I have been trying to give Lion an orgasm for a few days. We started on Saturday before we went to the casino. To be fair, I didn’t try all that hard then. I liked the idea of leaving him hanging. I tried Sunday and almost had him. My sinuses were hurting Monday, so I took the night off. When he suggested wearing the chastity device or masturbating as a way to make him hornier, I figured I’d give him an orgasm last night before locking him away. It did not go as planned.

We may have been making headway, but my arms started aching. When I stopped, he said he wasn’t really close. I don’t know how long I was sucking him, but I thought he should be close by then. He suggested using my hand, but it was a little numb and then fell asleep. I must have been in an awkward position because my shoulder hurt too.

Sadly, he was locked away without an orgasm to send him off. I guess we’ll find out if being caged makes him horny. In the past, I committed to unlocking him at least every other day for “exercise”. I’m not sure what the rules are this time around. I suggested having a random number of days to be locked and a random number of days to be wild. Lion doesn’t like the randomness. Isn’t it random when I decide to give him an orgasm? I don’t decide to give him one Friday at 6:15. I play it by ear. Random. Maybe tonight. Maybe not. I decided to give him one a few nights ago and that didn’t wind up happening. I do understand his aversion to being wild for a random amount of time. He wants to be locked up or not locked up. None of this wishy washy nonsense.

He said the Jail Bird is the most comfortable cage. I was expecting one of the newer ones when I asked him. To my surprise, it went on without issue. Once I got the screw to stay in my fumble fingers, it threaded right in. That never happens. Is this an omen that he’s stuck with the cage for the foreseeable future? I’m pretty sure it will annoy me at some point, and I’ll be done with it whether he is or not.

Speaking of which, he wants me to want him in the cage the same way he wants me to want to spank him. He said if I feel possessive about his weenie, maybe I should pay more attention to it. I guess I’ll have to figure out how to make the cage a game.

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