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He starts to open the chest, but can't do so. He gives a sheepish grin. "Locked," he says. Giving the lock a careful once-over, he sets about unlocking the chest. The lock is separate from the chest and another lock can easily be substituted if necessary or desired.
Upon opening, it is apparent that this is no ordinary chest. In fact, as Dantes can confirm, it holds an extra-dimensional space within! As he unpacks the chest, Dantes stands by with detect magic running, identifying the magical goods. Inside are the following items:
- a ship's figurehead that resembles a mermaid wearing the skull of some odd creature with horns (radiates faint necromancy)
- two wooden tokens with the image of a feather engraved upon them (radiate faint conjuration magic)
- a pair of silk slippers (radiate faint transmutation)
- an ornate crown crafted of platinum with blue-black whorls
- a jeweled box filled with jewelry
- enough goods and plunder to fill your ship's hold (silks, furs, raw gold and silver ore, spices, etc.)
All of these items are as dry as if they had been stored in a temperate room protected from moisture. Further inspection and investigation shows that the extra-dimensional space is about 250 cubic feet in size!
Perception: 1d20 + 11 ⇒ (12) + 11 = 23
Disable Device: 1d20 + 15 ⇒ (16) + 15 = 31

Chumtooth |

"We must know what each thing of magic does. The rest we can sell when we make port," Chumtooth says. "The crew will want payment, and the ship will need repairs. The rest, we can spend ourselves."

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Sorry, was out of it due to illness.
This figurehead must be mounted on the prow of a ship function. Once per day, a ship carrying Besmara’s Bones can inflict a curse on an enemy ship struck with a successful ramming attack. The target ship must succeed at a DC 14 Will save or its pilot takes a –4 penalty on Profession (sailor) checks to control the ship. In addition, the cursed ship can never gain the upper hand in ship-to-ship combat (Skull & Shackles Player’s Guide 9). The curse inflicted by the figurehead cannot be dispelled, but it can be removed with a break enchantment, limited wish, miracle, remove curse, or wish spell. In addition, once per day, Besmara’s Bones can be used to cast false life (CL 5th) on the captain of the ship carrying the figurehead. A ship may not have more than one figurehead, magical or otherwise, mounted on it at one time.
The tokens each form a huge flapping fan, causing a breeze of sufficient strength to propel one ship (about 25 mph). This wind is not cumulative with existing wind speed. The token can, however, be used to lessen existing winds, creating an area of relative calm or lighter winds (but wave size in a storm is not affected). The fan can be used for up to 8 hours. It does not function on land.
When worn, a pair of these slippers enables movement on vertical surfaces or even upside down along ceilings, leaving the wearer’s hands free. Her climb speed is 20 feet. Severely slippery surfaces—icy, oiled, or greased surfaces—make these slippers useless. The slippers can be used for 10 minutes per day, split up as the wearer chooses (minimum 1 minute per use).
Find a port to sell your plunder is easy, though getting there will take a little time. The three closest ports to you are Little Oppara (roughly 30 miles to the north-northwest), Ngozu (roughly 40 miles east), or Goatshead (roughly 50 miles to the east).
Little Oppara is the only settlement on the Taldas Isle in the Shackles. The little town was a small pirate haven but, in 4656 AR, Danziul Maxeme took control of the island and remade the town to mirror the opulence of far-off Taldor. Little Oppara's fine taverns serve delicacies from across Golarion, and richly attired men and women frequent plays and operas at the famed Blooming Rose Theater.
Ngozu is home to a sizeable fleet of pirate vessels crewed by sailors of Mwangi heritage, nearly all of Bonuwat descent. Residents of the town are loyal devotees of the ancient Mwangi faith of juju, a religion committed to congress with the spirit world of wendo. Ajuoga Baas is the chief wendifa and ruler of the settlement.
Ngozu tolerates non-Mwangi ships, but Ngozu's rules are strict for non-natives, and most laws involve "blood price" punishments.
Goatshead is the main settlement on the Firegrass Isle in the Shackles. It was founded In 4642 AR by a trio of pirate captains who settled on the island. The Pirate Council laid the blame for all and any pirate misbehavior against Sargavan vessels on the Firegrass island buccaneers. Made the scapegoats of every Sargavan complaint, these three captains named their settlement Goatshead and adopted a flag with a white goat's head on a black field.

