Disclaimer: This is a work of fiction and as such is a product of my imagination and not real life. I beg your pardon if there are historical inaccuracies. The story will include descriptions of sexual activity between teen boys, and in later chapters, activity between men and boys. If material of this kind might offend you then please stop reading. To all others, enjoy! You are welcome to send comments or story ideas to Playbuddy123@yahoo.com
Tortuga Gold - 10 t/t
It was eight days later, late in the afternoon, that Chandler heard a look out call "Land, ho!"
Tom was in the rigging and both turned to look in the direction the sailor was pointing. Chandler could barely make out a slim grey outline on the horizon.
Tom finished his work and scurried down. "Bet that's where we'll meet up with the Soledad," he smiled.
A crowd of men gathered on deck to have a look. Not long after, the Captain ordered men and boys aloft to shorten sail.
"Why's he doing that?" Chandler asked as Tom hurried to his post.
"He probably wants us to come in slow so we arrive just as the sun is coming up tomorrow."
The news spread quickly that land had been spotted and Chandler could see the excitement in the faces of the men. He had to admit that he too was feeling a rush. The only question that remained was whether the Soledad carried good news about their prey.
Just as Tom had predicted, the Tortuga made the tiny island just after first light. They circled an oblong shaped patch of lush trees and white sand beaches until spotting a smaller ship at anchor on the lee side of the island.
Chandler was below at his station in the galley. "We'll take on fresh water and see if there is any fruit," Thatcher explained to half a dozen members of the crew.
"What's my job?" Chandler asked softly as the others were dismissed and headed topside.
"How good are you at climbing?" Thatcher smiled.
Chandler shrugged.
"Grab a machete, you're in charge of coconuts."
Chandler's eyes widened.
The sun grew warmer as the day went along. Captain Searle, Crandall, and the Master Gunner welcomed two men from the Soledad aboard and then promptly went below to the captain's cabin.
Three long boats were lowered from the Tortuga to look for provisions. The men from the galley joined others picked by the purser to scour the island. Most were armed with swords or pistols.
"The Soledad isn't very big," Chandler whispered to Tom as they manned an oar on one of the boats headed to shore.
"She's small but fast. My guess is that the Captain will want her to run out ahead and then we'll close in with our big guns. But the Captain won't want to shoot."
"Why?"
"He'll want to take her without doing damage."
"You sound pretty confident," Chandler said with a worried look.
"Captain Searle is one of the best. We usually hunt alone, so if he's bringing the Soledad along, it's for good reason."
Chandler nodded in the direction of one of the other boats, "Tawse looks confident too!"
Tom made an angry face and pulled extra hard on the oar, "We'll see how long that lasts!"
With both ships safely at anchor and freshly provisioned, the Captain allowed all but a hand full of crew members the choice of spending the night aboard or on shore. Both Tom and Chandler had chosen to stay ashore.
"Did you get your land legs back yet?" Tom smiled at Chandler.
"Still feels strange not to be swaying from side to side."
"You'll get used to it soon enough."
The crew had built a large fire halfway between the high tide mark and the tree line. As soon as they settled in, the jugs came out, and the drink flowed. The sun set and then the moon slowly came up over the horizon. Between the firelight and the moon there was plenty of light for Chandler to see Tom's face.
"Nice night," Chandler whispered, running his toes through the warm sand.
"That it is," Tom grinned. "Look, Thatcher is giving you the eye," Tom said as he took a swig from a jug.
"I think he's about due," Chandler laughed softly. "Three days and he's looking for it."
"So how long has it been since the last time?" Tom grinned.
"Day before yesterday."
"So, the Cook's Boy is going to be busy tonight." Tom laughed.
Chandler gave Tom a sheepish look. He snuggled a little closer, "Will you wait up for me?"
"Think you can take him and still have some left for me?"
Chandler grinned. "Who says I'll be the one getting it?"
"Well, Thatcher doesn't go the other way!" Tom laughed, "Fancies the girls, he does."
