Lion and I seem to have similar questions. He wants to know if I will stop something if he asks me to. I’d like to know the answer to that as well. But I also want to know if he’s asking to see if I will stop, or if he really needs to stop. As I said, I’d be happy if we used the nasty clothes pins every once in a while. He seems hell bent on enduring them on a nightly basis until he can master a full ring of them. To what end? Once he manages that, what’s next? Do we do another ring closer to the tip? All the way down the shaft? Do we put them away for use every once in a while? I don’t understand the game. It’s OK. We’re very far from his being able to take more than one of them, so the game continues.
Last night was punishment night. I caught Lion eating before me. He just charged right in without even looking at me. In his defense, we were having the leftovers of his wonderful mushroom barley soup so he couldn’t wait. When I went to administer his punishment, I didn’t restrain him. After four hard swats he started to move. Once he settled in again I gave him a few more swats. More movement. Settled, swats, movement. Settled, swats, movement. He told me it was enough. I told him when he stopped moving it would be enough. I guess that must have been the answer he was looking for because he held still for the final few swats. If he wants punishment, he needs to be able to take it. Yes, I could have restrained him, but I want him to be able to hold still. Punishment may be his idea, but I get to put my spin on it. [Lion – Painful spin]
Is that what he’s looking for? Does he want me to run with his ideas? I can do that to some extent. I just worry about going too far. What if he sets this lofty goal of taking the tiny clothes pins in a ring around the head of his cock and can never get there? Do I push him to do it no matter what? What if he gets halfway and can’t go any further? Will he feel he’s failed? Will he feel he’s failed me? He can never fail me. First of all, this isn’t life or death. Even if he said he absolutely can’t take another tiny clothes pin ever, he’s nowhere near failing me. Clothes pins would be out. Move on to the next thing.
On the other hand, I don’t want to fail him. I have to walk the fine line between cheer leader and realist. I know you can do it, but if you can’t it’s OK. You’re doing very well, but now you’re bleeding. The Velcro makes your cock look very angry, but now gangrene has set in. Yes, that’s extreme, but that’s what I think about. He wants me to keep going, but I don’t want to go too far.