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Dammit... I have buyers remorse. Lol. That 20 would have gotten me a horse. Oh well. Options for the future
Wait, so, a horse doesn't actually makes us faster? It just changes the roll to Animal Handling? I think I'm having buyers remorse getting one....
Handle Animal!: 1d20 + 1 ⇒ (6) + 1 = 7
"Wait, what am I doing? I don't know how to ride this." Gorn gets off his horse and offers it to Grim.
Obstacle?: 1d20 ⇒ 11

Evendur "Grim" Greymantle |

The priest, trying to get distance just sprints, yelling, right past the proffered reins...
Seems appropriately silly and cinematic

Evendur "Grim" Greymantle |

Can't everyone just ride a horse? Or is it more animal handling due to crowded streets etc? In any case my handle animal would be -1, lol

GM Infinity |

The animal handling check is to make the horse attempt a Dash. Everyone can ride a horse, barring an obstacle of some sort you automatically advance one. The idea is that its a crowded metropolitan chase with a non-linear path, stuff/people jumping out all over etc. Bolting through such an environment with rapid course corrections takes some skill with animal control, forcing it to run someone over for example might go against its training.
But yeah, didn't want horse to have a clear advantage. Wanted to give you guys a chance instead of just saying 'you run, uh ok, horses move 80ft, boom, you all get arrested.' Just a bit of abstraction if you can swallow it.

GM Infinity |

Donal turns back to keep Amrik on track, just as Mal falls through the ceiling onto some praying orphans. Tiberius however, with the slithery speed of a dragon, quickly shimmies down a drainpipe and disappears. Tiberius reached rank 5 first with 2 consecutive successful dashes, and has eluded the guard. The Watch has already sent reinforcements and are coordinating with whistles openly on the streets, but do not know your current position.
B3
Dash: 1d20 + 5 ⇒ (15) + 5 = 20
Obstacle: 1d20 ⇒ 5
Pole!: 1d20 + 5 ⇒ (12) + 5 = 17
The guard hot on Tiberius' tail is served a flagpole to the nuts, but his codpiece saves the day. Unfortunately, the dragonkin is simply too quick and he can't find him after the distraction.
B1
Taunt: 1d20 ⇒ 10
Obstacle: 1d20 ⇒ 12
The guard closest to Mal steps forward over the broken roof, for a moment having trouble spotting the halfling among the children, saying "Give it up! The entirety of the Citadel will soon be upon you! It will take more than nimble steps on loose shingles to save you now..." Taunting Mal. Mal needs to make a wisdom Insight check DC 10 or have disadvantage on rolls for 1 round (not including obstacle roll).
Amrik
Dash: 1d20 + 4 ⇒ (12) + 4 = 16
Obstacle: 1d20 ⇒ 16
Amrik had kept sight of the noble and sought to arrange a similar escape for himself, using Donal's hesitation to get a few moments ahead.
B2
Dash: 1d20 ⇒ 20
Obstacle: 1d20 ⇒ 7
Oh hi!: 1d20 + 1 ⇒ (15) + 1 = 16
The other guard dashed forward to follow him, knowing his ass would be served well done if he lost the Duke's son. An arm of the great raven flock broke off suddenly in a dive bomb, but the nimble warrior somersaulted forward after his quarry.
End of Round 2 Group A Positions:
5
4 Girl(m), A1, Grim(m)
3 Kenku, A2, Gorn
2
1
End of Round 2 Group B Positions:
5 [Tibs, escaped]
4
3 B3, Amrik, B2
2 B1
1 Mal, Donal
Reminder, every turn roll for action, then roll raw d20 for obstacle and consult list.
Dash: Player choice Athletics or Acrobatics check (DC 13) that moves you two positions ahead. Can be used only twice per character, not counting failed attempts.
Jab: Attack roll vs Mounted AC. On a hit, no damage, but Dex save or fall from the mount. Jab can only be used on chasers who share the same position number. The mount is free to take after.
Taunt: Intimidation vs Insight contested. Loser gets disadvantage on actions. Can be used on any adjacent (position wise) rider.
Trip: Player choice Athletics or Acrobatics check (contested). Fail means chaser on foot stumbles and loses position.
Movement check = choice of Athletics or Acrobatics. Animal Handling if mounted.
1 Blockade. A short wall of wood and debris blocks your path. Make a DC 12 movement check. If failed, you stumble and lose a position rank.
2 Banana Peel. You actually slip on a banana peel, if you don't make a DC 13 dexterity save. No position gain.
3 Mud Slick. Make a successful DC 13 movement check. If failed, you lose a position rank and may not Dash on your following turn.
4 Puzzling Pedestrians. A massive crowd appears and you must quickly navigate, DC 13 int investigation check or gain no position.
5 Pole! You must make a DC 13 athletics or acrobatics check. If failed, you are dragged off of your mount, losing a position rank. If unmounted, you stumble from a slam to the face and do not gain position.
6 Vigilante. A random citizen with a stink in his eye works against you, make a charisma persuasion or deception check DC 13 to escape his ire.
7 Oh hi! A sudden person/obstacle swings down in front of you. Make a DC 14 Dexterity saving throw. If failed, you are dismounted and lose a position rank. If unmounted, you also lose a position rank.
8 Glass pain. Some idiots are hauling a huge, exposed pane of glass across town for some reason. DC 13 strength save to break through clean, or lose position picking out the pieces.
9 Praying Orphans. Make a DC 13 Wisdom saving throw to navigate the praying orphans. If failed, you and your mount fall, costing you two position ranks.
10 Didn't eat my Wheaties. You or your mount is suddenly tired of the chase. DC 14 Con saving throw to power through, or lose position.
11-20 No Obstacle. Nothing Happens.
Group A Inits, Round 3:
Kenku, A1, A2, Girl <--UP
Gorn, Grim
Group B Inits, Round 3:
Mal, Tibs, Donal <--UP
B3, B1
Amrik
B2

