Disclaimer: This is a work of fiction and as such is a product of my imagination and not real life, please forgive any historical inaccuracies. The story will include descriptions of sexual activity. One brief scene hetero, and the rest will between teen boys, and in later chapters, between men and boys. If material of this kind might offend you then please stop reading, all others, enjoy! You are welcome to send comments or story ideas to Playbuddy123@yahoo.com
Tortuga Gold -- A Pirates Tale (b/b, M/b)
Born on the last day of October in 1656, the child came into the world on a stormy night in a dimly lit room of a public house. The lass, barely nineteen, had become pregnant by an unknown man. It often happened in her profession. She gave the boy the name "Chandler" after one of her more frequent visitors. She thought the town's candle maker was a pleasant enough sort, and chose the name with him in mind. Starting life under such circumstances didn't offer much hope for a bright future.
In the fourteen years since, Port Royal Jamaica flourished. The town, seized by England in 1655, was now known as a place of such debauchery as to have no rival in the Caribbean. In fact, it was said of Port Royal, that it was the `wickedest city on earth'.
The Black Dogg tavern, Mr. John Starr proprietor, served a variety of social classes. The solidly built three story brick structure had a grog room for merchants, one for seaman and tradesmen, and a third for conducting business of a more personal nature. The most recent census listed twenty one white women and two Negro women in Mr. Starr's employ. They did a great deal more than serve drinks.
"Chandler!" Mr. Starr yelled across the noisy room.
"Yes, sir?" the lad placed four pewter mugs down on the table at which several deck hands from the "Tortuga" were sitting, and then hurried over.
"See that Mary gets back down here. She's been too long upstairs. That sod's time is up."
Chandler made his way through the crowd, the patrons so intent on their drink that they paid no attention to the slender boy. At little more than five feet tall and barely a hundred pounds, the lad was small for his age. As he climbed the steps, Chandler noted that the thick tobacco smoke, the smell of rum, and the sound of laughter seemed to follow him. Arriving at a room at the top of the stairs, he pounded his fist against the door.
"John says time's up! He wants you downstairs, now!" he yelled.
"This bastard's so drunk he can't finish his business!" Mary answered.
Chandler slapped the door a couple of more times with an open hand. "Tell him he's got five minutes, or John will be up here!"
Chandler knew he didn't need to finish the sentence. John Starr was well over six feet, and sported two hundred and fifty pounds of muscle. Mary's current customer wouldn't be the first to be thrown down the stairs, slammed against a wall, and then tossed out into the mud of the street. Nor, thought Chandler, would he be the last.
The Tortuga (Turtle) had sailed into port the previous day after a successful time at sea. The crew called themselves "Privateers," as distinguished from "Pirates." Their captain had received letters of authorization from the governor which sanctioned their murderous activity. It was a subtle difference to be sure, but it was useful for appearance sake. Whatever the name, privateer or pirate, all were welcome in Port Royal.
After raiding a Spanish treasure ship, the crew of the Tortuga had been rewarded with a share of the spoils. Their new found wealth probably wouldn't last long however. It wasn't uncommon for a man to spend his entire fortune in a few days on rum, women, and gambling. The Black Dogg was having a very profitable night.
"So what's going on in the house then?" A voice called from the shadows.
Chandler stopped mid-pee, the stream trickling to a few drops as he stood outside the back door of the tavern.
"What?" he turned to look over his shoulder, "Who's there?"
"Thomas Piper," came the answer.
"Better come out or I'll call John."
A figure slowly emerged from the darkness.
"Go ahead, finish your pee."
Chandler saw that the voice had come from a boy not much older than himself. He was dressed like he'd just come off a ship or spent a great deal of time around the harbor.
"What are you doing back there?"
"Dunno do I? Just woke up, not sure how I got there," the lad chuckled.
Chandler stood with his dick in one hand and the other holding his breeches down in front.
"So are you going to just stand there with your cock out?"
Chandler blushed, turned toward the wall and tried to finish what he had started. But now with an audience, his kidneys became bashful and things wouldn't work. Closing his eyes, he settled himself down, and with a second effort met with success. Shaking the last drops off the end he tucked it away.
"Are there any pretty ones in there?" Thomas asked as he pulled a pipe and a small rag from his pocket. He carefully unwrapped the cloth, picked up a pinch of tobacco, and pushed it firmly into the bowl.