Chumtooth |

After hearing about the nearest ports, Chumtooth says, "I think Little Op-puhra would be the best place to go, but I would hear each of your words on this choice."
He looks to each of his officers to voice their opinions.

Dantes Goldforge |

"I would say Little Oppara is a strong choice. Perhaps the luxurious marketplace would fetch a decent price for our high end goods." The shrug he uses to punctuate the end of his sentence says that he's certainly open to other opinions too.

Janus Ult |

"Well captain, it seems you have your answer. But, for my own council, I am the voice of dissent among a sea of agreement. I would see us sail to Goatshead and make our home their. If we live among the opulent conditions of Oppara our men will find themselves fat and cultured for sure, better by half to take to a port that will not make them soft."

Chumtooth |

”Your words have weight, Janus, and are not unheard,” Chumtooth replies. ”But we will make no home in any port, only sell what we have taken and buy what we need. Goatshead is nearly twice the distance. I do not think a short stay in Little Oppuhra will soften the crew. Perhaps it will make them hungry for more plunder.”

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Carrying on while Dantes looks over the items.
The trip to Little Oppara takes a half-day (15 hours) and you arrive just as the sun starts to set. As the crew is released for shore leave, Kroop approaches Chumtooth and the other officers.
"Beggin' yer pardons, sirs. If ye are ever to be considered free captains, ye'll want ta send word to Port Peril and arrange a meeting there with Kerdak Bonefist, the Hurricane King of the Shackles. I expect that he's had his eye on us and will be looking to meet with ye. But beware, the Hurricane King is not known as Bonefist because o' his handshake! Ye'll also want to send a small incentive with yer messenger (4 points of plunder should be sufficient)."

Chumtooth |

Chumtooth nods in acknowledgement of Mr. Kroop's recommendation.
"Come then," he says to his officers. "We should find buyers for our plun-dah and then send a letter to the man with fists of bone."
Intimidate, Negotiating prices: 1d20 + 14 ⇒ (8) + 14 = 22

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You can sell your plunder (other than the bribe being used for the Hurricane King), pay your crew, and take on whatever supplies are needed or desired. This is a good time for shopping, as well. Once everyone is ready, I'll move you ahead to Port Peril.

Faengrim |

Faengrim can help with negotiations. He'll stand behind Captain Chumtooth with a sharky grin.
Aid to Intimidate +10 (auto-success)

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Okay, with a little intimidation, you get slightly more for your booty than normal. The group earns an extra 10% for a grand total of 31,782 gp (not including the crown). After paying your crew, you still have 30,782 gp to divide amongst the officers, which works out to 6,156 gp and 4 sp each. I'll kick off Book 3 tomorrow.

Chumtooth |

Chumtooth sees to a few more details before the party leaves port: He instructs the crew to mount to magical figurehead to the ship, he gets the crown and jewels appraised to determine if they are of sufficient worth to bribe the Hurricane King, he seeks out a magical craftsman who can merge the powers of the two harpoons, and finally, he cedes the remainder of his share to Dantes, so that he may purchase items that will aid him in battle.
He turns to the rest of the crew and says, "Ready yourselves. We will be leaving for Port Peril soon."

