I know I've had fantasies before, where I think, "I'm going to put on my white dress and some panties and go to the store..." For me, it's a white hot fantasy at the time, imagining how naughty, pretty, and dangerous it would be, but I've realized through experience that my fantasy seems to have blinders on in a way. My vision is narrowly focused on the personal aspect of the crossdressing, and seems to disregard the fact that going out in society means interacting with people.
On the few occasions when I actually have gone out dressed, and pulled up in the parking lot of a store, it quickly became apparent to me that the reality of the situation wasn't as tidy as my fantasy. People were coming and going, a mother was loading her purchases into her car, and the kids were looking around at people going by. Someone rushed by to put their cart away, and a car drove past looking for a space, and the whole time, I'm in a dress wondering if I should get out of the car.
It's at that moment, when all those people are there, I can smell the exhaust from the car, the sounds of the cars grinding by on the road, that I realize that this is very real. This isn't some neat fantasy in my mind. The teen girl standing there by her mother looks at me in my dress and heels walking by. Does she know, or is she just wondering why on a day when 99% of the people are wearing shorts and tees, someone is dressed up nicely to go shopping.
I like pushing myself, but I'm doing this for fun too, and I don't want to feel too uncomfortable. That's not fun.
What I usually do now, before I go out dressed to a place I haven't been before, is to visualize myself in a dress in a given setting. For example, I went to the mall today in my male clothing. I've done it so many times, I usually just tune out most of the stuff I see there as I walk through because it's nothing new to me. But if I were in a dress, it would seem different, and I know my senses would be heightened and my awareness of my surroundings and everything happening around me would be on alert.
Visualizing the situation in the safety of my male clothing helps me to decide whether I would be comfortable in a given situation, and to pay attention to what the experience is really like, so I am not paranoid when I hear a giggle of a girl going by.
Entering the mall, I imagined what it would be like if I were in heels, a dress and a wig. I felt myself in my familiar clothes as I entered, I paid particular attention to the people around me.
People walked by, I looked at them. They looked at me. If I were in a dress, I would be scared at the stares, but I guess people just naturally stare...and laugh, and say various things. It's most likely not about you, but if you're nervous, you can take all of these things personally.
The mall was busy with people going in every direction at the same time. As I walked along, and visualized being in a dress and heels in this environment, I realized that it would be a very big step for me to dress as a woman and be in this type of hustle bustle.
So before you get all dressed up in your sexiest dress, and impulsively stepping out of the house, use some visualization in the setting before you go. It might help you not to be surprised when you actually decide to go out dressed.
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