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 - 8 t/t t/m/t
Tom stirred and opened his eyes. Chandler was right next to him, still sleeping soundly. They were on their sides, lying like spoons in a drawer. Tom used his finger to tenderly brush at a few strands of hair on the back of Chandler's neck.
"Are you glad you signed up?" Tom whispered, playing with the curls.
He edged closer and snuggled his crotch tighter against Chandler's rear. Chandler wiggled in his sleep, seemingly enjoying the feel of Tom's crotch.
"So, you like me pushed up against your bum, eh?" Tom chuckled. He slid his hand down the boy's side and softly felt his ass. "You know you're making me hard!"
Chandler, still sleeping soundly, sucked in a breath and made a soft snorting sound.
Tom ran his hand over his friend's ass for several more minutes, pausing from time to time to give it a tender squeeze. "Now you've done it," Tom laughed softly, "it won't go down," he grinned, giving the front of his britches a feel.
Making up his mind, Tom leaned over and tenderly kissed Chandler behind the ear. "I promise I'll go easy," he said quietly, reaching around to undo Chandler's pants. Moments later he tugged them down, baring the boy's rear. He gave the soft globes a feel, pausing to run a finger up and down the crack.
With Chandler's ass now exposed and waiting, Tom undid his own britches, kicked them off, and snuggled up tight. Tom's cock naturally settled into the crease between his friend's cheeks. Tom once more kissed Chandler on the neck and then put the head of his dick on the target. Satisfied he was in the right spot, he eased forward. The tight ring resisted his advances. Tom pushed harder but still made no progress.
"Thought you'd be loosened up bit more by now," Tom mumbled, and pulled away. He crawled out from under the blanket. "I'll be right back," he said to the sleeping boy and hurried off.
A few minutes later he returned. "Greased it up a bit," Tom said proudly as he lay down once again behind his friend. Chandler still hadn't moved. Tom stuck a slippery finger into the boy and gave it a turn before withdrawing it. Finding the spot once again with the head of his dick, he pushed forward for the second time. It slid in with ease. He paused with the head just inside the tight ring.
Chandler grunted, and pulled his ass back as if wanting to get the thing out of his bum.
"Steady," Tom whispered, rubbing Chandler's side.
Tom put his hand on the boy's hip, holding him in place. He eased forward, burying another couple of inches in the fourteen year old. The warm tunnel of Chandler's rectum felt wonderful as it squeezed Tom's dick.
Chandler groaned softly and stirred. Then he spoke. "Wha..? He asked, still half asleep. "Tom, is that you?"
"Yeah," Tom whispered and offered another kiss.
"What are you doing up my bum?"
"You made me hard, I had to take care of some business." Tom chuckled, and pushed in a little more.
Chandler groaned as the teen's cock slid deeper. "Least you could have done is wake me," he grumped.
Tom pulled back, paused, and then shoved his entire length up Chandler's ass in one long push.
"Oooooooo," Chandler sighed contentedly.
"You like the feel of that, don't you?" Tom whispered, giving his cock a gentle thrust.
In response, Chandler pushed his ass back against the other boy's crotch, making sure the thing was well lodged. "Yeah," he groaned.
There was a quiet pause.
"So now that you've got it all up there, are you going to do something with it?"
Tom chuckled, "That's the proper attitude," he grinned, and started to fuck.
Chandler braced himself as best he could, but the roll of the deck caused him to stagger as he made his way to the Captain's cabin with morning tea. The wind had picked up and the ship was starting to pitch and roll. It didn't help that his ass was sore from Tom's wake up call. Still, he managed to reach the door, steady himself, and knock.
"Come!" the Captain responded.
Chandler opened the door and stepped inside. The Captain was pulling on his shirt.
"Tea, Sir"
"Over there," the Captain motioned.
Chandler put the drink and biscuits on the desk. He looked over to the bed...uh, rack when he heard a sleepy yawn.
"Hi," the Captain's boy, Stevens, smiled when he caught Chandler's eye.
Chandler smiled back. He noted the young man's voice was higher pitched than he remembered.
The boy crawled out of the blankets and Chandler wasn't surprised to see that he was naked. What did surprise him was how swishy and effeminate he seemed. Chandler hadn't noticed the last time they met. The boy giggled in a girlish kind of way, and padded over to the desk. His limp plaything swung gently from side to side. Chandler couldn't help but chuckle.
Stevens seemed to enjoy having an audience. With a mischievous look and a twinkle in his eyes, he tucked his cock and tiny ball sac back between his legs hiding all signs of his boyhood. He posed, and with no hair down there, he made a convincing image of a pre-pubescent girl.
Chandler giggled. He had never seen a show like that.
The Captain gave the boys an amused look.
"Will there be anything else, Captain?" Chandler said softly.
"Tell Mr. Thatcher you won't be working in the galley today."
"Aye, Sir"
The Captain looked at Stevens. "Take him to the Master Gunner; you're both assigned to him today."
