My rediscovery of crossdressing all began again with a pair of panties. One pair turned into two, then a few weeks later I added a bra. For some reason, my next purchases were some thigh high stockings and some heels. Standing there looking at myself in the mirror, I knew that it somehow looked incomplete.
I needed a dress or a skirt, but debated about my growing secret stash of clothing. One night while online, I saw a dress that I needed to have - a pink dress with a wide, flared skirt. I wanted it so badly, and on impulse I clicked on the online button and purchased it.
Flash forward to today, and I have so much clothing that my secret stash isn't a secret anymore. I can dress freely when my wife isn't home, but lately I've had the urge to step out.
Don't get me wrong, being dressed at home is fine for the most part, but my fantasy begged me to step out that door. It was almost as if I were dressed up with no place to go.
Several times, I played with the idea, and stood on the threshold of that door as if there were some great abyss on the other side. Several times, I chickened out, but the thrill of the thought was more than enough to drive me crazy.
One night, I got the courage to finally do it, and snuck outside in a dress, wig, some decently applied makeup - but probably not the best either - borrowed from my wife's makeup bag.
Feeling the fear and the thrill as I stepped past the door was intense. "I can't believe that I'm actually doing this! This is crazy! I mean I know I'm daring myself to do this, but I'm actually doing it!" my feet entered the hallway, and I was officially out of the house as the door closed behind me.
I felt tense walking down the hall of my building. The sound of my heels on the hard floor at night scared me, since I didn't want to draw attention to myself. I really didn't want anyone to catch me. As I walked, my heart beat, and my senses were on alert. It was thrilling, but mostly scary. My heart beat in my chest. Still, there was that thrill of actually doing it. At times, I looked around and marveled that I was actually in a dress walking down to my car. I was actually outside in my panties and a dress. There was such a naked and vulnerable feeling in being dressed like this. There was no hiding any truths if I got caught.
I got in my car and drove around a bit, and every now and then I'd look down at myself and realize that I was driving my car while wearing a dress.
"Wow, I can't believe I'm actually doing this," I thought to myself. I never would have imagined that I would be doing this at some point in my life.
In a way it was thrilling, but in another way it was almost a bit underwhelming too. I kind of built up so many expectations for this moment, but the world didn't stop spinning, lightening didn't come down from the sky. The only thing that happened was that I had taken a step further down the road of my femininity. A question was answered, but many more began to pop up in my mind.
I finished my dare, and drove back home and snuck back into the house. (Not being caught coming back in the house was another peril that I needed to avoid.
That night was memorable but almost forgettable. Basically, all I did was drive around at night, it just happened to be in a dress. I guess to me, it showed that it wasn't such a big deal after all, but the realization of this fact is a big deal, the kind that can change a person forever.
And of course there is the nagging urge to do it again...
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