Chastity and orgasm denial discussion

My boy and I tried to keep him locked for two weeks (which would have been our longest yet), but I was getting restless by day four. It took eight days before he finally came inside me. He gave me multiple orgasms each day, we were intimate almost every night, and still, I couldn’t last the full time. So, how do you keyholders manage it? How can you go that long without sharing in that release with your partner??