Sierra? - It's Part Of Who I Am

By Sierra Romeo

I first started dressing when I was young. I would occasionally borrow some things from my mother or sister at times when I was alone. I never understood why I liked it, but I just did. Still, I also felt guilty and ashamed by it and would often go for long periods without dressing, even if I had plenty of opportunities. This would go on and off until my late teens when I eventually outgrew what I had available to me. I just took that as a sign to stop completely. Still, I was interested in the concept of crossdressing, and I liked to watch movies, read stories online, or look at pictures of it. It was a way of enjoying crossdressing without actually dressing up, and it worked for me for a long time.

I had eventually found my way to Flickr, and I enjoyed viewing the photos of the lovely ladies there and leaving comments on their pictures. At this point, I still had no interest in dressing up, but I did enjoy browsing through the girls' photos and reading some of their background stories on how they got started. After a few years of seeing these ladies modeling some beautiful dresses and seeing how much fun they seemed to be having posing with friends, I began to think about trying it again. Still, I never seriously considered it and always put that thought aside until later. Eventually, I made a few friends there and would message them occasionally. After a few questions from one girl who suspected that I had more than just a passing interest in crossdressing, I told her about my past and that I had been somewhat thinking about dressing again. After that, I was more open to other girls and told more of them about my past.

Things really changed for me with the help of a sissy friend named Jenny. It was a sad situation, but she told me that she would be moving and she wouldn't be able to take her girl's clothes with her. She didn't like the idea or cost of keeping her things in storage for a long time, and knowing that I liked her clothes and that I was interested in dressing up again, she asked me if I could take them. After some initial hesitation, I agreed. She sent me her things, and in June of 2014, I was able to dress up again for the first time in at least 15 years. I was a bit scared about getting back into this, but once I was dressed, I realized that this is a part of who I am, and it is never going to go away. I was able to enjoy dressing up occasionally and sharing my pictures with some friends, but with no makeup skills, I wasn't too happy with my appearance. I eventually went to a makeup artist who used to run a dressing service to get a makeup lesson and my first makeover. I was amazed with the results, and this was the first time I had ever really seen myself as a girl. After that, I started practicing makeup on my own and started sharing my pictures online. The response from the community has been overwhelming, and it's been very exciting to see how I've been developing in these few short months. I've been making a lot of new friends, and now I've been asked to be one of Rachel's Cover Girls.

As far as my style goes, it's very feminine with a lot of very pretty dresses. Since the clothes that I really started with came from my sissy friend, most of the things that I had were in a style meant for little girls. I do like the sissy look in other girls, but I never really saw myself as a sissy. Still, I found it to be a lot of fun to try on those cute sissy dresses with a gorgeous petticoat. I joked with my friend saying that maybe it's appropriate that I start out with little girl clothes since I am something of a new girl right now. I have more clothes now, and I tend to prefer more adult or age appropriate looks, but it's still fun to play as a little girl at times. When I dress up, I enjoy being as feminine as I can be, and I have no interest in pants. I don't always have a lot of opportunities to dress up, but when I do, I always have a lot of fun taking pictures and sharing them.