After gagging Jim with the open mouth gag, I left him there to drool all over himself for the next hour. I watched him struggle as he attempted to not shove the huge 10 inch dildo in has ass even deeper than it already was. He had to lean forward to prevent it from plunging deeper into his hole which meant there would be no relaxing for him for the entire hour.

After the hour was over...

Me: "Has your cocky attitude dropped down a few pegs yet boy?"

Boy: "Mmmmmm!"

Jim was nearing the end of his 2 hour sentence on the wooden horse, after he arrived 1 hour late for his session. He had already asked me a few times how much longer before I would let him down off the wooden horse. He seemed very curious as to what time it was, since he was blindfolded and had no way of knowing how much longer he would be there. He had 30 minutes remaining, but I didn't tell him that.

Boy: “Come on man, do you realize how fucking uncomfortable it is to sit on this wooden edge? Let me off of this thing! And my dick needs some attention! Why don't you suck it for me?”

Me: “Oohhh, that almost sounded like a safe word, but not quite. Remember, if you want to remain locked in that chastity cage for at least a week, all you have to do is say that little 3 letter word. Then you'll be released from all of this, except that chastity cage of course, per our agreement.”