So like any Crossdresser I have a vivid memory of my first dressing experiences, and since I just started this blog I figured it'd be a good place to start. I remember first became interested at the idea of wearing women's clothing by watching television. Several TV shows featured young male characters dressing as women (usually portrayed in a comedic manner), this was my first exposure to the idea that men and boys are not necessarily being forced into wearing male clothing. Watching men on TV wear dresses and makeup got me wondering what it felt like to wear women's clothing. Additionally I'd never been a particularly big fan of men's wear, (or technically boys wear, since I was probably like 8). I always found male clothing very uncomfortable and unflattering, and inevitably when I was old enough to start picking my own clothes I mostly wore simple t-shirts and gym shorts as they were the most comfortable clothes I could find.
So at this point I had developed a fascination with men wearing women's clothes and a distaste for clothing designed for males, however I'd only ever seen a man wearing women's clothes on TV, never actually in person, that is until 4th grade. I was sitting outside my classroom in the morning waiting for my teacher to arrive when I hear laughter down the hall. Upon looking up I saw a 5th grade boy wearing a short flowy black halter dress, It was the most mind blowing and exciting thing I'd ever seen: a boy wearing a dress in real life! While all the other students were laughing with him, (in what was obviously intended to be a funny prank), I was in awe of him. I had so many questions, how did it feel to wear, what were you wearing underneath, why did you choose that dress over others? Unfortunately after only a few moments a teacher arrived and escorted him off to the front offices undoubtedly for making such a ruckus, and wearing a dress to school. Although my exposure to a boy in a dress was brief it opened my eyes to the possibility that anyone could do it, any boy could dress like a girl.
Now for the inciting incident: at this point I was completely enthralled by the idea of wearing women's clothing and was looking for any excuse to do it. I found that excuse in the cartoon show Codename: Kids Next Door. In the series teenagers act as one of the villains of the show and they wear bras that have armor come out of them. Mind you the boy teenagers wore these armor bras as well! I had my excuse, I needed to know what wearing a bra felt like. So one day when I had the house to myself I went to my mother's closet (I was an only child, no sisters to borrow from unfortunately) and found her drawer full of bras. I pulled out the pinkest one she had and tried in on. It felt absolutely amazing, the soft fabric hugging my chest giving me feminine curves. Now I was still pretty nervous about what I was doing so after a few minutes of enjoying the bra I quickly took it off and left my mother's closet.
Well now that I experienced a taste how amazing women's clothes could feel I needed to try more. So on another day when I had the house to myself I went back into my mother's closet. Of course I immediately slipped on a bra, and then I slipped into my first pair of panties, pink microfiber Hanes bikini panties. Again the feeling of euphoria flooded over me, wearing women's panties felt soooo goooood! But I wasn't going to stop there, I wanted more! I kept combing through her drawers and found her collection of slips, so I tried them on, and loved the way the soft nylon fabric covered my body. After trying on her collection of slips I had come to my big moment, trying on a dress. My Mom had them all lined up in a row in her closet, just waiting for me! I chose a blue one with white spots and tried in on, the way the fabric brushed over my legs, and curved over my bra creating the illusion of breasts. I was absolutely hooked, there was no going back, I belonged in women's clothes.
So after that I took every opportunity to wear my mom's clothes that I could. This went on for years, slowly trying on new and different clothes in her closet. Additionally I discovered the crossdresser communities on Youtube and Flickr which inspired my to keep dressing. Inevitably the time came when I would move out for college, and this finally gave me the opportunity to fully dress in my own clothes, and in a wig and makeup. Of course it took some time to perfect things like makeup and clothing sizing, but I'll probably have separate blog posts about that. That pretty much catches you up to today, if you read that whole blog post hope you enjoyed it! Look forward to more feminine fun posts soon!
-Carly