You cannot select weapon specialization (grapple). Grapple is not a weapon.
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Yes you can:
"Weapon Specialization (Combat)
You are skilled at dealing damage with one weapon. Choose one type of weapon (including unarmed strike or grapple) for which you have already selected the Weapon Focus feat. You deal extra damage when using this weapon.
Prerequisites: Proficiency with selected weapon, Weapon Focus with selected weapon, fighter level 4th.
Benefit: You gain a +2 bonus on all damage rolls you make using the selected weapon.
Special: You can gain this feat multiple times. Its effects do not stack. Each time you take the feat, it applies to a new type of weapon."
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Perhaps I'm misunderstanding what your trying to say, but we do make damage rolls while grappling:
"Once you are grappling an opponent, a successful check allows you to continue grappling the foe, and also allows you to perform one of the following actions (as part of the standard action spent to maintain the grapple)."
One of the actions:
"Damage: You can inflict damage to your target equal to your unarmed strike, a natural attack, or an attack made with armor spikes or a light or one-handed weapon. This damage can be either lethal or nonlethal."
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I think it does nothing. My reasoning being that you don't make damage rolls while using grapple.
But you do.
Once you are grappling an opponent, a successful check allows you to continue grappling the foe, and also allows you to perform one of the following actions (as part of the standard action spent to maintain the grapple).
Damage: You can inflict damage to your target equal to your unarmed strike, a natural attack, or an attack made with armor spikes or a light or one-handed weapon. This damage can be either lethal or nonlethal.
I stand corrected. That seems very odd to me.
Yes, maintaining a grapple would do an additional 2 damage. Pretty simple.
It is clear that you can weapon spec (grapple), I would not allow the weapon spec damage (grapple) and (dagger) to stack though. Weapon focus doesn't stack, and while that is intended not to stack on the same weapon, I'd argue that that is exactly what you are doing (albeit in a roundabout way).
I am not so sure of that ruling that I cannot be convinced otherwise - I can see a couple of meritous counterarguments.