Freedom on the Sea

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
108 Followers

McNally glared death at me but walked off without a word. Lawrence took me by the arm and hauled me down below towards the brig. "Boy, you keep that up and you will be shark bait."

"How is it my fault that toothless waste of skin can't handle losing an argument?"

Lawrence only shook his head and pushed me into my cell. The other survivors from the Sprite were here, and they ignored me. They'd heard how I was going to help the pirates and considered me a traitor. I'd tried to convince them to wake up and offer to join but they'd refused to hear me.

So I was back to languishing in the dank brig. But this time I wasn't feeling hopeless. In a few days I'd be in Havana putting my scheme into action. And provided all went well, hopefully earning my place on the crew.

Even though I was technically being disciplined for my confrontation with McNally, I was going to enjoy the afternoon I now didn't have to spend doing whatever demeaning task the pirates decided to heap upon me. I decided to sleep.

How long I had been asleep I don't know but when I was awoken, none too gently, it was dark. "Sleep well brat?" snarled a voice. McNally's voice.

"Oh go away McNally."

I was punched in the face for that. "You don't give me orders! Haul him up! It's time to teach this fucker a lesson!"

I was hauled to my feet and dragged out of the brig. I was brought up on deck. Nobody was in sight. "No Cap'n, no first mate, and nobody to help you. Night crew is all my men. And we've decided to show you your place."

"Small men trying desperately to prove they're superior," I scoffed.

"You're the one who's small!" McNally hit me two more times, both in the gut. "And you're the one who will know his place now boy," he promised.

I coughed from the hits but showed no other reaction. But when McNally revealed a whip I understood. They were going to flog me. They turned me back toward the mast and one of them each grabbed one of my hands.

"What's a matter boy? No clever words now?"

"You're not worth it."

That's when they cracked the whip. An explosion of agony hit my back like fire. I'd been threatened with a flogging before by Captain Brussels but I'd never actually endured it. McNally hit me four times before he started talking. "Little English shit, talking shit to me, thinking he's deserving of being in this crew. I don't know how you tricked the Cap'n into believing you but you will be this ship's doom!" I was whipped five more times in rapid succession. I made no sound, determined to give the toothless pirate no satisfaction. I lost count of the whippings I took after the tenth strike. My back felt like it was on fire. My head lowered and I could see blood dripping down to the deck of the Defiance. Then McNally hit me again and my head shot up. I still refused to utter so much as a moan or a sound. I could tell my the way McNally was gnashing swearwords through his toothless mouth that my lack of response was infuriating him. This was his revenge and he was getting no satisfaction from it.

McNally whipped back again. But a shot fired through the air and the pirates holding my arms let go. I slumped against the mainmast and managed to turn my head to see Captain Cold Eyes and first mate Lawrence coming onto the deck with about twenty others. Cold Eyes looked like she'd been woken very abruptly and jumped out of bed. He shirt was unbuttoned in a few places and her toned midriff was visible. Her hair as disheveled. Lawrence looked as refined as ever. Spasms of pain then overtook me and I screwed my eyes shut in pain.

"McNally," snarled Cold Eyes. "Who on the world gave you permission to flog the boy? Who gave you permission to draw the cat from it's bag? What in the hell do you think you're doing? Flogging a prisoner who is the key to a rich haul for us? For what? Some petty bullshit dislike?"

"Fucker needed to learn some respect!" protested McNally.

"Respect is earned you stupid Mick! Leo Sanfino may be a boy but you're the one acting like one!"

"I-"

"I'm done with you and your fighting with him! I made my choice to keep him and I refuse to tolerate this anymore! Lawrence, get the cat from him! Now he's gonna feel it's lashes!"

I opened my eyes to see one of McNally's pirates standing slightly in front of me. His pistol was sticking out of a pocket. With a surge of rage fueled by pure pain, I lunged up, smashed an uppercut into the man's groin, then yanked the pistol out of the pirate's pocket. Several of Cold Eye's pirate's yelled a warning and McNally turned to see me. The pirate I'd nutted dropped to his knees and I took the pistol and fired at McNally. I'd never shot a gun in my life, ever. So when my shot took the toothless Irish prick right between the eyes, it shocked me as much as anyone else watching. McNally fell to the deck, dead as a tree cut down. Cold Eyes looked at me with her blue cold eyes widened in surprise. All the rage fled me as shock at what I'd done set in and then I realized the other pirates had their pistols aimed at me, I tossed mine to the deck and sank back against the mainmast.