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You folks can retcon getting any supplies that are needed.
It takes several days for you to arrive in Port Peril, where you are met at the docks by a strapping half-orc who introduces himself as Tsadok Goldtooth. He smiles broadly, displaying the reason for his name. A sizeable crowd has gathered to witness the proceedings.
"I am here as a formal representative of Kerdak Bonefist, the pirate king of the Shackles! You want your letter of marque, you have to first impress me! It is most unusual," he turns to address the crowd,"though not unheard of, for a successful, but relatively unknown ship to request a letter of marque without the sponsorship of a recognized free captain." He turns back to you. "So, since you have no sponsorship, there will be a couple of tests to determine your mettle and worth of being free captains yourselves."
"Your first test is simple enough. One of you will climb the foremast and unfurl and set the sail from the top yard without assistance..." He pauses for dramatic effect. "[u]Before[/u] my man can do the same on the mizzenmast. No flight magic is allowed, and you can't conjure creatures to do it for you. You must unfurl the sail yourself."
"I'm sure I don't need to explain to you "experienced" sailors the means by which this is done, so choose one of your crew who will perform the task. When I give the signal, start your climb."
Climbing the mast requires a DC 10 Climb check for the lower 45 feet and a DC 15 Climb check for the upper 15 feet. Contestants must then make their way along the yard, which extends 30 feet out from both sides of the mast, untying sail as they go. Contestants can use accelerated climbing (–5 penalty on the check) to increase their climbing speed from one-quarter speed to half speed. Moving along the yard requires a DC 10 Climb check, or a contestant can walk along the yard at half speed with a DC 15 Acrobatics check (or move at full speed with a DC 25 Acrobatics check). Climbing or balancing requires one skill check per move action.
The sail is tied to the yard at four locations, 15 feet from the mast and 30 feet from the mast on both sides. Correctly unfurling each of the four areas of sail without it snagging or tangling requires a DC 15 Profession (sailor) check and takes a standard action. A contestant who succeeds at a DC 18 Profession (sailor) check realizes that untying all of the sail on one side of the yard will cause loose sailcloth to flap about in the breeze, making the job of setting the remaining sail more challenging. To avoid this problem, the sail should be released in stages on one side of the mast and then the other. If one side of the sail is completely unfurled first, the DC of the Profession (sailor) checks to unfurl the remaining sail increases by 5.
DUe to the stress involved, you cannot take 10 on actions.

Chumtooth |

"I accept your Challenge," Chumtooth replies, holding is chin at a proud angle. "I am Chumtooth, Cap-i-tan of the Keesss of Ven-jensss!"
He readies himself to move at the signal, bending his legs slightly and standing on the balls of his feet, as if ready to spring.

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Magic use was addressed within the rules. Since he didn't specifically call out buffing, you can assume that it is not cheating, though it would be considered unsporting. If you want to cast the spells surreptitiously, make a Stealth check.
Tsadok blows a whistle and the contest is started! The process is described above. The other pirate begins his climb, moving quickly. It takes him three rounds to get 45 feet above the deck. He slows down as he climbs the last 15 feet, taking a total of five rounds to clear the mast.
Haines accelerated Climbing: 1d20 + 12 ⇒ (6) + 12 = 18 15 feet
Haines accelerated Climbing: 1d20 + 13 ⇒ (19) + 13 = 32 30 feet
Haines accelerated Climbing: 1d20 + 13 ⇒ (17) + 13 = 30 45 feet
Haines Climbing: 1d20 + 13 ⇒ (17) + 13 = 30 52.5 feet
Haines Climbing: 1d20 + 13 ⇒ (2) + 13 = 15 60 feet

