Ironperenti's Skull and Shackles

Game Master Ironperenti

Character Treasure Tracker

S&S on roll20

Disrepute 3 Infamy 3

Crew Perilous Pearl 28 of 20 (Guillaume, Orslaw, Beket) Goblin's Prize 28 of 20 (Bessie, Bleepos, Nasifi)


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DM / GM / The man behind the curtain

The most recent lord of Tidewater Rock was Bertram Smythee, captain of the Vale and three other brigs. Like his predecessors, he held Tidewater Rock as his seat, but controlled a few other small castles on surrounding islands as well. Over a decade ago, “Iron Bert” Smythee went to sea with his small fleet in a feud with Free Captain Carola Antiochus and was never seen again. Word came back that Antiochus had lured Smythee into the edges of the Eye of Abendego and ambushed him with the help of a previously unknown ally—one Barnabas Harrigan—and that Smythee’s fleet was cut to pieces between the enemy f leets. Though Captain Smythee managed to sink Antiochus’s Pergador, he was last seen on the deck of the crippled and sinking Vale at the mercy of the Eye’s
hurricane winds.

Captain Harrigan claimed the remainder of Antiochus’s fleet and took control of several of Smythee’s undefended castles. He made an attempt to take the Tidewater Rock as well, only to discover that Smythee’s able widow had taken charge of its defenses. She managed to fend off his attack with such alacrity that Harrigan decided to leave the widow to rot in her tower.

Although Tidewater Rock remains a secure base and harbor, it does not command the reputation it once did. The current owner of the Rock is Agasta Smythee, widow of the late Iron Bert.

Windward Isle is 2 miles long by 1 mile wide and is almost entirely surrounded by rough shingle and gravel beaches. Its central elevation never rises above 100 feet, so the tower of Tidewater Rock commands a good view of almost the entire island. The harbor of Windward Isle is a quarter-mile-wide channel that runs just south of Tidewater Rock and ends in a lagoon. Tidewater Rock is a fortified tower house over 70 feet tall.


F Human Cleric of Besmara 5 | HP 28/28| AC 13 TO 11 FF 10 | F +4 R +2 W +8 | CMD 15 | Init +1 | Perc +5

Bessie tries not to react upon hearing Harrigans's name again. Apparently they just cannot escape their former Captain, such as he was. Although, that was long ago.

Can we learn if Harrigan still controls the other castles, and exactly what he did to attack the castler that failed?


DM / GM / The man behind the curtain

Information about the attack is not available


CN Male Goblin Rogue (Unchained Pirate/Scout) 5 | HP 43/43 | AC 20 TO 18 FF 13 (CSFD 25/23/13) | F +3 R +10 W +2 | CMD 18 (CSFD 23) | Init +6 | Perc +10 DV | Rogue's Edge: Acrobatics

Since Bleepos assisted Bessie, I'll assume he heard the same things as she did

Hmm... - thinks the goblin, clearly alarmed by hearing Harrigan's name, but pretending everything was fine - Maybe we do different approach! Maybe we don't try to attack rock. Longlegs Female Widow probably hates Harrigan as much as we do.

He circles around Bessie for a moment, thinking way too hard for such a simple concept.

Bleepos say we try to talk to Longlegs Female Widow. Enemy of my enemy and whatnot.


Male Tiefling Bloodrager 4 (Primalist, Steelblood)

Guillaume is quite concerned with the revelation that Harrigan had tried and failed to make the Rock. When Bleepos speaks up, he nods and points to the goblin. "Now that's good thinking, me lad. Let's talk to this widow and see if we can strike a deal with her."


F Human Cleric of Besmara 5 | HP 28/28| AC 13 TO 11 FF 10 | F +4 R +2 W +8 | CMD 15 | Init +1 | Perc +5

That's my helmsman! Good Idea! I agree. Perhaps we can reach an accord with the good widow, safe haven as allies against Harrigan.


