Under the Black Flag Ch. 02

Story Info
The boy's torment continues.
5.5k words
4.44
18.8k
12

Part 2 of the 4 part series

Updated 06/10/2023
Created 05/31/2020
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

The 25 year old boy lay curled in the corner of the brig listening to the gentle waves and patter of rain on the side of the ship. He focused on the rhythm to distract himself from the pounding ache in his head and ruined ass. He had drifted to sleep for only a few minutes before he woke in a start, his mind replaying the horror of what the captain had done to him. In the dim light he could see two other members of his old crew, the bars of the cage, and something behind the bars. He blinked and squinted. It was the huge man with the bandana tied around his head covering one eye. The boy pushed himself up, ignoring the screaming from his head and ass. He rubbed the side of his head to calm the pounding. Keys rattled as the door was opened. The man with the bandana motioned to the two other men in the cage. They glanced at each other than at the boy before stepping out of the brig. The boy started to stand, but the door was slammed shut with an ear ringing clang. He leaned his head back on the wall as he listened to the footsteps fade up the steps.

He was alone for the first time since his violation. He took a deep breath and slowly put his hand into his pants. An ache came from his balls where they had been squeezed. He adjusted himself gently, swallowing the lump in this throat. He braced himself and slid his hand behind him and gingerly placed a finger on his tender hole. His breath hissed through his teeth and a searing pain raced up his body. His asshole was slick and slightly loose. He could feel the sticky cum, spit, and blood that still coated the entrance. He prodded around gently fighting the urge to cry again at the ache in his bowels.

"Need a minute?" A deep gravelly voice came from the darkness. The boy yipped and jerked his hand out of his pants.

"No! Wh.. who's there??" the boy said loudly, feeling his face turn crimson as he snapped his head up. He stared into the gray eye of the man with the bandana.

A deep chuckle that was almost a grumble answered him. The huge man leaned on the brig, slipping his arms through the bars nonchalantly. The boy pressed back against the wall of the ship staring at the bands of muscles running along his forearms, almost hidden under thick red hair. Tattoos ran up both arms forming full sleeves on the man. How could someone so huge manage to be so silent? The boy thought to himself.

"Got yerself a name?" the man asked. His voice sounded like a barrel of rocks thundering down a hill.

The boy hesitated before answering, "Ma.. Mathias." he said, feeling fear spread through his stomach. He couldn't go through a rape by another man.

The man stood back, flipping his long red braid over his shoulder before pulling some items from a pouch. He rolled a cigarette, taking his time as the silence stretched on between the two of them. When he was finally finished he lit it, taking a long, savory drag. He exhaled and the thin stream of smoke drifted around the man, snaking its way to the boy. It smelled of tobacco and mint, a strangely comforting scent, the boy thought.

"M'names Max," the large man said, extending his hand through the bars towards the boy. The boy shakily stood and hesitated before stepping forward. He stuck his hand out and put it in the paw of the other man. He looked up from the hairy fist enclosing his to look into the man's face. In the dim light he could see the massive scar running from up in the man's hairline, under the bandana, down his cheek, and through the corner of his mouth. The man gave a firm and short shake before releasing the boy and returning to leaning on the bars.

"S'one helluva shiner, ye got ter," Max said, gesturing towards the boy's face. The boy ducked his head and reached up to touch his swollen face.

"Musta had an interestin' first night." Max grumbled before grunting and spitting to the side. "Ol' Capin' Judge ain't all bad. Jus rough round teh edges."

The boy blinked. Captain Judge. He had heard tales of the wicked pirate captain, but never heard of him having a taste for abusing asses. The boy flushed a bright red again as he hoped Max didn't know what had happened in the room with the captain.

"Yeah, we had a disagreement on joining his crew." the boy lied lamely. He swallowed trying to tame the knots in his stomach. He glanced up in the eye of Max trying to read his silence, but could not tell anything from the dark expressionless gaze. The boy dropped his head and moved to the back of the brig. The silence was finally broken by an enormous grumble from his stomach.

Max grunted and pulled out his pouch again. After rummaging around for a bit he stuck his arm through the bars again with a small piece of jerky extended to the boy. " 'er boy. Savor 'at bit der. Meals of meat 're few." Max watched the boy carefully chew the dry plain piece of meat. "If'in Judge ain't killed ya yit, you'll be 'round for a spell."

