Chapter 4: In the Shadows of Oldtown
The Meeting
As night fell, Sam made his way to the docks, following the directions the hooded stranger had given him. The area was quiet, with only the occasional creak of boats and the distant murmur of voices. A shadowed figure stood by a pile of crates, looking every bit the part of a secret informant.
The stranger gave Sam a curt nod as he approached. "Right on time. I hope you're ready. This job isn't one for the faint-hearted."
Sam kept his voice steady. "Tell me what I need to know."
The stranger handed Sam a small, weathered parchment. "Your target is Lord Vaith. He's staying at an inn just off the main square, and he's carrying important documents—information on trading alliances in the Reach."
Sam raised an eyebrow. "You want me to steal from him?"
"Not just that. We need you to gather any information on his alliances with other noble houses. A quiet operation—don't get caught."
Quest Updated: Spies and Schemes
Objective: Infiltrate the inn and gather intelligence on Lord Vaith without being detected.
Rewards: 800 silver coins, +5 Reputation, Stealth Skill boost.
Sam's pulse quickened. This was the kind of high-stakes mission that could either make him a valuable asset or turn him into a target. "Anything else I should know?"
The stranger shrugged. "Just keep your wits about you. Vaith is careful, but the men he travels with aren't as sharp. Use that to your advantage."
With that, the stranger disappeared into the shadows, leaving Sam alone with a sense of both anticipation and anxiety. This mission was unlike anything he'd tackled before. He would have to rely on his instincts—and his newly acquired Stealth skill.
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Scouting the Inn
As he approached the inn, Sam activated his Stealth skill, moving carefully, avoiding eye contact, and blending into the evening crowd. The system flashed notifications, tracking his progress.
Stealth Level 1: Minor concealment in dimly lit areas. Avoid making direct eye contact with guards.
The inn was modest—a two-story building with flickering lights visible through small windows. Sam ducked behind a stack of crates nearby, watching as a few men in dark clothing exited. They looked like guards, probably Vaith's hired muscle.
After a few minutes, he spotted Lord Vaith through one of the second-floor windows. The lord was deep in conversation with another man, their expressions serious. They seemed distracted—perfect for Sam to make his move.
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Breaking In
Circling to the back of the inn, Sam found a narrow alley where a drainpipe ran along the wall. He checked the window above him; it was open just a crack, likely left that way to keep the room cool.
The system pinged.
Skill Check: Climbing
Success Rate: 75%
Sam took a deep breath, gripping the pipe as he began to climb. He moved carefully, testing each grip and foot placement, and within moments he'd hoisted himself to the window.
Skill Check Successful: Climbing Level +1!
Easing the window open, he slipped into the room, careful not to make a sound. Inside, he took a moment to steady his breath. This was Vaith's room, all right. A set of fine robes lay draped over a chair, and a small, unsealed chest sat beside the bed.
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Searching for the Documents
Sam moved quickly, scanning the room. The chest caught his attention first, and he carefully opened it, finding a stack of parchment tied with a leather cord. His system flashed a prompt:
Knowledge Check
Analyzing Documents…
He skimmed through the papers, noting details on grain shipments, alliances with minor houses, and most importantly, a mention of trading routes through Dorne.
Intelligence Gathered: Trading and Alliance Records.
Sam tucked a few of the key documents into his bag. Just as he was about to slip out, he heard footsteps echoing down the hallway. His heart pounded as the footsteps stopped outside the door.
The system displayed a warning:
Alert! Enemy Approaching. Stealth Mode Engaged.
He froze, instinctively slipping behind a wardrobe. The door opened, and a guard entered, grumbling to himself as he looked around. Sam held his breath, praying the guard wouldn't notice anything amiss.
The guard gave the room a cursory glance, scratched his head, and left, muttering under his breath about the drafty windows.
Stealth Check Successful: Avoided Detection
As soon as the guard's footsteps faded, Sam crept back to the window, clutching the documents tightly. He slipped out, descending the drainpipe as quietly as he could. The street below was empty, and he quickly moved away from the inn, breathing a sigh of relief once he reached the darkened side street.
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The Exchange
Returning to the docks, Sam spotted the stranger waiting by a darkened alley, just as he'd promised. Sam handed over the documents, and the man gave them a quick once-over before nodding in approval.
"Well done. I wasn't sure you'd manage it, but you've proven yourself."
Sam's system chimed with a notification:
Quest Complete: Spies and Schemes
Rewards: 800 silver coins, +5 Reputation, Stealth Skill +1!
The stranger handed Sam a small pouch of silver, along with a folded note. "Take this to the wine merchant in the eastern quarter. He's expecting you."
