What are some of your favorite chastity games to play with your keyholder? During the NFL season, my wife will tell me what reward I'll get if my favorite team wins and covers the spread and what punishment I'll get if they fail to cover the spread or flat out lose. The rewards/punishments increase in scale based on how much they are favored to win/lose by. Needless to say, if they're a large favorite and lose, it's a bad experience for me but it gets her interested in the game more which is fun.
My former Mistress was multiply orgasmic. She would enjoy an oral worship session, and at the end, make me guess how many orgasms she had.
If I guessed correctly, I would get to cum too.
My problem was that she could cum 20-30 times in an hour, which made counting difficult.
And orgasms almost obtainable.