So, Grumpy is pretty much in chastity all the time. However, I like to be hands on about it so I do Assignments . Outside of them, life is pretty day to day. We wake up, go to work, eat, clean, watch TV just like everyone else. The difference being he does so wearing a cage. Inside of assignment , things are a bit more strict. Yes, we still work , eat , clean and watch TV but now he has requirements to fill.

He recently came up with the idea of spinning a wheel on assignment. So I added it to this one. These are the options on the wheel.

  • Earn 6 hours
  • Add 12 hours
  • Cage Free T&D
  • No T&D
  • Earn 1 day
  • Add 3 days
  • Reward
  • Spin 2 more times

I wrote them to intentionally be Not in his favor. He is to spin the wheel once every three days , which coincides with inspection day.  He has spun twice now in this assignment and the first spin he earned one day. The second he won Reward. I set up Reward to be he can suggest what he would like his reward to be ( orgasming being completely out of the question) and I can approve or deny it. He was completely baffled and I expected as much. He has never been great at asking for things himself so while getting a Reward might seem on the surface to be a good thing, its kind of a double edged sword for him.

I put a fair bit of thought into what was going on the wheel and why. Knowing he was going to have a hard time coming up with something, I initially intended to not help him at all. However, I didn’t expect he was going to have as hard of a time with it as he did and I just can’t be that much of a bitch. So, I clarified for him that his reward could be anything he wanted and didn’t have to be related to chastity. He was required to come up with something by 11pm so he could log it and he was running out of time. I think that made it even harder on him.

I adhere to assignments strictly. Once in place they cannot be altered. It was technically not in the assignment ( as written ) that I would not help him but it was the intention. I just didn’t expect him to struggle so much and really didn’t want to see him lose his reward AND get punished for not logging it. So I told him he should just bank cage free T&D and maybe think of some other things in case this happens again.

My Grumpy wants for so little, so I rarely deny him of anything, except orgasms. I was hoping a Reward might make him think about the things he does like or are special. Though in retrospect, because he wants for so little and on the rare occasion he asks for something , I let him have it , this was going to be much more difficult than I expected.





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