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Actually, you just want the edge of the razor to be in light contact with the strop. Pressing the razor down against the strop will only dull the edge. You really only need the weight of the razor...

Based on what I've read here in the beginner's guide and the stropping threads, it seems that most (including me) strop before every shave, and quite a few (also including me) strop post-shave as...