"I guess," Chandler shrugged, though it occurred to him he had never really looked at the women in the house in that way.
"I could do with a bit of fun," the boy smiled.
"You're out of luck, we're closed."
"Shame, that," Thomas shook his head, "I was in the mood for it! So what are YOU doing here?"
"I live here."
"Your mum is one of them then?"
"Don't really know, no one ever told me who my mum was. They all kind of raised me." Chandler shrugged.
"What's your name?"
"Chandler."
"Chandler what?"
"Just Chandler, there's no more"
"Well, nice to meet you, Just Chandler," Thomas smiled.
The boys stared at one another a moment longer. There was something in the way Thomas looked at Chandler he couldn't describe. Perhaps it was curiosity, or maybe something else. It was difficult to tell.
"Maybe I'll come round tomorrow then."
Chandler nodded, "John will take of it, he'll make sure you find what you want," Chandler said, turning for the door.
"We'll see about that," Thomas chuckled.
The following evening, Chandler looked up from wiping a table to see the young man from the night before.
"I came to see what there is then..."
"John's over there, he'll help you out," Chandler answered as he picked up an empty wine bottle.
"Not like I've done this before," the boy said with considerably less swagger.
The look on the boy's face told the story. It was his first time in such a place.
"Come on then," Chandler nodded and headed for the owner.
"What's this about?" John grunted, wrestling a small cask toward a corner of the bar.
"I'm looking for a bit of fun."
Chandler chuckled, "Better see the money first!"
The boy gave Chandler an annoyed look, reached into his pocket and dropped five Spanish doubloons onto the counter.
John got a glint in his eye and smiled. "I'm sure we have just what you're looking for, sir," he said picking up one of the coins. "Chandler, fetch Sara."
Chandler nodded and went upstairs.
Starting around age twelve, Chandler had become more interested in the business that took place on the second floor of the house. He was curious about the coming and going of the men and women. As boys will do, he eventually found ways to see things for himself. After the initial surprise wore off, he found that he enjoyed watching the men as they drove their hardened members into the curly hair between the girl's legs. He'd stayed too long a couple of times and had gotten his ears boxed, so he made sure his visits were brief.
On one occasion however, he had stayed longer than usual. He had become so intrigued by what he was watching he had started to rub his own bulge. Before he had known what was happening he had rubbed it to such a state it had burst, making a mess in his breeches. The wonderful feeling that had washed over him that first time had been indescribable. He instantly figured out what had been such a mystery. The meaning of the sounds and words coming from the girl's rooms finally had made sense.
"No wonder they keep coming back," he had thought as he smiled and hurried off to clean himself.
"I'm Sara," the young girl said sweetly as she led Thomas up the stairs.
"I'm Tom," the boy replied softly. He reached out and placed his hand on the girl's bum as they climbed the last few steps.
"My, aren't you a bold one!" the girl giggled.
Tom smiled, "So how long have you been doing this then?"
"Since I was thirteen, going on about four years now."
Sara showed the boy into the room and motioned him toward the bed. She started to close the door but caught movement out of the corner of her eye. She smiled and left it open a tiny bit. Moments later an eye appeared.
Sara stepped to the bed where Tom was anxiously waiting. "Let's see then," she giggled as she started to undo the lad's shirt.
Tom blushed slightly and hurriedly undid the buttons, tossing the garment to the floor.
"Very nice," Sara said, running a finger slowly down the boy's smooth chest. "How old are you?"
"Sixteen."
"Have you been with many girls then?" Sara smiled sweetly as she reached for the button on his pants.
"Only two," Tom whispered as Sara's hand slipped inside searching for him.
"Don't worry, you'll do fine!" She whispered. She kissed him sweetly on the cheek as her fingers wrapped around his dick. "Mmmm, you have a big one."
"Oh, that feels good, that does!" Tom moaned.
Sara pulled the lad's penis a few times and then lightly pushed him backwards, urging him to lie down. She glanced over her shoulder. The door was open further than before.
Sara soon had the young man naked, extremely hard, and groaning under her touch. She stroked the sizeable shaft, pushing the skin back and forth over the head. Satisfied the lad was ready for what came next she sat back. She quickly pulled her dress over her head, removed her petticoat, and climbed naked onto the bed.
"These are pretty," Tom said reaching up and softly rubbing her breasts.
