One of my favorite themes for a game is “nobody knows if you gonna cum, not even me”. 😄 Setting him up for a situation in which it would be immensely difficult to achieve an orgasm, but not impossible. Now that I said that, I think it’s the same why I opted for “rare sex” over completely pussy free. The end result is borderline the same, but mentally the difference is massive. Because if he knows there is a chance he will try his best. And not just physically. I want him to participate as much as possible. I want him to try to reach the almost impossible goal. Because if he fails, I know he has been edged and denied much harder than I alone could ever do it. And if he somehow manages to cum I would be most happy to let him have it, because it would be earned and it would open up other things for me to tease him with 😈

For the longest of times, I wanted to start playing with bit of a anal. Since his dick is almost always locked it would be great to use another very sensitive area, but still having the mindfuck of keeping him caged. Nipples work nicely, and they are very sensitive. But I was thinking something more “down there”. Something that’s connected to the same cluster of nerves as the penis is, so it has a little bit of familiarity, but it’s still vastly different feel. A while back I bought a prostate massager as I think it’s a good starting point. We tried strapon before and while it was hot, it was too much for a start. The prostate massager on the other hand was a success. Last time I used it he had a massive orgasm, but it was with a little bit of help from the hand on his dick. So I was wondering what would happen if I kept him caged this time. 😇

First I did let him play with the massager alone for a while, but without the vibrations. Just so he can explore the feeling of having something inside him. I wanted him to take it slow, so he could appreciate the feeling of a toy pressing on his prostate. I was thinking maybe I’ll get him a buttplug for training at home. I kinda like the idea of being able to order him to wear it on command any time 🤭Anyway, when he was ready for the session I could see he was already quite aroused, but somewhat nervous. It’s still something new, we don’t do too often.

I kinda liked the idea of pairing it with a little bit of bondage. I know he’s always playing with his nipples, but I wanted to be the one who had it under control this whole time. I know I didn’t make it any easier for him. But that’s kinda the point. I didn’t want him to have it easy, I wanted to have it barely possible. He was completely allowed to cum. If he managed it just by having a buzzing toy in his ass 😈 I honestly hoped to see it. A few times I thought he was almost there. I can see it on him when he’s close. And Luke later told me himself, that one or two strokes of his dick would send him over the edge for certain. Well, too bad I didn’t let him have them 🤭 It was either ass or nothing 😈 And unfortunately, he didn’t make it this time. But it was so damn hot. The frustration was almost tangible. To even give him a chance I made sure he was horny before we started, so he’s beyond horny now. 😄 He’s virtually melting away. Like I said, I couldn’t edge him like this myself. Only he can do it when he hopes he can cum. I would have stopped way sooner. I love when he’s putting all of this effort into it, but it only takes him so so close, but still not enough 😈

Now the only thing I am wondering is, I’ve seen people cum like this. So, was it a lack of training, or does he need to be even hornier to make it happen? 😇I guess we will find out in time.