When I create a new chastity assignment for Grumpy, I use a random number generator to determine how long it will last. This last assignment was a mere 23 days. LAME! To make it worse , he earned 4 days off of that. So this last assignment lasted only 19 days. I didn’t tell him how long the assignment was going to last and I could see the disappointment on him when I told him his assignment was over. I was just as disappointed.
Typically within about 24 hours of his assignment ending we play and I let him orgasm, unhindered. After this one, neither of us have pursued it, still 8 days after his assignment has ended. During this time, there has been no T&D. During our post assignment conversation we both agreed that this was the most unfulfilling assignment ever.
We had to go out of town shortly after this assignment started ( which pauses assignments) and it normally takes him a few weeks to ‘get into it’ So he was barely settling into it when it ended. For me the whole thing was like awkward foreplay ending in bad sex.
One would think the answer would be to just start a new assignment and pick the number myself. However, its not as simple as all of that. I tend to let him have at least one orgasm between assignments. When we talked about this again a few days ago, he told me he doesn’t feel like he deserves one and well.. I agree. So at this point I guess I should figure out how to make him earn one so we can get past this stalemate and put this crappy assignment behind us.
I’ve said the words ‘Chastity is not always fun’ more times than I can count in the more than 20 years I’ve been doing this ( Holy crap! when did I get old? ). Though its rare I have to say it to myself. Okay, I am done mourning the loss of this assignment, time to move on!