Chumtooth |

Chumtooth sprints for the mast, and begins climbing quickly.
Accelerated Climb, DC 15: 1d20 + 14 ⇒ (17) + 14 = 31 15'
Accelerated Climb, DC 15: 1d20 + 14 ⇒ (10) + 14 = 24 30'
Accelerated Climb, DC 15: 1d20 + 14 ⇒ (1) + 14 = 15 45'
Accelerated Climb, DC 15: 1d20 + 14 ⇒ (5) + 14 = 19 60'
Chumtooth hurtles up the mast without slowing down.
Profession Sailor: 1d20 + 11 ⇒ (15) + 11 = 26
Realizing he needs to loose the sails in stages, rather than one side at a time, Chumtooth makes his way out to the far side of one mast.
Acrobatics, DC 15, half-speed: 1d20 + 14 ⇒ (15) + 14 = 29
Acrobatics, DC 15, half-speed: 1d20 + 14 ⇒ (9) + 14 = 23
He then begins to unfurl the outermost portion of the sail.
Profession, sailor: 1d20 + 11 ⇒ (16) + 11 = 27
Having done so, he makes his way back across to the far side of the other mast.
Acrobatics, DC 15, half-speed: 1d20 + 14 ⇒ (15) + 14 = 29
Acrobatics, DC 15, half-speed: 1d20 + 14 ⇒ (17) + 14 = 31
Acrobatics, DC 15, half-speed: 1d20 + 14 ⇒ (7) + 14 = 21
Acrobatics, DC 15, half-speed: 1d20 + 14 ⇒ (1) + 14 = 15
He then begins to unfurl the outermost portion of the sail on this side.
Profession, sailor, DC 15: 1d20 + 11 ⇒ (18) + 11 = 29
He then makes his way back towards the center, and begins unfurling the remainder of this sail nearest the mast.
Acrobatics, DC 15, half-speed: 1d20 + 14 ⇒ (7) + 14 = 21
Profession, sailor, DC 15: 1d20 + 11 ⇒ (14) + 11 = 25
He then moves over to the last portion of sail, and works to unfurl it.
Acrobatics, DC 15, half-speed: 1d20 + 14 ⇒ (9) + 14 = 23
Acrobatics, DC 15, half-speed: 1d20 + 14 ⇒ (1) + 14 = 15
Profession, sailor, DC 15: 1d20 + 11 ⇒ (14) + 11 = 25

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As Chummtooth begins to undo the sail from the far side of the mast, a boom comes loose and suddenly swings into his mast! Chumtooth, you need to succeed at a DC 20 Acrobatics check to keep your balance. Failure means that you slip and must succeed at a DC 20 Reflex save to catch the rigging or fall. The fall is into the harbor’s water, not onto the Stingray’s deck. If you do not fall, the DC of all remaining Profession (sailor) checks to set the sail increases by +2 because of the tangle of sail and lines now pressed against the foresail.
Because Haines plays it safe, you will easily best his time unless you fall, so go ahead and make your Acrobatics check (and Reflex save if necessary). In any case, so long as you don't fall, your Profession (Sailor) checks will easily meet the qualifications, even with the DC increase.
Dantes Perception: 1d20 + 0 ⇒ (9) + 0 = 9
Janus Perception: 1d20 + 11 ⇒ (1) + 11 = 12
Alexander Perception: 1d20 + 11 ⇒ (7) + 11 = 18
Faengrim Sense Motive: 1d20 + 1 ⇒ (16) + 1 = 17
Faengrim Perception: 1d20 + 13 - 5 ⇒ (18) + 13 - 5 = 26
Dantes Perception: 1d20 + 0 - 5 ⇒ (1) + 0 - 5 = -4
Janus Perception: 1d20 + 11 - 5 ⇒ (15) + 11 - 5 = 21
Alexander Perception: 1d20 + 11 - 5 ⇒ (1) + 11 - 5 = 7
Faengrim Sense Motive: 1d20 + 1 ⇒ (3) + 1 = 4

Faengrim |

Faengrim goes over to the cheating sailor. "If my captain gets hurt, I'll gut you and serve him your heart."
Intimidate: 1d20 + 10 ⇒ (8) + 10 = 18

Alexander Valdell Caladir |

Alexander takes out an ornate flute and looks to the spectators.
How about a little music then? Before starts whistling out a shanty melody.
Alexander will try to subtlely use his still water ability.
Still Water (Su): At 3rd level, a sea singer can use performance to calm rough waters within 30 feet, reducing the DC for Profession (sailor) and Swim checks, as well as for Acrobatics and Climb checks aboard ship, by an amount equal to the bard’s level (to a minimum of DC 10) for as long he continues to perform. He can extend this duration to 1 hour by playing for 10 consecutive rounds. This ability requires audible components.
This performance replaces inspire competence.
I will let Chumtooth choose the mount to lower the DC, I have lingering performance, so I will lose 1 performance every 3 "rounds", if it goes over 8, I would just use the 10 consecutive rounds to make the effect last an hour. Any checks you want from me to make it seem like just normal music?

