Welcome To The Working Week

Students are not the only ones who dread the month of September – teachers, too. And there are no exceptions for crossdressing ones. With the 2012-13 entering full swing next week, the frequency of my complete crossdressing will most definitely slow, which is unfortunate – but I’ll just have to make the most of the times I am fully en femme.

Perhaps it was the start of the school year that led my girlfriend to posing the question “If you could go to work fully dressed, would you?”

Before I answer the questions, first I want to analyze the motives of its asking. I believe they could be one of two things:

  1. She asked because she was curious about how involved I would let my crossdressing become in a school environment – specifically – would other teachers ever know, or even students?
  2. It was a broader question judging just how serious I am about crossdressing, and if it would ever become something more.

(Please note, girlfriend who will probably read this, that I felt no ill-will when you initially asked, and likewise I hope that none is felt in reading this.)

I think her actual motives might have been a little bit of both – it is an interesting question and situation, enhanced all the more by the work environment of a school. I also think it was a good question to force me to think about my future in crossdressing, without actually asking that.

Let me say this – I am a crossdresser, and in one sense, I have always been a crossdresser. (Is the act of dressing necessary for one to consider themselves a crossdresser – or is it just the want? I’ll save that question for another day.) In addition, I will always be a crossdresser – even if I stop dressing (and in this I am sure.) I have no plans to ever stop, and see no reason. Why change something about yourself that you like? I was taught never to give into peer pressure – and that will continue, regardless of what my family might think if I tell them, or if in some bizarre unthinkable circumstance my school tries to use it as grounds to fire me. My happiness comes before theirs.

Now, back to the original question – if I could, would I go to work dressed up?

It all depends on the environment at work – if it’s a utopia, and everyone, students and teachers, welcomed it with open arms – sure. I hate wearing a tie and women’s clothing, to me, is more comfortable. There’s also more variety and fashion. Women, at the school where I work, also have the ability to dress for a wider range of weather than men. Yeah, I can wear a polo when I want to dress down, but I’ll never be able to wear “fashionable” sandals to work. Socks and dress shoes all day are uncomfortable.

Outside of this perfect utopia – in the actual world, where I actually work… well that is a different story. Right now, no, absolutely not, I would never go to work crossdressed. I wouldn’t even wear girl’s underwear under my pants in lieu of boxers. There’s too much risk for too little reward. And yes, I have ripped my pants at work. Twice, actually.

I also want to note that I am untenured. Ignoring any debates about what you think of tenure – it would be much easier to fire me if I was “found out” as a crossdresser, and find some other reason to justify it. I think, as educated individuals, most of the administration in my district would support someone who crossdressed, but in a society with a feral news media that often demonizes teachers and high strung parents who are overprotective, having a crossdressing teacher is not a good PR move. Also note, that most people think of crossdressers as deviants, not normal people who enrich their lives with a creative hobby.

Maybe one day, crossdressing will be more widely accepted and I will be able to wear a skirt and panty hose to work. Maybe that day is closer than I think. Recent articles, like this one about German father Nils Pickert and his crossdressing son, or the New York Times piece on “gender-fluid” children are heartening to read and hopefully signal a changing perspective on what it means to be a crossdresser. (One quick nitpick – the NYT article does not once use the word “crossdress” – is this intentional? Some kind of rebranding with a push for acceptance? I don’t know.)

There you have it. Would I crossdress at work? Yes and no. I love dressing up, and would do it more often than not in an ideal world, but it’s not an ideal world, and to be honest the frequency at which I’m dressed right now is more than enough for a crossdresser like me, who was in the closet to everyone just two months ago.

In my next few longer entries I want to do a write up on how the internet influenced me as a young, closeted crossdresser, and  also how Halloween is essentially Christmas for crossdressers.