Stevens whined, "He'll make us clean the guns and turn over the powder."
The Captain shot the boy a stern look.
"Sorry, Sir," Stevens quickly apologized, biting his lip.
"Go get it," the Captain said firmly.
Stevens gave the man a pleading look, but got no welcoming response. He rolled his eyes, and then reluctantly walked over to a trunk and retrieved a leather strap. Chandler made to leave, but the Captain stopped him.
"I expect my orders to be obeyed without comment. Stay here and watch what happens when you don't," the Captain said calmly.
Stevens walked over to the Captain and handed him the leather. He gave the man one more pleading look, but then accepted his fate. He turned around and bent over, placing his hands on his knees and closing his eyes.
There was a snap as the strap landed on target. Chandler winced and Stevens let out a high pitched squeak, but didn't say a word. There was a second and a third snap and the boy's rear end began to glow bright red. The fourth lick was clearly the hardest, and then it was over.
"Get your clothes on," the Captain said firmly but without anger. He dropped the strap at the boy's feet.
Steven's picked it up and quickly returned it to its spot in the trunk.
The Captain took a long drink of tea and left the cabin.
"Should have kept my mouth shut," Stevens whispered as he rubbed his ass. The way it stuck out reminded Chandler of one of the girls back at the Black Dogg.
Chandler couldn't keep from smiling.
"Go tell Thatcher you're on Captain's orders and meet me back here in ten minutes," Steven's said in a boyish sing song voice.
Chandler nodded, "Are you all right?" he smirked.
"I've had it way worse than that, haven't I?" the boy giggled, "Really, I'm surprised he didn't give it to me harder!"
Chandler shook his head and chuckled.
Stevens led the way forward from the Captain's cabin to the ladder that would take them to the gun deck.
"The Master Gunner, Mr. Hobbs, used to be in His Majesty's Navy. Captain Searle showed him a bag of gold coins and he signed up with us real quick," the lad chuckled.
"So are we really going to clean the guns?"
"Yeah, pretty sure we will."
"Just the two of us? There's what, twenty eight cannon?" Chandler looked around.
"We won't be alone. Some of the gun crews will be there for practice and the other powder monkeys will be there too."
Chandler was confused.
"The boys that run the powder up from the magazine are called powder monkeys." Stevens giggled.
When they reached the gun deck they found it was filled with activity. Perhaps twenty men and six boys were already at work. Crews were running the guns in and out and practicing the loading sequence. Others were busy with other tasks. Chandler saw the young oriental boy, Quan, was busily ramming a wet cloth down the barrel of a gun.
Stevens noticed Chandler's look. "Haven't seen many like him I bet?"
Chandler shook his head `no'
"Captain took a ship as a prize a year ago; most of the crew was killed. Quan was hiding in the hold. Captain brought him aboard and told him he'd give him a chance. Captain said the crew could use a bit of entertainment. But he warned him if he caused any trouble, he'd be tossed over the side."
Quan looked up, and grinned. The boy's smile was beyond description.
"He's cute," Chandler chuckled.
"He's a little bitch if you ask me,"
"Huh?"
"I think he's after MY job," Stevens said bitterly.
"He is?"
"I don't know for sure. But I don't trust him!"
Chandler gave the boy another look.
"He's great with his hands though," Stevens said reluctantly, watching him clean the cannon, "he does magic tricks."
Chandler turned.
Stevens whispered, "And he puts on other shows, too. He can suck his own dick."
Chandler looked at Quan wide eyed.
"Yup, he's so limber, he can twist every which way."
By the tone in his voice, Chandler could tell Stevens was definitely jealous.
"That'd be something to see," Chandler said with wonder.
Four long hours went by and Chandler's arms were aching. Cleaning the guns was hard and dirty work. Each gun was first cleaned inside and out with a long ram soaked in sea water and then rinsed clean with fresh water so as to not leave any salt residue. Then they were dried. Each was carefully inspected by the Master Gunner and then by the crew that fired them. Every inch had to be free of rust, dirt, and soot from burned powder. If not, it was cleaned again.
"Right! Now the six of you to the magazine and we'll turn the barrels!" The Master Gunner ordered.
The boys groaned.
"What's that mean?" Chandler asked Stevens.
"We have to turn over each barrel of powder to make sure the ingredients don't separate."
Chandler gave him a puzzled look.
"It's dirty work, and you'll have that black shit up your nose and in your throat for days."
Once again the thought went through Chandler's mind that he might have made a mistake in signing on.
Work done, and after cleaning up as best he could, Chandler found Tom and they got their evening meal. They took their food on deck to enjoy the evening air.
"Looks like you was on the gun deck today. Tom laughed.
Chandler gave him a frustrated look. "Just another one of those things you didn't tell me about."
Tom grinned.
Chandler explained how he had gone to the Captain's cabin that morning and what had happened to Stevens.
"Got the strap did he?"
