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.

Lion has presented a choice, of sorts, to me. Obviously, I don’t have to accept either one. He suggested being locked in his chastity device or being allowed to jerk off without having an orgasm. In effect, I guess, he’d be edging himself. The experiment is whether either of these ideas would make him hornier/easier to arouse.

When pressed, I told him I could lock him up if he wanted me to. I dislike having to lock and unlock him. I fight with either the cage, the lock or both. That said, I do love a good experiment. However, what I realized this morning is that, just as I’m stingy when it comes to not sharing his cum, I don’t really want to share his weenie either–even with him. Weird, right? [Lion — I don’t know if it’s weird, but it does eliminate a lot of options.]

If his masturbating is out, that leaves the cage. I guess that means I’m locking him up again. (Insert grumbling here) As I was reconciling this in my mind, I wondered how to put my own twist on his twist. What if the length of time he’s in or out of the cage was random? A roll of a die, perhaps. Random number generator. Deck of cards. He’s locked for X number of days. He’s unlocked for Y number of days.

I’m sure Lion had something different in mind. He probably wouldn’t mind being locked for X number of days if it was based on the roll of a die. Six. Damn. I don’t think he’d like a similar roll for being wild. I may be wrong, but I think he wants to go right back into the cage once I’m done doing whatever it was I unlocked him for. [Lion — Yup.]

The problem is that the cage is such a pain in the ass to me. I’ve found myself not wanting to unlock him because I’ll just have to lock him back up again. Yes, I agree it’s stupid to think that way. I don’t know. It seemed like a compromise when I was thinking about it. There’s nothing saying we can’t try it both ways and see if one works better than the other. The cage part, not his masturbating. His weenie is still my toy. Mine, all mine.

[Lion — I wrote my post for tomorrow morning before I read this. It talks about how I feel about being locked. I never liked the idea of some sort of random period for lockup.]

I spent the morning at an in-person meeting for my company. I think something like 73% of us work from home now. Once a year the CEO travels to the big offices for a town meeting. This was my first one and it was another meeting that could have been an email. Well, maybe not, but definitely a video conference. They hype it as a good way to see your coworkers. Most of my coworkers are scattered all over the place. As far as I know, most of them have never met each other. Anyway, it was the first time in a long time I’d been anywhere for work.

We didn’t do anything sexual last night. I don’t know why. Maybe I was making Lion sweat it out. I know he wants an orgasm. (I hear you over there yelling, “Make him wait!”) Don’t worry. I’ll torture him again tonight. I probably won’t make him wait. I can’t promise he won’t be edged once or twice. That will just make it sweeter when he finally has a long-awaited (in his mind) orgasm.

The other day, Lion suggested playing a game. It seems like a good idea. We’d have to work out the details. I think he forgot, because we haven’t played in a long time, that we do have another game – Spankardy. I’m not sure I remember the exact rules, but I’m sure we can come up with them to play again. It actually sounds like a good game to play on Tuesday or Wednesday since those days don’t have punishment swats coming. Would it be bad if I gave him his elusive orgasm after work and then spanked him for our game later? He might not submit to that spanking as readily as if he was horny. On the other hand, does he have a choice?

When I was in school and had to write an essay, the rewrite was always more difficult for me. I’m having the same problem at work. I do a task, pend it, then a trainer goes through and grades it. I get a list of what I did right and what I did wrong. It was hard enough to figure out the first time through. Now I have to go undo what I did and fix it. My head is spinning. I forgot all about writing a post until Lion mentioned it.

Yesterday’s football games didn’t go very well. I don’t know how many swats Lion wound up with [Lion — 418], but they were mostly for Eagles points. Yuck! Spanking him added insult to injury. We have two weeks for his buns to prepare for the Super Bowl. Needless to say, we’ll be rooting against the Eagles.

I said in yesterday’s post that I’d either tie Lion’s balls up or use clothespins. I also wanted to suck him. He insists I can suck him on the massage table. I don’t see how that will be comfortable for either of us. I prefer being on the bed. Since I was sucking him, I tied his balls. It’s easier to avoid hitting clothespins with a hand job.

It’s so difficult to tell what’s going on with him when I’m sucking him. He rarely makes a sound. Sometimes I can tell by his movements. I thought he was getting near the edge early on based on how he was moving his hips. Nope. Then he seemed to get softer. I stopped and asked if he was losing it. Nope. A while later, my arm was going numb from being in one position for too long. I had to stop.

I didn’t think he was near the edge. He said he was pretty close. He was bummed that he didn’t get an orgasm. I let him in on a little secret: he wasn’t going to have an orgasm. If I’d gotten him to the edge, I would have done it again and left him hanging anyway.

What a bitch!