The girl leaned closer, gave him a brief kiss and then moved lower. When her mouth reached the throbbing shaft, the boy groaned and thrust upwards. She held him in her hand as she licked the head and then sucked. The boy thrust upwards again and with a bit of effort managed to take him all in. There was an appreciative moan. The talented girl continued her work, but sadly only a few short strokes later it was all over.
Tom grunted, closed his eyes and held her head tight to his crotch.
Sara moved her mouth up and down as the boy groaned. There was no doubt what was happening. Moments later, when his moans ceased, she pulled off and wiped her lips.
"You're a quick one!" Sara laughed, getting up from the bed and reaching for her clothes.
"No, no, wait! I can do it again," Tom begged, "We're not done are we?"
There was a muffled giggle from the hallway. Sara turned and chuckled. "What do you think, Chandler? Shall I give him another go?"
Tom's eyes grew wide. He quickly sat up. "Chandler?"
There was a playful laugh and the door clicked shut.
"You shouldn't spy like that," Tom said with a blush as he sat down at the table. Chandler was clearing it of food.
"Wasn't much to see," Chandler laughed.
"I suppose you could do better then?"
This time it was Chandler's turn to blush. He didn't say a word.
"You've never done it, have you?" Tom guessed.
Chandler turned and busied himself with his chores.
"I've done it hundreds of times," Tom boasted.
"Liar, you said you've only been with two girls."
Tom gave Chandler a knowing look. "I've been to sea, haven't I?"
Chandler looked confused.
"Living in a place like this and you don't know what happens on a ship?" Tom laughed with a roll of his eyes.
Chandler didn't know what he was missing, but Tom certainly seemed to know something that he didn't.
Tom pulled his pipe and tobacco from his pocket. "Get us a drink then," he winked and reached for the candle to light his smoke. "I've got some stories to tell!"
It was quiet in the house. The last of the customers had been shown out and Chandler was comfortable in his bed. John was in his room at the end of the hall and six women shared the remaining three rooms, two to a bed.
Lying on his back, Chandler thought about the things Tom had told him occurred at sea. At first he had been surprised. For some reason he had never considered the possibilities that a boy would do things with another boy. As Tom told him of the secret adventures he had shared with the cook's boy, Chandler had grown hard. The stories seemed to grow as they went along. He had even told of things that had happened with the men.
Thinking of the stories once again aroused Chandler. He reached down and took his cock into his hand. His penis, like the rest of him, was slender. It was however of good length for his age. He looked at the candle flickering near the bed. His cock was nearly as long and slightly thicker. "But, not as big as some I've seen," he thought sadly as he slowly stroked himself.
The image of Tom on his knees, taking another boy's cock into his mouth, caused Chandler's heart to race. His breathing quickened as he thought of his own dick sliding between the older boy's lips. He had watched the girls take a man into their mouth many times. The thought of Tom doing that deed was more erotic than Chandler could imagine.
"Suck it, then," Chandler whispered, closing his eyes and imagining holding Tom's head as Chandler pushed the end of his cock into the wetness of Tom's mouth. "It would be warm," Chandler thought as he used his other hand to play with the heavy sack beneath.
The fourteen year old worked his dick with practiced efficiency. He twisted his hand as he pulled on the shaft, rubbed his thumb over the soft head, and raised his ass off the bed from time to time, thrusting the stiff rod through tightly clenched fingers.
Chandler flashed back to the scene he had witnessed through the crack in the door. Tom was lying on his back, Sara pleasuring him, and the sounds of his voice as he groaned. Visions of other men and boys crowded out the one of Tom as Chandler grew closer and closer.
"Suck it," Chandler whimpered as he climbed to the top. When it came, the spasms of pleasure shook his entire being. It seemed as if the stuff pouring out was being drawn from a well and it kept bursting out in one long shot after another.
Finally, after what seemed like an eternity, the moment came to an end.
"Gawd, that was a fucking good one!"
Chandler ran a finger through the puddles on his chest and lower stomach, pushing the slippery white goop around on his belly. He raised his hand and stared at the wetness, several drips falling and forming new puddles.
"Tom said there was more to tell," Chandler whispered as he pushed the covers aside and carefully climbed from the bed in search of a rag. "What else could there be?" he thought and shrugged.
