Stepping Out As Jessica – The Final Frontier

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Pardon the title please, I just saw the new Star Trek movie this past weekend with my wife.

When it comes to crossdressers, some are fine wearing underwear under their man clothes, some dress head to toe inside their house, and yet others venture outside into the world. What does it mean to make this leap from closet to curb, and how in the world can one muster up the courage to do so?

A little background on my ‘public’ crossdressing, if you can call it that. I’ve been fully dressed as Jessica only once outside of my own home, during a counseling session. I changed in the bathroom across the hall and then proceeded to my one hour session. I was anxious and scared but at the same time a bit relieved that I could be myself. Other than this one time, I’ve underdressed (women’s underwear) only a few times in my life. Some of us really enjoy doing this, but for some reason I’ve never felt the same affection for it.

You may be asking yourself, “Well, Jessica, how about Halloween?”. Indeed, I’ve considered this special day but have never had the courage or strategy to go through with it. Perhaps one day I can go as Wonder Woman or Chun Li, we shall see. But while Jessica has bounced around the four walls of my apartments, her heels have never touched the grass, concrete or asphalt.

What would be the consequences of doing so? In other words, if I decided to transform into Jessica and step outside of my apartment to grab a cup of coffee at the local Starbucks. How would I feel and how would others react to me? Do I even want to do this, or am I just conforming to what I think a crossdresser should do? These questions are all valid and must be answered before actually making a decision. Additionally, I have my wife and her feelings to consider, as I never make a crossdressing decision without her consent.

Well, after some consideration, I have decided that I would in fact like to see what it’s like to be Jessica out in public, if only just once. From there, I can sort through my emotions and reactions in order to assess the situation and whether or not it is something beneficial.

So then I turn my attention to the details. It is necessary to choose a wig, outfit, makeup scheme, and shoes. Then, where to go? What to do? Luckily for me the where and when have been taken care of. What do I mean by this?

The Be-All conference takes place every year in suburban Chicago. I learned about it shortly after moving here, but for one reason or another have never attended. However, this year I started seriously considering attending. Like most graduate students, though, I am broke and going to Be-All would require registration and hotel fees. I was feeling a little sad about not being able to afford it, when I came across their scholarship page. I read it over and discussed it with Rebecca. She thought it was a great idea and encouraged me to apply.

I received a response within a couple of days, informing me that I had been awarded a scholarship to attend the 2009 Be-All! I would finally be able to socialize as Jessica among my fellow sisters. All that I needed to pay for was the hotel fees, which I could easily afford as they had a special rate for the conference.

This is quite an exciting time for me, and I will do my best to document everything as it occurs while trying my best to enjoy it.