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If you wild shaped into a Giant Octopus while you have sky swim and are flying 25ft in the air, if you grapple an enemy would he be brought up into the air and then dropped (if you choose to release the grapple)? Would the enemy than just take falling damage? So essentially this octopus could attack with its tentacle, grab, release, attack, grab, release (thus incurring falling damage each time on top of normal damage) until all your attacks have been used?
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I will say cant do that. Cause the corpse not haste to the land. Its time fall down. (Betwen 1-2 secs)
1 round is 6 secs. Cant fall 8/9 times. Maybe 2-3 times being waiting betwen attacks. But waiting its lose time and that could mean lose attacks. Its something to think about.
Another option is start the grapple=end the full round attack.
It depends on how RAW you're being. By the rules, falling short distances is instant. The rule: "If you attempt to place your foe in a hazardous location, such as in a wall of fire or over a pit, the target receives a free attempt to break your grapple with a +4 bonus." only applies to moving the foe on purpose after you've already grappled them.
If you're the sort of GM who likes to add a bit of realism ("No, you can't sunder the giant's hat: you're three feet tall and he's mounted on a Purple Worm.") then you can certainly add a "can't fall repeatedly in the same round" rule.
If you want to disallow it within the rules, the nearest I can think of is "You can perform one or more free actions while taking another action normally. However, there are reasonable limits on what you can really do for free, as decided by the GM." E.g., you don't get to grab as a free action, release as a free action, an unlimited amount of times.