M Human Fighter (Corsair) 5 | HP 31/49 | AC 20 TO 13 FF 17 | F +6 R +3 W +2 | CMB +9 (11 Overrun) CMD 21 | Init +2 | Perc +1

"So we just hoist the white flag with the black skull and wait til they agree to parlay and pray to Besmara they don't start shooting?" Orslaw nods "That sounds like a solid plan to me. Though if we are hoping to do this to build our reputation are we looking to have her join us or try and convince her to surrender Tidewater Rock to keep Harrigan out?"


| Speed 30ft | Active conditions: None | HP: 12/12 | AC: 17 (13 Tch, 14 Fl) | CMB: +5, CMD: 17 | F: +4 R: +2 W: +2 | Init: +2 | Perc: +2, SM: +2 | Combat Stamina: 3/3 |

Beket nodded in agreement with the others. While parley was not his particular style, he had to admit that they were still outclassed by their former captain. If he was unable to take Tidewater Rock by force, then they would have to rely on their cunning.

"Let us not wait then. Rally the crews and let us set sail."


DM / GM / The man behind the curtain

The burgeoning fleet sets off for Windward Isle and Tidewater Rock. It is a short trip, taking only a day and a half. The ships come into view of the island near midday. A tower rises like a solid block from the sea at the edge of this island. The pounding surf rolls around its base and partially covers the steps that lead up to its front gate. A few arrow slits pierce its walls here and there, and a single shuttered window opens high upon the face of the fortress. A roof of metal shingles rises from its battlements where sentries keep lookout and siege weapons stand ready on corner turrets. As per the description learned at Goatshead, a long channel leads to a lagoon at the base of the Rock.

How do you approach?


Male Tiefling Bloodrager 4 (Primalist, Steelblood)

Knowledge (Nature): 1d20 + 5 ⇒ (14) + 5 = 19

Can I tell, either visually or from looking at the layout of the area, whether there are likely to be sharks in the area?


DM / GM / The man behind the curtain

@Guillaume: big ones might possibly be in the deep water but doubtful in the channel and the lagoon. the occasional one probably wanders in but it would not be regular. It is likely there are some small sand sharks in the tide pool.


Male Tiefling Bloodrager 4 (Primalist, Steelblood)

After giving the area a good look over, Guillaume turns to a crewman. "Get me a parley flag." Once the man returns, Guillaume takes it and turns to Beket. "Follow me" he says, and then jumps overboard.

I'll swim right up to the steps leading to the gate unless something attacks me (not easy, given that I can take the run action for 120 feet/round, also I have Blindsense 30 in the water, so hopefully I'll knowit's coming.). I doubt the garrison will while I'm underwater. Once I get there, I'll try to arrange safe passage for the ship, or dive back into the water if they attack.


F Human Cleric of Besmara 5 | HP 28/28| AC 13 TO 11 FF 10 | F +4 R +2 W +8 | CMD 15 | Init +1 | Perc +5

Bessie has Bleepos maneuver the Goblin's Prize into the agreed upon position and prepares for whatever the discussions from Guillaume lead to.


| Speed 30ft | Active conditions: None | HP: 12/12 | AC: 17 (13 Tch, 14 Fl) | CMB: +5, CMD: 17 | F: +4 R: +2 W: +2 | Init: +2 | Perc: +2, SM: +2 | Combat Stamina: 3/3 |

Beket would give his captain a nod, his skin shifting into that dark, shark grey as his fingers grew webbing. He would dive in after the captain, following his lead towards Tidewater Rock.


DM / GM / The man behind the curtain

The guard on the battlement peers down and calls, "What do you want?"

Those on the ship see Guillaume come up out of the water and raise his white flag. They can also see additional men manning the ballistae (there are two).


| Speed 30ft | Active conditions: None | HP: 12/12 | AC: 17 (13 Tch, 14 Fl) | CMB: +5, CMD: 17 | F: +4 R: +2 W: +2 | Init: +2 | Perc: +2, SM: +2 | Combat Stamina: 3/3 |

Beket would rise out of the water alongside with Guillaume, his eyes scanning the top of the fortress. Rytys screeched loudly, soaring high above them all and keeping a watch out. His more vicious nature did not like the idea of negotiations but even a shark knew better to attack a well-protected prey.

"I have your back, captain." The large man muttered, staring upwards at the man who addressed them both.


DM / GM / The man behind the curtain

After Guillaume states his intent, the guard says something over his shoulder. After what feels like an hour but is likely little more than a few minutes, a pair of shutters about halfway up the tower open. A woman looks out upon the two standing at the edge of the water.

