Stepping Out: Before the First Time

Of course I didn't just step out of the house in a dress one night out of the blue.  There were all kinds of test runs leading up to that moment, but the incident described in my last post was the first official time that I stepped outside in a dress - no safety net - but there were definitely some memorable events before that.

I guess everyone starts under-dressing with panties.  That's how it all begins.  The first time I did it, I was so nervous that someone would see, or my pants would come down for some reason.  It was one of those decisions where I was like, "Should I wear these pettipants under my clothes today?"

Pressed for time, I gave in to my morning impulse, and zipped up my pants, forcing myself to have to wear women's underwear for the entire day.  That day, I was so distracted with making sure my pettipants weren't showing, I was constantly secretly checking them, and making sure my shirt was tucked in.  It was more of an uncomfortable feeling than I had anticipated.  I remember being invited to lunch with some colleagues that day, and the whole time I was anxious that the lace hem was showing through my thin, nylon pants.  I kept rubbing it and feeling it to see if it was showing. 

Now I wear panties almost without thinking about it, but at first it was nerve-racking.

After getting used to panties, I would safely find adventures, maybe wearing a bra under a thick shirt or coat (although I'll post another story about that later.)

Eventually, I felt the need to get a little more adventurous.  I guess the first time I really went out fully dressed, I put on a thin, little skirt under my shorts, and a frilly blouse under a flannel, buttoned shirt.  When I got to my car, I discretely stripped out of my male clothes and began driving.

In my mind, I was safe and in a car, and no one would notice, but I soon realized the number of people who actually look at you while you're driving.  There are the cars next to you, and there are people on the street.  Even a guy several feet away at a gas station was looking at my car.  I wasn't wearing a wig or makeup, so I'm guessing that he either saw the shirt and perhaps thought I was a girl, or was wondering why a guy was wearing a blouse with floral appliqués on it, with a bra showing through.

Obviously, I turned right around after only two minutes of driving, and went back to the drawing board, knowing that I better get a wig and some makeup if I was going to go out again.  This was getting more complicated than I thought!