That is the universal question. As soon as he finds out he's in trouble, every boy about to find his bottom stinging seems to want to know exactly what he's in for.
And it's always such a dilemma, because it's not a question I can answer.
I don't really use set numbers for spanking. I feel they are counter productive.
It's understandable that the boy wants an answer. Having a number helps cut it down to size. A clear definition takes a spanking from being the big scary unknown to something manageable, bearable. They know the exact size of the challenge and can gird themselves to meet it.
But sometimes that's not what you really want. It's not what he needs. If the goal is true penance, true remorse, then a challenge the mind can embrace and defeat is the worst thing you can have.
Such things have their place, but when you're trying to take someone into a specific emotional space the mind is an obstacle, not a ally. It is the mind's job to protect those vulnerable emotional spaces. Uncertainty helps soften the barriers the mind puts around them and makes letting them down easier than it otherwise would be.
This isn't just about making it easier on you. It's about making it easier on him. The harder he fights, the higher the risk that you may actually do harm. This is not desirable. We want to gently bend, not break.
Still, even with the walls softened it is hard to know exactly what getting past them will take.
Everyone is different and even someone I have spanked many times is different from time to time. I have a very good idea of what they can take and how they will react but nature has it's own way.
If I were to set an absolute number of strokes I might low ball it and not push him far enough to achieve the catharsis he needs.
And after he's taken though 10 or 20 or however many and it's not enough I can't very well stand there and say "oh, I've changed my mind, you need 20 more." That breaks trust and erodes credibility. Not healthy for a relationship at any stage.
Or if I guess too high then we are faced with the unpleasant choice of my either having to again change my mind, or he may be forced to ask the scene to stop and even though that's 100% ok, he'll likely still feel he failed if he can't get through the whole number.
Or worst, perhaps, if he forces himself to go through with more than he can or should take he may find himself either physically or emotionally damaged.
No, there's just no good option there.
So when he asks how many, I say "it depends", "we'll see" or just "I won't count, I'm just going to keep going until you're good and sorry."
That way I make sure he gets exactly however many he needs and not one swat more.
And he can always be a brave boy and take it, because the challenge can just happen to be whatever he can take right then.
That way we both win.
I like that.