Monday, September 3, 2018

Once upon a time....

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...


  1. Thanks Becca, always great to reminisce on a start. That caption is as good now as it was then. Shows too how good Paint was. It’s still popular despite being deprecated by Microsoft since July 2017.
    Let’s think story for a minute. Wonder how Jamie is now after 26 years? :-)

    1. Thank you for your kind words. Hmmm, interesting idea, if the right picture comes along we may have to revisit Jamie.

  2. Very cool to see old school caps and the history behind them!

  3. Love to see the old ones! I did my first caps in 98, also unaware that anyone did them. I've posted some old ones from time to time......funny how so many of us came up with the idea to do them.