GM Infinity |

Kenku
Dash: 1d20 + 4 ⇒ (9) + 4 = 13
Obstacle: 1d20 ⇒ 11
The shadow assassin has one final trick up his sleeve, as his body contorts almost into the form of a pure liquid, gushing through the tiny hole in a sewer drain. Kenku assassin has escaped.
A1
Trip: 1d20 + 5 ⇒ (17) + 5 = 22
Obstacle: 1d20 ⇒ 4
Puzzling Pedestrians: 1d20 ⇒ 19
The guard hot on the girl's steps lunges forward "Gods damnit, out of the way! Citadel business!" scattering a large crowd and yanking the woman's reigns...
Girl vs DC 22: 1d20 + 5 ⇒ (1) + 5 = 6
...the horse kneels suddenly and the girl flips forward, getting a face full of hard cobblestones. A1 forward 1, girl back 1. A1 is now blocking your escape.
A2
Dash: 1d20 + 5 ⇒ (13) + 5 = 18
Obstacle: 1d20 ⇒ 13
His partner quickly rushes to his side, to reinforce the barrier. "Now halt! All of you. Its over. Surrender your arms." A2 also reaches 5, blocking your escape.
Group A Chase over. Surrender or fight.
Group B still going, Mal and Donal up.

Donal the Seeker |
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Donal shoves the guard off of him and scrambles to his feet, dashing forward to catch up to Amrik! Athletics: 1d20 + 4 ⇒ (12) + 4 = 16
Obstacle: 1d20 ⇒ 10
Con save: 1d20 + 4 ⇒ (20) + 4 = 24 I ate me wheaties today!

Evendur "Grim" Greymantle |

Group A Chase over. Surrender or fight.
*Laughs in Gorn* They have us surrounded! They can't get away now!

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Gorn chuckles, casually twirling Shellcracker in his hand. "Heh. It looks like they have us...
...right where we want them.
You sure you wanna do this here, guys? Yer a loooong way from base, and ain't no one getting here real soon. Ain't you worried about me?"
Intimidation!: 1d20 + 5 ⇒ (1) + 5 = 6
Unfortunately, during the chase Gorn got a pair of bright lacy pink panties caught on his head, and the gay splash of color on his crown makes the whole effect more laughable than anything else.

