Cross-Dresser Finds Life Purpose While Dressed as a Girl

Hello there! If you are new here, you might want to subscribe to the RSS feed for updates on this topic.

Over the weekend I had the wonderful opportunity to dress up for the third time in the past four weeks. Quite the turnaround, eh? Just in case you don’t know what I’m talking about, I went through a drought of not dressing from October to March and it was tough to get through.

Since then, however, I have femmed myself up every single Saturday except the one before Easter and it’s been great for me. My life is feeling much more balanced and combined with exercising, spending time with my wife and things going well at work I am much more happy.
For the first time in my life, I’ve found something valuable to do with my time dressed as a woman. . .

The Status Quo

Before I get into that new purpose, let me first debrief you on how my sessions en femme would normally go. I would take a couple of hours to get ready — shave, apply makeup and put my clothes and accessories on. I suppose that because in my lifetime I really haven’t transformed into Jessica an awful lot, for a while the preparation process took center stage. Once it was done, there wasn’t much else to do.

Oh sure, I would certainly enjoy gazing upon the gorgeous reflection in the mirror and the obligatory picture taking, but outside of that it was pretty bland. This is because I never did anything of significance. Under no circumstances would I open the front door, not even to take a few steps, which meant that I would be forever confined inside of my four walls.

It’s perhaps because of this that I haven’t ever developed a healthy frequency for my cross-dressing. Sure, it was fun and sure being in a skirt and makeup would make my heart flutter like butterflies in a beautiful garden, but it was just irresponsible to dedicate an entire night to, well, nothing.

Please don’t get me wrong, because I do feel that expressing yourself through clothing and cosmetics is pretty powerful. It’s just that in my case I needed something more if Jessica was going to ever start making regular appearances.

When I attended the Be-All conference last June, I was taken aback by my own analysis of the situation. Would I forever be limited to these (amazing) transgender conferences to be able to break out of the closet and actually participate in various activities?

My wife and I discussed this quandary time and time again but never could get to a valid solution. The result, more often than not, was time vegging out in front of the TV in drag. Big whoop, right?

A Perfect Storm

I had been considering making videos for a while, shortly after I began blogging, but I wasn’t 100% sure. When the time came to go to Be-All in June, I made sure to pack my camcorder alongside my wigs, dresses and makeup. As soon as we arrived at the hotel, I made the transformation and just before heading out, I fired up the video camera to document those exciting first steps.

At the time I was only doing it for private memories. I had every intention of keeping that motion picture between me and my wife. Later that same evening, just before I peeled my face off, I propped my handicam on the nightstand, sat in front of it and started my first vlog.

I had a lot to express that night and wanted to make sure that I never ever forget the feelings and new experiences. This was also to be confidential, though in the back of my mind I kept alive the possibility for public broadcast.

After that day, the tapes sat dormant in the back of my closet, kept hidden so they wouldn’t be accidentally viewed by the wrong eyes. Looking back, I don’t even think I watched them more than once or twice.

Fast forward a few months, and my blog’s going stronger than ever. I’m confident and proud to share pictures of myself in drag and suddenly the video idea resurfaces. I made the decision and before I knew it I was actually driving my car around town en femme with my wife doing most of the filming.

After some thoughtful editing I posted my first YouTube video on November 13th of last year, to rave reviews. During that week, as the positive comments and encouraging messages rolled in, I revisited that fateful June weekend.

I popped the cassette into my camera, rewound a bit and hit the play button. Whoa, cool, my vlog! Just as I began to take it all in and relive that time, blam!, a new scene began — oops, we recorded over Jessica Who’s first vlog. I hastily went back to the beginning of the tape, dearly hoping that the other footage was in tact.

Luckily, it was, so I transferred it to my PC and did some fun editing, adding sound effects and background music. Exactly seven days after my first video went up, its successor was online. It was quite magical for me, as my original idea for making YouTube videos back on June 5th of 2009 had finally come to fruition.

Incidentally enough, that very first production is far and away my most popular video to date, at over 17,000 views and counting.

Couldn’t Possibly Keep Up

As you can see, my big picture goal was to post a new video every single week, but due to several factors (most of which my living situation at the time) it was highly unfeasible. So unfortunately, Jessica Who? HD went dormant for several months.

I still had every intention of picking up where I left off, and began formulating a scheme to accomplish just that. Equipment and supplies were purchased and each idea that came to me was recorded on paper.

At last, things came together last month and I was able to reboot my YouTube channel. The plan is simple enough — one new comedy video each and every Tuesday. Carrying it out, however, is a different story.

It’s a bold endeavor indeed, especially for someone who works full-time and doesn’t often get to dress up like a girl. Nevertheless, filming, editing and releasing these videos has been exhilarating and is now merging with my drag time, forming a mutually beneficial relationship.

I now have more motivation to set aside time to go from male to female, and I’ve made proper arrangements to keep my weekly promise going strong. Sure, I may miss a week, but I can assure you that it won’t be anytime soon (currently, I have three brand new videos ready to go).

My wife and I joked that Jessica now has a “job”, and it is making funny videos. I’ve got a laundry list of ideas, I’m constantly inspired and keep something with me to jot down my thoughts wherever I go. There are numerous grand plans in the works for my YouTube channel, most important of which is….well, I’ll get into that later, I promise.

For now, I leave you with my very first screen time as Jessica, and thank you for reading my post, watching my videos, and giving me your support and encouragement. I’m dead serious when I say this, I couldn’t do it without all of you.