"Ah, so I can count on you to be a good mate and give me a rest. I'll be the one doing you!"
"Nah, I don't think so." Tom shook his head.
"Better get it ready," Chandler warned with a mischievous smile, "I'm coming calling."
Tom leaned back, rested his hands in the sand, and stretched his legs out in front of himself. "Well, you take care of Thatcher and we'll sort it out after that."
Chandler got to his feet. "I promise you're gonna be the one face down and ass up."
Tom just shook his head in amusement.
Later that evening Chandler approached Tom and nodded in the direction of a sand dune. Tom followed his gaze to a spot hidden from the others. Chandler got there first and Tom moments later.
"Thatcher all taken care of?" Tom teased.
"Yeah, he'll sleep well tonight." Chandler smiled.
"So, did he do you up the bum?"
"Yeah, but it didn't last very long. He was too worked up!" Chandler chuckled.
Tom settled himself on the sand and Chandler sat beside him.
Chandler looked at the moon, now well above the horizon. The light sparkled on the ocean and cast a glow over Tom's face.
Tom leaned over and gently kissed the younger boy on the lips. The kiss was soft and very tender.
"Do you think that's enough to keep me from going after your bum tonight?" Chandler teased.
Tom smiled, leaned in, and kissed his friend again. This time the kiss was longer and more probing. He pulled back and gazed into Chandler's eyes. "You can have whatever you want," he whispered.
There was no look of lust or boyish sexual need in Tom's eyes, all Chandler saw was tenderness.
It was quiet for a moment.
"Do you think boys can love other boys?" Chandler whispered, wrapping an arm around Tom and leaning his head on Tom's shoulder.
Tom wrapped his arm around Chandler's waist and gave him a soft squeeze. "What do you think?" he asked tenderly.
Chandler thought a moment. The silvery glow of the moon, the waves lapping against the shore and the warmth of the boy next to him... it was all so intoxicating. "Yes," he whispered.
The kissing had gone on for over an hour. Chandler thought it was an all too perfect romantic moment. Both boys lay on their sides facing each other, gently touching here and there. When the clothes came off, the warm sand acted like a blanket. Chandler sensed Tom was ready for more.
Tom got to his knees and waited as Chandler took the hint and stood up. Not a word was said. Tom reached for Chandler's cock as the younger boy softly pushed it forward into Tom's hand and then into his willing mouth.
"Ugh," Chandler whispered softly, gently pumping in and out. He spread his feet in the sand and bent his knees as he pushed the head of his dick between Tom's lips.
Tom whimpered happily, and then skillfully used his tongue and mouth to pleasure his friend. After several minutes, Tom took his mouth off the boy's cock and looked up. "Ready to come calling?"
Chandler smiled.
Tom got down on his hands and knees and turned to face away. Then he bent low, rested his head on his arms, his ass raised, open and inviting.
Chandler got to his knees behind him and lovingly felt each cheek. "I don't get to do this very often," he whispered, feeling Tom's ass. He reached lower and played with the heavy sac hanging between the boy's legs. "Sure you don't mind?"
Tom wiggled his bum, "fair's fair," he said softly; the tone of his voice leaving no doubt he was smiling. "Show me a good time."
Chandler ran his finger up and down the crack and paused at the wrinkled ring in the center. He felt something slick there. "Did you get it ready?" he chuckled, "Or am I feeling something else?"
"I brought something along," Tom said, "but I thought it was going to be for you!"
Chandler giggled, edged closer and pushed his finger into the warm hole. Tom grunted, but Chandler didn't stop until he had gone as far as he could reach into Tom's rectum. He twisted his finger around, pulled back a bit and then probed again. He felt his cock swell when he thought that soon he'd be stuffing every inch of it up there. He played with the tight hole for a couple of minutes as Tom dutifully stayed in place, head down and ass up for him.
"Ready?" Chandler asked, his voice throaty and husky.
Tom grunted, and Chandler took that as a "yes".