"Get the boy patched up Lawrence. I'll deal with them," said Cold Eyes to her first mate.

Without so much as a word Lawrence and two others hauled me up and took be below deck. They rousted the ship's doctor, a former Royal Navy surgeon named Rodrick who was one of the many that had gone pirate after England's war with Spain had ended and all the privateers had found themselves out of work.

"He took all this and didn't make a sound?" asked Rodrick, called Roddy by the crew.

"Aye, so I heard," said Lawrence.

I was face down as Roddy applied salves to my lash marks so they wouldn't get infected. "Pretty boy's tougher than he looks," said Roddy.

"Aye he is. And who knew he could shoot? Shot McNally clean between the eyes!"

"First time I've ever fired a gun," I said my voice muffled by the pillow my face was on.

"That was your first time shooting?" asked Lawrence.

"Yes."

"I don't believe that!"

"It's true."

"No way could you be that good a shot on your first ever shot!"

"Some say rage helps focus if you don't let it overwhelm you," said Roddy. "I've seen it before. Heard that Blackbeard is like that. Only gets more focused and clear minded when angry. When he's not drunk of course. Them is the ones you want to watch out for. The ones who get focused, rather than unfocused, as the temper flares."

Lawrence, I could see through the side of my gaze, was looking at me with a mingled look of newfound respect, curiosity, and caution. I was patched up with bandages and as I was getting to my feet and about to put on a shirt Lawrence had helpfully provided another pirate came in. "Cap'n wants to see the boy. Now."

I ignored the shirt and walked bare chested to the captain's cabin, followed by Lawrence and the others. Lawrence went in first to talk to the captain. He was only in there for a few minutes before he came out and ushered me in, closing the door behind him.

Captain Cold Eyes had fixed her appearance and no longer looked disheveled. For a brief second, she eyed my lean, strong sailor's body and bare chest before she started speaking. "Lawrence says you've never shot a gun until tonight. I have trouble believing that."

"It's true Captain. Brussels didn't train us ship's boys to fight. Nor would my father for fear I'd use that training on him."

"Given what I just saw you do, I don't blame him. Well Leo, I have dilemma about you once again."

"And let me guess," I said, noting how she called me 'Leo' not 'boy' right there. "The other pirates want to lynch me for killing McNally because he was crew and I'm still just a pretty boy with a big mouth and no proof I can actually deliver on my grand idea to make you all a lot of gold? Is that it?"

"That's it Leo. That's exactly it. You killed crew. And you ain't crew. That has to be answered."

"Then M'lady the Captain can do as she sees fit."

"You don't seem worried."

"I've just been flogged. You can't really do much more to me without killing me and kissing that rich haul goodbye, Captain Cold Eyes. Only McNally's diehard friends will want me dead. The others, from what I've seen, disliked McNally a lot and will insist I be disciplined, punished, but not killed. They can smell the gold in the wind. With me dead, the wind blows in a different direction."

"You are a merchants son Leo, if the way you argue is any indication," she laughed.

"Merchant's know what they're worth Captain. I'm no different even though I sell no goods. Do as you see fit."

She sighed, looked me up and down again, then spoke. "Tomorrow we're tying you to the top of the mainmast for a day. That's punishment. After that you will have a day to recover. I need you looking somewhat alive when I send you into Havana."

"I think looking weather beaten will work in my favor. After all, it will look like I've been at sea for a long time. And shipwrecked."

"Is that the story you plan to sell?"

"Yes that I was shipwrecked and floated to shore. Then made my way to Havana."

"Which shore?"

"Some nameless island. The Caribbean is loaded with them it won't be questioned too much. I managed to piece together a decent piece of wreck and float to Havana's shores."

"What ship wrecked you?"

"A pirate attack. Which will be no lie when you think about it. Or not a total one anyway."

"What pirate ship?"

I knew now she was testing me to see if I'd give her away. "Not Blackbeard. He's know to not leave any survivors. Calico Jack and the ladies he sails with, Anne Bonny and Mary Read. Or some other. There is no shortage of pirates in the Caribbean."

"Believable," she nodded.