"I am Lady Smythee, what do you want?"


CN Male Goblin Rogue (Unchained Pirate/Scout) 5 | HP 43/43 | AC 20 TO 18 FF 13 (CSFD 25/23/13) | F +3 R +10 W +2 | CMD 18 (CSFD 23) | Init +6 | Perc +10 DV | Rogue's Edge: Acrobatics

As they wait, Bleepos gets a little distracted chasing a seagull around the ship. The goblin's stomach growls - as per usual, he's hungry.


F Human Cleric of Besmara 5 | HP 28/28| AC 13 TO 11 FF 10 | F +4 R +2 W +8 | CMD 15 | Init +1 | Perc +5

Bessie watches the scene at the tower, the approach of Commodore Coeur-de-Lion and Beket. The appearance of the woman in the balcony window. Bessie smiles as her helmsman goes chasing seagulls, a welcome relief from the negotiations going on on shore. She says a prayer to the Pirate Queen, thanking her for the gifts and her favor upon the Peril Crew, and their additions. And then adds a promise that they shall remain worthy of such blessings. As captain, she then moves among her crew, encouraging them to be ready and making sure that the Goblin's Prize is ready for a fight if needed!


M Human Fighter (Corsair) 5 | HP 31/49 | AC 20 TO 13 FF 17 | F +6 R +3 W +2 | CMB +9 (11 Overrun) CMD 21 | Init +2 | Perc +1

Orslaw does his best not to focus on what is going on at the tower and begins calling out orders to the crew. He aims to keep them busy and near a point where they will be needed if things go south. Lots of additional knot tying and tidying up on the deck. However, he makes sure that it doesn't look like he is standing by the ballista at the ready, he just happens to be calling out most of his orders from there.


Male Tiefling Bloodrager 4 (Primalist, Steelblood)

"I am Commodore Guillaume Coeur-de-Lion. My crew and I are, largely, escapees from the lash of one Barnabas Harrigan. I hear that he is your enemy as well as mine, and I believe that we may be able to help one another." Guillaume says, with a bow.


DM / GM / The man behind the curtain

"How many crew do you have?" Smythee asks. Once she receives an answer she says, "If you wish to talk terms send a good faith hostage this afternoon unarmed. Then you may join us for dinner, you and up to five of your ship's officers."


Male Tiefling Bloodrager 4 (Primalist, Steelblood)

Guillaume turns to Beket. "Given that you are already here, would you mind remaining? It's not as though they can actually disarm you." He says quietly, with a smirk.


DM / GM / The man behind the curtain

The question lays hanging in the air so Guillaume lets it go and they head back to ships. Discussing the situation with the ships' officers, Kroop offers to act as hostage. "If anything should go wrong I'm one of the most easy to replace and the least capable of taking the fight to the tower." the old cook adds to support his case.


| Speed 30ft | Active conditions: None | HP: 12/12 | AC: 17 (13 Tch, 14 Fl) | CMB: +5, CMD: 17 | F: +4 R: +2 W: +2 | Init: +2 | Perc: +2, SM: +2 | Combat Stamina: 3/3 |

"I will let myself be taken, captain. If I need to, I will escape to the roof and plunge myself into the sea." Taking off his club and other weapons, he offers them to the captain and awaits to be taken into the tower.


DM / GM / The man behind the curtain

Beket can go in as hostage or you can take Kroop up on his offer. Also, who will attend the dinner?


F Human Cleric of Besmara 5 | HP 28/28| AC 13 TO 11 FF 10 | F +4 R +2 W +8 | CMD 15 | Init +1 | Perc +5

A noble offer, Mr Kroop, but I don't think you or any of the crew is easily replaceable. Havin' someone that can call down the fury of lightning and the spirit of the sea to bring the fight from within rather than simply be a hostage to rescue may be helpful, but by the same note having such a fierce warrior represent us during negotiations will show that we can be powerful allies. Bessie give Beket a respectful nod.

I believe that Nasifi and I from the Goblins Prize should join you. And I know formal dinners are not his strong suit, but I want my helmsman with me. Bessie nods to Bleepos. Just in case. she adds with her lopsided grin.

Bessie would probably want Beket to be the hostage - but I would rather the party be the ones at the dinner, if Kroop is hostage we all can attend and contribute to the negotiations - tried to give Guillaume an option to select Kroop as hostage and still stay true to Bessie's character.


