Johng2,
First let me say congrats on your first step tward be who you are!

I have been wearing skirts out and about for sometime now. It was my female counslar that got me to understand one thing. "The only thing stopping me from wearing a skirt or being me. Was me!" I know that may not make much sense but here is the thing I have figured out. If you go out looking like a guy, but you are wearing a skirt most people won't even give a seconond look. You have to be comfortable with yourself and understand that you are not doing nothing wrong and that is just how you felt like dressing. Now if you go out and are acting scared or act ashamed of how you are dressed that is what is going to atract the most attention. The worst mastake you can make is try to hide the fact that you are wearing a skirt, that just send the wrong signal to people. That just makes people think you are ashamed of what you are wearing. Here is a good example of what I am talking about.
For some reason about 3 weeks ago someone backed into the front of my brand new car at work. So on my next day off I decied to take it to a body shop and get an aprasal done. The body shop I went to was part of a local car dealer. This is what I wore. I wore a dark blue jean skirt that has a slit in the front not the back and is knee length (see some of my other post for some pictures of this skirt), Suntan hose ( I for some reason don't feel comfortable wearing a skirt with out hose, I think it has to do a little bit with mainting somemore modesty), a blue and black silk like shirt that has a great big skull on the front, and a pair of loafers (yes they are womens but you could never tell). I drove my car to the shop and walked in to have someone come out and give me an aprasial. When i walked through the door there was someone there waiting to pickup her car. I walked to the counter said what I needed to and sat down. The women did glace over but said nothing. While I was sitting there waiting that lady got her car and left. Shortly there after a nother women come in once again nothing was said. Then it come time to go out to my car with the appraser who was a guy. I walked out to the car with him and just acted like I normally would. I never acted nervious or scared at all. As a matter of fact the biggest problem I had was i was quite brezzy out that day so the wind kept wanting to blow open the front of the skirt, it proably wasn't a good idea to wear that skirt that day. Now as i was back in the waiting room the other girl that worked there was out on the shop floor with a few of the workers. I could see that they where looking at me and talking about me as I was standing there at the window waiting on the guy to finish the quote. Now here is where it got funny the 2 guys that she was working with and talking to made it a point to go outside and smoke just as I was leaving. I walked out to my car and I was watching them out of the corner of my eye. They where damn near breaking there necks to look at me and the funny part is they where trying to act like they whern't. I got in my car and left.
So as you can see it's all about what kind of attitude you bring to the table when you are wearing skirts. I mean let think about it like this. When women wear a mans shirt or mens pants they still look like women right? So the same holds true for men if you wear a skirt you are still going to look like a man. The thing that makes men and women look diffrent from each other is there body's.

So my best advise to you is be you and don't worry about what others might think or say.