Here’s a Chastity Game that my bud “ChicagoGear” is doing with his boy., “RubberCuffs“. Very clever.

Well it’s a craps inspired game. Jake started with a target of 14 days in chastity. On day 14 (Monday) he got sleepsacked and rolled a 12 sided die to get to cum. The setup is that before he gets in the sleepsack on the 14th day he rolls the die himself to obtain his “target” number. Then once he is in bondage I roll (he says when I drop the die), and if he hits his target #, or /- 1, he gets to cum. If he is not in the range then he gets teased and left in chastity. On the 2nd day he gets to try again for the target #, but this time he gets a /- 2 spread which will get him to cum. The third day /- 3 and so forth until he cums. If enough days pass then eventually he is guaranteed to win. Rolling a target of 1 or 12 is bad because it dramatically decreases his chances. Jake ended up rolling a 1 for his target on Monday. He hasn’t managed to get a cum-worthy roll yet. He has rolled 9,9,9,8 this week. Tomorrow he needs to roll 1-6 to win, so he’s up to 50 percent chance at least!

You should also know Jake is in the cb6000, first chastity he has ever been comfortable in long term. The other day at work he told me he forgot we was wearing it. I changed that quickly.