CN Male Goblin Rogue (Unchained Pirate/Scout) 5 | HP 43/43 | AC 20 TO 18 FF 13 (CSFD 25/23/13) | F +3 R +10 W +2 | CMD 18 (CSFD 23) | Init +6 | Perc +10 DV | Rogue's Edge: Acrobatics

Oh, Bleepos knows everything about dinners, formal or not. - said the goblin, obviously lying to his teeth, and barely hiding the fact he was excited about the prospect of eating.


Male Tiefling Bloodrager 4 (Primalist, Steelblood)

My impression was that the hostage would be included in the dinner party. If that's so, let's go with Beket. If not, we'll send Kroop.


DM / GM / The man behind the curtain

I did not make it clear but the hostage will be held separately, that way they can be executed in case you get out of hand.


| Speed 30ft | Active conditions: None | HP: 12/12 | AC: 17 (13 Tch, 14 Fl) | CMB: +5, CMD: 17 | F: +4 R: +2 W: +2 | Init: +2 | Perc: +2, SM: +2 | Combat Stamina: 3/3 |

Then I'll let Kroop do it, though Beket likes his cooking.


DM / GM / The man behind the curtain

Therefore, that afternoon the men row Kroop ashore and he is "welcomed" into the keep. That evening, the ships' officers are rowed into the lagoon giving access to the Rock. They are cordially greeted and escorted inside.


DM / GM / The man behind the curtain

You are welcomed in by what may be the man at arms. He is dressed in finery over the top of his chainmail. You initially step into a room that takes up the entire floor. The floor is of dirt and it is filled with various items to include a rowboat hanging from the rafters. He then goes through a small opening to the right where a vertical ladder leads up.

"Follow me. We have your shipmate under lock and key and he will be the first to die if you cause trouble. The Lady Smythee welcomes you in to discuss mutual gain, not to be set upon." With that, he leads on and does not speak again.

Climbing to the next floor you see a guard in the adjoining hall before going through a door into a small waiting room. Two more guards stand waiting in there. From there you pass through yet another door into what appears to be a small smithy. A man in filthy clothes and smelling of goats smiles at you. Crossing the smithy, you pass through another door and into a stairwell up. It spirals around and you see a door to the third floor but you don't stop there. Instead, you continue to the fourth floor where the stairwell door opens on a medium sized room with a large table.

The man at arms walks to the head of the table and stands next to who you assume is Lady Smythee. A gentleman dressed in common yet clean clothing gestures toward the two at the front of the table and says, "Her Ladyship Agasta Smythee and her Sergeant at Arms Royster McLeagh. I am Albers. If you need anything during dinner, please let me know."

There is a Soldier flanking Lady Smythee and yet another in the back corner whom you notice when you walk in. Once the ships' officers enter and sit there is very little room.

"So Captain," Lady Smythee says opening conversation, "What brings you and your merry band to our shores."

Map has been updated


Male Tiefling Bloodrager 4 (Primalist, Steelblood)

"Well," Guillaume begins, thinking over what he wants to say, "We are a rather new pirate crew. Many of us were press-ganged by a certain Barnabas Harrigan until recently, but managed to get loose and acquire a ship to boot. We're out to make a name for ourselves and, if we're lucky, get back at the bastard. We hear you're no friends of Harrigan here, and thought that perhaps we could find ways to assist one another." After a momentary pause, he speaks again. "But I should introduce you to my compatriots. This is Beket, Druid on my flagship the Perilous Pearl." He says, motioning to each in turn as he introduces them. "Bessie, who captains our other ship, the Goblin's Prize, and a priestess of the Pirate Queen. Orslaw, the Pearl's Master-at-Arms. The short one is Bleepos, helmsman of the Prize, and finally Nasifi, our expert in ship's weaponry."


| Speed 30ft | Active conditions: None | HP: 12/12 | AC: 17 (13 Tch, 14 Fl) | CMB: +5, CMD: 17 | F: +4 R: +2 W: +2 | Init: +2 | Perc: +2, SM: +2 | Combat Stamina: 3/3 |

Beket follows his captain inside of the veritable fortress, his rags and armor cleaned as best as they could be for 'polite' company but the smell of sea salt still clung to him. There is a low growl at the mention of killing Kroop but no action is taken; Beket has grown accustomed to the cook's renewed passion in food and with it, his fondness of the man. He would have to eat the man who killed such a blessed cook.

