This is a game I play with my sub - When we are in bed at night, I have him put his hands on his head and spread his legs. I then reach down between his legs and begin squeezing and torturing his balls. I keep up my torturing while he squirms. I love to hold one of his balls between my thumb and forefinger and squeeze until he is moaning and withering in pain. If he removes his hands from his head to try and stop me, or closes his legs to try to avoid my torture, I penalise him by adding more time to his 'Chastity Time'. I like to keep up my torture until he is truly suffering and moaning in pain. I especially like to make my torturing very painful to try to make him break my rules when he only has a day or two to go before he is allowed to orgasm. I also enjoy how pathetic he looks squirming around on the bed naked, unable to get away. He has lost count of how many days it has been now.
MissCharlotte, we, my Mistress and i, have very similar habit. I also have to put hands on my head and spread legs. Then instead of squeezing my balls She puts 3 electro rings on my cock and balls (see picture below) and switches power to most paiful pulse mode, when i feel like a needle penetrates my cock each second. Usually She starts at a middle current level but if i remove hands from the back of my head or try to close my legs She adds current and so pain.
Chastity is all fun and games, until your keyholder fully grasps their power and moves from his fantasies to Her pleasures. How wicked!