Very clever idea, thank you for shairing.
One of the most challenging dares I had to do was place clothespins on my nipples and then knock them off with a wooden spoon, thus effectively spanking myself on the breasts as well.
It was much harder to knock them off then I thought. Each slap was quite painful. Even worse, however, was that with each failure there was the horrible realization that I would have to do it again, but this time with even harder force.
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