This guy wanted to hang out with mistress Lyen and princess Nikki. On that front he managed but it was not what he had thought about. The mistresses turned him into a foot slave and he was made to lick their dirty boots as well as do other demeaning things. He regretted why he wanted to hang out with the mistresses in the first place as they were not what he had thought they were.
When a slave has two mistresses, he has a lot to do. Lady Anna Solis and Princess Rachel are happy to go out. They spent their day shopping and eating. When they are tired, they go to the park and have their slave service their feet. He licks and sucks their toes, taking the sweat and soreness with him. He also licks the spit off the sole of Lady Anna Solis's shoe.