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So I currently have a smartcarry and a crossbreed supertuck and I love to ride my '08 Vulcan! My concern is that I'm not sure if the retention on the supertuck would hold where I wear it at whick is between my right pocket and my back pocket with a forward cant. I just don't want my .40 to go flying on the highway while I'm flying down the highway. Would the smartcarry be the solution in this case or will the supertuck hold it and I'm a pansy?

I rode my little brother's brand new Honda Rebel 250cc bike home from the dealer for him with my Px4 in a Crossbreed Supertuck without a problem. Kinda stuck to the speed limit with the bike being brand new and all. Idk how it would have held up on my ZX-6R or R6 since I sold both of them before I had my license to carry.

CrimsonSoul
My only ride is a Wing, but I do have a back rest on it.
My small Kahr CW40 and/or XD .45 rides very well OWB and under my " HAWAIAN" shirts ! The back rest helps retain them, sooooooo....
Just a thought, maybe some sort of lanyard for ya' - a quick easy attachment to the belt ? ? Heck, maybe a heavy duty rubber band
around the grip. Attach it just before your ride ?!!?
Mac .40 >>>>>>> *:+*

I carray a glock 26 in an IWB comp-tac - no problems shifting or moving.

will be moving to OWB holster and don't anticipate problems, but I also don't ride without an armored jacket so I don't worry about it coming out.

A friend of mine uses that same setup with no problems. He also carries in a shoulder holster. Good luck.