Evendur "Grim" Greymantle |

Oh damn boys... trust me, if he gets swinging? You're all gonna die... Gorn! Focus!
Advantage for Gorns intimidation?

Evendur "Grim" Greymantle |

Thought he was trying to get them to break or run... but hey, even advantage on the first round wouldn't hurt :)

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Gorn turns to Grim, and the motion makes him aware of the lacy undergarments clinging to his crown. He grabs them and throws them in disgust at a small black bird scrapping at ground. The force of the thrown lingerie kills it instantly.
"Two on two, chummers. That the kind of odds you thought you'd have when this started? Why don't you run along and we'll forget this all happened."
Intimidation Advantage!: 1d20 + 5 ⇒ (10) + 5 = 15

"Mal" Malaric |

on a biz trip.
insight: 1d20 + 1 ⇒ (14) + 1 = 15
Dash: 1d20 + 3 ⇒ (19) + 3 = 22
Obstacle: 1d20 ⇒ 1
Acro: 1d20 + 3 ⇒ (3) + 3 = 6

GM Infinity |

The two men standing in the way of Gorn and Grim's freedom at first seem honor bound to their duty...these disciplined warriors wouldn't easily be swayed like some power-for-hire Fist. But when the pink chemise instantly decapitated a rusty grackle, which proceeded to erupt from its naked nape a bright red fountain...well, s#+# like that makes a man think twice.
"Let's rip out of this scene, Cosmo. It's Amrik we're after."
The other one seemed eager to fight, already gripping a longsword in one hand and a triangle pointed gladius in the other, but ultimately lost the staring contest and broke with his mate to follow after the nearest whistle.

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"Well that was easier than I expected," Gorn rumbles at Grim.
"Let's make like a tree, and get outa here."
He pauses to look at the bird he killed.
Rusty Grackle: Inedible, comes across his internal HUD, and he turns away to follow the WarCleric away from the scene.

Evendur "Grim" Greymantle |

"Well that was easier than I expected," Gorn rumbles at Grim.
"Let's make like a tree, and get outa here."
He pauses to look at the bird he killed.
Can't believe I'm gonna say this..., he says then sighs.
Lets try and guess where they are heading, aided by the whistles, see if we can't get ahead of them and create chaos for their pursuers? A bit of gold to a pack of beggars or a panicked horse cart might help
A whole new chase for you DM with different skill checks ;)

GM Infinity |

B3
Trip: 1d20 + 5 ⇒ (12) + 5 = 17
Obstacle: 1d20 ⇒ 7
Oh hi!: 1d20 + 1 ⇒ (8) + 1 = 9
Too winded to dash, one of the guards rips up a ceramic tile, tossing it like a frisbee at the back of Donal's knee...DC 17 athletics or acrobatics check or lose position.
Just after releasing his sun baked projectile, a flying snake thwaps him in the face from out of nowhere and he rolls backwards as the tail penetrates his left nostril.
B1
Trip: 1d20 + 5 ⇒ (13) + 5 = 18
Obstacle: 1d20 ⇒ 5
Pole!: 1d20 + 5 ⇒ (3) + 5 = 8
The one taunting Mal watches the slippery halfling shrug it off, and pursues with a renewed anger. He leaps forward and grips the short legs with both arms.DC 18 athletics or acrobatics Mal or lose position
The grip is short lived however, as a chimney flute to the face halts the honorable man's advance.
Amrik
Trip: 1d20 + 4 ⇒ (14) + 4 = 18
Obstacle: 1d20 ⇒ 16
Amrik, at least by appearances, seems just as eager to escape the Watch, footsweeping one from behind... Opposed: 1d20 + 5 ⇒ (18) + 5 = 23 ...but the only effect is a brief knee taken as the athlete keeps his balance.
B2
Dash: 1d20 + 5 ⇒ (3) + 5 = 8
Obstacle: 1d20 ⇒ 11
The athlete tries to push ahead in a final burst, but an unfortunate arrow wound from years ago combines with the weather to cause a jolting cramp, and instead he limps ahead uncertain.
Current Group B Positions:
5 [Tibs, escaped]
4 Amrik, B2
3 B3, Donal
2 B1, Mal
1
Mal and Donal up.

