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This came up in a boss fight this evening, so I figured I would ask, as the four GMs playing at the table were not in agreement on the answer. This is taken from level three of Thornkeep
Each claw on grappling also can eviscerate and does 2d6 sneak attack damage.
couple questions came up:
1) If the medium sized creature hits with a claw on another medium size creature, and makes his Combat Maneuver check to grab, does he inflict his sneak attack and ability damage immediately?
2) I cannot find where this is codified in the rules, but if said monster was say in melee range of 3 seperate PCs, and took a full attack action with 4 claws, and hits all three, does he get a chance to grapple all three of them at the same time? Yes or no, and cite rules where you find this. Given what we could determine at the time, I am inclined to believe that since each claw has grab, on a full attack action if he attacks 3 seperate creatures he can hold all 3 if he hits each of them.
1) Yes. Unless the ability specifically says that there's a delay to when the sneak attack damage happens, it would happen right away.
2) You're not going to get any rules citation, because the rules don't list any limit to the number of people you can grapple, regardless of # of arms. So RAW the answer would be yes, but I do think it would be a reasonable houserule to put a cap on the number of people who can be grappled by the same enemy.
And that's what I've given you. The answer is that you're looking at the possibility of adding two restrictions that don't exist in the rules. Hence there is no rule citation that will apply.
When you attack with a longsword, it does 1d8 damage if you hit. Just because the rules don't specifically indicate that that damage is done the same round, doesn't mean it's ambiguous. Any effect should be considered to take effect the same round as it's initiated, unless the rules specifically state otherwise.
Relevent text, provided the monster doesn't have special text of its own.
Grab (Ex)
If a creature with this special attack hits with the indicated attack (usually a claw or bite attack), it deals normal damage and attempts to start a grapple as a free action without provoking an attack of opportunity. Unless otherwise noted, grab can only be used against targets of a size equal to or smaller than the creature with this ability. If the creature can use grab on creatures of other sizes, it is noted in the creature's Special Attacks line. The creature has the option to conduct the grapple normally, or simply use the part of its body it used in the grab to hold the opponent. If it chooses to do the latter, it takes a –20 penalty on its CMB check to make and maintain the grapple, but does not gain the grappled condition itself. A successful hold does not deal any extra damage unless the creature also has the constrict special attack. If the creature does not constrict, each successful grapple check it makes during successive rounds automatically deals the damage indicated for the attack that established the hold. Otherwise, it deals constriction damage as well (the amount is given in the creature’s descriptive text).
Creatures with the grab special attack receive a +4 bonus on combat maneuver checks made to start and maintain a grapple.
I don't have a copy of thornkeep so I don't know the exact answer because I don't know the monster. Edit: And here's the grappled condition text.
Grappled
A grappled creature is restrained by a creature, trap, or effect. Grappled creatures cannot move and take a –4 penalty to Dexterity. A grappled creature takes a –2 penalty on all attack rolls and combat maneuver checks, except those made to grapple or escape a grapple. In addition, grappled creatures can take no action that requires two hands to perform. A grappled character who attempts to cast a spell or use a spell-like ability must make a concentration check (DC 10 + grappler's CMB + spell level), or lose the spell. Grappled creatures cannot make attacks of opportunity.