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Piercing Grapple (Combat)
You can use small but deadly weapons to restrain a foe, forcing it to choose between pain and capitulation.
Prerequisite(s): Dex 13, Improved Grapple, Improved Unarmed Strike, Quick Draw, Intimidate 7 ranks.
Benefit(s): You can draw a light or one-handed piercing weapon and stab your opponent with it when you initiate a grapple. You take a –2 penalty on your combat maneuver check to initiate the grapple, but since you pull the weapon out as part of the grapple, you don’t take the usual –4 penalty. If you succeed, you grapple your opponent as normal, and the weapon doesn’t count as being in your hand either for the purposes of the –4 penalty or for dealing damage while maintaining a grapple. If your opponent successfully breaks the grapple, it takes an amount of damage equal to the base weapon damage of the weapon you used to initiate the grapple plus an additional 1d4 points of bleed damage. A successful DC 15 Heal check or any magical healing ends the bleed effect. If you choose to end the grapple, you can opt to not deal the bleed damage, but either way, your opponent still takes the base weapon damage. While maintaining this grapple, you gain a +2 circumstance bonus on all Intimidate checks made against your opponent.
Hamatula Strike (Combat)
You can catch your opponents on your weapon and hold them in place.
Prerequisites: Improved Grapple, Strength 13, Base Attack Bonus +7.
Benefit: Whenever you damage an opponent with a piercing weapon, you can immediately make a grapple check; success means the opponent is impaled on your weapon and you both gain the grappled condition. While the opponent is impaled, as an attack action you may make a grapple check on your turn at a -4 penalty to damage the opponent with your weapon, even if your weapon cannot normally be used in a grapple.
So I can stab with weapon
Free grapple (Hamatula strike)
Free stab with weapon (piercing grapple)
Repeat?
Keep in mind that Piercing Grapple only triggers when the opponent breaks your grapple, or when you end it. I'd assume this means that your failed check doesn't trigger the feat.
Other than that, it seems to work.
Looks legit.
Piercing grapple is weird. It says you stab your opponent as part of initiating the grapple, but you deal damage only when the grapple ends, and you have no way of choosing not to deal said damage so it's hard to say how the feat goes about "forcing it to choose between pain and capitulation."