Freedom on the Sea

The man's eyes narrowed. "She doesn't understand English well, and even if she did she knows better than to talk. I own this brothel."

"Forgive me for being cautions. I had no idea the captain kept brothel owners as her contacts. I'm Leo. As you know."

"I do indeed. And my name will remain blank. I pass along information that comes from the sailors downstairs to Cold Eyes. Now, I have work to do and you are slowing things down. What do you have?"

I told him as quickly as I could. Rosita kept smiling naively. Either she really didn't understand or she was indeed as loyal as the brothel owner said. "Give me another week and I'll have the date for the bulk shipment," I finished.

The man appraised me for a time, then nodded. "I'll relay it. But one more week is all boy. After that, your chances are up." He made to leave.

"What about her?" I asked pointing to Rosita.

"Have her if you want her. I told the Madam she'd be upstairs for a while." Then the owner was gone.

Apparently Rosita understood enough and pulled her dress down. Her big breasts spilled out, tiny dusky nipples displayed proudly. I began to get hard instantly. I motioned for her to come to me and she came. I pulled her nipples to my mouth and sucked on them. Her hands found my pants and rubbed my growing erection. Small gasps escaped her as I suckled her nipples, pulling her dress down the rest of the way.

Rosita was soft, her pubic hair dark, her ass round. I smacked it and made her squeak enjoyable as she produced my hard shaft from my pants and stroked me. I'm not bad, cock size wise. I'd seen bigger on black slaves and sailors of course, but no woman I'd had had ever complained. "Suck," I said pulling my mouth from her now-erect nipples.

Rosita knew enough English for that command and fell to her knees, using her dress as a cushion. She swallowed my cock deeply and began working hard. The skill of a experienced whore. I moaned loud and leaned my head back. I wondered if Captain Cold Eyes ever sucked cock like this? She was a woman after all! Forget her you idiot! I scolded myself again. Focus on the one actually pleasuring you! Not the one you'll never have!

Eventually I needed more and pulled Rosita up. She knew what was next and bent over, clutching the bedpost. Her cunt was tight looking and as dusky as the rest of her but when my cockhead prized her lips apart, there was pink in there. She moaned as I filled her and I moaned as I hit as far as I could go. Grabbing two handfuls of her ass I began pumping her deep. Rosita began moaning loudly as I pumped her quickly. Even though I was pent up from months at sea and work, I knew how to control myself and not spew in seconds. I began going harder and Rosita moaned all the louder. I knew whores likely practiced on moaning like they were in ecstatic pleasure, lest the offend a customer, but I like to think that Rosita's moans were genuine. Then again, she hadn't cost me a dime so who cares?

I pulled out of her and laid down on the bed. Rosita came without a word and mounted me, straddling me and sliding up and down on my cock, Her face was lit with pleasure and she fondled her bouncing breasts with both her hands. I reached up and moved her hands aside, squeezing her round breasts myself. She moaned loud and her head leaned back, her back arching. I brought my hands down to her hips and helped her bounce deeper, taking me into her more and more. Her moans were non stop and her hands resumed squeezing her breasts hard, pinching her own nipples. I pulled her down and planted her breasts in my face as I really started pounding the little whore deep.

Rosita's moans were loud in my ear. Her cunt was clutching and squeezing at my cock and I felt her begin to convulse. I rammed harder as she screamed loud and shook, orgasming hard. A few seconds later I yelled myself as all my pent up weeks erupted out of my cock and into her cunt. I clutched her too me, burying my face in her breasts, until I shot my last drop.

I gently pushed Rosita off me and saw the guard at the door looking in through a crack. "What?" I asked jokingly. "Not used to hearing your girls have real orgasms? Probably only used to hearing them fake it." I smiled.

The guard shut the door without a word.

I laughed and looked at Rosita. She was flat on her back, lightly rubbing her cunt as some of my seed leaked out her hole. "Senorita happy?" I asked.

"Si Senior! Si!"

"Good. I come again to see my favorite Senorita."

"Si!"

I squeezed her breasts one more time each then got up and redressed. I let myself out and winked at the guards on my way down. I waved to the madam and headed back to the street, making my way to the tavern I was staying at. It was sunset and Havana's usual intense heat was cooling to the point where it was almost pleasant.

Once the pleasure of fucking Rosita faded my mind returned to my task. I had one week to get that manifest and ship timetable!

Chapter 5: Breaking And Entering.

