I have spent the better part of my adult life with a boy in chastity, sometimes more than one. They were all very different as people and our relationships were equally different. Their reasons for wanting/needing it were all different as well. However, there were a few things they all had in common. Me and a kind of bittersweet feeling about ‘Release Day’.
I’ve always been the sort to take a fairly active role in their chastity. Assignments started with the very first cage I locked on and have continued since. They, like the boys wearing my cages are all very different as well. Catered to the boy, so to speak. Now is a good time to pimp my boys blog where he logs his chastity assignments. https://grumpylionsdenial.wordpress.com/
With assignments comes Release Day and while that meant something different to all of them, they all expressed the same feeling. ” Yay! Assignment over!” and “Crap! Assignment over!” For my Grumpy , Release Day typically means he gets to orgasm. Full on, unhindered and not ruined orgasm. So Yay, right ? Not so much. The Crap part for him is that he has to start over.
I have always tried to make Release Day special for them in some way because of that bitter part. SH1 was typically a trip to a fine dinning restaurant followed by prostate milking and then a nice bubble bath together. SH2 was excused from his chores and was allowed to have sex with me as often as he wanted for 48 hours. Though really, I was trying to make it special for me too and for the same reason. Sure, I am thrilled to have sex that involves a living flesh penis that ejaculates. However, I really love the interactive nature of chastity assignments. That interaction brings me and keeps me close to them. Not that the exact same things aren’t done outside of assignment but its easy to push them to the side when life gets a bit too lively. SH2 would frequently ask to go on assignment by saying ” I miss you , please don’t let me cum for X months?” when life on the farm had us very busy.
I was asked recently why my relationships that don’t involve chastity don’t last. I responded with something along the lines of ” I get bored and lose interest” Thats not entirely true. I guess I just have never found a non chastity way to have chastity assignments to keep me close so I don’t drift off when things get stale or when life gets difficult.