Freedom on the Sea

Story Info
Ship's boy seeks plunder, finding more than just gold!
18.8k words
4.76
13.4k
31
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
Dave2526
Dave2526
106 Followers

Chapter 1: Captured

Cannons fired all along the ship as I ran across the under deck of the ship. Our ship's cannons were good but not enough. The captain of the ship was a blasted idiot and hadn't even waited until the ship's starboard side cannons were lined up with the pirate ship that had come upon us. It had come completely out of nowhere, out of a fog bank that was set around a small series of nameless islands that dotted the Caribbean.

The ship rocked as the enemy ship's cannons returned fire, men dying as the pirate ship's port side broadside tore into our ship's starboard side. A cannon tore through the sailor beside me. His body was blasted apart in front of my very eyes. As I shoved the corpse off me I wondered how in the hell I'd ever wound up here.

My name is Leonardo Sanfino. I'm the son of an Italian silk merchant that took his business to jolly old England in order to take advantage of trade in the New World. I was taken from Florence Italy to London with my father and his business when I was only seven years old. My mother, she was a peasant girl fro the Tuscan country side that I never knew. My father's current wife was chosen for him. I have three half siblings, two brothers and a half sister. And as far as my dear father was concerned, I was a wretched mistake he made when he was younger. Why didn't he just cast me out then? I wondered that a million times. He never liked me. I was a bastard to him in all but name. But he apparently had a use for me. I became the caretaker of my younger half siblings and my father's personal workhorse. I worked like a dog, taking care of terrible snotty children that were taught from as old as they could remember that I was only a half brother, and therefor not really one of the family. I did all the menial work that was too good for him. All the menial work he was too cheap to hire actual help for. My step mother disliked me. My life was pretty miserable to be honest. No I suppose it's not really a surprise then that I jumped at the chance to get the hell away from them all.

I heard gunshots now and the sounds of swords clashing together. The pirates had boarded the ship. I jumped to my feet, scrambled over the dismembered body of the sailor and ran for the lower deck. I was no fighter, never had been. Never learned to use a sword. Never learned to shoot a gun. My father hadn't wanted to train me in anything, perhaps fearing I would use it against him and my rotten half family. So I ran. Was I a coward? Oh yes I was! But cowards were often the ones that survived! I ran into the cook's pantry and tried to close the door but then the cook himself knocked the door open and closed it, then turned and started when he saw me. "Why aren't you out there?" he asked.

"I could ask you the same."

"I'm a cook, not a dammed fighter! I ain't going to fight pirates!"

"I'm just a ship's boy, so neither am I!"

"You signed on for that!"

"I signed on to get away from my father, not fight pirates! Captain Brussels never trained me, nor did anyone on the ship! So what exactly could I do besides be another body for the pirate to play target practice with? Or sword practice with? I don't get paid enough for that!"

"Get out there boy! That's an order!"

The cook, a fat man named Charles glared at me but I just laughed. "Take the order of a fat cook who feeds us slop while Captain Brussels dines on roasted meat? Fuck you, you fat sack of blubber."

That made Charles, who's always been insecure about his weight, take a swing at me. I'm no sword fighter but I've been in enough dock side tavern fights in my life to know how to defend myself. I caught that fat cook's fist and yanked him forward. His momentum did the rest and he crashed headfirst into a barrel of lard. His head got lodged in it. I laughed as he tried to extract his head but then realized his thrashing and moans would bring the pirates to me. The sounds of battle were dying out above and that meant the pirates were winning. So I unlocked the pantry door and left.

Only to run into two dirty pirates with swords drawn. "Well lookie what we got here!" said one of them. Missing his front teeth and scarred. His accent was Irish. Wonderful. Me a pretty English ship's boy meeting an English-hating Irish pirate! "A cowering little brat?"

"I surrender!" I said.

"What makes you think we're here to take you alive?" asked the other one. A black man, one of the many former slaves that took the life of piracy rather than go back to the chains.

"Captain Cold Eyes orders, that's what!" said a third pirate, this one looking a little more refined, but hardly any nicer than the first two. "We take them that surrender alive, see if they're worth anything."

"This brat barely looks like a man! A pretty punk like him? He can't be worth much!" protested the toothless Irish pirate.

