While I dabbled in cross-dressing from when I was a young child, I really didn't get into completely transforming myself until my mid 20's. By then I was married and had an established life and had the self confidence that was strong enough not to be rocked by concerns about being thought of as strange. Also, about that time we had gotten the internet and I was able to see how many others like me there were and how well some CD's could create their illusions.
I didn't have a digital camera back then but wanted to have photos to look at after the fact and be more objective in my opinion of how I looked. I'd take my film to a local grocery store and drop it off. Then come back a week later and nervously pick it up, all the time trying to read the faces of the clerks to see if they had looked at the pictures.
Of course, with film I had to be very selective when taking pictures as to not waste film. And many times I would get pictures that were out of focus or had poor poses. Things are so much easier now that you can have instant feedback and make corrections and adjustments either by retaking the picture or editing with software.
Tips & Tricks
Read more about my first times getting out of the house on the blog pages. "Out" "Out2" and "Out3"