Sam took the note, confused. "Another job?"
"A new contact," the stranger replied with a knowing smile. "Consider it an invitation to the world of noble games and shadowed deals. If you survive, that is."
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New Connections and Reflections
Back at the inn that night, Sam counted his silver, satisfied with the reward. His reputation in Oldtown was growing, but so were his risks. He'd crossed into a dangerous world, where trust was rare, and betrayal was the norm.
With his system's help, he reviewed his new stats:
Sam Wilson - Merchant and Spy
Charisma: 6
Trading: 13
Persuasion: 9
Endurance: 3
Melee: 4
Stealth: 2
Knowledge: 3
Reputation: +15 (Noble Circles Unlocked)
The upgrade in Stealth gave him a little more confidence, and his Persuasion skill had increased too—he'd been learning from every deal, every conversation. But he knew he couldn't rely solely on numbers. Westeros was full of unpredictable forces, and all the stats in the world wouldn't save him if he made a careless mistake.
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Meeting the Wine Merchant
The next day, Sam made his way to the eastern quarter of Oldtown, where the wine merchant was set up in a quiet alley. The merchant was an older man with a knowing smile and sharp eyes. He greeted Sam with a nod, glancing briefly at the note from the stranger.
"Ah, you must be the newcomer," he said, his voice soft but firm. "I hear you're quite the resourceful one."
Sam shrugged. "I try."
The merchant chuckled. "Good. I have a task for you—nothing too difficult, just a bit of information gathering. There's a rival merchant who's been undercutting my prices. I need someone to find out where he's getting his supply."
Quest Alert!
Market Rivalry
Objective: Investigate the rival merchant's supply chain and report back.
Reward: +200 silver coins, and access to better trade goods.
Sam agreed, feeling a little more at ease with this job. Investigating supply chains was less dangerous than stealing documents from lords, and he could use the extra silver to invest in his own trades.
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The Investigation Begins
Sam spent the rest of the day shadowing the rival merchant, using his upgraded Stealth skill to stay hidden as he moved through the crowded market. The merchant seemed completely unaware, going about his business without suspecting he was being followed.
After observing for a few hours, Sam noticed that the rival was regularly visiting a shop at the edge of town. The shopkeeper, a middle-aged woman, handed over small, well-wrapped packages each time, and they exchanged a few words before the merchant moved on.
Sam's system displayed a new objective:
Optional Objective: Speak with the shopkeeper to gain additional information.
With his Persuasion skill in mind, Sam decided to take the risk. He approached the shopkeeper casually, striking up a conversation about her wares.
"Seems like you've got a steady customer," he said, gesturing toward the merchant who'd just left. "He must get good deals here."
The shopkeeper chuckled, glancing at Sam. "He's one of my best customers. Good business is all about loyalty, you know?"
Sam flashed a friendly smile. "Couldn't agree more. Any tips for a fellow merchant?"
Persuasion Check: Success!
The shopkeeper relaxed, clearly flattered. "Oh, it's no secret. I just offer a fair price, and he keeps coming back. A steady supply from the Arbor helps too, of course."
Bingo. That was exactly the information Sam needed.
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Reporting Back
Sam returned to
Reporting Back
Sam returned to the wine merchant with his findings, feeling a sense of accomplishment. The merchant greeted him with a satisfied smile as Sam recounted the rival's source—shipments from the Arbor, a prized region for wine and known for its quality.
The merchant's eyes gleamed with approval. "The Arbor, you say? Clever. I knew he had some secret supplier."
The system chimed, and a new notification appeared:
Quest Complete: Market Rivalry
Reward: 200 silver coins, +2 Reputation, Access to Enhanced Trade Goods
The wine merchant passed Sam a pouch of silver. "You've done well, friend. I'll make sure you get access to my best trade goods from here on out."
Sam thanked the merchant, already calculating the potential gains he could make by leveraging these new goods. Access to quality supplies meant he could undercut other merchants in Oldtown or even set up exclusive deals.
As Sam counted his coins later that evening, he felt a renewed sense of purpose. He wasn't just surviving in Westeros—he was beginning to thrive.
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Developing His Network
With his growing influence, Sam's contacts expanded rapidly. Word spread among the merchants and traders that Sam Wilson was the man to go to for discreet tasks and profitable trades. He earned not only coin but valuable connections with people who had ears in every corner of the city.
Each successful mission felt like leveling up in his own real-life game. He spent his downtime training with Tom, focusing on Melee skills and Stealth, knowing that in Westeros, the ability to fight and avoid detection could be the difference between life and death.
