OH how lovely to be asked, what fun!
Well we have Locktober coming up so how about next week in the run up, you unlock him this weekend, and he has to try to ruin as many orgasms as you can, or he can do it or share the job.
If he manages 7 ruins he can cum at the end of the September. Otherwise, well might as well lock him up early, give him a ruin at the end of Locktober and then, I’d say Christmas is looking good for his next orgasm!
Have fun and let us know how you get on,