From what I can see, each of us had his own unique path with the razor.
I find your stories very interesting and if I wasn't sly already I would have definitely wanted to try out the look.
Although I have been craving to be totally shaved smooth for ten years, my first head shave was totally spontaneous. I went from 4inches of hair to shaved smooth when my roommate jokingly said "let's shave your head" after watching a head shaving scene in a movie we were watching on cable. We don't have clippers that time, we made use of office scissors and 3 disposable razors. I got a few nicks and cuts but it was well worth it.
I'd been fascinated with the idea of a shaved head since I was a teenager, when (with the exception of Kojak and Yul Brynner) shaved heads were neither common or "acceptable".
In the 90's, when buzzes and shaves became the style, one day I finally summoned up the nerve to go from a caesar cut to a buzz. That first #4 buzz seemed so radically short when I got it. But after awhile, I decided to go shorter and came home with a #2. Within an hour, I'd decided that it wasn't what I really wanted and had an overwhelming urge to shave it all off. I only had a little battery powered beard trimmer in the apartment and it took forever for the wimpy thing to take off that last quarter inch of hair. But when that was finally done, I lathered up and shaved bald for the first time.
Since then my hair comes and goes. I shave it off at least once every year and then keep it shaved for anywhere from a few weeks to a few months. Grow it back to some sort of buzz style until I feel like being bald again. Sometimes I do the deed myself. Sometimes I "call an audible" when I'm in the barber chair and instead of asking for my regular cut I tell him to shave it all off. He's gotten used to it and isn't even surprised when I ask for it.