Chandler carefully centered the head of his cock against the opening, and ever so slowly pushed forward. The entrance held firm for just a moment and then gave in and let the head inside. He paused to make sure Tom was comfortable, and then pushed the rest in until his crotch hair kissed Tom's ass.
Chandler rubbed Tom's back as he held himself buried to the hilt. He felt his dick flick upwards several times, eager to get going. He pulled back just an inch or two and then tenderly returned it to its place. Using the same technique Chandler progressively lengthened each stroke until he was deep dicking Tom's ass. He slowly and methodically fucked in and out of the hot confines of Tom's rear end, taking every opportunity to probe and explore.
Tom made soft moaning sounds as Chandler got down to it. "That's the way," he grunted under his breath, his hands digging into the sand as he pushed his ass back toward the hard shaft.
Chandler, holding Tom's waist, closed his eyes and pumped in and out in a steady but unhurried pace.
"Fuck, that's nice," Chandler moaned.
The fourteen year old's ass cheeks clenched tight with each push and relaxed with each pull back. His boyish stomach curved softly down to where his hard cock protruded, splitting the firm globes of Tom's ass. He watched as his penis disappeared up Tom's bum with each thrust.
Tom spread his knees wider to give Chandler the best angle possible. "Stuff it back in there," he whimpered, the need apparent in his voice when Chandler accidentally pulled back too far.
Chandler pushed his dick back into place and sped up. He slammed in more forcefully and Tom grunted in appreciation. Chandler fucked harder, groaning as his passion grew. Tom's ass was now his, and he intended on using it.
Tom lifted himself up to all fours. He arched his back as Chandler plowed into him. "Deeper," he whimpered, begging for more.
Chandler gripped Tom close to his hips and roughly pulled him back onto his cock. He pounded away with such enthusiasm his ball sack slapped against Tom's bum. "Still want it hard? He grunted.
Tom moaned.
"How's this?" Chandler grunted, thrusting as hard as he could into Tom. He loved the feeling of being in charge and using Tom's ass any way he wanted. He decided that what he wanted was his cock as deep in that hole as he could manage.
The boys' grunts, groans, and sounds of sex drifted over the dunes. The rhythmic pounding of the waves created a background to their activity. As wonderful as it all was, Chandler knew it couldn't last. Chandler's breathing quickened, and his moans came in throaty gasps. He slammed hard and fast into Tom, noting his dick slid easily on the thin layer of grease. "Almost, almost," Chandler whimpered.
Tom put his head down and lifted his ass higher, offering it up for Chandler to do with as he pleased.
"Do it, do it" Tom chanted again and again as Chandler pounded away. "Cum in my ass!"
Chandler grunted, slammed in several more times and then groaned, "Gaaawwwwdd!"
As Chandler shuddered behind him, Tom pushed back. "Shoot it up my bum," he groaned, "put it all in there."
Chandler aimed his cock to one side and thrust in deeply one last time, wanting to make sure that what he had just deposited in Tom's insides would stay there.
Several long moments of intense pleasure and then it was over. Chandler reluctantly pulled out and rolled to the ground.
Tom looked over as Chandler settled onto his back.
Chandler looked up at the stars. "One of the best ever!" he sighed.
Tom smiled and then snuggled close. They kissed softly.
The kisses, tender and loving, continued for a time.
Chandler reached down and found that Tom was still hard and throbbing. "You didn't get off?"
Tom shook his head.
Chandler looked up and smiled. He spread his legs and pulled them back a bit.
Tom crawled onto Chandler's chest and moved until their cocks were touching. They kissed a bit longer.
Chandler playfully wrapped his legs around Tom. The other boy smiled and nudged the head of his dick just under Chandler's. Both knew where this was going.
"Do you mind if there's some of Thatcher's juice still up there?" Chandler smiled.
"Nah, it'll just make things easier." Tom laughed softly.
As they looked into one another's eyes, Tom poked his cock around until he found the spot. Chandler pulled his legs back further. Tom fisted his cock, centered it, and eased forward. In one steady push Tom snuggly buried himself deep in Chandler's hole.
