I came across this game. It essentially plays like monopoly but each space requires something of the sub. your Domme can set the beginning chastity time and set the penalty time that can be added. The sub is sometimes asked to take a photo as proof that the Domme can login and check on. /http://ms-cassandra.com/proctor/ Let me know what you think
I tried that earlier this month. It was fun at first, but the novelty wore off rather quickly. Maybe it would be different if I had a Domme checking up on me, and enforcing the outcome. I will give it another try if it ever gets updated beyond "Beta1" The same site also has a Chastity themed dice game, and Slot Machine.