I put it all together and looked in the mirror, it was the first time I really saw Jill staring back. She wasn’t gorgeous, but she definitely had potential. I started taking photos and created a Flickr page in early 2015. Inspired by the supportive feedback I was receiving, I decided to go get an actual makeover and scheduled an appointment with Amnesia Sparkles at Genderfun in Brooklyn. I was so nervous as I sat outside in my car beforehand, but I shouldn’t have been. It was so fun, and she was just amazing. I can’t say enough great things about her. I just loved my results so much. For the first time, I was that smart, beautiful, and sexy woman I had dreamed of, since I was young!

What’s next for Jill?

I can’t believe how far she has come in the last year and a half. Placing 2nd in the Kitten category of Glamour Boutique’s, Glamour Girl Picture Contest. This has been a big confidence boost and I think it is time she spreads her wings and ventures out and about FOR THE FIRST TIME. I would also love to attend Keystone next year and meet in-person some of the wonderful friends I have met online,.So, there will be definitely more to come from this girl!”

If you would like to hear more about Jill, check back on our newsletter for more updates on Jill!

See the rest of the 2016 contest winners here.