It’s probably the first time Luke has really begged me to let him cum. I am not sure if it’s becasue I teased him a bit extra “hard” lately, or if it’s becasue his last orgasm was just cumming with the anal wand. 🤔 I think it might be the latter because I always try my best to keep him completely out of his mind. I like when he’s horny and his mind is a bit pliable, it’s makes him more devoted to serving me, he’s extra attentive and he’s extra sensitive to any sexual stimulation. But that’s been his new normal for quite some time and I think he had to make peace with the idea that he won’t ever not be horny. 😇 But to reward him, keep the positive feedback going and keep a sliver of his sanity, I let him cum, one way or another every few weeks or so. I don’t keep check really, I prefer to just watch how “ripe” he is for cumming and then give him a taste, of something most guys have daily 😈

Of course, the longer we go, the more desperate he is and I can usually tell when he’s nearing his limits. I know that any orgasm, or release I provide isn’t going to last long. Usually, it’s mere hours or days at best. But it gives him a break. I wonder if the anal orgasm he had has been different. He came like a firehose, that’s for sure. But could it be because I didn’t even touch his dick? The only dick I own is his, so I don’t know firsthand how it works 🤭

Lately, I’ve been getting hints, that he’s really and I mean really horny and that he can’t take it anymore. Of course, my first reaction was “So, what’s going to happen when you can’t take it anymore, but I keep you locked” … Well, the answer is that he’s going to keep taking it. Which is exactly what I love about chastity. 😈 “Awww, you are going to lose your mind if I don’t unlock you? Well, then go ahead. There is no escaping. You either learn how to deal with it, or you don’t deal with it… but the external effect is the same. You don’t cum.” Well, at least I think. I didn’t see him spontaneously cum in the cage. Some people claim it can happen, but most people I’ve talked to never managed to cum in the cage just because they were too horny. Anyway, I am sidetracking, because I too am horny, when I think about those things 🤭 So back to the point. After I told him, that that’s too bad. I’ve started paying attention to see how bad it actually was. Interestingly riding his face without unlocking last time, probably didn’t help him either. I could tell he was getting really desperate. Though I kinda liked it, because he’s been all over me, helping doing my every whim. I am starting to suspect that prolonged chastity is the closest we could get to telepathy 🤭

Anyway, I am not (completely) evil. So after ignoring him for a while, just to confirm he’s that desperate I’ve decided that it’s time to give him some relief. I would have started considering it anyway since it’s almost a month since he came last time. Too bad he had chosen to beg me to let him cum, because now I am confronted with a dilemma. I can’t let him think begging is working on me, but at the same time, I think he deserves some relief. 🤔 So I’ve decided I will let him have it, but I’ll keep him flaccid the whole time.

Boy needs to cum so bad? Ok, lets make you cum, just sit on the stack of towels, so you don’t accidentally get erect. I didn’t hear anything about needing to be hard or using the penis in any meaningful way. The lack of orgasm is frustrating you too much? So, let me fiddle with your pale and soft dick until it starts dripping cum, so I can lock you right back in. 😈

Haha, I hope it wasn’t too unsatisfying 🤭 What more did you expect? You were begging me, that the pressure is unbearable. The cum is gone, the pressure is gone, this is all the sex you need and all the relief I’ve decided to provide. I would say I hope it’s going to last you a few weeks. But like I said before, it doesn’t matter, since I am the one holding the keys 😈 So “It IS going to last you a few weeks”. … how many weeks? Well, for the sake of keeping you motivated, let’s say it depends on how your behavior. (at least little bit).

P.S. I am aware I switched the person from “him” to “you” mid-way through the journal. But I am used to talking mostly to him about the ways I am going to tease him, that it feels natural to me, to “talk” to him in my notes as well. I know. At least you can put yourself better in his shoes (or cage, your pick) 🤭