(How close are the pirates to 'Naut at the top of the round? He was attempting to intercept all of them so that he'd be close to every one, but I'm not sure if that goal succeeded or not.)
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"Ignorance is bliss, and you look absolutely miserable."
(How close are the pirates to 'Naut at the top of the round? He was attempting to intercept all of them so that he'd be close to every one, but I'm not sure if that goal succeeded or not.)
(Jack was about 10 feet behind the others because he really didn't want a fight to begin with, while the other three were very gung-ho on murdering Gridolpho.)
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'Naut wraps their fingers around Jack's throat and drags him towards the other pirates. As they do so,a low humming begins, and the pressure in the air around them increases dramatically. This begins ramping up and up, as 'Naut drags Jack around to face the nearest wall. It finally culminates in a blast of force radiating out from all sides around 'Naut, striking the pirates and Jack, and threatening to blow them back.
(Casting Thunderwave, but shoving Jack up against the wall so that the knock back doesn't break the grapple, instead blasting him into the wall but keeping him within 5 feet of 'Naut. Using 15 ft. of movement to catch as many pirates within the spell's radius as possible.)
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"Ignorance is bliss, and you look absolutely miserable."
Areleo will bust into the alley but not with his sword instead you see him grow in size and stature slightly and his hands grow into claws.
"Today bandits will have the honor of combat against Areleo the Warrior." and he will jump into melee with the tiefling.
As a bonus action, he will rage activating his bestial form with claws and making his two claw attacks
The first claw attack is 19 to hit and 7 damage
the second attack is a 19 again with 6 damage
total damage is 13
Trying to not kill him.
For the DM below about the claw attack:
Claws. Each of your hands transforms into a claw, which you can use as a weapon if it’s empty. It deals 1d6 slashing damage on a hit. Once on each of your turns when you attack with a claw using the Attack action, you can make one additional claw attack as part of the same action.
As the wind blows, 'Naut holds on, then moves Jack around so that the wind now blows out into the open street, and shifting the wind will end up pushing 'Naut into the wall they're next to instead of far away, keeping them close to Jack.
This post has potentially manipulated dice roll results.
Sayyida stayed standing just within the doorway watching the fight with interest; Arleo was a terror and the...Naut?...terrifying in its own way they would be good assets in a mutiny.....Gridolpho.....seemed to be skilled only at getting into trouble. But it remained to be seen how he went now cornered...
Merigar...she was almost certainly going to have to kill once the job was done...but perhaps...she needed to know more...
As she watched she whispered, " Smooth waters and clean winds shipmates."
The thief draws his rapier ("Pokerface") and a dagger and slashes at the thug on his tail. He then gets out of the way to let everyone else have a chance.
The crewman gasps in pain as Gridolpho stabs him... but the rogue is too quick for him to retaliate! So instead, he throws himself at the Triton, swinging rapidly with a mace!
Crewman 1 - Attack: 9 Damage: 8
Attack: 18 Damage: 4
The second crewman decides to help Jack out and lunges towards 'Naut, swinging at the armored creature with all his strength!
Crewman 2 - Attack: 7 Damage: 4
Attack: 8 Damage: 3
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I think all the PCs except Emrys have taken their turn, so I'll go ahead and take Merigar and the Tiefling's turns.
Merigar casts acid splash, hurling the glob of acid at the tiefling and Crewman 1, dealing 3 acid damage if they fail a DC 12 Dex save.
Crewman 1 Dex save: 5 Slim Dex save: 6
Whether he's hit or not, the Tiefling decides to cast Armor of Agathys at 2nd level with his action and attempts to run away from the fight with his movement (he provokes an attack of opportunity from Areleo, but if Areleo hits him the Barbarian he will automatically take 10 Cold damage from AoA)
Unless Emrys has something he wants to do, it's the end of round 1.
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So, now that the fight has already been going on for a round, I finally got a map to help you guys visualize what's going on. If any of you want to adjust where your characters are, just let me know where you want me to put them.
(Yes, I'm aware I got some of the distances wrong in my estimates).
(Areleo is still entitled to an Attack of Opportunity against Slim if he so chooses, this is the map for the start of round 2)
(Uhhhh... K'den, I'll go ahead and roll Jack's Acrobatics check on the off-chance he also manages to roll a nat 20, along with is Initiative).
Acrobatics: 5
Initiative: 20
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Initiative: 16
(How close are the pirates to 'Naut at the top of the round? He was attempting to intercept all of them so that he'd be close to every one, but I'm not sure if that goal succeeded or not.)
"Ignorance is bliss, and you look absolutely miserable."
(Jack was about 10 feet behind the others because he really didn't want a fight to begin with, while the other three were very gung-ho on murdering Gridolpho.)
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Initiative:
Jack - 20
'Naut - 18
Areleo - 16
Gridolpho - 13
Crewman 1 - 11
Crewman 2 - 7
Merigar - 6
Slim - 3
Will Sayyida and Emrys be joining the fray or are they hanging back for now?