My week was nearly up. This thought went through my head a dozen times a day as the date got closer and closer. But I had to wait for the right moment before I could break into Senior Robert's office. I was no burglar. Nor a lock picker. I had to wait and take my chance when the moment was right.

"Are you with me?" Diego asked suddenly.

"Oh," I shook my head, realizing I had lost in thought. "Sorry Diego, thinking of Rosita," I lied.

"Don't fall in love with a whore," he said going back to his list.

I forced a smile. I'd visited Rosita twice more since my initial visit. Apparently she was quite popular and how much I had to pay reflected that. But she was my only stress relief. And now even that wasn't working. My deadline still invaded my thinking process, even as I was mid thrust in her cunt!

I'd become her favorite. Or so she said. I'm sure she said the same to all her customers so how true it was was debatable. I never questioned it but I was probably pretty high on her list. Her orgasms were quite wet. And the other whores began to wonder, but I'd see only Rosita. Maintaining my cover was paramount and I'm sure that man was watching me. So I kept up the pretense of young boy, and every young boy has a thing for a whore at some point. Usually their first one. Though Rosita was not my first whore, I pretended such.

"Leonardo," said Diego's voice. "You're off again. We need to get this done!"

I shook my head again and resumed my work, a inventory check. This was a sign that the silk shipment was leaving soon. So my deadline was running out in more ways than one. I had to get solid information! And since Diego was an underboss, I was hoping he knew something!

With that in mind I started talking. "Why are we taking inventory now?" I grumbled. "We just did this last week! Why is Senior Robert so paranoid?"

"Big shipment," said Diego.

"Hopefully it sails soon so we can take a breath!"

"In five days the ship comes for the massive order," says Diego.

"Which ship?"

"Only the Senior knows and he doesn't say," Diego looked at me. "Why so curious?"

"I'm only asking so I know when he'll put the whip away and we can relax!" I said going back to my list. It was a reasonable answer and Diego didn't question it. I'd gained a little, I knew now that the ship was coming in five days. But not which ship. Dammit! It was no good. Tomorrow was my last day of my deadline. I needed that schedule! So it was time to act! "Is the Senior away?" I asked.

"Stepped out for lunch, he should be back soon."

"Oh good, I can sneak off to Rosita and be back before he notices!"

"Leonardo you can do better than a harlot," he sighed.

"Well if you know anyone more respectable I will gladly meet them. Until then, I'm off! You can turn me in if you don't like it!"

He only grumbled. Diego wouldn't turn me in. Without me, his job was a million times harder. He never visited whores, or so he said. I wondered what his release from the daily stresses was because I'd never seen him drink either. No drink, no women. Nor did he smoke Havana's famous tobacco. He was a true workhorse. I slipped away and waited until I knew he would be engrossed in his work again before making my way toward Senior Robert's office. The door was locked as I learned when I tried it but the window, though shut, was not securely shut. It must have been left open in a hope of a breeze.

Praying no other workers were nearby I pushed. The window slid open noiselessly enough. I slipped in.

The office was lavish, but one could expect nothing less from a silk merchant. I remembered my father's well enough, Lush, lavish, bordering on the ridiculous. And my stepmother's kleptomaniac love for shiny things only made it worse. Shaking off the bitter memories I started opening drawers. Searching shelves. If I was caught now, I would be arrested for thieving. But being killed my Captain Cold Eyes for not coming through on what I'd promised was far worse. I didn't destroy the office, that would be a give away that someone was in here. I made sure I jostled no papers and out everything back in it's proper spot once I'd searched through it.

If Senior Robert had kept the schedule, I was done fore. There was no way I could pry it from his person, he kept hold of it like it was his first born son. This was my last chance. If it came up to be nothing, I would have to run. Or sell Captain Cold Eyes to the Spaniards. And THAT, for reasons I could not explain even to myself, I would not do. I'd given her my word and that was all I had in this miserable world! I was going to keep it!

I stepped across the floor and heard a board creak. Looking down I pressed. A loose floorboard! Clever Senior Robert, I thought to myself pulling the board up. No one would expect a stuck-up Spaniard to rely on such cheap tricks. Bringing out a box I pulled the lid off. It was the schedule! "Oh thank you God, even though I've cursed you a million times," I muttered out loud. I searched pages and found the one I was looking for. "The ship's name is the Hermione. Huh. Good to know." I closed the book, put it back where I found it, put back the floorboard and made for the window. Getting outside the room and closing the window I couldn't help but jump up and down. I'd done it!