"Do I need to tell Captain Cold Eyes you're disobeying her order?" asked the third pirate. The other two shut their mouths instantly and then grabbed me by the shoulders and brought me along.

"You'll find the cook in the pantry, with his head stuck in his own lard. And I don't mean his fat ass." I said. I suppose I should feel bad about selling out a ship mate but that fat fuck had it coming. Not that I was thanked for my information, the Irish pirate promptly punched me in the gut. All the air left me in a huff and I decided to keep quite for the rest of the way back up topside.

"Merda," I said to myself in Italian, which I still spoke fluently despite having half grown up in England. As I was dragged top deck I wondered if escaping my father had been really worth it? I was as welcome there as the plague and had to endure my bitch step mother and her snot nosed bratty children but at least I had my own room and bed. As I got older I did more work for shit pay for my greedy merchant father. He hiked up his prices and stated they were because of the cost of importing silk from Italy. And the prices he charged for merchants to sail the silk to the New World were even higher! But money, and the affection of my cunt stepmother were the sole things in his world that mattered. After hitting my early teens I began looking for a way out. My father told me I'd be his workhorse forever but horses couldn't travel on water! So I began looking to the sea to escape.

It was a typical dream. Especially in the two hundred years since the discovery of the New World. Escape across the no-long-thought-to-be-believed-as endless Atlantic ocean. But actually getting taken on was no picnic. Boys looking to escape miserable fathers and lives were as common as rats on the streets of London. I was growing up good looking, as I'd learned from young girls who thought I was some Italian beauty from Venice or something equally ridiculous. Speaking Italian was the only real asset I had besides working hard. I spent two years trying to get away. As my step siblings were growing up I finally got a yes. From a merchant captain named Brussels. Captain Jack Brussels. His name had caused me to bite my tongue to avoid bursting into laughter. Who keeps the name of Brussels on the sea? But I held my tongue, lest it cost me my freedom.

Some freedom, I thought to myself as the sun hit my eyes. The deck as covered in the dead crew of our ship, the Sprite. Captain Brussels himself was among the dead. The pirates were hauling the ship's cargo over to their ship, which looked like a frigate class ship. The black flag flew behind the ship. As well as at the top of the tallest mast. I'd heard the name Captain Cold Eyes from the pirates below but his name didn't ring a bell. Thankfully I'd not been captured by Blackbeard, or Charles Vane, or Calico Jack. Hopefully this Captain Cold Eyes was merciful. Or at least, not as brutal as the other pirates on the Caribbean sea.

This was freedom, I reflected as they dumped me in with what other prisoners had surrendered or been beaten into submission. Mostly younger crew like me. My big dream to escape my father had only put me in the hands of another tyrant. Captain Brussels was a former Royal Navy officer that had been discharged from the Royal Navy for something that the crew neither asked about nor, if they knew what it was, spoke of. Brussels ran his ship like he was still Royal Navy. He flogged sailors for not giving him way, or speaking out of turn. He firmly frowned upon anyone other than his officers coming up with ideas, whether they were good or not. He insisted the ship be meticulously clean at all times. I've spent an entire week on deckhand duty on this trip alone. He and his "officers" if that's what you wanted to call them ate like kings in the captain's cabin while the crew and other ship's boys gurgled gruel. Brussels forbade the crew from singing any shanties to pass the time, denied rum or any kind of other alcohol on the ship, you worked from sun up to sun down with no exception. Unless you were night shift, in which case you worked from moon up to moon down then! The pay he paid the sailors and crew was well below Royal Navy pay, despite his Royal Navy standards. Oh yes, this was freedom alight!

For two years I've been enjoying this "freedom" and wondering every day if I wasn't better at my father's mercy. But I'm legally a man now, having turned eighteen a few months ago. And thus, like all men, I must live with my choices.

The rest of the captured crew was silent, like I was. All of us wondering what was about to happen to us no doubt. Then the pirates began muttering and I looked up to see their captain walking across the boarding plank.