The boy grimaced and finished the jerky feeling the pounding in his head get worse. He slid down the wall and sat shifting to ease the burn in his ass. Max straightened up with a deep sigh.

"Git sum rest, Mathias." Max said as he stepped away and disappeared up the steps. Mathias sat alone in the brig with the sound of his own name running in circles in his sore head. The way Max had said it. It was like he had tasted every syllable, savoring the word. He closed his eyes to try and drift to sleep.

...

Mathias paced in the brig for hours as the sun rose the next day. No one was returned to the cage. He was alone. A member from the pirate crew brought him some food, or what you might call food, he couldn't tell what it was, but the ache in his stomach from hunger drove him to eat it all. He licked his dry split lip and savored the little amount of water he was given. He figured his old crew as gone, either off the ship or had joined the pirates. The only thing to pass the time was to listen to the crew move around above him. Every so often the silence would be broken by a muffled shout or boots thudding on the floor above him.

Darkness fell, bringing with it the queasy feeling of unease as he remained alone. He had finally settled into the corner when he heard the thud of boots coming down the steps. Mathias jumped to his feet and glared at Max as he moved to the door. Keys clanked as the door was unlocked.

"Where is my crew? Where has everyone been? Why am I here? Are you going to kill me, yet? Answer me!" Mathias' questions seemed to fall on deaf ears. Max only grunted and stepped aside to let the boy out of the brig. Mathias felt rage well up inside of him as he was being ignored. It boiled over and he swung a forceful punch at Max's head, hitting him in the corner of his mouth as hard as he could. Max didn't even move his head at the punch. He paused before turning his head and spitting a bit of blood on the floor. Mathias growled and threw another punch, this one was caught in the giant hand of Max as he snapped his arm up and over his head, pinning him to the bars of the brig.

"Easy, boy." Max growled into Mathias' face. His hot breath spilled over his face, smelling like mint and tobacco. Mathias struggled for a beat before sagging against the bars. Max released his grip on the boy and stepped back.

"Strike 't me ag'in." Max said deeply. His gray eye smoldered as he stared into the boy's eyes. Mathias raised his fists before lowering them again, defeated. His head hung low. Max turned on his heel and went up the steps. Mathias followed, his breathing quickening as he hoped it was truly death that awaited him this time. He took in a deep breath of the fresh sea air as he stepped on deck once again. Max stood by the door to the captain's quarters and knocked twice before glancing over at the boy. His dark hooded eye stared into the wide brown eyes of the terrified boy. Max grunted and spit to the side as the door opened. The boy swallowed before stepping into his nightmare for the second time.

Captain Judge closed the door behind the boy and pushed him towards the table. The boy gasped and stumbled forward. The captain lazily sunk into a chair opposite the boy while gesturing to the spread of food. Mathias felt his mouth begin to water as he looked at the food with longing. It had been months since he had had food even half as good as what was in front of him. The pirate life must feed better than the English life, he thought as he slowly sat. He reached towards the meat only to have his hand smacked away.

"You earn the right to eat." the captain growled, returning to his lazy slouch in the chair. The boy swallowed, looking between the captain and the food. After all of the abuse he had experienced the night before he had begun to feel numb to more trauma. His mind tried to race with ideas to get out of his predicament, but he was starved and dehydrated.

"Well boy?" the captain said, breaking the boy's lost train of thought. The boy jumped and stared at the food. He wouldn't be able to survive much longer on the thin gruel they had fed him earlier, then his eyes fell on the water.

His thirst drove him to reply, "Yes, Sir." while he dropped his head.

"Over here, boy." the captain said, cocking his head to the side as he watched him. Mathias hesitated before standing and walking around the table to stand in front of the captain.

"Now, get to work." the captain commanded, leaning further back in his chair and pushing the bulge forming in his pants towards the boy.

Mathias swallowed feeling his stomach tighten and his head start to spin. He couldn't bring himself to look up into the captain's face. He only stared at the man's growing bulge. The captain tipped his head to the side with a cocky smirk spreading across his lips. The boy sank to his knees with a soft sob, his whole body trembling. The captain rested his hands behind his head making it clear the boy would have to choose his fate tonight.