"Leonardo?" asked a voice. Diego was standing behind me looking shocked.

Oh fucking hell! "Si?" I asked unable to form any other words.

"What were you doing? Fucking you whore in the Senior's office?"

"Yes!" I said grabbing hold of the line he'd just given me. "Revenge for so much extra work!"

"Where's Rosita then? I should meet this whore who's got your attention."

Oh come on! "She's getting dressed."

"Fine, I'll wait."

This could not be happening! "I uh, told her to go out the front."

"Then Mr. Sanchez would have seen her, he's at the front desk. In fact," Diego's eyes narrowed. "He would have likely heard you two. Whores are loud."

"Maybe he's been engrossed in the same level of hard work we have?" I asked. Feeble lie Leo, he's not an idiot.

"I highly doubt that. What were you doing in the office?"

Now I was fucked. I had to hope I could spin this. "Truthfully Diego, I was captured by pirates," I confessed deciding to go straight for the honesty. It would shock him, hopefully, and give me a chance to think of something else. "By Captain Cold Eyes. She wanted to kill me but I convinced her I was a chance at a rich prize. So she sent me here to learn what I could to steal Senior Robert's silk."

Diego looked baffled but angry. "If pirates captured you, you'd be dead. Captain Cold Eyes? Never heard of her. And her?" he put heavy emphasis on the word. "A female captain pirate? Such a thing is impossible."

"Tell that to Anne Bonny and Mary Read."

"Neither of them are captains. No man would willing submit to a woman as captain. Such things are not done. Nor acceptable. Nor tolerated. You're spinning elaborate lies to try and confuse me! You're from our business rivals aren't you! I dammed spy I've been calling a friend all this time!"

I couldn't help it, I laughed. I'd told him the God's honest truth and he hadn't believed me. In his defense, my story is farfetched to those who didn't see it happen. But the ridiculousness of it all made me laugh.

Which was the exact wrong thing to do. He seemingly became convinced at my laughter that he'd guessed it all right. "You're done," he said. "Senior Robert will hear of this. So will the soldiers! You'll hang!"

Sorry Diego, I thought to myself. I did the last thing he'd likely expect. He was clearly expecting me to run. So I lowered my head and charged full speed. I hit Diego in a crash and we fell to the dirty street. Diego was about my size but he was a underboss, and had never done any real hard labor. I could out strength him. And did. I rolled him over and locked my arms around his neck in a choke. "Believe it or not Diego," I said in his ear as he thrashed. "I was telling the truth. I'm sorry about this. But my life's on the line. In more ways than you know." I tightened my grip and squeezed. His thrashing was subsiding. He was running out of air.

If I killed him, I knew I'd never be able to explain it all to anyone. Killing Diego was not my plan. He had been my friend and I felt bad that it came to this. But he'd been wrong place, wrong time. Diego passed out finally. I smashed his face off the ground to ensure it. Then I picked him up, threw his arm around my shoulders and hauled him onto the street, making for the brothel.

Street goers stared. "Too much to drink, drunk too early!" one person said. I nodded and eventually they stopped looking and I was able to get him to the brothel without much more attention. Once inside though, it was a different story. The madam came to me at once. "I want no trouble in here and-"

"Go find the man in charge. No don't give me that perplexed look, the man who owns this brothel," I snapped as she tried to look dumb. Then I hauled Diego's unconscious form up the stairs and into a room. A man was in midst of being sucked by a topless whore on her knees. "Take it to another room!" I snarled. They both jumped but something in my face told them to go. I dumped Diego onto the bed and waited.

Sure enough, the nameless man arrived. "What have you done?"

"Gotten the ship name and it's schedule for the silk haul," I said. "But there was a complication. He found me out. Assumed I was stealing for a rival company. I had to take care of him. He's not dead. Dead would bring more questions. But I couldn't leave him."

"The ship name and schedule?" the nameless man asked irritably.

"Ship's name is the Hermione. It arrives tomorrow. Five days it will be loaded with silk and from it departs Havana for Florida, then on to Spain."

"I must admit, I didn't think you'd pull it off."

"I'm sure you're not the only one."

"What do you expect me to do with him?"

"My employer will notice his missing, that's unavoidable." I said thinking fast. "I can't risk him panicking and altering the silk ship's schedule forward. I'll explain that Diego isn't feeling well and went home sick."

