When she started seeing this guy, lady Pascal had thought that old guys were tougher than the younger guys. But this particular one was not and the mistress had to do something. The mistress felt that she had to toughen him up and she did this by trampling him and caning him. He was caned butt naked and he was also tied. So he could not even help himself. He had to toughen up as it was not optional.
Mistress Reell did not want a slave who did not add value to her life. He was a liability to her as he ate a lot but he did little. So she caned his hands and his butt to make sure he learned to sit on his butt less and to use his hands more. That way, he would not have to suffer the pain and humiliation of being caned butt naked.
Empress Victoria did not want to deal with a spy. When she found out that this guy was a spy, she had to torture him. And she did it by forcing him to strip naked. She had him tied up before she caned him so that he did not try to resist what she wanted to do to him. He learned never to spy again as the consequences were grave.
Mistress Lyla and her friend were asked for money by this loser and they made him a deal he could not refuse. The mistresses told him they would give him the money and he did not have to pay it back. But he had to agree for them to cane him naked. He was in dire straits and he had no choice but to agree to the deal the mistresses offered.