It was a woman! I blinked several times to ensure that the sun wasn't playing tricks on my eyes. It really was a woman! Long fiery red hair hanging low. For a second I thought she was Anne Bonny, and I'd been tricked somehow but there was no sign of Calico Jack whom she sailed with and was rumored to be lovers with, nor Mary Read, the only other female pirate I'd ever heard of. Whoever this woman was, she was something new! The redhead female pirate captain began conversing with her crew which allowed me to take a better look. Her hair shined. She was dressed in well worn sailor's clothing. Two pistols, one on each hip. A sword. A black hat shade her white skin from the unmerciful Caribbean sun. Slim and slender but not soft. No pirate could ever be soft. She looked fit. And easily as tough as all her men.

As I thought that she smacked the man she was talking to across the face and he fell to the deck of the Sprite. "I told you idiots to take the Captain alive! He was ex Royal Navy! Someone was bound to want him back and it would have been a good ransom! Now we're stuck with a bunch of nameless crew that nobody will miss and a few boys by the look of it! Useless!" She snarled at the fallen man. All the other pirates, except the ones guarding us prisoners fled, suddenly finding things to do. I swear I heard the toothless Irish pirate mutter something about going to get the cook's head out of the larder! Captain Cold Eyes was just as fearsome as she looked.

She'd have to be. Women at sea are usually regarded as bad luck. Captain Brussels had believed in that and allowed no woman on his ship, whether docked in port or at sea. I blinked my brown eyes as she came closer to inspect her "useless" prisoners.

Her eyes were as blue as the sky above, and as cold as her last name signified. Her eyes ran over all the others then rest on me. "Who're you pretty boy?" she asked.

"Leonardo Sanfino, M'lady."

"'M'lady'?" she repeated laughing. "That's a compliment I don't think I've ever heard before! I'm no lady boy. Nor will you flatter me with such talk. I'm a Captain and you will remember that."

"As M'lady the Captain commands," I responded, then wanted to bite off my waggling tongue.

But she laughed even louder than before. Her breasts jiggled underneath her white shirt. "Oh like you pretty boy. You at least can laugh on death's threshold." she said. "Your name is Italian but your accent is clearly English. Where are you from?"

"London by way of Florence Italy, M'lady the Captain," I answered. My only hope of not being keelhauled or worse was to keep her amused. So I kept the joking comments coming and made myself sound unconcerned that she'd just all but said I was going to die.

"And now you're in the Caribbean? My you are quite the traveler."

"Not by choice, M'lady the Captain. My father is a silk merchant that left Italy to trade in London and take advantage of the New World. I took up sailing to escape him and my wretched step-family. And so, here I am. The price of freedom," I gestured to the dead bodies on the deck and the rest of the captured crew held with me.

She laughed again. So did some of the pirates guarding us. I was sweating, and not just from the sun burning my neck but kept on going. "If it pleases M'lady the Captain, would she please have messaged delivered to my father, Giovanni Sanfino, in London?"

"A last will?"

"No. A last 'fuck you'."

That made them all laugh even louder. "Well I can respect that," said Captain Cold Eyes. "But I'm not going to kill you. If you father is a silk merchant, then he should pay for your return."

"I highly doubt that. He regards me as nothing more than his workhorse. Which is why I left. If you'd captured one of my step brothers or step sister, he'd pay heaven and earth to get them back! But me? He'll laugh at the ransom and ignore you from then on. So I'm afraid, M'lady the Captain, that ransoming me would be a complete waste of your time."

She stared at me. "You do realize, boy, that by saying such you are practically signing your own death warrant? If I can't get anything out of you, why should I keep you? Your pretty looks don't translate into gold for me or my crew."

I shook my dark hair out of my sweaty face. "I am well aware of that fact, M'lady the Captain. And if those are my options, just shoot me now please. Anything is preferable than going back to that man. My fate is in M'lady the Captain's hands."

She stared for a moment. "How long have you been a ship's boy?"

"Two years now. At eighteen, I'm technically a boy no longer."

"Toss him in the brig with the others," she said to the pirates. "If he's got some actual experience, he may be useful."

"He's a brat!" protested one of the other pirates.

Captain Cold Eyes promptly turned those cold eyes for which she was named onto the man. "I said, put him in the brig. We lost some men taking this ship. They will need replacing. Besides," she looked back at me. "He's pretty. And funny, which is more than I can say for any of you. Now move it!" She turned and walked away.

Well, I thought to myself, you've avoided death for one day Leo!