Trembling, the boy reached up and began to unlace the man's pants, gently pulling the erect cock free. The angry purple head pointed straight at his lips, demanding to be attended to. After another long pause the boy leaned forward and put the offensive cock between his lips. His tongue touched the soft flesh and he retched. This brought an evil chuckle from the captain.

"Good boy." The captain purred. Enjoying the show the boy was giving him.

More cock slipped past the boy's lips as he squeezed his eyes shut. He tried to ignore the humiliation as he sucked another man's cock for food and water. Was this what his life would become? Nothing but a cock sucker to be used and abused for entertainment? The dick in his mouth reached his throat and the boy began to bob his head up and down. He tried to think of what girls used to do for him at port to satisfy the man. The boy retched again thinking of what may be in store for him. The retching brought up more saliva and made it easier for his lips to slide along the shaft.

He continued for what felt like hours, but was only a few minutes before the captain shifted and placed his hands on the back of the boy's head. He tangled his fingers in the shaggy blond hair before gripping hard and forcing his cock deep into the boy's mouth and into his throat. He felt the throat spasm and tighten around his member and he moaned deeply. The boy began to panic as he was held in place with a cock suffocating him.

After a few beats the captain began to throat fuck the boy. Drool dripped out of the corners of the boy's mouth and onto the floor. Squishing, squelching noises filled the room along with small sounds of discomfort and agony from the boy as his jaw began to cramp and he struggled to breathe. The captain quickened the pace with which he was pulling the boy onto his waiting cock. Finally he stilled, holding the poor boy with his nose buried in the black pubic hair, throat stuffed with cock, as he unleashed his cum. He squirted two ropes down his throat before pulling out and dumping the rest of his load on the boy's tongue. The boy retched and gagged, but didn't spit out the nasty hot cum on his tongue as the cock slipped out of his mouth and hung in front of his face, slick with his saliva.

The captain kept his hands buried in the boy's hair as he watched the boy close his mouth and swallow the present he had given him. He chuckled to himself watching the discomfort and pain on the boy's face as he stayed between his knees.

Judge finally nudged the boy with the toe of his boot. "Eat." he ordered the boy as he tucked his deflated cock into his pants.

The boy moved to the chair on the other side of the table and began to tear into the food. He tried to wash the taste of semen and shame out of his mouth with cool water and food. He refused to look at the captain, but could feel his eyes burning into him.

The captain stood and slowly walked behind the boy. "Stand and bend over." The boy froze and began to shake again.

"Stand and keep eating." the captain barked. The boy jumped and did as the captain commanded, his fists resting on the table as he waited for his next violation. The captain pushed the boy's pants down around his ankles and ran a hand up his thigh to his ass cheek. The boy felt himself begin to flush red as his breathing quickened in terror. The hand moved to his asscrack and pulled the cheeks apart, admiring his handiwork on the boy's asshole. It was red and inflamed, with a tiny tear on one side of the puckered ring. The captain spit on his finger and rubbed the used star. The boy gasped and tensed his whole body.

"Hush and eat." the captain growled as he slid his finger inside the boy. The boy was still tight. The captain reached over the table and grabbed a large carrot. He slid it down the crack of the boy and stopped on the tiny hole. He rubbed the vegetable around the ring as he leaned over and dribbled more spit onto it. He pushed the carrot inside the boy, watching his back tense and his knuckles turn white. He fucked him slowly, watching him tense and try to relax against the invasion. He ran his hand over the boy's ass and lower back as he plunged the vegetable in and out.

The hard carrot forced the boy's asshole to conform to it, not giving him any relief. The assault continued and soon the carrot was sliding in and out much easier. The boy grimaced as the hard carrot was replaced by the larger, but more forgiving cock. He felt the captain grib his hips as he drove into the boy slowly, savoring the way he stretched around him. The captain reached up and tangled his fingers in the boy's shaggy hair as he pulled back making the boy arch his back for a tighter fit. He thrust long and slow, taking his time, enjoying the boy thoroughly.

