I decided that before I try any of it for pay, I'd do a bit of amateur Dominatrixing.
I found my first "client", who I later called my Cherry boy, on-line. Or rather he found me. We met in person at Earwax, a hip little cafe in Chicago. It was a sunny day so we sat out on the patio. I was wearing my best friend's low-cut black vinyl dress, 'cause I didn't have my own, and looked uber-pro-Dom. Fortunately, it was also short and strappy so I didn't get too warm. Cherry was incredibly hot and tough looking. He was also quite the snazzy dresser with a biker / rock-a-billy flair and had a menagerie of tattoos cascading down his arms. When I got him back home I'd find out that there was green and red oriental dragon crawling up his back. His voice was rich but his words were halting as he'd just moved here from Japan a few months before. And though he'd not had much experience, he had lots of enthusiasm and ideas.
"I did have one time with this woman from Germany. We met in hotel and she would not let me walk the whole time I was with her. She put me to my knees and made me crawl and beg her to do what she wanted with me. She tied me up and she beat me on my bottom. She used a dildo in my ass, I had never had anything there before. She called me her little virgin slut girl and made me eat her pussy. After she came, she saw I was hard and told me how naughty I was. She beat my cock until I cried then tied my cock and balls to each other and put me in a skirt and called me a sissy girl."
(as it's almost midnight, I'm ending things here. More tomorrow!)