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After a successful grapple, can you make an attack with melee weapons, ie dagger(s) or shortsword(s)? Or are you left with continuing the grapple vs ending it?

I'm not sure how best to describe it so here is a picture to give a general idea.

example weapon grapple

Additionally, would this be considered a normal attack or something else?

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    \$\begingroup\$ I was certain this was asked somewhere else but I am having a hard time finding exactly where. There are some questions on the "Related" sidebar that seem close, though. \$\endgroup\$ – Javelin Jun 15 '17 at 18:18
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Yes

Grappling

When you want to grab a creature or wrestle with it, you can use the Attack action to make a special melee attack, a grapple. If you’re able to make multiple attacks with the Attack action, this attack replaces one of them. (PHB p.195)

For example, if you have a 5th level Champion, you can try to grapple your opponent, and if you succeed with the grapple attempt then the second attack (with a weapon like a war hammer that you have in your other hand) is available. Note that you can't now have a shield unless you have a third hand, and it has to be a weapon you use one handed.

Using at least one free hand, you try to seize the target by making a grapple check, a Strength (Athletics) check contested by the target’s Strength (Athletics) or Dexterity (Acrobatics) check (the target chooses the ability to use). If you succeed, *you subject the target to the *grappled condition** (see appendix A).

The condition remains until it ends. The target is grappled until either it escapes the grapple (which requires the target to use an action) or you voluntarily release the grapple.

Grappled
• A grappled creature’s speed becomes 0, and it can’t benefit from any bonus to its speed.
• The condition ends if the grappler is incapacitated (see the condition).
• The condition also ends if an effect removes the grappled creature from the reach of the grappler or grappling effect, such as when a creature is hurled away by the thunderwave spell. (PHB Appendix A, Conditions)

Hold 'em by the arm and smack them in the head with your hammer, for as long as the target is unable to get free of you.

From your comment:

So I can't use my legs to (for argument's sake) lock over the shoulder and under the arm and strike with 2 daggers using the dual wielder feat?

No, you need to use at least one free hand per the rules. If you want to use cool judo moves, or cool wrestling moved, you'll need a DM ruling for that. As to your picture, the feet wrapped around the waist of the target don't matter, per the rules.

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  • \$\begingroup\$ Even if the hand is not actually grabbing the grappled creature, you can bet one hand is used for support or balance. This is an attempt to make a loophole for free hands that clearly goes against the rules. Want to use a greatsword while grappling? roll a Kreen. XD \$\endgroup\$ – Mindwin Jun 15 '17 at 23:21
  • \$\begingroup\$ @Mindwin No, it does not clearly go against the rules. You hold onto the target with one hand and (if you have an attack) you hit with the other. At lower level, you have to wait to next turn for that hit, and the target gets to try and break the grapple. THis is one of the ways martial characters are given a modest bit of flex in trying to get an edge but there is no free ride, no easy button. You have to make the roll, and you have to beat the "get free" check. \$\endgroup\$ – KorvinStarmast Jun 16 '17 at 3:05
  • \$\begingroup\$ @Mindwin What loophole are you talking about? The picture in the question or my explanation of how grapple works? Nowhere did I say that you can use a great sword to do this. Maybe take another look at the answer. Arrgh, didn't realize this was a dupe. :( \$\endgroup\$ – KorvinStarmast Jun 16 '17 at 3:06
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Yes.

We could dig into the grapple rules (PHB p.195) to show it's so, but I think there's an easier place to see it: the Grappler feat (PHB p.167).

You have advantage on attack rolls against a creature you are grappling.

Clearly, then, one can attack the target of a grapple.

Looking back to the grapple rules we see that initiating a grapple requires a free hand. It doesn't exactly say that you need to continue using that hand to grapple, so there's a judgment call to be made as to whether you can attack with a two-handed weapon while maintaining the grapple. ("I tuck their forearm into the crook of my knee and kneel down, effectively trapping his arm, and raise my maul high overhead with both hands..." for instance.)

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