"Can I go now? I'd like to sleep before I spend the day being shit on by sea gulls. I'll work on my story more when I'm sailing up in the clouds."

She laughed again. "Leo sometimes I swear I'm almost attracted to you."

"Well I'm not crew and, I flatter myself, somewhat attractive. You are a woman beautiful woman with womanly desires. It's understandable."

She scowled. "Then I think sometimes I dislike you intensely."

"The truth can be painful," I smiled.

That earned me a hard glare that told me I'd pushed it too far, so I decided to get out of here. "If the Captain will permit me, I will be on my way."

Wordlessly she turned away. I was taken back to the brig and tried to ignore the pain and sleep. I'd ducked death again, and managed to earn a shred of respect from Cold Eyes. McNally was dead, and having to spend an entire day tied to the mainmast of the ship was well worth that. Rest in pieces you toothless piece of shit! May the sharks feast on your corpse.

Despite the pain, I could feel sleep closing in. By last thought was how Cold Eyes used my name and had looked at my body. I was experienced enough to know when appraising eyes were on me. The truth did indeed sting! But I wasn't deluded enough to push that any further.

Not yet.

Chapter 4: Havana

"So boy, any other clever ideas?"

"Oh I have plenty. But I've been snarled at enough for being smarter than Senior Havierez today. Farewell Diego."

"Farewell Leonardo."

I waved and left the merchant's warehouse and made my way into the blistering Havana heat. The sun was still high despite it was well past midday. I took a drink of water from my canteen and then put on my hat, making my way down a street.

I was doing very well for having been in Havana for two weeks now. I'd arrived, weather beaten, and worked my way into Senior Robert Havierez's silk shipping business. My story had been only vaguely questioned by Spanish authorities. I'd altered my story to say I had no idea who the pirates were that had attacked and sunk Captain Brussels's ship. Then the Spaniards had, out of the goodness of their hearts, given me a coat and sent me on my way. After that it was up to me.

Using a little money the pirates had given me (I had told the Spaniards I found it on a corpse that washed ashore on the island I was wrecked on) I got a hot meal down my stomach then set about finding work. It wasn't hard. Luscious silks from Havana were in high demand. As were workers. Mind you, there was no shortage of both men and women wanting to work silk wool but when I had shown up at Senior Robert Havierez's business and managed to correct no less than a half dozen things he was doing wrong (both with his trading practices and his business sales) with such calm and knowing experience the hotheaded prick had (begrudgingly) hired me on. As a junior supervisor.

That had been two weeks ago. In two weeks, though he still didn't like me, I had done much for my boss's business and managed to ring a raise out of the prick, if for no other reason than to keep me from going to his rival's business. I'd gotten a raise for Diego Quantano too, who had fast become a good friend. Diego was Robert's nephew and therefor was the 'underboss' as he put it. It was from him I'd learned just about every detail of the business his uncle ran.

I won't lie, I do feel bad about lying to Diego and using him this way. I guess I'm not a total pirate just yet. Though for Captain Cold Eyes I would willing burn Diego's uncle's business down to the ground with him and his prick uncle inside it. I smiled to myself. Even having only been with the red haired pirate for a week, and seeing little of her unless I was in trouble at that, I knew I was already caught under her spell. And though she would deny it, she was a caught under mine a bit too. Hopefully caught enough to give me a share of the treasure of even let me stay on! I had some ideas for hauls once they had accepted me! Including robbing my father of everything he was worth!

But that is getting way ahead of yourself Leo, I scolded myself. First you have to pull this off. Cold Eyes said she had a contact in Havana. He had yet to make contact with me. She told me it would be at the two weeks mark.

I knew much but not enough to plan a successful piracy act yet. I needed to get my eyes on Senior Robert's shipping manifest, which contained all the dates for shipments of his silks for the next three months. Most were small, but according to Diego he sent off one bulk shipment every three months to some extremely rich noble back in Spain. The kind that needed fresh silk made for each of his three estates every couple of months. THAT was the haul I needed to get a timetable on! Unfortunately he never sent the bulk shipment of flawless silk on the same ship. It was always by a different merchant on a different ship. No doubt to avoid someone (like me!) figuring out his timetable and selling the date to it, or stealing the shipment outright! I had to get a look at his personal books! But no one, even Diego, was allowed into Senior Robert's study. He made us all call him that, Senior Robert, at all times. Stuck up, arrogant Spaniard. But then what did one expect? Ever since the war more than a decade ago, the British Empire had begun to take more control of the New World, especially the Caribbean. The Spanish Empire had lost it's control of the throne of France as well as it's slave trade in the New World. The Spanish Empire was declining. And had been for years. Spain was as mighty a superpower empire as ever, or at least so was the pretense they put up. But the glory days were fast ending. Though no one said it aloud here in Havana of course. The Spaniards may have lost the war but they had not, and likely never would lose their sense of pride. Even at the expense of their own empire!