Evendur "Grim" Greymantle |

Ones chasing the in the alleys etc in general seem more of a threat to our fleeing friends, and while taking the high ground and their eyes away from them is likely best, leaping roof top to roof top in platemail or balancing on rooftops without acrobatics is not gonna end well. So ground patrols it is.

"Mal" Malaric |

Missed that Mal was up. Sorry
DC 18 athletics or acrobatics Mal or lose position: 1d20 + 3 ⇒ (2) + 3 = 5
Mal's short legs have struggled keeping up with Amrik, but he finally finds a window of small spaces to catch up.
Dash: 1d20 + 3 ⇒ (18) + 3 = 21
Obstacle: 1d20 ⇒ 20

GM Infinity |

Donal
Dash: 1d20 + 4 ⇒ (20) + 4 = 24
Obstacle: 1d20 ⇒ 7
Dex vs Oh hi!: 1d20 + 2 ⇒ (2) + 2 = 4
Donal jumps a narrow rooftop gap effortlessly, skidding to a stop some 15 ft down from the longer line of pyramidal tile stacks...sliding right into a bizarre Siamese cat whose arched back did little to blunt the momentum.
Group B Positions:
5 [Tibs, escaped]
4 Amrik, B2, Donal
3 B3, Mal
2 B1
1
Group B NPCs to go.

GM Infinity |

B3
Trip: 1d20 + 5 ⇒ (20) + 5 = 25
Obstacle: 1d20 ⇒ 9
Sweat pouring down his face, the winded interceptor lunges at the halfling "C'mere you little..." contested vs DC 25...
But he was so worked up he didn't notice the little praying orphans were chasing after him, protecting Mal as one of their own...vs Orphans: 1d20 + 1 ⇒ (17) + 1 = 18...nearly consumed by the tiny hands. Net loss of 1 position
B1
Dash: 1d20 + 5 ⇒ (19) + 5 = 24
Obstacle: 1d20 ⇒ 10
No Wheaties?: 1d20 + 2 ⇒ (1) + 2 = 3
The other guard that had been lagging far behind suddenly sprinted forward like a professional athlete, each step true and sound, his biceps femoris pulsing and bulging, inflated by pint after pint of oxygen rich blood...until his empty stomach groaned the moan of the damned, and his hamstring twisted and ultimately broke free of its tendon anchor. Net gain 1
Amrik
Trip: 1d20 + 1 ⇒ (3) + 1 = 4
Obstacle: 1d20 ⇒ 7
vs Oh hi!: 1d20 + 4 ⇒ (7) + 4 = 11
Unarmed and with his hands bound, Amrik had little choice but to remove his boot with his other foot and fling it into the face of the closest guard...vs Boot: 1d20 + 5 ⇒ (1) + 5 = 6...who, charging forward, swatted it away like a fly. To add insult to injury, the charming noble stepped barefoot on a nocturnal possum in slumber, startling the small creature only half as much as Amrik himself.
Net gain of zero! Amrik did not escape this round.
B2
Trip: 1d20 + 5 ⇒ (2) + 5 = 7
Obstacle: 1d20 ⇒ 18
The last guard following Donal makes the same daring leap across the gap, attempting to land on the Tormtar's knee with his shield...Donal contested: 1d20 + 4 ⇒ (9) + 4 = 13...but the faith guarded acolyte rolls sideways at the last moment. The guard nonetheless is quick to block Donal's only way forward...B2 has reached 5th.
Chase is over, Mal and Donal (and Amrik) surrender or fight.

Evendur "Grim" Greymantle |

Whistles sounded, people shouted and chaos reigned.
With the guards that chased Gorn and Evendur slinking off for easier prey, the two were left to either flee or try something stupid. Evendur proposed something stupid.
Lets try to head them off! Whistles are heading north... If we tear up this street cut through the market and tear east down one of those alleys? We can catch 'em! Let's go!
They rushed through the crowded streets, made more difficult to navigate thanks to people rubber necking.
Athletics: 1d20 + 4 ⇒ (6) + 4 = 10
They weren't making rapid progress. You'd think a pair of warriors, one smelling strangely of herbs and spices, would make more speed but 'twas not to be.
As the whistles and shouts grew louder, and more rapid, conveying the excitement of a cornered quarry, they tried something different, darting between carts and horses in an effort to make up time and ground...
Trying to double down
Dexterity saves: 1d20 ⇒ 3... characters apply own Dex mod.
Instead Grim is knocked down and trampled by a wagon hauling ox!
Damage: 1d6 ⇒ 3
Dazed he staggers to his feet, checks on Gorn, then orients himself in his desired direction but knowing he is likely too late...