Through winding hallways and up a ladder they went, his eyes watching the various people they passed along the way until they entered a decently sized dining hall. With the numbers there, however, it seemed rather cramped. Settling into his seat, he watched the warriors in the room carefully as Guillaume spoke. Scarred hands gently rapped at the table before his name was called.

He gave the older, handsome woman a nod as his captain introduced him. Socializing was not his best aspect and while he had become a better storyteller, he was not quite the one for diplomatic meetings. He knew his purpose for being here though; he was here to fight if things went horribly wrong.


DM / GM / The man behind the curtain

"Good to meet you all. Albers did our introductions. Yes, I am no friend of Barnabas Harrigan but how do you propose to assist me in that?" Smythee asked.


F Human Cleric of Besmara 5 | HP 28/28| AC 13 TO 11 FF 10 | F +4 R +2 W +8 | CMD 15 | Init +1 | Perc +5

With the pause, Bessie jumps in...
Lady Smythee, you have a safe harbor. We have two ships. We all hate Harrigan and know he will be coming for us both. We are stronger together. So the question becomes, what does Tidewater Rock need from us?

Diplomacy: 1d20 + 10 ⇒ (12) + 10 = 22


DM / GM / The man behind the curtain

"Well, I want my forts back, I want Harrigan dead and most of all, I want the ability to take ships again. We are in an excellent position to observe trade moving into and out of the shackles. All we lack is a small fleet with which to attack the choice ones. Without it, my income is very mean." Smythee responds.


CN Male Goblin Rogue (Unchained Pirate/Scout) 5 | HP 43/43 | AC 20 TO 18 FF 13 (CSFD 25/23/13) | F +3 R +10 W +2 | CMD 18 (CSFD 23) | Init +6 | Perc +10 DV | Rogue's Edge: Acrobatics

It feels as if we were all made for each other! - says the goblin, trying to assist Bessie in their diplomatic efforts.

Diplomacy: 1d20 + 3 ⇒ (7) + 3 = 10 To assist

Yet, most of the time the goblin seems to be frantically looking for food, eating without much worry. He smells the food before ingesting it, but mostly to enjoy the smell as well.


F Human Cleric of Besmara 5 | HP 28/28| AC 13 TO 11 FF 10 | F +4 R +2 W +8 | CMD 15 | Init +1 | Perc +5

Bessie smiles, My helmsman is correct. You need a fleet and we need a harbor. I am sure that taking your forts back would be a way to weaken Harrigan. Seems like a perfect opportunity for business partnership. That little goblin pirate is truly a blessing from Besmara.

Bessie looks to Guillaume, With Commodore Coeur-de-Lion's approval; I propose Tidewater supplies a safe harbor; and identifies trade ships to target for the Perilous fleet. We provide naval protection to Tidewater and support the Lady Smythee in retaking her outposts. We claim all ships until and provide shares to Tidewater for each successful looting... Bessie will negotiate on behalf of the Perilous fleet so long as Guillaume allows, but will defer to him for final agreements and decisions.

Bessie would propose a number of terms to the agreement; not sure how specific we need to get but will add proposed points to discussion.


Male Tiefling Bloodrager 4 (Primalist, Steelblood)

After listening to Bessie wheel and deal, Guillaume nods. "Continue, Captain Rogers. The Pirate Queen has gifted you with a silver tongue that I never had. It does indeed sound" he says, with a nod to Bleepos, "like our forces were made to help each other. All praise be to Besmara for bringing us together."


DM / GM / The man behind the curtain

Lady Smythee considers the offer and then says, "I am in a difficult position. To have allies can be a blessing or a curse depending on their reputation and capabilities. Since his one time attacking us here, Harrigan has left us alone as have other pirates. If you do have history with him you well may draw his ire down upon us were we to join forces. At the same time, I have no genuine indication that you would be capable of stopping Harrigan or any other free captain from assaulting what is left of my late husband's legacy. So, I would submit that you prove your capabilities by taking the light house on Derby Hill. It is the nearest of our forts that was lost and likely the most secure. If you do that, then I offer a Shackles marriage contract with your Master of Arms for one year. That will give him the title of Master of the Rock during that time period. Should our endeavors be successful, perhaps we could extend the arrangement after the first year." Then she looks the table over for the ships' officers reactions.

