Last night , there was some discussion about starting another chastity assignment. The last assignment was such a horrid fail, I am finding myself struggling to get us back on track again. Though I don’t think I expressed that as clearly as I wanted to when he and I talked. I went to bed shortly after we talked and woke up to a message from Grumpy that basically asked if we could wait on starting the next assignment until after we try prostate milking again.

During the last assignment he had asked if prostate milking was allowed while he was in assignment. My response was “For you, no.” Of the many strange  things the human body does, prostate milking may possibly be near the top of the list. For some men its the most mind blowing orgasm and others it is nothing at all. Some years ago I had two boys in chastity at the same time. SH1, got so much out of it  that it would drop him to his knees. This made me laugh, so of course I always did it with him standing. However, DB got nothing from it at all. He said it kind of felt like he just peed a little. So for him I did it as a means of keeping him healthy during long assignments while SH1 watched in undeniable envy. That also made me laugh, of course. For my Grumpy, while we’ve not tried much yet, I already know he is going to be the former, so while in assignment, no milk for you!

Grumpy and I have only been together a few years and yet I still find myself surprised by the things we haven’t done. Though to be fair, I am also surprised by some of the things we have done. He makes me proud on a regular basis. Prostate milking is one of the things that leaves me a bit surprised. More often than not, I am the first active keyholder for my boys. If they had had any experience with it at all, it was the ‘lock it and leave it’ kind ( which sucks! ). Because of that, I tend to let them set the pace. Grumpy has only had 3 real assignments , I am not counting the last one because it was absolute shit. However, prostate milking typically comes up long before we even start assignments. I think, at least in part that this hasn’t come up much is because he simply just doesn’t ask for things for himself. While changing my mindset in how I work with him might seem like the right answer to that issue, its not really. Not only does he not ask for anything for himself , I can’t think of a single occasion where I have brought something up and he has even hesitated with saying yes. He didn’t even blink before happily saying “Sure” when I brought up injecting saline into his scrotum. Really, I couldn’t be more proud to call this man mine.

Ah, I wandered off topic again. So, I think I’ve only tried with him caged and I’ve not met a man yet that can while wearing his cage. So, if you are reading this and happen to be a guy who can be milked while caged, let me know. I am now finding myself terribly curious if something about the cage prohibits milking or if I’ve simply not come by one yet.





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