If your DM will allow a you as a 4th level Druid of the Moon to wildshape into a Giant Octopus (can say how you saw/interacted with one in your backstory) and be able to wield a shortsword then you can do this build.
Advance to 4th level as a Druid of the Moon. Take the Skulker feat.
Advance to 2nd level as a Rogue.
This is how you do the craziness:
Cast Pass without Trace and then wildshape into a Giant Octopus on turn 1... or as prep. if you can right before a fight.
On turn 1 or 2 (depending on when you cast and wildshape.) you can hide as a bonus action (due to Cunning Action).
To calculate your Stealth check you can use your character's (expertise from Rogue) Stealth instead of the +5 from Giant Octopus (due to the rules of wildshape). This should be +9 at 6th level. (4 druid/2 rogue) Don't forget to add the +10 from pass without trace and Skulker let's you try to hide when only lightly obscured (such as the wood elf examples from mask of the wild feature... or any instances of dim light. (or even in complete darkness against those with darkvision),
Before you wildshape you can drop a shortsword on the ground and pick it up after as a free action. Make a shortsword attack (can add sneak attack damage due to wildshape rules.) from hiding (+19 stealth and can try to hide in dim light).
As you level up in Rogue you can do more and more sneak attack damage.
Not sure what the purpose of this build is other than to have some crazy fun with a Giant Octopus that can Sneak Attack.
I would say that you have no proficiency bonus to using the weapon in octopus form. Humanoids (including Primates) have opposable thumbs, which are incredible. Normal weapons are designed to be used with them. Try to spar with a sword, spear, or basically any other weapon with your thumb and forefinger taped together.
Octopuses should definitely be able to use a normal weapon, their tentacles are great. But they do not have an opposable thumb, so I would say no proficiency bonus. I would still allow the sneak attack.
I would however allow you to special order a tentacle short sword, designed to be held by a tentacle. Maybe charge you 125 gp for it. That sword would work in EITHER human hands or tentacles.
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If your DM will allow a you as a 4th level Druid of the Moon to wildshape into a Giant Octopus (can say how you saw/interacted with one in your backstory) and be able to wield a shortsword then you can do this build.
Advance to 4th level as a Druid of the Moon. Take the Skulker feat.
Advance to 2nd level as a Rogue.
This is how you do the craziness:
Cast Pass without Trace and then wildshape into a Giant Octopus on turn 1... or as prep. if you can right before a fight.
On turn 1 or 2 (depending on when you cast and wildshape.) you can hide as a bonus action (due to Cunning Action).
To calculate your Stealth check you can use your character's (expertise from Rogue) Stealth instead of the +5 from Giant Octopus (due to the rules of wildshape). This should be +9 at 6th level. (4 druid/2 rogue) Don't forget to add the +10 from pass without trace and Skulker let's you try to hide when only lightly obscured (such as the wood elf examples from mask of the wild feature... or any instances of dim light. (or even in complete darkness against those with darkvision),
Before you wildshape you can drop a shortsword on the ground and pick it up after as a free action. Make a shortsword attack (can add sneak attack damage due to wildshape rules.) from hiding (+19 stealth and can try to hide in dim light).
As you level up in Rogue you can do more and more sneak attack damage.
Not sure what the purpose of this build is other than to have some crazy fun with a Giant Octopus that can Sneak Attack.
I would say that you have no proficiency bonus to using the weapon in octopus form. Humanoids (including Primates) have opposable thumbs, which are incredible. Normal weapons are designed to be used with them. Try to spar with a sword, spear, or basically any other weapon with your thumb and forefinger taped together.
Octopuses should definitely be able to use a normal weapon, their tentacles are great. But they do not have an opposable thumb, so I would say no proficiency bonus. I would still allow the sneak attack.
I would however allow you to special order a tentacle short sword, designed to be held by a tentacle. Maybe charge you 125 gp for it. That sword would work in EITHER human hands or tentacles.