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There's no rule, but lots of people use 20-40 laps on fabric, then 40-60 laps on leather before shaving.

Maybe you just need to strop more . . . Try it, won't cost anything.

...

. . . Besides "it'll nick me", how do you assess whether the blade is sharp?

. . . How much stropping do you do between shaves? On what?

What you're describing _could_ be caused by a blade...