There has got to be a better way. I've got the regular ol' grease gun with the fitting on the end that you have to hand tighten with your finger tips once you get it on the zirk. Does a better gun exist? Do they make one that clamps on to the zirk somehow without having to tighten it and fight it?

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most grease guns nowadays have a push on type fitting that is easier to use. some even have a 90 degree fitting to get to those hard to reach areas. go to your nearest auto parts store and have a look in the grease/oil aisle. you could even replace just the hose to update your grease gun. they have a firm steel ones and flexible hose replacements.

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If you have or can get a compressor you can get a grease that hooks up to air, then you only need two hands instead of three. Just push the end on the grease nipple and squeeze the handle.