I do it with my beard since i shave head haha. It works, especially if you are squirming like crazy, and you can adjust it to be more or less punishing as you seem fit
Another thing that you should consider is a minimum duration for commands, so that you get the time to enjoy the single commands and it doesn't gets out of hand having you continously change what you are doing (for commands that are not compatible with others).
The compatible ones like cage or hair bondage could be modifiers and the most intensive one could be like timed sessions that stack. When the total time of the full game is reached, you stop getting commands and do them in the order they came in.