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'Naut wraps their fingers around Jack's throat and drags him towards the other pirates. As they do so,a low humming begins, and the pressure in the air around them increases dramatically. This begins ramping up and up, as 'Naut drags Jack around to face the nearest wall. It finally culminates in a blast of force radiating out from all sides around 'Naut, striking the pirates and Jack, and threatening to blow them back.
(Casting Thunderwave, but shoving Jack up against the wall so that the knock back doesn't break the grapple, instead blasting him into the wall but keeping him within 5 feet of 'Naut. Using 15 ft. of movement to catch as many pirates within the spell's radius as possible.)
"Ignorance is bliss, and you look absolutely miserable."
(Con 14 or 2 thunder.)
"Ignorance is bliss, and you look absolutely miserable."
(Are you kidding me)
"Ignorance is bliss, and you look absolutely miserable."
Areleo will bust into the alley but not with his sword instead you see him grow in size and stature slightly and his hands grow into claws.
"Today bandits will have the honor of combat against Areleo the Warrior." and he will jump into melee with the tiefling.
As a bonus action, he will rage activating his bestial form with claws and making his two claw attacks
The first claw attack is 19 to hit and 7 damage
the second attack is a 19 again with 6 damage
total damage is 13
Trying to not kill him.
For the DM below about the claw attack:
Claws. Each of your hands transforms into a claw, which you can use as a weapon if it’s empty. It deals 1d6 slashing damage on a hit. Once on each of your turns when you attack with a claw using the Attack action, you can make one additional claw attack as part of the same action.
Jack CON: 16
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Jack's immediate reaction to being grappled is to cast gust of wind to try to get the horrifying armored monster off of him.
'Naut, please make a Strength save.
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Oh, almost forgot...
Crewman 1 Con: 4
Crewman 2 Con: 15
The tiefling is out of range.
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Str save: 15
"Ignorance is bliss, and you look absolutely miserable."
As the wind blows, 'Naut holds on, then moves Jack around so that the wind now blows out into the open street, and shifting the wind will end up pushing 'Naut into the wall they're next to instead of far away, keeping them close to Jack.
"Ignorance is bliss, and you look absolutely miserable."
Sayyida stayed standing just within the doorway watching the fight with interest; Arleo was a terror and the...Naut?...terrifying in its own way they would be good assets in a mutiny.....Gridolpho.....seemed to be skilled only at getting into trouble. But it remained to be seen how he went now cornered...
Merigar...she was almost certainly going to have to kill once the job was done...but perhaps...she needed to know more...
As she watched she whispered, " Smooth waters and clean winds shipmates."
Action- Bless on Naut, Arleo and Emrys.
Initiative- 8
The thief draws his rapier ("Pokerface") and a dagger and slashes at the thug on his tail. He then gets out of the way to let everyone else have a chance.
Rapier: 15
Damage: 8
Sneak Attack: 4
Bonus action Disengage and move out of the way.
DCI: 3319125026
The crewman gasps in pain as Gridolpho stabs him... but the rogue is too quick for him to retaliate! So instead, he throws himself at the Triton, swinging rapidly with a mace!
Crewman 1 -
Attack: 9 Damage: 8
Attack: 18 Damage: 4
The second crewman decides to help Jack out and lunges towards 'Naut, swinging at the armored creature with all his strength!
Crewman 2 -
Attack: 7 Damage: 4
Attack: 8 Damage: 3
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I think all the PCs except Emrys have taken their turn, so I'll go ahead and take Merigar and the Tiefling's turns.
Merigar casts acid splash, hurling the glob of acid at the tiefling and Crewman 1, dealing 3 acid damage if they fail a DC 12 Dex save.
Crewman 1 Dex save: 5
Slim Dex save: 6
Whether he's hit or not, the Tiefling decides to cast Armor of Agathys at 2nd level with his action and attempts to run away from the fight with his movement (he provokes an attack of opportunity from Areleo, but if Areleo hits him the Barbarian he will automatically take 10 Cold damage from AoA)
Unless Emrys has something he wants to do, it's the end of round 1.
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So, now that the fight has already been going on for a round, I finally got a map to help you guys visualize what's going on. If any of you want to adjust where your characters are, just let me know where you want me to put them.

(Yes, I'm aware I got some of the distances wrong in my estimates).
(Areleo is still entitled to an Attack of Opportunity against Slim if he so chooses, this is the map for the start of round 2)
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Areleo would let Slim go as he turns to the one who hit him slowly. The first hit but seemed to do very little damage the second missed completely.
Areleo smiles with sharp jagged teeth like a shark, “Little bandit dares to face Areleo? Areleo will give little bandit what little bandit desires.”
I will make my claw attacks on him.
First attack 18 and damage is 9
second attack is 12 and damage is 6