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I usually carry a CZ-75D-PCR in a nemesis pocket holster in the weak side, inside breast pocket of my riding jacket. This is my preferred carry location when riding. Although I'm not using a small "pocket" pistol, and it certainly fills up that pocket in all three of my jackets, it hides well there, is not poking me while riding and I think it's easier for me to deploy from there than IWB which would require me to completely unzip the jacket on all of my riding jackets. If I'm going on a very short ride and then doing something immediately upon arrival, or if there will not be an easy way to change from jacket pocket carry to IWB once I get there, I'll either rig up IWB before I go or keep the jacket with me the entire time (which is a pain, I rarely do this).

Also, I've recently acquired a Ruger LCR. I haven't carried it while riding yet, I know it would fit the same pocket even nicer than my CZ does.