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No checks necessary, Alexander. The pirates have no reason to assume that it is anything other than a man whistling.
The bald sailor merely shrugs. "Don't appear like 'e's been 'urt," he grins.
Alright, next is a little game of cards," Tsadok says, taking out a worn deck of cards and handing them to a nearby pirate. "One of you, I don't care which, is going to play me in a game of Bastard's Fool."
Bastard’s Fool is a popular game on pirate ships, and is played using a deck cobbled together from several partial decks. Even a down-on-his-luck sailor who doesn’t even have a full deck of cards can play Bastard’s Fool, as each player brings whatever cards she has, and combines them with other players’ cards to create a new deck. Bastard’s Fool is a bluffing game similar to poker.
"An' just ta' make it a little more interesting, we'll play by Port Peril rules. The winner of each hand must drink a ration cup of Gutburn rum."
Each player starts with a stake of 100 platinum pieces. You must supply your own stake; Tsadok has brought along a moneychanger to exchange currency or plunder if needed. Each hand, gamblers receive a starting hand and place their initial bets. They may then discard some of their cards and draw more to improve their hand and bet again. Once all bets are matched, the gamblers reveal their cards and the best hand wins.
To simulate an actual game of Bastard’s Fool, each player rolls dice, trying to get a score as close to 20 as possible without going over. At the beginning of the hand, each player pays an ante of 1 pp and secretly rolls a d20, representing her starting hand. A round of betting ensues (minimum bet is 1 pp; maximum bet is a player’s entire stake, called “all in”). To represent the discard and draw, each player may then secretly roll another die of her choice (d4, d6, d8, d10, d12, or d20) to improve her score (the larger the die, the more cards drawn). This is followed by another round of betting. A player can fold at any time instead of betting—in this case, the opposing player wins the hand. If the total of both dice is 20 or less, that is the gambler’s score. If the total is over 20, the gambler’s score is only the highest number on a single die (representing a poor draw). The highest score wins the hand. On a tie, no one wins. The pot remains on the table, and a new hand begins, with bets added to the existing pot.
Participants may improve their position using expertise, insight, misdirection, or even legerdemain. A gambler can make one of the following checks each hand (all DC 15): Bluff, Profession (gambler), or Sense Motive. A successful check adds +1 to the gambler’s score, with an additional +1 for every 5 points over the DC (even if this pushes the gambler’s final score over 20). A failed check reduces the gambler’s score by 1, with an additional –1 for every 5 points under the DC.
The gambling PC can also make a DC 20 Sleight of Hand check to cheat and increase her score by 4 points.
Each time a hand is played, the winner must drink a shot of rum. Each drink after the first requires a DC 10 Fortitude save (the DC increases by +1 for each additional drink). The drinker takes a –1 penalty on all skill checks for each failed saving throw. Once the character has consumed a number of drinks equal to 1 plus double her Constitution modifier, she is sickened (taking an additional –2 penalty on skill checks) for 1 hour for each drink beyond this maximum.
The poop deck is empty except for the dealer, Tsadok, and the participating PC. The dealer announces the revealed cards and wagers to the crowd who cheer and shout advice. Tsadok sits with his back to the harbor.
The way we play it is, we each make a d20 roll publically. Then bets are placed and the player rolls his or her chosen die behind a spoiler. I will roll behind the GM screen, which you will not see (that way you have no idea if Tsadok is cheating unless you notice it in-game with a Perception check (if, in fact, he is)). Bets are made again and then (and only then) I will read your spoiler and let you know what happens.
"Choose your champion," Tsadok sneers.

