Black Sail

Eh heh… well… I wrote this story long before I did “Long Night” … and well I didn’t expect to get reviews… to tell the truth… and I wasn’t planning on writing another chapter… it was written in boredom you see… So… While I’m debating on writing another chapter I’ll let you guys enjoy this little Story… it’s not finished… but yah.

No lemon in this chapter… but be warned the next one… well it’s pretty much all there is in it! Lots of lemon!!! ^-^
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A cat call echoes over the quite waters of the harbor as a dark figure silently approaches the ship towering over the docked fishing boats. White ocean battered letters glimmer dully in the full moons soft rays. The words name it “the Black Sail.”

Short choppy brown hair hides under a large dark green hat and a slim female figure is hidden under a loose male shift and baggy trousers. Dark sapphire blue eyes peer up at the ship’s hull under brown messy bangs. A look of hope and fear crossed the females face. Jessica knew this ship was her last and only chance to continue living.

After her home had been burned down in a grass fire her entire had life burned down along with her home, she had lived on her own for two months eating what ever she could get her hands on. At first she hadn’t to much trouble surviving on the food she had in her satchel from when she had tried to run away from home, but after all her food was depleted she found that the grass fire had burned down anything editable for miles.

Her stomach demanding she give it something she had decided to head to town while still wearing her big brothers clothes that she had run away in. She would try and get a job as a boy at the Harbor. She soon learned that what would have taken a day by horse turned into a week’s trip on feet. It didn’t help that she was terribly week from loss of food and she often had to sit down to rest.

Once she had come to the harbor things didn’t become as easy as she had thought. Her dirty and grimy clothes only got her judgmental glances and little to no work. Sleeping on the streets with little to no food had caused her once plump and round figure to become a skinny figure with her ribs showing. She had to find some way to get a steady job so she could survive. There was no doubt in her mind that if she continued this life style that she would die a slow and painful death.

Then luckily she had over heard two merchants men talking about the Black Sail that was said to be coming to the harbor in a few weeks. She had been deathly still as they had talked about how it was a Trade ship for their country and a pirate ship for other countries. It was just rumor they said, but some people were sure that it was in deed a pirate ship in disguise.

Listening to more rumors Jessica had learned of how the Cabin boys often did little to no work. They were to warm the bed of the Captain every night until he tired of them. Once they were finished with their trip and had returned back to harbor the cabin boy would leave with enough money to have to never work again.

Knowing that rumors were only half truths Jessica decided to try and become the new cabin boy for the Black Sail. She had nothing to loose. So saving up money over the few weeks before the ship arrived Jessica had managed to arrange a meeting with the first mate about becoming the next cabin boy. With the money she had saved she was able to get her clothes and her self washed the day of her meeting.

And here she was waiting under the full moon for her interviewer. A loud constant taping of some one’s boot against wood filled the night as a large burly man moved down the catwalk towards Jessica. She watched him silently as he approached her coming out of the thick fog that floated about the harbor.

“Ya he’r f’r ta job?” the man asked with a thick rolling accent just barley understandable.

Jessica nodded trying to hide her immediate disgust at the terrible smell which floated about the man like a terrible perfume that was been sprayed on too much.

“Yes.” She said softly her voice lowered an octave to give the image of a young man or boy.

The man looked Jessica up and down analiyzing her and finally nodded, “A’lright… ya gt ta job. Wha’s yu’r name lad?”

Jessica stopped for a moment, she hadn’t thought of a name… “Jess” She said spouting her brothers nick name for her.

He grunted nodding pointing a finger at himself, “Ol’ Jimbo’.” He motioned for her to follow him as he turned back up the catwalk. She followed him to the ship and along the deck to a well carved mahogany door. He opened the door and nudged her to go in which she obediently obeyed. She listened as his footsteps fell away from the door before she took to looking about the room.

Her mouth was left open at the plush carpet, drapes, paintings, a desk and a large pillowed bed with velvet soft comforters on top. She had heard that the captain treated his cabin boys well but she hadn’t thought it to be THIS well! She yawned tiredly as she heard a man walk by the door saying something about them heading out tomorrow morning.

Jess was having trouble keeping her eyes opened and crawled her way to the bed. She was hungry but she figured she would get something to eat in the morning. Crawling out of her heavy clothes and left in nothing but undergarments she shifted under the blankets of the bed cuddling up in the warmth of the blankets and the softness of the bed. She swiftly drifted off to sleep oblivious to the man entering the room.

A tall man well muscled with black tumbling hair, a clean shaven face and wearing a red tailored cotton jacket over his white shirt and tight fitting black trousers stood talking to another man. His name was Captain Arin of the Black Sail. Arin finally dismissed Herk, his second in command, as he headed to his bed chamber. He knew that Jimbo had arranged for a new cabin boy to warm his bed on their new and very long trip, Jimbo was one of the best men he had when it came to choosing good cabin boys. They were often pretty and screamed erotically every time he bedded them. He wondered what type of a treat he would have this time. He hoped it was a really pretty one to keep him entertained for the next few years, for they didn’t plan on coming back to this harbor for a long time.

Depending on how well of a job Jimbo did he just might be entertaining himself tonight to take the tension from playing a trading ships captain. Perhaps he would tie the boy down to the bed as he introduced the boy to pleasures never experienced before. He smiled lazily at that thought as he slowly opened the door to his room.

His eyes wandered about the room as he closed the door behind him locking it. He didn’t want his new cabin boy trying to escape once he found out what his true purpose was. His violet eyes spotted the slim figure of the cabin boy on the bed. a hungry smile lit his face as he looked over the boy. His short ragged bed mussed hair framed a beautiful oval face, and the pale skin showing through the undergarments caused his pants to become tighter. Jimbo had done a very good job.

