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GROUND PEPPER
Steak should have some moisture to it, so seasonings should stick to it pretty well. I have heavily salted and peppered my steak before searing it before and had no issues with the seasonings sticking. Perhaps it is the type you are using? Is it very coarse? Sometimes it helps to kind of "pat" it on, if that makes sense.
Pepper it and put on a hot skillet with the pepper side down
Cook it longer on one side and apply lots of pepper.
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