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Its been this way all my life, even after switching to straight/DE shaving. my old multi-blade tool of death used to give me really really bad ingrown hairs and that was painful.
I've done ATG for...

This is not an ingrown/razor bump issue, but I'm not sure what it is.

I've tried using a straight razor and a DE, both have the same problem. I take plenty of time to prep (I use kyle's prep)...