Full attack and Improved Grapple

[Elder-Basilisk]

That's the rule I meant. Anyway, I referenced it to demonstrate that it is possible to be grappling more than one person at once. The improved grab rules for a creature with two improved grab attacks (such as the brown bear) are the only rules necessary to initiate a grapple with more than one person at once.

If the bear hits the first character, it gets a grapple check. It takes the -20. If it wins, it pulls the character into its square and the first character is considered grappled (although the bear isn't. The bear then hits the second character, taking the -20 and still wins. It pulls the second character into its square and that character too is now considered grappled (although the bear isn't).

Assume that neither opponent escapes during their actions.

On the start of the bear's next turn, both of those characters are considered grappled. If the bear doesn't take the -20, it is too. However, the bear's failure to take the -20 shouldn't change the status of either character; both are grappled until they escape.

That sequence of events appears sufficient to me to be considered initiating a grapple with more than one opponent. Where's the problem with it?

I don't see an "entering a grapple" rule, but perhaps I'm missing something. I do see a "joining a grapple" rule, and it's this:

Joining a Grapple

If your target is already grappling someone else, you can use an attack to start a grapple, as above, except that the target doesn’t get an attack of opportunity against you, and your grab automatically succeeds. You still have to make a successful opposed grapple check to become part of the grapple.

Since it states that you're attacking someone who is already in a grapple, I don't think that pertains to your comment. Of course, you're welcome to rebut if you're seeing something I'm not....

 

[Kershek]

I'm pretty sure it means exactly what it says. If the creature takes the -20 penalty it is not considered grappled itself. So if the other creature wants to achieve a grapple result against it other than "escape" they must grapple normally - and go up against the creature's whole grapple bonus.

Interestingly enough, I just noticed in the 3.0 FAQ that it says when you take the -20 penalty it applies to all grapple checks you make until your next turn.