Chandler wrapped his arms around Tom as Tom started a very slow fuck. He looked up at the stars, then Tom's face, then back at the stars. "A really great night," he grunted softly as Tom thrust deep into him.
At first light the chase was on. All crew members were ordered back aboard and shortly after that the order was given to make sail. The Soledad soon pulled away from the larger and slower Tortuga. Tensions grew as day turned to night and back again.
"Captain had me on the gun deck all day," Tom muttered as he dug into his evening meal.
"I heard the Master Gunner yelling all the way down in the galley," Chandler said with a mouth full of food.
"We must have practiced running out the guns, loading, and firing a hundred times."
"Why did YOU have to do that?
"If they lose a man, then other's have to step in and help out," Tom said softly.
It was at that moment Chandler realized the danger they would face. "You mean if someone gets killed," he whispered.
Tom looked at his friend and nodded.
Chandler's eyes grew moist. "I couldn't bear to lose you," he choked.
Tom gave the boy a reassuring look. "Mates look after one another. We'll come through it just fine. Wait and see."
Chandler still felt worried, but not a word more was said.
Seven days of hard sailing and still no sighting of the prize or of the Soledad. The men were growing restless. Just when Chandler thought things couldn't get more worrisome, the wind died down and then stopped all together.
"What do we do now?" Chandler asked as he and Tom stood at the stern looking up at the now empty sails.
"Wait." Tom sighed.
"How long?"
"As long as it takes."
Hours passed. An eerie calm settled over the ship. The sun climbed higher in the sky. With no breeze, the air grew close. If you were on deck the sun beat down, if you were below deck it felt as if you were in an oven.
"It feels a little better now," Chandler offered as he and Tom sat together late that evening on the crew deck. As usual the drink was flowing freely.
"Not by much." Tom fanned himself with a thin piece of driftwood Chandler had seen him pick up on the island.
The men were listless, weary of the wait and the oppressive heat.
"We need us some entertainment!" Tug yelled to no one in particular. Other men looked over and then cheered in agreement.
"We know your idea of entertainment!" A voice called from the back. A man stood and groped himself. The other sailors laughed.
Tug flipped him a sign with his hand and the crowd roared.
"Time for a horse race," Tug laughed.
The chant "Horse Race, Horse Race" was picked up by the men.
Tom looked at Chandler and shook his head.
"What's a horse race?" Chandler whispered to Tom.
"Two boys will have to strip down in front of this lot and wank."
Chandler didn't understand.
"The one that holds out the longest is the winner. They'll make bets."
Chandler looked over at a small circle of sailors forming in one corner. "That's it?" Chandler whispered again.
"Not quite, the loser will have to take it up the bum as everyone watches."
Chandler sank lower, trying to hide. "Which boys?"
The answer came a moment later.
Tug quieted down the crowd. "Captain's boy!" he pointed toward Stevens, "See that the lads draw lots, the two shortest will be the ones."
The sailors hooted and laughed, all seemingly pleased with the method of choice.
The game had been played before, so all it took was for someone to pull the strands of rope out from where they had been stowed. Stevens made the rounds of all the powder monkeys, the ends of the strands peeking above his tightly closed fist. The first short line was drawn by a lad about Tom's age with red hair and an Irish brogue. He wasn't very tall. His compact stature made him an excellent choice for working the gun crew.
"Gallagher!" Stevens announced, and the crew cheered.
Tom held his breath as he pulled his line from Steven's hand. He let it out with a soft grunt when it turned out to be long. Chandler did the same, and was thankful his also was long.
"Didn't fancy having to be doing it in front of the whole crew," Chandler whispered.
Tom agreed.
The second short string was drawn by a tall, sturdy lad. The blond hair, fair features, and solid build suggested he had a German heritage. His muscled arms and firm chest hinted that he wasn't just a horse, no doubt he was a stallion.
Stevens, the pris that he was, grinned happily and stuck his tongue out to taunt the blond boy. "Lang!" Stevens yelled, and the match was set.