Alexander Valdell Caladir |

apologies, had medical things I had to take care of past weekend. Also, I think I understand how this works.
well, if that is the case, then how could one resist
He gives a slight bow, the purple feathered parrot looks over the other man with one black eye.
He sits down giving a smile to the other player as he places his bet before drawing his hand.
bluff: 1d20 + 14 ⇒ (11) + 14 = 25
19 total score.
well, lets start a little slow then? he murmers before tossing another 4 PPs into the pot.
this could take a while, do you want to up the min bet to 5pps? Or did you have an idea for how to do this without turning it into a potential 30 post game hahs.

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Yes, let's go ahead and up the bet to 5 pps. The book suggests that we run a few hands to let you get a feel for it and then I ask your basic strategy and use that to describe an accelerated sequence of play.
Tsadok also draws his hand, before tossing 4 extra platinum into the pot.
Initial Draw: 1d20 ⇒ 6
Tsadok growls at his sour luck, but puts another 5 pp into the kitty.
He takes three cards, grins broadly and bets another 5 pp.

Alexander Valdell Caladir |

if I understand correctly, once I match his bet, that round is over yes? I'll go ahead and do my next hand this post.
hmmmmm. What do you think voilet? Alexander muses to his parrot, the parrot merely lets out a small whistle in response.
He taps his fingers as he thinks before tossing another 15 pp into the pile, for a total bet of 20.
I truly don't want to drink a lot of that seawater, its just not suited for my palate.
However the first hand goes, Alexander keeps a smirk on his face.
hand2: 1d20 ⇒ 11 Alexanders smirk twitches slightly, before he toss 5 pp into the pot.
draw: 1d8 ⇒ 7
bluff: 1d20 + 14 ⇒ (10) + 14 = 24
Total of 20.
perception: 1d20 + 12 ⇒ (5) + 12 = 17 keeping an eye out.
fort: 1d20 + 6 ⇒ (4) + 6 = 10 in case I won first round

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Tsadok reveals his cards (you may read the spoiler above; he got a total of 8) and Alexander shows his cards. The pirate eyes Alexander darkly as the swashbuckler scoops up his winnings. It seems that he is playing a fair game.
"Take a shot," he intones flatly. Tsadok meets the ante, and new hands are dealt.
Initial Draw: 1d20 ⇒ 2
"Blast!" he shouts, throwing down his cards. "Take it! (He got a total of 22.)
"You owe another drink."

Alexander Valdell Caladir |

fort: 1d20 + 6 ⇒ (16) + 6 = 22
cheers Alexander says before turning the drink up. He grimaces at the drink, but manages to keep himself collected.
He draws again after tossing the obligatory 5pp into the pot.
hand: 1d20 ⇒ 19
perception: 1d20 + 12 ⇒ (11) + 12 = 23 keeping an eye out.
No other rolls.

Chumtooth |

Concerned that some other act of sabotage might occur, Chumtooth watches the area around the game, rather than the game itself. He watches for anything that could be a potential danger to Alexander or the other members of his crew.
Perception: 1d20 + 10 ⇒ (7) + 10 = 17

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Draw: 1d20 ⇒ 13
Tsadok bets 5 pp and then draws a single card (he gets a total of 18). Alexander notices that the dealer is subtly (and ineffectively, apparently) stacking the deck in favor of Tsadok.

Alexander Valdell Caladir |

apologies, I didn't realize I was up.
fort: 1d20 + 6 ⇒ (12) + 6 = 18
Alexander will wait until he can make eye contact with the dealer before giving him a quick wink before Throwing the min bet and drawing.
1d20 ⇒ 7
1d12 ⇒ 12
19 total.
After the draws, he will tentatively look to the man across from him before giving a very small smile, and betting another 10pp.
if you wanted to finish the rest in a single post, Alex will never roll for additional cards, only roll to improve his hand if he is 18 or less, and only "cheat" if cheating can get him a 18-20. Alex also doesn't want to drink a lot of the grog, so would try and finish it up quickly.