The sun was well up, in fact, it was past mid-day when Chandler woke, dressed, and left the tavern. He had a few coins in his pocket. They had been left on tables as tips, or forgotten in the drunkenness of the night before. He made his way down Queen Street, past High Street, and through the narrow lane along Lime Street. Hugging the harbor, Lime Street was filled with shops, vendors, people, and the every day stuff of a busy port.
The smell coming from the butcher turned Chandler's nose. Live chickens squawked in their cages, pigs milled about a small pen, and freshly slaughtered beef hung from hooks. Meat wouldn't keep in the heat, so the animals were dressed when the money was paid.
Chandler stopped at one stall for fresh bread, some fruit at another, and wine at a third. With breakfast in hand he searched for a spot to sit down and eat. He headed for a place on the sea wall so he could look out at the ships.
The Tortuga was swinging slowly on its anchor in a protected corner of the large harbor. The 36 cannon of Fort Charles protected the entrance and made the place safe for ships of opportunity. Whether pirate or privateer, the Crown felt it was important to protect the vessels that had, for years, been the only way to protect the island from a Spanish attack. It was a marriage of convenience.
As Chandler ate his meal, he wondered about the boy that had told him all those stories. He looked closely and tried to make out if he was on board. The ship was some ways off and it was impossible to know for sure. The fresh air of the harbor helped moderate the stench coming from the market. The bright sun was beating down and it promised to be another muggy day. The harbor was active with five ships being re-supplied and a number more biding their time until their captain decided it was time to set sail once again.
Chandler finished his food and tossed the scraps over the rock wall into the water. He had made up his mind and turned back to the busy market place.
Chandler was starting to lose hope of ever finding the boy when he almost literally stumbled upon him.
"What are you doing down there?"
Tom was seated on the ground, his back against the wall of a blacksmith's shop. His body was slumped over as if in death, but the occasional snort told Chandler he was in fact alive. "You're drunk," Chandler said with a look of disgust.
The boy didn't look up. Even when Chandler nudged him in the ribs with the toe of his boot he didn't move. Leaning down, Chandler found that Tom was passed out. What looked like his dinner was a smelly mess on his shirt. There was no doubt he had thrown up.
"I should just leave you here," Chandler said to no one in particular. He looked around and it was clear no one else was going to bother with a drunk in the street. Chandler took pity on him. "Well, let's get you home then," he sighed, struggling to wrap an arm around the lad and get him to his feet. Tom stirred a bit but couldn't walk. Chandler half carried and half dragged him back to the Black Dogg.
"What's with him?" Sara nodded as she looked up from where she was straightening some plates.
"Found him drunk in the street," Chandler grunted as he dumped the boy into a chair.
"He's a mess, he is!" Sara laughed softly.
"Will you help me clean him up a bit?"
Sara laughed, "It'll take more than a little bit, I'll wager!"
Between the two of them they managed to get Tom up the stairs.
"Into the bath with him," Sara sniffed and turned her head away. The smell of sick and rum was overpowering.
They dragged Tom into the room and sat him down near the tub, a large whisky barrel cut in half. Chandler found the smell almost more than he could manage. With Sara's help, Chandler unbuttoned his breeches, and pulled them down and off. He then got the lad's long shirt undone, pulled his arms through, and tossed it on the floor. In such a warm climate there was no use or need for any undergarment.
Sara took the boy's feet while Chandler took him under the arms, and they deposited him in the barrel. "Fetch some water," Sara sighed as she scooped up the clothes.
Six pails of water later, Sara scrubbed Tom's hair with soap as Chandler did his feet and legs.
"Want me to do his naughty bits?" Sara giggled as Chandler eyed the better than seven inch dick lying limp and lifeless between the boy's legs.
"No, I'll do it," Chandler whispered with a blush. He pulled the skin back from the head, rinsed it with water, and then with soaped hands, went at it. Tom still had not been roused from his drunken stupor. Vigorous scrubbing, another rinse, and Chandler finally finished his work.
Out of the tub, dried, and with a clean shirt, Tom was unceremoniously flopped face down on Chandler's bed. The boy's ass peeked out from beneath the shirt, it was a soft shade of pink.
"Let him sleep it off then," Sara said softly.
Chandler took one last look and closed the door.
There hadn't been much room, but Chandler wasn't about to sleep on the floor. Very early the next morning, after they closed the tavern, he had stripped down to a night shirt and slipped into bed next to Tom. Exhausted, sleep came quickly.
