A little bit of background before I begin divulging the profoundly sensitive experience that occurred when a longtime family friend discovered my cross dressing. I will refer to the family friend as Sam who was an elderly widower (since passed) whom our family has known for 20 years. Our family lived in the same area as Sam but moved out of state about 6 years ago. We still have remained close though, and I have stayed with him over the past few years since, I still have business connections in the area.

Sam’s immediate family other than one daughter lived about three hours away and generally visited about once a month. Since losing his wife he has had one romantic interest but she had to move across country due to her illness to live with her family, as they were the primary care givers.

I most recently stayed with him about two months prior to his discovery of my cross dressing. It was during this visit that I had lost a USB stick with some pictures of me in feminine attire, while I was staying with Sam. The loss of the USB stick led to a heart stopping email and eventually to a close empathetic relationship between my feminine side and Sam.