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Monday, January 10, 2011

Crossdressing Thoughts & Reflections - Jessica Who?

Who better to close out our series on crossdressers than Jessica Who? And who is Jessica Who? I think a lot of our readers know already—from her blog and from her videos on her YouTube channel. She is a humorist who makes a point, or perhaps someone who makes a point with humor. Either way, we are entertained while we understand what she writes and speaks about. Her video on labels is classic! Check out what she has to say here.

- Ariel

A couple of years ago I found myself in a difficult situation, one that others would die for. There I was, a lifelong crossdresser with all the struggles and strife as all the others, with the ultimate blessing—an accepting fiancé (now wife). The problem was, I still couldn’t accept myself.

Although I was sure of some things and semi-confident with how I looked as a female, there was a huge block preventing me from enjoying my full gender identity, which as of yet was still unknown. This created conflict with my wife that shouldn’t have existed. I needed to find my way, and soon.

So I began blogging, an undertaking that I had tried once before in 2002. Back before blogging was huge, I was blogging on GeoCities. My thoughts and experiences were shared with the digital world but were erased one day in an e-purge.

With my wife's blessing, I started my blog Jessica Who? quite uneventfully. The typical starter posts were uploaded, but soon my creative energies really took off. I didn't intend it, but soon my articles were laced with sarcasm, humor and satire and others took notice.

I didn't realize that I was writing with this humorous tone until readers and other bloggers told me. In reality, I was just being myself. Before long, I began to focus heavily on the humorous side of the trans world.

Then, at the end of last year, I started making videos and posting them to YouTube. I decided that they would almost exclusively be comedy from my transgender point of view.

Somewhere along the way as I was authoring crossdressing articles and creating transgender comedy videos, I really found out who I was. My true gender identity, which is extremely difficult to put into words, took shape and thus I was able to start expressing it accurately.

This also led to the birth of my stand-up comedy career. I perform as a guy and as a trans girl, and my humor comes from the many facets of life that are real to me. Comedy, a hobby of mine since 11 years old, was now becoming my guardian angel.

It hardly ever works out like this. All my life I thought it would be books, therapy and intense meditation that would help me in finding my way. At times the possibility of never finding a balance seemed likely. In the end, it was writing blog posts, acting like a fool in front of a video camera and stepping on stage that did the trick for me.

I am now much more open about being a crossdresser, many of my friends and family are aware of it and fully accept me. I come out of the closet with the enthusiasm of a kid chasing an ice cream truck. Am I naïve? Nope, I know that not everyone will agree with this, but I don’t care anymore.

Comedy has that affect on those who perform it. You shine a spotlight on anything that you are self-conscious about and soon enough, the anxiety fades away. When you make fun of yourself by ripping into your insecurities and ridiculing your experiences, nobody can hold anything over you.

I raise a mirror up to myself and also to the rest of the TG world. I satirize how society views us but also how we view ourselves. By pointing out the (in my opinion) exceedingly extreme seriousness with which we discuss our nature, I hope to help others accept themselves by laughing a little.

Among the issues I've lampooned are—the various transgender labels, wondering why men crossdress, the notion that all crossdressers eventually transition, crossdressers pressuring other crossdressers to develop a female voice, gender stereotypes and crossdressing being considered disgusting. Not everyone understands my humor, but that’s okay because I do what I want artistically and aim to make most of my videos with a social message.

Instead of worrying what my crossdressing means or what label(s) suit me best, I am simply myself—an intelligent yet silly person who is responsible but also immature who feels like a guy sometimes, a girl other times and a combination of both the rest of the time.

My approach won’t work for everyone but I think we’d all be better off if we took ourselves just a tad less seriously. Don't get me wrong, there will always be a need for serious research, discussion, protest, rallying, struggle and defense. But every kingdom needs a Royal Jester. I am ze.


  1. Love your attitude, Jessica. A smile goes a long way in this life, and the people who remind us of that are the guardian angels of our mental health. Thanks for this post and all you do.


  2. Funny, intelligent, adorable........what's not to like about Jessica?

    Love the videos. Love your sense of humor! Keep up the good work, girl!

    Melissa XX

  3. The royal jester generally has far more depth of passion, understanding, wit, and wisdom than are apparent at first glance. Those who look no further than the comedy are missing out on a wonderful treasure.

    You, Jessica, are indeed that treasure and I thank you for brightening my day on a regular basis.

  4. You bring a much-needed lightness to this too often serious issue of transgenderism. Keep up the good works...

    Hugs, Elly

  5. Great post. What is the use of doing anything if you are not going to be happy doing it. I love dressing and the fun it brings and I enjoy your site. You count your blessings and have a good time doing it.
    Keep up the good work.

  6. Thank you all so much for your wonderful comments, they are so sweet and you honor me with your kindness :)



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