When you put the knife on the undamaged tomato skin there is no weak point it is all resisting being cut evenly. Once a cut has been made only two very small points are resisting being cut. The flesh is much weaker than the skin as well. That is why it seems effortless after breaking the skin each time. Also you are using a dull knife if a tomato needs to be squished at all to cut through, and serrated knives are a lazy answer.
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