Every time I want to give Lion an orgasm I think I should just do it. You know, the long buildup and then the orgasm. But now it feels like there’s pressure to edge him first. Tease him and edge him every other day. Tease him further than last time. There’s always the possibility of a ruined orgasm. Then there’s the possibility of whatever we had the other night which was more than a ruined orgasm. Then there’s last night which was beyond that. I pushed him way too far and he didn’t get his orgasm that he had been anticipating for eleven days.

He’s disappointed. I’m disappointed. We tried again about an hour later, but whether it was really not possible or he was just too upset, I couldn’t get him hard again. Maybe we could try in the morning, but Lion has never been a morning sex kind of guy. In this case, that really sucks because we’ve got a seven hour drive ahead of us and he’s wild and he’s disappointed and I’m mad that I disappointed him and now I’m awake at 5 in the morning writing this and you can imagine how much fun this drive will be.

The worst part is that for a few minutes he thought I was actually trying to push him too far. Why would I do that when I know he’s been waiting eleven days? Why would I do that when he specifically said he didn’t want to come a day early because he was looking forward to “a big send off” for our last trip? I should have just played with him enough to get him excited and then given him his orgasm. Nothing fancy. But I feel pressure to make it fancy. I don’t want him to have a boring orgasm after waiting so long and with him anticipating “a big send off”.

He’s been telling me how much better I am at edging him and how interesting it feels to have multiple ruined orgasms. Do more. Do it more often. He says I’m starting to enjoy things. I think I’m just getting more confident that I can do what he wants and not hurt him. And then something like this happens and the rug is pulled out from under me again.

I’m sure he’ll read this and think we should just stop or that I want to stop. I’m just irritated that I disappointed him and for what? So he could have a better, less vanilla orgasm? Yeah, that worked out. I know I can make him come tonight, but it was supposed to be last night. And I was already thinking about making him come tonight anyway.

I think I’ll go back to my less confident way of doing things. In some ways I feel safer with my insecurities.

Now from the title you’d probably expect that I caved in and gave Lion his orgasm a day early. I did not. What I did do, however, was allow him to give me an orgasm. Quite a few in fact. And how is that a treat for him?

Lion gets a big erection when he gives me orgasms. Had he been uncaged he probably would have gotten one last night. My intent was to make him hornier by proxy. I hope I made him more aware of the cage and the fact that he can’t come without permission. And he loves to give me orgasms. And I love to get them. Win-win.

Yesterday, I emailed him partway through the day that I would be needing his tongue or fingers later on. I asked him if that woke up Mr. Weenie. He said it certainly did. Bingo! He was now in anticipation mode. Of course he had no idea whether he would be uncaged for the festivities. I wasn’t sure if he would be either. It crossed my mind to unlock him so I could ride him when I was done with my orgasms. I love feeling him inside me. But, given my recent track record of ruined orgasms and the fact that I have no self-control, I probably would have given him a full orgasm. So I figure the Lion riding will wait till tonight.

After he was done with me, or I was done with him, I was playing with him through the cage and he said it’s too bad the cage covers the more sensitive parts of his cock. Poor boy. If I could touch the more sensitive parts then he could too. Not a good idea. It is a little frustrating for me to try to tease him through the bars, but I have the key and I can get to any part I want at any time. He shouldn’t be able to. Besides, he’ll have five days without the cage so he can touch anywhere he wants. But that doesn’t mean he should touch himself.

I haven’t decided how long Lion’s next wait will be. I do know that there will be opportunities for time off or time added. I’m going to enjoy our final trip of the summer and he can enjoy his wildness. Then I’ll decide.

Sometimes it’s as difficult for me to control myself as it is for Lion to hold back his orgasms. I should know by now that my mouth is no match for his cock. I didn’t really have specific plans for him last night. I just figured I’d edge him a few times and that would be that. But did I do that? Nope.

I don’t know what made me decide to tease him with my mouth. I told him right from the beginning that he was not allowed to have an orgasm. I knew he was over-the top excited. His erection didn’t fit all the way in my mouth. But I kept going anyway. So it was really no surprise that he couldn’t hold on. Whatever the point is between ruined orgasm and full orgasm, we hit it. No amount of squirming on his part kept him from oozing out a little. But the good news is, he’s horny again this morning so I didn’t go too, too far.

Afterwards he said he thought it was me who couldn’t wait to give him an orgasm. I told him I could wait and that maybe I’d make him wait another week. He agreed that I could. Then a few minutes later nervously asked if I would really make him wait another week. I just smiled at him. Would I do that to him? Probably not. I’d have to listen to him whining and grumbling for another week. Even though I’ve relieved some of his pressure over the past week in the form of ruined orgasms and whatever that was last night, he’s still tree-humping horny. And he’s been a very good boy. While I have been working late, he’s been helping out around the house. And since I was already set to leave him wild for our last trip of the summer, I don’t really want to change those plans. However, I suppose I could leave him wild and unsatisfied until Friday. That way he may not be distracted by the cage pinching him but he may be distracted by the fact that he’s still a very horny boy. Too many choices!

The truth is, I don’t need him to wait another week. From my point of view, the whole reason for the cage is to keep us focused on our sexual relationship. Well, to keep me focused. There’s no reason for monumental waits on his part. Punishment really does nothing for me, but I understand the allure for him so extending a wait time is probably somewhere in his future. It’s true that the threat wears thin unless you follow through. I guess I’ll list that as a goal for me.

Lion can rest assured that he will have his orgasm as scheduled on Thursday night and he will indeed be wild for our trip. Of course, he’ll still need to be on his best behavior. I do have paddles and the shock collar at my disposal even if he’s not caged.

Lion is a very horny boy. The other day, in the middle of the kitchen, I started fondling his butt. He was purring so much I wonder if he tried to get an erection. Then yesterday I unlocked him to do some manscaping. Of course, I never just do manscaping. I always play with him a little bit. A few strokes of his cock, some ball squeezing, a little more rubbing his buns. When I was working on his backside he let the tip of his penis poke between his legs. I don’t know if it was on purpose or not but I couldn’t let it go unnoticed.

When I was done I informed him that he would remain wild until he showered and eventually I would play with him. He asked if I thought I could trust him. I told him if I started to play with him later and he wasn’t immediately at attention I’d know he’d been naughty and he might get some of that punishment he craved. He promised to be good. He was, indeed, a good boy. Hours later, after his shower, he was ready for some exercise.

I got a small bag of tricks, as I like to call it, with clothes pins and Velcro in it, and proceeded to make his balls look like a porcupine. I’m sure not all of the clothes pins hurt but some of the more strategically placed ones hurt a lot, and I’m pretty sure the ones that don’t necessarily hurt add to the overall pain. And just to make sure, I pull on them all to heighten the experience. Eventually I swapped out some of the regular clothes pins with ones that have the no slip tape on them. Similar to Velcro, it’s like hundreds of tiny teeth biting into the delicate skin. Of course, I stroke his cock from time to time to keep him happy. The movement also causes the clothes pins to wiggle and I’m sure that reminds him they are still there.

Eventually I took them all off and just concentrated on playing with his cock. I always think I’m just going to tease him and not edge him. Just enough to get him hard, but not enough to really get him going. And then I give in and edge him anyway. It’s nothing he’s doing. I just have limited self control when it comes to teasing him.

I’m not sure how I feel about multiple ruined orgasms. I like watching him squirm, but it increases the chance of my going too far and giving him an actual orgasm. We’ll have to play with it and see. Luckily I have a willing guinea pig to experiment on.

At this point, my Lion remains horny. And he will stay that way until Thursday night