Chastity and orgasm denial discussion

Hello all, It’s been some time since I last visited the mansion. Hubby and I are getting back into our Chastity play with a bit more zest. I’ve discovered something we’re both enjoying, especially me! I wanted to share it here. To us, Chasity is much more enjoyable when there are activities that keep us both involved. Recently, I started playing a new game: First, he gets unlocked and lubed up. Then, like the video below, my goal is for him not to cum while I stroke him in time with the beat of the music. The whole routine takes about 6 minutes total: roughly 45 seconds of stroking followed by 30-second pauses. He agreed he needed strong motivation to give it a shot. So we set these terms:

1. I get to decide when it ends, and we’ll continue until he wins at least one session. He didn’t think it would be that hard; he was sure he could outlast me this way so he wouldn’t just say “no more” after six losses. Now I needed a reason for him not to cum. IF (and it’s a big IF) if he manages to stay dry, I’ll leave him unlocked for 4 straight days and let him have all the orgasms he wants, in any way he likes from me. But if he fails by cumming, I lock him RIGHT BACK UP AND the poor guy suffers through this:

1. He gets gagged, blindfolded, and restrained with some tight nipple clamps.
2. Twenty firm swats on his rear that WILL hurt. This is serious motivation for him because he doesn’t enjoy hard spankings. (You can pick something you dislike as your own motivation.)
3. He must make me cum using his tongue before anything else happens, and only after his spanking does the gag come off!
4. He stays locked in his loris and willing to lick me to an orgasm whenever I want until I’m ready to let him try again. No sooner than 4 days (to give his bottom time to recover) and no later than 7 days so he has to try once more. The clock is always ticking. If he refuses at any point to give me an orgasm, I can start a session regardless of how much time has passed. Together we agreed these terms are serious motivation. Here’s an example of the beat to stroke along with…

I wear thigh-high heels and a leather corset, among other things, to add to the challenge. He, like most men, is very visual and loves how I look in this outfit so it’s sort of cheating but I enjoy unfair advantages so I use them. It has been one month now and he still hasn’t won even once out of five tries. Though he got awfully close last session; I thought for sure he might win, that final beat was just too good—he couldn’t hold on. I am having such fun with his punishments. I never realized this part of myself before but I really like doing it. Now here’s where it gets interesting. Since there are 30-second breaks sometimes he will start to cum during a break which ruins everything completely. It frustrates him greatly. Other times though, he manages a good strong orgasm. The punishment is clearly working because he lasts longer in his attempt to avoid cumming. I can tell he’s getting worried it’ll be more challenging than he thought. Lucky me but he agreed.. He will outlast this sooner or later and I need a plan to keep it going for a little while longer. Any ideas from this wonderful group of like-minded enthusiasts???