In honor of back to school for most, here is a school related caption. For those that are wondering, this is one of the first cross-dressing captions I ever created. Circa 1992. At the time I had no idea anyone else did anything like this nor imagined I would ever share them. Since I was young I would see a picture and create a little story around it, eventually I had a portfolio type book where I kept the pictures and hand written stories on notebook paper. By the time I was in college I had quite a book full of stories, although they were all family friendly. When I got my first computer and discovered "Paint" the rest was history. Eventually a picture "spoke to me" and my first cross-dressing caption happened. I still create my family friendly stories that I share with my family but when the right picture comes along...
Anyway here is one of, if not the first for me...