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Tsadok draws and looks at his hand, then back to the dealer with a scowl. He meets the bet and takes four cards. He again meets the wager and reveals his hand with a grin that quickly turns to a scowl as Alexander shows his cards.
Draw: 1d20 ⇒ 5
"You're bad luck," he points accusingly at the dealer and snatches the cards from his hands. The next several hands proceed in a similar fashion, with Alexander handily beating Tsadok each time (honestly!). The game proceeds for a good hour as Tsadok's pile of coins dwindles and Alexander's grows. Finally, the pirate goes all in.
Alexander's Draw: 1d20 ⇒ 13
Tsadok's Draw: 1d20 ⇒ 7
The cards are dealt and each player draws, Alexander again besting Tsadok. As Alexander collects the remainder of his winnings, Tsadok throws his hands up in surrender.
Alexander Cards: 1d8 ⇒ 6
Tsadok Cards: 1d20 ⇒ 1
He snarls, "Okay, you've proven yourselves agile and clever, but this next test is for all of you to participate in. All you have to do is to keep my boarder from defeating you and standing aboard your vessel." He smiles a predatory grin. "Let me know when you are ready."
I've placed everyone on the ship, but I'll let you reposition yourselves as desired. When you are ready, let me know.

Dantes Goldforge |

(Looks fine to me. Ready to go!)
Chumtooth, would you be okay if I changed positions of Chumtooth and Dantes? I'd prefer to stand behind Chum or Faengrim to buff and support them. If not, I'll get my axe out and do my best to hold the position.

Chumtooth |

Chumtooth wrote:(Looks fine to me. Ready to go!)Chumtooth, would you be okay if I changed positions of Chumtooth and Dantes? I'd prefer to stand behind Chum or Faengrim to buff and support them. If not, I'll get my axe out and do my best to hold the position.
That makes sense. Go ahead and switch us.

Janus Ult |

If you would be so kind as to move me to the focsle deck, I would like a good range and eye on things. Also, I would hand Chum and Faen a cure serious and Alex and Dante a cure moderate for them to use if needed. Extracts are useful. Also Also, can I drink a truestrike extract as Chum signals ready? That way I can start the round with truestrike.

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I've moved you, but you should have permission to move yourselves. Yes, you may drink as the signal is given.

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Tsadok whistles and a giant cage is rolled out onto the dock. Within is a true monstrosity (this). It stands about 11 feet tall, with cold, black eyes that stare out from its fish-like face. It is a hideous green-skinned, web-fingered, and obese giant.
"Fishpork! Dispose of these folk, if you would please." Tsadok says, opening the cage and retreating to the mainland. The giant seems to only dimly understand the command but hefts a giant boulder from within the cage.
INITIATIVE
Faengrim
Alexander
Fishpork
Chumtooth
Dantes
Janus
Faengrim and Alexander are up!
Dantes Initiative: 1d20 + 1 ⇒ (4) + 1 = 5
Janus Initiative: 1d20 + 0 ⇒ (2) + 0 = 2
Alexander Initiative: 1d20 + 4 ⇒ (7) + 4 = 11
Faengrim Initiative: 1d20 + 2 ⇒ (18) + 2 = 20
Fishpork Init: 1d20 + 3 ⇒ (4) + 3 = 7

Alexander Valdell Caladir |

Alexander rummages around in a pack as he steps up to get a clear line of sight to the giant. Finally, pulling out a red ball, tosses it a couple of times in the air and then throws it at fishpork, upon contact it erupts into showering blast of glitter.
Casting Glitter dust DC 17 will save, or be blinded.

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A dumbfounded look overcomes the giant's face and it rubs its eyes, trying to clear them. Finding that it cannot do so, it roars in anger, chucking the boulder that it was clutching at the last place it saw targets (aiming for Alexander). The rock hurtles through the air, but Alexander sidesteps it at the last minute and it smashes into the deck, through the port railing, and sinks to the bottom.
The party is up! Chumtooth, Dantes, and Janus, then Faengrim and Alexander again.
Rock vs. Alexander: 1d20 + 12 - 2 ⇒ (17) + 12 - 2 = 27
Miss chance (high good): 1d100 ⇒ 48