I don't have enough to act yet, I mused to myself pausing in the shade of a balcony. But I do have enough to keep Cold Eyes from declaring this whole scheme a failure. I did need to make contact with her contact, whomever that was. All she'd said was he'd approach me.

"Two weeks from when you arrive in Havana," she'd told me before she'd sent adrift on my makeshift piece of ship hull that was to help sell my shipwrecked story. "My agent will make contact. He'll be watching when you arrive on the beach, and he'll keep an eye on you all through Havana. If you sell us out, he'll see you dead."

"I'd expect nothing less Captain," I had responded.

"Exactly two weeks from when you arrive on Havana's shores you will go to a brothel, the Spanish Fly, and wait for him to make contact. Tell him what you've got. He'll judge if it's good enough and relay it to me. I trust you understand what happens if he decides it's not enough."

"I do indeed, M'lady the Captain."

"I actually think I'm going to miss hearing that. Now off with you!"

And that had been that. I had searched the city during my first couple of days here to find the Spanish Fly and had done so. A typical brothel in the Caribbean that catered to sailor's base needs once they came ashore after months at sea. As well as relieve the sailors of their hard-earned coin too. I decided to go to the Spanish Fly and await my contact.

It wasn't hard to find once you knew the layout of Havana's streets. Ironically there was a church at the other end of the block. Sin and sainthood within spitting distance of each other! The irony made me laugh as I approached the brothel. The ladies eyed my fine clothes, a benefit of working for a silk merchant. Senior Robert Havierez would not have anyone on his staff that looked like a vagabond, so I was properly clothed in fine clothes for the first time in my life. My looks also attracted their attention. The girls were all dressed, though loosely. This brothel was one of the more respectable ones. No sexual acts were in the common room (the occasional cock stroke or breast cup non withstanding) all the lewd acts happened behind closed doors. I was a new face so I caught attention.

The madam arrived shortly after my arrival. "Welcome my dear boy," she said. She had the look of a lifelong whore who was now too old to be considered desirable and now ran the business and cared for the girls. "I don't think I know you. You are far too pretty to be a sailor and too well dressed also."

"Actually M'lady I was a sailor until I was shipwrecked. Now I work for a silk merchant."

"Oh my, such manners. Who are you?"

"I am Leonardo Sanfino."

"That sounds Italian."

"It is. I'm a long way from Florence for sure."

"Well, Rosita is waiting for you."

I blinked. "I wasn't aware someone was waiting for me."

"Oh yes, your name is distinctive. I was told to give you a room when you arrived. Now go on, you're distracting my girls and angering my other customers."

Sure enough she was right. The other whores kept winking at me. The other customers were glaring. So I went up the stairs, passed the rather large pair of men who worked security, and went into the designated room.

Inside was a typical Havana girl, brown hair, dusky skinned from all the sun, in a red dress. I did like her dress. Having been at sea with Captain Brussels for months, then with Captain Cold Eyes for a week, then ashore in Havana working my way into Senior Robert's business, I'd not had any time to visit women for that urge. Rosita's breasts were large and her smile was inviting. "Someone paid for you to be with me?" I asked.

"Si Senior," she responded.

"Do you speak English?"

"Little, Senior."

"Fortunately for you I'm fluent in both," I promised in Spanish.

She smiled but before I could say anything else a door opened from the balcony. In walked a man with dark skin, dark hair, and small dark eyes. His clothes were unremarkable. His face unremarkable. He could have been any one of such men on the streets of Havana. "So boy, what do you have for the Captain?" he asked in English.

This was Captain Cold Eye's contact. Or was it? Was this a test? "Which captain?" I responded.

"Captain Cold Eyes."

"A mysterious captain to say the least," I said. "Once doesn't even know if he's real."

Dave2526
Dave2526
108 Followers