"That excuse will work for today boy but not tomorrow or any other day. No I'll work it out."

"How?"

"I'll make it look like he was set upon by thieves after work, robbed and killed. It'll look like a robbery."

"I don't want him to die!"

"His death was signed the moment he found you out, boy. And yours, I might add, is still not out of the woods! You're lucky you showed up. Cap'n Cold Eyes said you were to die at midnight if you hadn't come by today's end! But you delivered. So you've bought yourself some more time. For now. We'll see if your scheme actually works. Now get lost. I'll deal with him."

Angry, I stormed out. Rosita was waiting for me. "Senior have time?" she asked with a smile.

"Senorita fuck off!" I snarled. She jumped and ran and I stormed out of the brothel. I went to an ally and kicked a barrel as hard as I could. Diego was my friend, he didn't deserve to die!

But I'd done it! I'd delivered on my promise!

At the cost of his life.

But what did that matter? Mine was secure!

No it wasn't. And there was no assurance that it would be even after I was able to deliver on the silk ship! I'd extended my time again, nothing more. For what? So Captain Cold cunt could make a profit?

I sat down on the barrel I'd kicked over. Such was the price of freedom. No wonder all the pirates were hard cases and pieces of shit. You had to be such to live this way. Diego Quantano was a good man who only ever been my friend. And I'd signed his death.

Enough, I ordered myself. Enough. It can't be helped. Now, go back in there, apologize to Rosita, and be ready for questions when Diego's body is found. I stood up. As I went back to the brothel I began to wonder if I was really cut out for life of piracy after all. All that shit I'd hoped would come true, robbing my father, becoming respected, and (I couldn't deny it) fucking Captain Cold Eyes, all that didn't seem worth the price of Diego's life. I hoped I'd feel better after an ale and Rosita's lips around my cock. But I somehow doubted it.

I was in to deep to back out now.

Chapter 6: The Cold Eyes Warm

I woke up the next morning to a banging outside my door. Images of Spanish soldiers outside with muskets ready and loading, looking to arrest me for Diego's death flashed across my mind and I quickly looked for an escape but there was only one door and one window. Both were likely covered. The banging was getting quite insistent. I took a breath and answered it.

It was Mr. Sanchez, Senior Robert's secretary. "Where is Diego? He hasn't reported for work yet."

I put the most innocent expression I could muster onto my face. Mr. Sanchez was bald and thin, his hands soft. He looked like a good gust of wind could knock him off balance. He'd been Senior Robert's secretary for years now. He didn't really like me. When we thought I was street trash. Then when I corrected both him and Senior Robert on some of their techniques on the merchant business, his opinion of me became bottom-of-the-ocean low. But he never contradicted his boss (which was why Senior Robert's business was so easy for me to find flaws in) so he was loyal to a fault. "I have no idea where Diego is sir." I said.

"This is most unlike him! Today's a big day!"

"I don't have a clue sir," I said.

"When did you last see him?"

"Yesterday after work. I was going-"

"To visit your whore I assume," he interrupted. I nodded without answering. Mr. Sanchez scowled. "Wasting time in sin when you could be working harder and gaining God's favor." He scolded. He, like Senior Robert and most Spaniards, was a devout Catholic.

"We parted ways yesterday, I have not seen him sense," I said ignoring his scathing tine. "That was the last time I saw him."

"Well forget it, if he shows up then Senior Robert will hand him his head, family or not! Now get to work, we're moving a lot of product today."

I nodded without answering and got to work at once. Working hard all day down at the docks to help load the ship. The easygoing conversations I had with Diego were not possible with the other workers, who shared Mr. Sanchez's opinion that I was trouble. It made me miss Diego more. I wondered when his body would be found, then shook the thought from my mind and kept working.

I'd delivered my information, gotten the schedule to Captain Cold Eyes but heard nothing sense. Perhaps she was going to leave me here and take the prize without me. She was a pirate after all! That would serve me right for being responsible for Diego's death.

I worked the day away and eventually the ship was loaded. The Hermione set sail full of Senior Robert's silk. I wondered how far it'd get before Captain Cold Eyes took it. I trudged back to my room, wanting to wallow in peace. But the sun had barely set before there was a knock on my door. No one from Senior Robert's organization bothered me at this hour. The images of Spanish soldiers flashed before my mind again but this time I couldn't even summon the will to be worried.