When he woke, Chandler saw Tom sitting on the floor near the bed.
"How did I get here then?"
Chandler yawned, stretched, and sat up. "Found you drunk in the street."
"Where are my things? My clothes? My Money?"
"You puked on yourself so we had to strip and bathe you. There wasn't any money."
"The hell you say!" Tom jumped up ready to fight.
Chandler scurried into the corner, still on the bed. "You were in the gutter by the blacksmith's; you didn't have anything with you."
Tom appeared to study Chandler for any sign of deceit, he calmed a bit, and then sadly sat back down. "Last I remember was being with two blokes from the ship," he said softly. He reached for his head as if in pain.
Chandler sat quietly, not wanting to prompt another outburst.
"Robbed! That's what's happened, I've been robbed!"
"How much was it?" Chandler whispered.
"Twenty pieces of gold," Tom said sadly.
Chandler didn't know what to say. Finally he said, "Sorry."
The two boys sat quietly for a moment.
"So, you brought me back here? Cleaned me up?"
Chandler nodded.
"Thanks," Tom whispered.
Chandler and Tom looked at one another for a long moment. Something seemed to pass between them, some understanding, that they were very much alike. Both were doing the best they could with whatever life threw at them. Lately, it hadn't been very easy.
Tom slowly got to his feet and crawled onto the bed.
Chandler tried to squeeze tighter against the wall, fearing that Tom would hit him. Instead, Tom drew near and staring Chandler in the eyes, slowly put his hand under the other boy's shirt and touched his dick. It instantly grew hard.
Chandler trembled with a combination of fear and excitement.
"What's this then?" Tom whispered as he wrapped his hand around the stiff member. The slender rod throbbed under his touch.
Chandler couldn't speak. His throat was dry and he couldn't find words.
"When a mate helps out another mate, like you done for me, the first one has to do something in return!"
Tom gently stroked Chandler's cock. "I know you've seen the girls put one of these in their mouth, but the way you was listening to my stories yesterday, I bet you've never had it done to you."
Chandler's eyes never left Tom's.
Tom stroked the boy a moment longer. Leaning over, Tom pushed the garment aside and stared at Chandler's dick.
"You've got a nice bit of hair around it for a boy your age."
"I don't think I want you doing this," Chandler finally managed. He thought of the times that drunks had grabbed at his ass or felt between his legs when he was younger. If John saw them, they were thrown into the street.
Tom slid the skin back from the head, hocked up a bit of spit and let it slowly drop from his mouth. It made a long string which landed onto the slit. "You want me to stop then?
Chandler was again speechless.
Tom smiled, "I thought so," he winked; expecting the boy to have spoken up if was serious about him stopping. Then, he slowly took him deep into his mouth.
Chandler groaned. His hands naturally fell to Tom's head. He remembered the scene when Sara had Tom in her mouth. Tom had been right, Chandler had no intention of asking him to stop. "Suck it then, if you're going to..." he whimpered.
Tom sucked, pulled back a bit and went back down. His hand slowly stroked the shaft as he expertly worked his tongue up and down.
Chandler moaned, and urged his new friend on. He could see Tom was skilled at this. "That's the way," he grunted.
Tom swirled his tongue around the head, stroked, and sucked for several minutes. Chandler's breathing was growing more ragged, his grunts more urgent.
Then without warning, the teen's cock was jerking.
"Oh, oh" Chandler panted. Four long squirts that seemed to come all the way from his toes, shot out the end of his dick and deep into Tom's mouth. Embarrassed at the suddenness and realizing what was happening, he tried to pull himself out, but Tom held him firmly in place and merely swallowed what he was delivering. Chandler's eye's rolled back, he groaned one last time, and surrendered.
The sounds of a door, footsteps in the hall and on the stairs, were background sounds to Chandler's heavy breathing. He slowly came to himself as Tom finished licking the last drops off his fast diminishing manhood.
"Bet you liked that," Tom laughed softly, as he sat back and wiped his mouth with the back of his hand.
Chandler, his eyes wide, could only nod, `yes'.
"Mates stick together," Tom said in a matter of fact tone. He smiled and then chuckled.
This is the first part of what may become a series of adventures between Chandler and Tom. Write me at Playbuddy123@yahoo.com with your comments. If there is enough interest, I'll write more. Thanks, Jon