Archive for the ‘Crossdressing’ Category

Jennifer makes her debut…

Back at the beginning of September, Jennifer, my feminine persona, made her debut at a private play party.  As Jennifer, I wore a navy blue sheath dress from Old Navy, along with the other effects that turn me into Jennifer, i.e. rice boobs, zentai, and wig.  Unfortunately, however, since I was still recovering from a broken bone in my foot about a month prior, I couldn’t wear proper footwear.  Therefore, rather than wear Jennifer’s shoes, I had to go with a pair of Crocs, since Jennifer’s shoes were too painful to wear with the injury still actively healing.  But hey, at least I didn’t have to wear a boot anymore.

Going out as Jennifer for the first time was kind of “eh”.  I knew the people that I was with, but I hadn’t been able to completely drop my inhibitions and relax.  I felt uptight, not quite knowing how to behave as Jennifer.  I mostly stood back and watched from the sidelines as others did their thing.  I think the biggest thing was becoming comfortable in Jennifer’s skin, and I suppose this first time was as good of a start as any.  However, I have a long way to go before I am really comfortable as Jennifer around others.  Becoming Jennifer at home is one thing, since I live by myself, and I’m just walking around the house feeling the fabric against my skin, and trying to walk convincingly in heels.  Being Jennifer in front of others is an entirely different matter.

Read more

Exploring the woman within…

As I’ve gone through my thirties, I have really been more open to exploring my inner self.  When I was in my twenties, I was more concerned about what “other people” might think.  Now that I’m in my thirties, I have come to realize that said “other people” are too busy dealing with their own insecurities, and therefore aren’t paying close attention to me.  With that realization, there’s a certain level of “fuck it, let’s do it” that comes to mind, because, after all, you only live once.  I also love the freedom that we have as children to do and explore whatever we want in the name of child’s play, and it makes me sad the way society then pushes us into conformity with certain gender norms as we get older.  It raises our inhibitions, and makes us less willing to go outside those norms.

I generally go through life as a cisgendered male.  I have the male anatomy, I dress in men’s clothing, etc.  However, when I was growing up, I remember thinking how much more interesting the “girl” toys that were advertised on Saturday morning were than the “boy” toys.  I also secretly envied the far more exciting and fun outfits that women got to wear.  I loved the clothes, and I loved the shoes.  After all, men’s clothing is pretty formulaic, and the shoes aren’t that exciting, either.  Not much in the way of excitement there.  When I was around 12 years old, I secretly tried on some female clothing, and it actually felt pretty good.  However, at that age, I kept that side well hidden, because, you know, middle school and all.  Then I unconsciously put it away for quite some time.

Read more

Return top