Melee Skill +1!
Current Melee Skill: 5
As his skills grew, so did the complexity of his missions. His system tracked his progress, suggesting upgrades based on his recent activities. One night, while Sam reviewed his stats, he noticed a new option in the system menu:
Skill Unlock: Intrigue
Cost: 50 silver coins
The Intrigue skill would improve his ability to navigate the complex political web surrounding noble families, increasing his chances of survival in high-stakes deals. Sam decided it was worth the investment.
Intrigue Skill Unlocked!
Current Intrigue Skill: 1
The system offered another quest:
Quest Alert: Into the Web of Intrigue
Objective: Use your new skills to uncover information on Oldtown's noble families. Gain allies—or eliminate rivals.
Reward: Increased reputation, access to political factions
Sam couldn't help but smile. His life had transformed from one of survival to one of strategy. He was learning to play the game of power, one small move at a time.
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The Next Challenge
The following day, Sam received a message from a young noblewoman named Lady Meryn. She requested his presence at her estate, a modest yet elegant residence overlooking Oldtown. Lady Meryn, known for her cunning and ambition, was an influential figure in local politics. A meeting with her could be a major opportunity—or a trap.
Sam arrived at Lady Meryn's estate at dusk. The air was thick with the scent of citrus and jasmine, and servants ushered him into a small study where the lady awaited.
Lady Meryn was as intimidating as she was beautiful, with sharp eyes that seemed to see through any deception. "Sam Wilson," she began, her voice calm yet commanding. "I've heard about your… skills. I believe we have common interests."
"Thank you for the invitation, my lady," Sam replied, careful to keep his tone respectful but confident.
She leaned forward, studying him with a critical gaze. "I have need of a man who understands discretion and loyalty. My rivals are becoming increasingly bold, and I need someone to… manage certain delicate situations."
A new quest appeared:
Quest Alert: The Noble's Favor
Objective: Assist Lady Meryn in dealing with her political rivals discreetly.
Reward: Noble connections, access to higher-tier missions, 500 silver coins
Sam weighed his options carefully. Involving himself in noble politics was risky, but the rewards were tempting.
"I accept," he said, nodding.
Lady Meryn's lips curved into a smile. "Good. There's a minor lord who has been meddling in my affairs. He needs a reminder that his actions have consequences. I trust you know how to deliver a message?"
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Delivering the Message
That night, Sam tracked the minor lord to a dimly lit tavern, where he was carousing with his friends, clearly unaware of the danger he'd invited. Sam's Intrigue skill kicked in as he assessed the situation, planning his approach.
He slipped into a shadowed corner, waiting until the lord's friends left him alone to find more ale. Seizing his opportunity, Sam approached, leaning in to speak quietly but firmly.
"Lord Aelin, my employer has grown… concerned about your recent activities," Sam said, his voice barely above a whisper. "She believes a change in your conduct would be best for all."
The lord's face blanched. "Lady Meryn sent you, didn't she?"
Sam's system displayed a prompt:
Intrigue Check: Success! Lord Aelin Intimidated
"I would advise you to heed her concerns," Sam continued, a dangerous edge in his tone. "For your own well-being."
The lord nodded quickly, his face pale. "Tell her… she'll have no further trouble from me."
Quest Progress: The Noble's Favor (Complete)
Sam returned to Lady Meryn's estate, reporting his success. She regarded him with a newfound respect, pressing a small pouch of coins into his hand.
"Well done, Sam. You've proven yourself an ally worth keeping."
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Evolving as a Power Player
With his newfound influence, Sam found himself increasingly embroiled in Oldtown's web of intrigue. Missions grew more complex, from securing alliances between minor merchants to arranging covert meetings between rival nobles. He earned silver, but more importantly, he earned trust and influence.
Each mission further honed his skills, and he could feel himself becoming sharper, more calculating. His system tracked every success, encouraging him to take on even bolder tasks.
Skill Growth: Intrigue +2!
Current Intrigue Level: 3
Through his experiences, Sam learned that in Westeros, power was rarely gained through brute force alone. His survival depended on his ability to navigate the labyrinth of alliances, betrayals, and deals—and he was becoming increasingly adept at it.
One evening, as he counted his latest earnings and reviewed his network of contacts, he received a message from Tom:
"Big opportunity. House Hightower has a job that needs a skilled hand. The reward? Enough coin to live like a lord. Interested?"
Sam's eyes gleamed with excitement. This was his chance to truly make a name for himself, to climb to the highest echelons of Oldtown society. He could see the path before him, a series of calculated moves that would bring him closer to true power.
End of Chapter 4