The pirates hauled me and the others up and trooped us across the boarding plank. The pirate ship was surprisingly clean and well kept, which was a stark contrast to the crew! All of whom looked like they'd been at sea for weeks easily. "Think you're special cause the Cap'n likes your face and jokes?" asked one of the pirates bringing us across. It was the toothless Irish one again. "Well you ain't! Don't be going and getting your hopes up you'll bed the Captain! She don't bed men at sea!"

"I wouldn't dream of trying to bed the captain. She'd likely shoot my balls if I did. I happen to like those very much! And as for her not bedding you, that's smart of her. She'd need to dive to the bottom of the sea to clean herself off if she did." I said before I could stop myself.

That little insult earned me three more punches to the gut and when I collapsed on the deck, a series of kicks were added. "I'm gonna kill you boy!"

A gunshot rang out and everyone stopped. Captain Cold Eyes was coming across with the refined looking pirate I'd seen below deck. "Did I tell you you could beat the prisoner McNally?"

"He insulted me! No pretty boy brat insults me!"

"He's got a mouth that one," said the refined pirate.

Cold Eyes looked down at me, then kicked me herself, twice, the second time in the face. "You don't get to run your mouth at my crew brat," she said.

"As M'lady the Captain commands," I managed to moan.

That only earned me a third kick. "Just captain from now on, boy. Next time you call me lady I'll stomp you until you're useless to any actual lady! And you McNally, don't you lay a hand on prisoners I've decided we may or may not need! Or you'll wind up in the bring yourself faster than you can blink!"

"Aye Cap'n," said McNally.

And after that I kept my mouth shut all the way to the bring. They tossed me into a single cell and then ushered the rest of the prisoners into the others. "I'm still gonna kill you!" McNally hissed at me through his missing teeth. Then he was gone.

Good job Leo, I told myself in the dank darkness of the pirate ship's brig. What little favor you may have had is gone now. You managed to cheat death today but increase your chances of it happening tomorrow at the same time! Good fucking job!

Chapter 2: A Plan

My face was aching because of her kick, and every time I drew breath my ribs hurt. Hopefully none of them were broken. There was no window and no lit lantern in the brig so I could see only the slivers of sunlight streaming down from above. I closed my eyes, tried to block out the pain, and do my best to rest.

I have no idea how long I was down in that dank brig but a sudden jerk to the ship told me we had started moving. Eventually the pain in my face started to subside to the point where I could yawn without pain. My gut was another story. Between my ribs hurting and my stomach growling, true sleep was impossible. I merely dozed in a senses of hazy pain and hunger. I half watched the slivers of sunlight coming down from below fade away as night fell. Night brought true black to the pirate ship's hold. Occasionally a light would pass the stairway above as a pirate crewman went by with a lantern but none of them ever came down below. If the other survivors from Captain Brussels ship were awake, they said nothing. I hadn't been really well liked by the sailors. When we would hit whatever port Brussels sailed us to, the dockside women always noticed me before any other crewmen, including Brussels himself and his so called officers. I'd know my share of easy women and whores during my two years. My good looks and ability to speak fluent Italian were good for something at least! But that same success made other crewmen of the Sprite jealous. Brussels, who didn't like me to begin with, now had an excuse to turn a blind eye when some sailor, jealous that the wench he wanted had eyes only for me decided he was going to teach me some respect.

I was jerked away with a start and a flare of pain from my ribs. There were pirates outside my cell. Thankfully the toothless Irish one was not here. The refined one was though. "Up boy, up. Cap'n wants a word with you."

I got up as quickly as I could and they let me out of the cell. The refined one led the way while two others followed behind to ensure I didn't try anything. Not that I would. We were still at sea, where could I go beside Davy Jones locker?

My eyes stung as I was brought above deck, stung by the morning sun. It was mid-morning if the light was any indication. Pirates went about here and there, tending the ship, securing the rigging, scrubbing the deck, or some other duties. McNally, I noted, was on the deckhand scrubbing bunch. He glared at me but I ignored him as the refined pirate led me toward the captain's cabin. He dismissed the other two pirates following me and closed the doors.

There was another set of doors just inside. It was like a small waiting area for those that wanted to see the captain. "Boy," said the refined pirate. "You'd best keep your tongue civil today. None of that 'M'lady the Captain' mouth that you ran yesterday. Cap'n's not in the mood."

Dave2526
Dave2526
106 Followers