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.

Then about a year ago, it just kind of hit me: I wanted a pair of women’s shoes.  That went through a bit of a thought process.  I wanted a pair of women’s shoes, but I didn’t really know what I wanted to do with them.  I also recognized that I have big feet, and so finding a pair of shoes that I liked and that fit me would probably be a bit of a challenge.  Casually browsing online, the shoes that I found that were my correct size were definitely not sexy.  I also couldn’t see myself just wearing the shoes by themselves.  It felt funny.  I ended up shelving the whole thing for a while, but the idea persisted.  I just couldn’t put it out of my mind.

I revisited the idea this past spring, and refined the idea a bit more.  It wasn’t just the shoes: I wanted to start crossdressing.  I had a feminine side that I wanted to explore, and to do that, I needed to make myself feel more feminine.  And I wanted to “pass”.  To that end, I developed the persona of “Jennifer” to embody the expression of my feminine side.

In order to make a believable Jennifer, I had to do a little shopping.  I got a few outfits, mostly from Walmart and from Old Navy.  I also got some embarrassingly cheap jewelry from Walmart.  After a few false starts, I settled on a relatively inexpensive medium-length wig that I found on Amazon for hair.  I didn’t want Jennifer to have short hair, but I also found that the really long wigs were more than I wanted to mess with.

I also did better research, and found four pairs of shoes that fit:

Beacon women's Newport casual shoes
These are Beacon’s “Newport” shoes, which are very low wedge-style heels.  I am still learning how to properly walk in these, because I don’t normally do anything with any sort of significant heel on it.

Bass Joanne sandals
Bass “Joanne” sandals.

Keds Champion canvas sneakers
Keds “Champion” canvas sneakers.  When I bought these, I also got an identical pair in a men’s size to see which fit better, and interestingly enough, the women’s size fit me better than the men’s size.  The men’s size was too long, whereas the women’s size fit my length and width pretty well.

I also got a pair of cheap flip-flops, but I’m going to assume that you know what cheap flip-flops look like.

In addition, I fashioned a set of breasts using rice and a pair of stockings.  The research that I did suggested that if you really want to make a convincing set of breasts, get silicone forms, but those are expensive, and I had already spent too much on shoes.  Rice and birdseed were suggested as alternatives, so I picked the rice.  The way I figured, I could always cook and eat the leftover rice.  Here’s how they came out:

Jennifer breasts (front)

To make these, I got the rice at a grocery store, and I got the stockings in one of those little plastic balls for less than a dollar at Walgreens.  What I did was put the bra that I had previously bought on, and then start filling the stocking with rice, making sure to pat it down periodically.  When I got the size that I wanted, I tied off the end of it, containing the rice inside.  Then from that knot, I pulled the remainder of the stocking back over the whole thing again, and tied it off on the other side.  The tie-off ended up looking like this:

Jennifer breasts (back)

All in all, I was pleased with how these came out.  The outward-facing side was relatively clean-looking, with the added bonus of the first knot’s slightly resembling a nipple.  And then the final tie-off is on the back, where nobody can see it.  I think that they work well enough, though if you touch them, they do feel a little bit firmer than real breasts.

I also got a skin-colored zentai suit to use as a base layer.  Besides the fact that I love zentai, it also helps me lower my own inhibitions.  When wearing a zentai, I can completely shed my normal identity, and become Jennifer.  No one will know that Jennifer is me – which is exactly how I want it.  In addition, when I look at myself in the mirror in a dress without the zentai, I think it looks goofy.  Put the zentai on with it, then it’s sexy.  Plus I have no desire to spend money on cosmetics in order to do nails and makeup at this time, nor do I particularly want to invest the time and effort that goes into shaving body hair.  This also means that I can completely remove all of the trappings of Jennifer when I’m done, and go back to my regular gender and identity on demand.

I’m going to hold off on showing you photos of Jennifer for now, only because the only photos that I have of Jennifer were taken in my home with a webcam, and the decor in my home is recognizable from other projects that I’ve done.  I’ll get some photos of Jennifer at a later date, taken in a different location, with a better camera.

All in all, though, I’m excited about Jennifer.  I think that Jennifer will certainly help me express my feminine side, as well as help me continue to explore and understand my own sexuality.