A tail, two pistols, and perhaps some desperation. Does this work?

[noble peasant]

Someone brought this up in a thread (ok technically they were talking about hand crossbows as they were the topic of discussion but I investigated the concept under the pretense of using pistols) I made and while the idea sounds wonderfully entertaining I don't think it works. The idea he brought forth was that you would be a tie fling who used TWF to use two pistols, while using prehensile tail/ grasping tail to hold one of the pistols after you fired to free up a hand and reload both pistols. There is two main thing I'm seeing that may just poop on the whole idea, those being that A) these tail abilities allow you to retrieve an item on your person as a swift action, that doesn't mean it can hold stuff, and B) IF I'm wrong about the first bit, reloading a pistol requires two hands, sure I could use a swift action to free up one hand and reload the pistol in the other, I doubt I could reload the second as I'm pretty confident my tail wouldn't count as a free hand.

While I think most of my statements on why this doesn't work are sound, I didn't want to presume I'm smarter/more informed than the person who brought up this idea, and wanted to double check, and hopefully be proved wrong as this sounds pretty fun. ;)

[cnetarian]

a tiefling fire routine with "grasping tail" feat

• begin with first pistol/crossbow in one hand and other hand empty
• make all iterative attacks with first pistol/crossbow, reloading with other hand which is empty
• drop pistol/crossbow on the ground so you have two empty hands
• swift action to draw second pistol/crossbow or use grasping tail to pick second pistol/crossbow off the ground if not the first round of combat and put it in the hand which has not attacked
• make all iterative attacks with second pistol/crossbow, reloading with the other hand which is now empty
• end of round as bookkeeping action change the pistol/crossbow in your hand from the second pistol/crossbow to the first and the one that is on the ground from the first pistol/crossbow to the second

note: many gunslingers put much thought and effort into figuring out this fire routine, and most people would never consider dropping a weapon onto the ground as a good idea.

[Cap. Darling]

To make this trick work the 6 second turn need to happen first for one hand and then for the other. If i, as a GM, want my players to be able to TWF with pistols i make room in the rules for pistols that can shoot several times with just one hand.

[lemeres]

You know that juggler bard lets you TWF reload with a 2 level dip without this complication (or the 'freak of nature' aspect of an alchemist with vestigial limbs), right?

And if you simply avoid dumping cha, you can grab cantrips. So a nice plus overall.