A Shackles marriage is an older custom where two pirates have a contractual marriage for a year. At the end of that year either side may declare a divorce or if they have actually grown close, then they may elect to continue the arrangement.


F Human Cleric of Besmara 5 | HP 28/28| AC 13 TO 11 FF 10 | F +4 R +2 W +8 | CMD 15 | Init +1 | Perc +5

Bessie raises a glass, looks at Orslaw and grins.
I can perform the ceremony!


Male Tiefling Bloodrager 4 (Primalist, Steelblood)

Guillaume turns to Orslaw and raises an eyebrow.


CN Male Goblin Rogue (Unchained Pirate/Scout) 5 | HP 43/43 | AC 20 TO 18 FF 13 (CSFD 25/23/13) | F +3 R +10 W +2 | CMD 18 (CSFD 23) | Init +6 | Perc +10 DV | Rogue's Edge: Acrobatics

Bleepos looks at Smythee, then turns his balloon head towards Orslaw. Slowly, his teeth start showing in an immense and somewhat terrifyingly childish smile.

Hee... Hee... Hee... - he let out unconsciously, almost inaudibly.


F Human Cleric of Besmara 5 | HP 28/28| AC 13 TO 11 FF 10 | F +4 R +2 W +8 | CMD 15 | Init +1 | Perc +5

You know its bad when the goblin is laughing at you.


M Human Fighter (Corsair) 5 | HP 31/49 | AC 20 TO 13 FF 17 | F +6 R +3 W +2 | CMB +9 (11 Overrun) CMD 21 | Init +2 | Perc +1

Orslaw has been mostly quiet and keeping an eye on things from a tactical standpoint. He nods in agreement at Bessie's negotiating points. When Lady Smythee first mentions the arrangement, it doesn't quite register with him as he is examining the equipment of the guards and mentally going through the inventory on the ship for possible upgrades. Then he notices Bleepos smile and feels the eyes of the others on him and the Lady's words sink in.

"Oh... Um..." he begins studdering. "Well Lady Smithee and Captain, I've heard about such arrangements but never really put personal consideration into the thought."

He gives a moment's consideration as he looks for any hint of warning in the captain's eyes. Seeing none, he turns to Lady Smithee, "I would consider it an honor and privilege."


| Speed 30ft | Active conditions: None | HP: 12/12 | AC: 17 (13 Tch, 14 Fl) | CMB: +5, CMD: 17 | F: +4 R: +2 W: +2 | Init: +2 | Perc: +2, SM: +2 | Combat Stamina: 3/3 |

Beket, for his part, had been eating quite eagerly. The food was good and was a decent change from the fare that Kroop made. Not that he would ever disrespect their chef by saying otherwise. When the mention of a Shackles Marriage between Lady Smithee and Orslaw, Beket sat back up and looked between the two of them. His eyes flickered between the mature beauty and Orslaw again and again before he gave a shrug.

"There's worse choices..." Beket mumbles. It was hard to figure out who he was commiserating with.


F Human Cleric of Besmara 5 | HP 28/28| AC 13 TO 11 FF 10 | F +4 R +2 W +8 | CMD 15 | Init +1 | Perc +5

Bessie stands and raises her tankard high, Then eat well Peril Crew, we will sail for Derby Hill to claim the prize in honor of the bride!

At some point later in the meal, she will request a map and details of Derby Hill from the Tidewater group. As it was one of their holdings, they should know the layout and defenses; at least how it was defended when they controlled the site.


DM / GM / The man behind the curtain

Eating proceeds with more small talk and no real details on the fort. After an hour and a small dessert Lady Smythee excuses herself, "I am going to retire now but Master McCleagh will provide you with the details we have of Derby Hill."

The fort in question is a lighthouse a few islands North of the rock. It is a heavily built lighthouse, much like the rock itself. Where the rock sits on a flat rocky island, Derby Hill sits atop a hill in the ocean with a spit of rock connecting it to a larger island.

More to follow, have to go to church. Map on roll20.

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