I have two answers to this. The first item I owned (but which was bought for me) was a school uniform. When I was in the process of getting my head around my cross dressing in my teens I was referred to a counsellor who pushed the idea of ?full immersion? so I was dressed as a girl full time for a good while.
My first born addiction (although it has expanded considerably since) was skirts and for that reason, the first item I bought myself was a purple pencil skirt.
