I was lucky enough to have a friend at a very young age that shared my interest in playing dress up. He had three brothers, and I had an older sister. At first we did not have anything real to wear. We would wrap towels around ourselves pretending they were skirts. I once borrowed two of my sisters bathing suits and brought them over to his above ground pool. We removed our swim trunks, and put on the bathing suits while we were in the pool. At that same time, I also remember looking at the Sears Catalogue and admiring the little girls full slips.
Shortly thereafter I moved away, but the door to my feminine side had been opened. Having a sister who got home from school later than me, and two working parents, I spent many an afternoon trying on her clothes. At that time her bras, pettipants, and crinoline slips were my favorite items to wear. As I got older, I believe that it was a combination of my male hormones kicking in, as well as my fear of being found out, but my dressing up went on the back burner until I got married. However, even before we got married, I had already been successful in getting my wife to stop wearing cotton bras and panties, and switch over to items that I found more arousing. My therapist told me that being around my wife and all of her pretty things was more than I could stand, and I just had to start wearing some of it. It was very early in our marriage that I talked her into allowing me to sometimes wear her panties when we were being intimate.
In answer to the question of what was the item of clothing that I was first interested in, I must say it was ultimately lingerie. However, I also know that as we develop and explore that side of our personality, we begin to purchase more and more things to make the transformation more complete. Then as we begin to go out, and are seen by other gurls and/or admirers, we need to have more than one outfit so that we are not being seen in the same outfit every time we go out. For many of us it is difficult to make these purchases, store them, and hide them from our spouses. I am lucky enough to have a closet in my basement all to myself with a variety of different items. I now have black, blue, pink, and red shoes and purses. I also have a red coat for winter outings. In short, I believe that we start with one item that allows us to express that side of us, and then it evolves into a need to buy everything that we need to allow us to try to pass as real women. Thanks Michelle.