GM Infinity |

The angry farmer wags a fist down at Grim "You there! What are you doing to my dear ox Sally?! Dag-blasted city slickers!" throwing a half-eaten roasted corn cob in your general direction.
Unfriendly citizen aside, the ground does give you a good perspective on the movements of the Watch. Their blue capes and the land's gentle slope upwards away from the bay make it easy to judge their distances. They seem spread out about 100 ft apart, covering a large area centering approximately on the post you fled from. You can even spot not far off some commotion atop the buildings, the human movements a sharp contrast to the sea of orange and red ceramics.
We may be a bit on hold until Aesh returns. In the mean time, continue to befuddle the Watch, make your way elsewhere, or anything else. I was hoping this chase would quickly wrap up this little Amrik scene but alas, it was not in the dice.

Donal the Seeker |

Sorry, I forgot to tell you all I was visiting family! I am back! I guess it is fight on the rooftops, then! Odds don't look good, Mal.
Mal, if this is where it ends... It was good to know you. Know that if I fall, disappear, Donal clutches his warmace and looks at the three guards, daring to come at him.
Initiative: 1d20 + 2 ⇒ (11) + 2 = 13

GM Infinity |

Malaric: 1d20 + 3 ⇒ (7) + 3 = 10
Amrik: 1d20 + 4 ⇒ (6) + 4 = 10
The Watch: 1d20 + 1 ⇒ (2) + 1 = 3
Amrik whispered "Cut my bonds, quickly!" to Donal and Malaric, offering up his wrists.
"Stay out of this, sir. We'll have you home soon." one interjected as the melee unfolded.
Don and Malaric up.

"Mal" Malaric |

The domesticated halfling turns around with a wide smile on his face.
With his hand on his crystal, he says, "hey, buddy. Long time, no see. How's it going?"
Cast Charm Person Wis DC 13 on a Watch

GM Infinity |

Wis vs Mal: 1d20 + 1 ⇒ (4) + 1 = 5
The trickery of Shar bored into the man's psyche, tactically disabling hostile neurons while enhancing childhood memories of friendship. Friendship blurred by the darkness of the shadow sorcerer...the mind was his. "Oh heya, Ace. What's new? Is your mom still growing them pumpkins east o'Cloak Wood?"

Donal the Seeker |

Insight: 1d20 + 3 ⇒ (18) + 3 = 21 Does it look like these guards have been ordered to kill Amrik and make it look like we did it? Or at least, does it look like that is what Amrik believes?

GM Infinity |

No, by his eagerness and eye-contact it seems more likely that Amrik is trying some last ditch trick to escape. Meanwhile the guards appear to know who Amrik is and are interested in protecting him and arresting you/Mal. The 'stay out of this sir' was a guard talking directly to Amrik.

"Mal" Malaric |

"She's doing great. Hey, what's going on? We've orders to escort Amrik. How about you?" The friendly rogue replies to his new friend.

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Best tell your friends to back off, Donal says, to Amrik or Mal, no one can say. We are having a talk with Amrik. You can have him when we are done.
Donal backs up a step, moving a little closer to the edge of the rooftop. Ready an action to throw any of them that come close enough over the edge to the cobblestones below.

GM Infinity |

Waving a hand as if its not that important compared to shooting the s#++ with you "Oh, some Flaming Fist arrested the Duke's son and everyone's gone nuts about it. Vanthampur's threatenin' to defund the Fist, but its probably just bluster. Need to get him into the Council's custody ASAP..."
"Ubaldo, snap out of it..." another frustrated guard calls over "Draw arms and secure that Lightfoot."
Ubaldo hesitates.