ElanSubdued
Posts: 1511
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Acephale,
Okay. Possibly to the chagrin of others, I'm going to give you a serious answer.
After reading your OP, my first thought was "what are you trying to accomplish"? The submissive broke an agreement the two of you made and it seems you're disappointed by this. If that's the issue, then I highly doubt the "punishment" you've devised will have much effect. When there are issues of this sort between D/s partners (online or otherwise), usually straightforward communication is required. You could ask the submissive to explain why he broke the agreement and you yourself can explain why you're disappointed and whatever other feelings you have. Get more feedback from him and make adjustments so this doesn't happen again.
Only you can decide, based on what the two of you agreed to and on the feedback you get, what the seriousness of the infraction is and what actions you should take. It's possible your submissive broke the agreement simply to get attention and if that's the case, giving him the kind of play punishment you've described is, in my opinion, the totally wrong approach. You'll just get more bad behaviour because you will, in effect, be rewarding him for the behaviour.
I suggest restating expectations, having the submissive repeat these, and asking if there are any issues that might prevent your submissive from doing as asked. Set reasonable expectations, not idiotic ones. Now, true enough, if you say "no masturbating without permission", that's clear and, depending on the submissive, it may be easy to follow. But, keep in mind that unless this achieves some kind of mutual goal and this goal is clear to both of you, it will be harder for him to follow a blind command. In fantasy D/s, the dominant issues a command and the submissive need not know why. Makes for hot literature. In real life, people usually perform better when they understand what is going on and what the goals are. Your goal may simply be to take control of his sexuality because it suits you to do so. Fair enough. If you've not explained this to him, I suggest doing so and I also suggest finding out if he wants to grant this kind of control to you.
You generally cannot force a submissive to do something they don't want to do. Yes, this goes against the pseudo-rulebooks, but that's the reality of human relationships of this sort. Therefore, if you've not done so already, I suggest having a chat about what you want and expect, and see how this lines up with your submissive's desires. As long as the two of your are reasonably on the same page, you can guide this boy toward what you want. But, if the two of you want completely different things, you're fighting a losing battle. And really, who wants to "fight" in their BDSM relationships anyway? This should be about exploring together, supporting one another, and having fun working toward mutual and reciprocal goals.
Now, having said all of this, I'll approach from a different angle. Perhaps you really do want to do a play punishment scene with this boy because it turns you on to do so or because you want to see him jump through hoops you set up. That's fine, but realize this is play and not actually problem solving. It's possible some small modicum of problem solving could be involved in the play, but I suggest keeping play for play's sake and problem solving as a separate activity.
So... you want to put him "on ice" (literally), have him take pictures, and, after he eats a red pepper, have him recite humiliating literature you've written and only after he finishes is he allowed fluids to rinse his mouth. Hmmm. I see at least two issues with this plan. First, continued exposure to ice will burn the skin. I'm talking about cold burns. Thus, as you've noted, you'll want to be careful as to how you expose him to this. Short periods may work, but you'll have to devise a mechanism to measure his reactions and to ensure he removes himself from the ice periodically. Second, regarding the pepper, have you ever eaten a super hot pepper? I have (mistakenly) and I couldn't read or do anything! My mouth burned so badly that even significant amounts of milk and water did little to help. As an alternative to the pepper, you could have him wash his mouth with soap and only allow him to rinse when he's completed his task. Toothpaste is another alternative as this isn't nice to have in ones mouth for long periods of time.
If you have a desired outcome but also set up the situation so failure is quite possible, this is something you should consider how to deal with. Just bitch-slapping someone for failing generally builds resentment so I'd figure out how to encourage success and how to deal with failure in a supportive, fair way so that if your submissive has to try again, he feels empowered by you and supported by you.
Good luck,
Elan.
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You only say that, because she wasn't in person, doing the deed ordered of her. 
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