Slave #66 was fortunate enough to serve Maya Sinstress on Her recent trip to Chicago. He was out of practice since he hadn't had any endurance pain training in a few months. Sinstress was gracious enough to work him back up. In part 1 of this 2 part clip, Sinstress puts an anal hook in his butt & anchors it to his collar. She then warms him up briefly with some hand spankings. Using a flogger, She tenderizes his skin even further. He's then upgraded to a leather slapper, used on his back and his ass. Next up, a dragon's tail!