The lad glared at him, his eyes blazing.
Lang and Gallagher took their places at the center of the deck. At Tug's command, they stripped down. Neither could resist reaching down and touching themselves.
The bets had heavily fallen on Lang, with the expectation anyone that well built, would certainly know how to use what God had given him.
The redheaded Gallagher initially seemed to confirm the heavy betting on his opponent, until he started to stroke. It turned out he was a grower, not a shower, and his dick swelled to a very respectable size.
Tug stood in front of the boys. "First one to mess the deck is the loser," he said with a stern look to both, "and ya can't just stand there, ya have to work it!"
The lads nodded, though Chandler could tell neither looked particularly pleased to be on display.
Tug counted down, and the game was on. Both boys closed their eyes and slowly stroked. The laughter and jeers from the crowd helped them stay calm for a time, but then the natural stirrings that come to teen boys appeared. Lang seemed to be the one struggling to control himself, while Gallagher appeared more relaxed. The crowd cheered both on, hoping to influence the outcome in their favor.
The minutes dragged on and still the boys went at it, stroking their cocks, pausing briefly and stroking again, hoping to prolong the moment and thereby become the winner.
The crowd grew impatient. Stevens, always wanting to be the center of attention, swished out to the middle of the circle, grinned and raised his two middle fingers. The crowd broke out in raucous laughter. Seconds later he was on his knees behind the two struggling boys. The men egging him on, Stevens got both fingers wet with spit and then drilled them deep into each boy's hole.
Lang grunted and tried to pull away, but Stevens pushed harder and gave his hand a twist. The Irish lad groaned but held his stance. Stevens gave each a twisting probe and no doubt a thorough rub. There were more moans. Stevens gave it another go and fucked his fingers in and out of both boys several times. Seconds after that, Lang grunted, stiffened and shot three long squirts of white goo out the end of his dick. The stuff flew in a high ark and splattered onto the deck.
There was a loud groan of disappointment from those that had made bets on the handsome lad. Stevens laughed and pulled his finger out of Lang and concentrated his attentions on Gallagher. With a couple of more twists, he too was shooting.
The crew howled in laughter when Gallagher held his fists up in triumph, his cock still partially hard.
Tom looked at Chandler and laughed. "Is that the way you figured it would turn out?"
"Nah, I thought Lang would win." Chandler chuckled.
The bets were settled, though there were more than a few complaints that the Captain's boy had influenced the outcome.
"Lost a week's wages because of him!" A gunner muttered and scowled at Stevens, "He likes to show off, let's see Him get buggered!"
All those that had lost bets joined in, calling for the boy to be done in front of them.
"All right, all right!" Tug calmed the crowd. "Captain's Boy gets it as well!" He smiled to the cheers of the crew.
Stevens' own smile faded and he made to run. One of the powder monkeys grabbed him from behind and hauled him squirming and complaining back to the others.
"Now we'll see what the Captain's been playing with," Tug laughed as he gave the boy's left bum cheek a firm grope. Stevens blushed.
It took the Irish lad, Gallagher, the better part of an hour to declare himself ready for another go. Two barrels were brought out, placed side by side and Lang and Stevens were bent over them.
"Who's gonna do the little one?" A voice called out.
Tug scanned the faces, and, with a grin, pointed at Luke. "He'll give us a show!"
The crew cheered when Luke dropped his britches and with three strokes made himself hard. The impressive dick stood out from his belly and a few drops of clear fluid lubricated the head. Stevens looked worried as Luke took his place behind him.
Chandler watched as someone whispered in Quan's ear who then scurried out and came back with a generous glop of kitchen grease. He carefully prepared each cock, giving it a playful tug as he finished. From the look, both were more than ready to get down to work.
Lang glared. "This isn't over," Chandler heard him tell Stevens as Quan stuck a slick finger up his bum. Lang took it without complaint.
Stevens on the other hand squirmed and blushed when Quan did the same to him.