Mathias felt his mind start to slip away as he was being taken. He heard his name echoing in his mind. The way Max had said it... Mathias felt a warmth grow in his belly as his name slipped around and around his mind. He could feel the heat spreading through his body, but snapped out of it as the captain drained himself deep into the boy's bowels. He let himself slip out of the boy and returned to his seat. He picked up a piece of meat and began to tear the meat off of the bone.

The boy shakily pulled his pants back up and sat down. He felt the blood draining away from his penis, shocked to realize he had been starting to get hard during the ordeal. He hoped the captain didn't notice. He went back to eating as much food as he could, trying to ignore the semen leaking from his asshole.

The two ate in silence until the boy finished eating. The captain took a drink of wine and leaned back in his chair.

"Okay boy, this is how your life on this ship will go." the captain said, staring at the boy who refused to look up from the table between them. "You will come to my quarters every night and let me do exactly as I wish to you. You will report to Max, who will put you to work on the ship. If I summon you, you will come and do as I say, understand?" his eyebrow arched as he waited for the boy to understand his place.

The boy weighed his options before nodding slowly. "Yes Captain." he whispered. A tear slipped down his cheek.

"Good," said the captain, "Max will take you to where you will stay. You may go." he waved his hand dismissively towards the boy.

The boy stood and pushed the door open and walked onto the deck. The stiff sea wind blew his shaggy hair back as he glanced around the empty deck. He shut the door and wiped the last of the tears from his eyes. He took a deep breath before launching himself towards the other side of the deck. He ran as fast as he could in the night, ready to launch himself off the side of the deck and to be done with this nightmare forever. He hit the railing and jumped before feeling the collar of his shirt pull tight behind him. He choked and fell back against the side of the ship, hung up over the side. He looked down at the inky water below, willing himself to be freed, but instead felt himself get hauled up and over and back onto the deck. He lay on the deck in a ball at the feet of Max.

""Da Hell you think yer doin' boy??" Max shouted at the form curled at his feet. He grabbed the boy by the shoulders and pulled him to his feet. He gave a mighty shake and saw the pain and agony on the boy's face. Max let the boy go and shook his head reaching up and rubbing the back of his neck.

"Liss'in 'er. I know you got'it tough here. Tougher'n most." Max paused not sure what else to say. He looked past the boy to the sea, lost in thought for a moment. "Lemme take ya to where you'll be livin."

He turned and walked a few steps before waiting to see if the boy would make a run for it again. The boy looked towards the sea before lowering his head and following the giant man. They went below deck, but not to the bottom of the ship where the brig was. Instead he was led into the main area where the rest of the crew lived. Max took him to the farthest back corner and showed him a ratty old hammock.

"Y'ull be sleepin' er'." Max motioned to the hammock below it. "I sleep 'er. If'n you run again, I'll catch ya." he stared at the small boy and watched his discomfort.

The boy nodded and climbed into the upper hammock. He sank into it, glad for the familiar swing and glad to be out of the brig. He pulled the thin blanket around himself feeling a false sense of comfort. He looked out at Max who was still watching him with his dark expressionless eye. His eyes grew heavy as sleep begged to take him away from this awful place.

"Thank you, Max." the boy managed to hoarsely whisper as he drifted into a fitful sleep.

Mathias awoke the next day with a start. Dim light filtered through the empty hammocks around him. He looked over the edge and saw Max's empty bed. He shakily got out and looked around the ship, listening to the bustle above him.

"Finally goin' teh join us, eh?" Max's booming voice made Mathias jump. He shrank against the wall as the giant man approached. "Well, don' jis stand der. Git yerself on deck so ye can git t' work." Max followed the boy up and into the sunlight.

The boy blinked in the bright sun. It was his first time in the light since his capture. He tried to keep his gaze from meeting the stares of the other pirates. Max soon had him scrubbing the deck and doing whatever horrible job that no one else on the crew wanted to do.

The days fell into a routine. He would wake early in the morning and begin whatever task he was assigned. He would work all day and eat one meal a day, usually Max would eat with him. Some days Max would tell a story and be quite animated, the next he would be silent, dark and moody.

The boy would dread the coming night as Max would escort him to the captain's quarters. The captain would entertain himself with the boy's body for as long as he would like. Some nights included a reward like food or extra water, but most nights did not. The boy fell into the rhythm, accepting his new role and taking his torture, feeling his mind going far away as the captain used him.

12