He stalked towards the boy watching the slim figure as he slept. He must have been tired to have fallen asleep by now, but no matter the boy would soon become much more so tired once he was done with the boy.

Jess snuggled further into the sheets happily falling into a dream were her mother and father were alive and had found her as she struggled to survive on the road. Arin lowered his hand down onto the boys shoulder shaking him, “Wake up boy.” Jess’s world was suddenly under the assault of an earth quake as she was shaken out of her dream.

Her eyes opened slowly in confusion, “Wha?...” She mumbled from tired lips.

Arin found himself smirking as he saw the sapphire blue eyes, the boy was much prettier than he had originally thought, “Hello there boy.” He sayed huskily.

For a moment Jess was confused and wondering why she was being called a he and even more so confused as to why she was being shaken awake. “Hello…” She muttered softly in reply to him.

“So you’re my new boy, hm?” He spoke as he looked her over, “Not bad… not bad at all.”

Jess was confused as to why this man was looking at her with such hunger and lustfulness, she nodded slightly still wondering what was going on.

His eyes narrowed, “Good.” His voice was low and husky as he crawled onto the bed covering her body with his. Before she could reply she felt his hands pulling the blankets off her and roaming all over her as his mouth covered hers preventing her from saying anything. She struggled against him but she felt him hold her tighter and something was poking against her thighs. Arin was enjoying kissing his struggling little treat as his hands roamed along the boys skin moving under his undergarments to pull them off and feel along the boys soft silky skin.

His tongue forced entrance into her mouth as his hands continued to tug her clothes off. She struggled harder but the more she did the tighter he held her down and that thing poking against her thigh grew harder. She made a whimpering noise against him and his hands moved to between her legs and he suddenly stopped. She was glad when he quickly pulled back but didn’t like the large amount of swear words that came from his mouth as he did so.

He sat back calming himself down before turning angry violet eyes towards her. Yes he was right. HE was actually a SHE. Her pale breasts and naked body glowed in the candle light.

“And just how did you get in here.” He asked angrily. Here he thought he had the perfect Cabin boy and his perfect treat turned out to be a female! His treat was suddenly very sour.

“J…Jim… jimbo…. Ne… new ca…cabin… b…boy…” she stuttered trying to cover herself.

“You aren’t a boy.” He stated angrily. She was supposed to be a HE!

Jess looked down in shame and shook her head, “No…”

“Why are you here then.”

“There was no other way I could get food…”

Arin frowned cutting her off, “And just why would I let you on here as a girl?”

Jess paused, she hadn’t thought this through… she hadn’t thought this through at all. “I… I was hopping I could go as a boy…” she said softly, “Disguise myself… I haven’t eaten anything for two weeks… please don’t kick me off.” She begged.

Arin growled, “You’re on a Pirate ship, not a mercy vessel!”

She winced as his angry words washed over her, “True…” She franticly tried to think of something to convince him to let her stay, “But you’re going to sail tomorrow morning… you don’t have time to get a new cabin boy.”

Arin growled as her words rand true. He saw Jess looking at him from under her ragged bangs her blue eyes shinning through them. She had heard that he slept with his cabin boys, she should have paid more attention to that detail! Jess thought. Now what was she going to do? He looked so slim and handsome, she almost didn’t mind if he decided to have her take the place of his cabin boys.


“I’ll do what ever you want me to do.” She says softly as her plea.

“Who says I want a GIRL to do anything for me?” He asked angrily growling at her.

Jess glared at him insulted he would think her so low, “I didn’t mean THAT type of work!” Arin shruged her comment aside as she continued, “Any WORK you want me to do. I’ll do it.”

“Maybe I don’t use my boys to work.”

She became pale as he just made the rumors become truth, “so the rumors were true…” She franticly tried to think of something anything to convince him to let her stay, “But… you could have extra help.”

He crossed his arms in a angry closed off way showing that he wasn’t listening to anything else she had to say.

With that Jess sighed her shoulders drooping as she give up, this was getting her no were and if they kicked her out she would die a slow and painful death. “Then please… kill me”

Arin paused, her hurt and hopeless voice hitting him some where in his dark hardened heart. What could be so bad that she would beg death?

“And if I let you stay?... what of it?”

Jess blinked hope starting to swell within her as she tried desperately to push it back down, “I’ll do any work you want me to do for food and nothing else.”

He was silent as he pondered over her words, free labor… He looked at her beautiful blue eyes looking up at him hope shining in their depths and he cursed silently wishing that she was a boy as he hadn’t seen women very much.

She bit on her lower lip as she waited for an answer between life and death. She heared him let out a small breath of air, “Fine” he muttered.

Jess smiled and in her excitement hugged him while still nude, “Thank you thank you thank you!” She blushed deeply feeling her breasts pressing against his chest and realized what she did and quickly jumped back away from him, “sorry…”

Arin had felt himself grow hot and excited as her soft body had hugged against him and he found himself a bit flustered “Hmph.”

“Um… were should I sleep now?”

“On the floor,” Arin replied.

“the floor?... Can’t I sleep with the rest of the crew?” She asked, wanting to get away from this man.

“They’d rape you in a second,” He smirked nastily at her.

“Oh…” She sliped from the bed quickly pulling her clothes on and laying down on the plush carpet curling up.

Arin lay himself down on the bed not very happy about not having his cabin boy for the night. Thoughts did enter his mind of having his way anyways. She seemed to arouse him just as his normal cabin boys did.

Jess laid curled on the floor just happy to be alive and quickly fell asleep on the soft carpet.