"Looking forward to this," Gallagher, the Irish lad, said with a smile to the boy bent over in front of him. Lang just lowered his head and spread his legs.
Chandler watched in fascination as first Lang and then Stevens had their cheeks pulled apart, and a hard cock head centered on their hole. Gallagher and Luke looked at one another and then, as if given a signal, both steadily pushed until they had completely buried their cocks deep inside their respective boy. With their balls finally kissing the upraised cheeks of the other boys' asses the two looked at one another once more, smiled, and started to fuck.
"Look at Stevens' face." Chandler laughed as the petite boy strained mightily to take the massive dick up his rear end.
"He's really gonna be sore after this." Tom laughed.
The cheers resumed as Gallagher and Luke put their full efforts to plowing the tight holes of the unlucky boys. Their grunts and groans were lost in the raucous comments, cheers and laughter.
The fucking was fast, hard, and meant to be entertaining, so both Luke and Gallagher made a show of it. The Irish lad did a few rabbit thrusts, then a couple of very hard and deep jabs, and then a slow deep push as Lang squirmed beneath him. Luke didn't have to do much more than push his huge thing forward and Stevens would yelp, squirm, and try to pull away. The crew loved watching him get his reward. As Gallagher and Luke did everything they could think of to humiliate the boy under them, the cheers grew louder.
"Look, I think those guys are up to something." Chandler elbowed Tom and pointed. Three powder monkeys were whispering and nodding their heads in agreement.
Moments later the three dropped their pants, stroked themselves hard, and joined Luke. One tipped over the barrel that Stevens was using to balance himself. Luke lifted Stevens up by the waist until just his toes were touching the deck.
Seconds later, Stevens' head was pushed down and a cock was shoved into his mouth. The other two boys stroked themselves, pointing the heads of their dicks over Stevens' back. The crew went wild.
Luke slammed in hard and held himself there as his eyes fluttered. Chandler knew he was shooting his stuff up Stevens' tight bum. The two boys on the sides sprayed their cum over his back, and the one in his mouth groaned, and unloaded as well.
"For fuck sakes!" Chandler laughed.
Tom howled.
The crew made so much noise it was deafening in the confined space. It couldn't have been better entertainment.
Before long however, it was all over. Gallagher finally finished, holding Lang tight against him as he pumped his bum full. He gave a playful final thrust and pulled out. Lang stood up and gently reached back, no doubt to see if any damage had been done. Gallagher put a gentle hand on his back as if to say, "Well done."
Luke on the other hand, made a show of slowly pulling his long cock out of the Captain's Boy and then slapped Stevens hard on the ass. The crew cheered. The humiliated and now cum covered boy turned purple, a mixture of embarrassment and anger on his face. As a final insult, a very drunken sailor poured rum over the kid's head to help wash everything off. It didn't work.
Stevens, all too ready to get out of there, looked down for his clothes and found they were gone.
"Guess you'll have to go topside starkers," Chandler taunted.
Stevens glared at him, and then made his way through the crowd and toward the ladder.
Tawse was minding his watch. "What the fuck happened to you?" he muttered when Stevens came on deck and headed for the rain barrel.
The boy glared. "Tug set Luke and some of the powder monkeys on me!"
"Tug did that?" Tawse pointed at the various cum stains on Stevens' body.
"Well, he wanted a show and made me part of it," Stevens said angrily.
Tawse' face grew stony. "Tug," he muttered and slapped the rail with the rope end that was always in his hand.
"You'll make it right?" Stevens' high voice squeeked.
Tawse nodded, but then jerked his head toward the bow, "Now wash up, and find some damn clothes!"
Stevens turned, put his head down and walked away, his boyish ass swishing from side to side.
"Little pris," Tawse muttered under his breath, "probably deserved it," he sighed and headed for the stern.
My thanks to James, John B., Hermes, Andrew, and those that have sent emails, offered encouragement or story ideas. Write me at Playbuddy123@yahoo.com with your suggestions or comments. Jon D.