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Now that I've been at this for a bit I figured I'd update this thread with and answer to my own question. Even after practicing on newspaper for days before using my strop...

First off Lynn was...

I'm sure I'll get it with practice and i plan on practicing with a simulated strop, I was just curious if it was possible to cut the strop even with proper blade positioning.

Follow up question:...

I've read more than a few posts where one of the seasoned members say that starting out you will cut up your first strop pretty bad...

I'm curious if this is due to accidentally leading with the...