"Yup,"
"Probably had it coming," Tom chuckled.
Chandler was quiet a moment. "He's a bit of a pris isn't he?"
"Oh for fuck's sake, he's more than a bit!" Tom laughed.
Chandler blushed. "I never saw a boy like that,"
"That's the way the Captain likes them," Tom laughed softly.
"Huh?"
"Young, not much hair, and all girlie like."
"But I thought you were the Captain's favorite?"
A twinkle came to Tom's eye, "I am!"
Chandler showed his confusion.
"You can't tell a soul," Tom whispered as he looked around to see if there was anyone near enough to hear.
"I won't,"
Tom leaned close to Chandler's ear. "Sometimes the Captain likes to be busy with a boy on his front side while another lad is busy doing for his backside!"
Chandler turned, wide eyed.
"I gots what the Captain likes when he wants it that way." Tom smiled, gripping his crotch and giving it a lift.
Chandler squirmed, recalling the feel of Tom's cock as it slammed up his bum earlier that day. He tried to imagine the Captain taking the very same thing in the very same place.
"No one else except a few of us boys knows," Tom said softly.
Chandler nodded, honored that Tom had shared the secret with him.
The next morning, Tom and Chandler stood side by side amidst a crowd of sailors.
"What's going to happen?" Chandler whispered.
"Captain's going to tell us where we're off to, and what we're going to be going after."
A few minutes later, the Captain called for quiet. He held up the leather wrapped parchment that Tom and Chandler had seen in Tawse' hands in the market.
"This.." the Captain said loudly, "is a secret communication from the government of Spain about a two ship treasure fleet that sets sail in three weeks time."
"How did he get it back?" Chandler asked hurriedly looking at the documents.
Tom carefully eyed the crowd and saw young Stevens standing next to Tawse.
"That little pris!" Tom said angrily.
"He's with Tawse?" Chandler gasped.
Tom nodded.
"We're going to rendezvous with the `Soledad' to see if she has any more news and then we'll hunt for gold!" The Captain yelled with enthusiasm.
The crowd cheered.
Chandler glanced over at Tawse, it appeared he was looking at individual faces in the crowd.
Tom noticed it as well. "So he knew what we were after," Tom mused. "What's his plan?"
Tom looked around the crowd and spotted Tug. They made eye contact and Tug indicated that he too had his eye on Tawse.
"What the fuck are you up to?" Tom whispered as he stared at the boson.
"Chandler carefully reached for Tom's hand and pulled him a little closer.
That night, Tom was called to the captain's cabin.
"Come," the man called a moment after Tom's knock.
Tom stepped inside and closed the door.
"Sit," the Captain said quietly and motioned to a chair. Stevens was on the bunk. The two boys exchanged glances.
No one spoke for several minutes. Tom looked at the Captain's boy, searching for any clue as to what was about to happen. Then there was another knock at the door.
The Captain nodded in the direction of the door and Stevens got up and opened it.
Tom saw that it was Quan.
Stevens gave the oriental boy a menacing, angry look.
Tom saw Quan was dressed in red and green silks. He had touched both cheeks with something red and had done the same to his lips. The effect was stunning. He looked like an oriental doll. His long black hair added to the illusion.
Quan stepped inside and Stevens again took his seat on the rack. The Captain gave Quan a tiny motion of his head and then sat down as well.
Tom watched as Quan drew two small fans from a slit in the side of the silks, flipped his wrist and the fans expanded. The boy's movements were slow, erotic, and ever so sensual. His entire body moved with quiet grace. Tom watched as he danced for the Captain, his eyes never leaving the older man. He was seducing him. The yellow color in the fans accented the reds and greens of the silks making a complete picture. Tom felt his cock stir.
The dance continued at an agonizingly slow pace. The boy was humming softly as he twisted and turned. Ever so slowly he unbuttoned the top of his costume and revealed his smooth almond toned skin, tender nipples, and firm stomach. Tom saw the look in the Captain's eyes. He was pleased, very pleased.
Dropping his shirt to the floor, Quan danced closer. With no apparent action on his part, his pants fell, revealing his boyhood. Naked, the boy covered himself with a fan and blushed sweetly. He turned and offered the Captain a tantalizing and erotic view of his backside.
The dance went on for a minute or two more and ended with the boy bent over looking backwards from between his spread legs. His ass was open and his sweet pucker seemed to wink.
Tom was fully hard.
The Captain stood and started to unbutton his shirt. He looked at Stevens and then back at Quan. He seemed to make a decision.
"I won't need you tonight," the Captain said, dismissing Stevens. "Be here after tea to clean things up in the morning."
Stevens shot Quan another angry look.
Quan rose from his bent over position and looked at the boy as he reached the door. Quan smiled sweetly. Stevens face grew red with anger as he stepped out.
The Captain looked at Tom, and Tom knew it was time. He stood and started to undress.
The Captain picked up Quan and carried him to his bed. He laid him on his back, his head propped up with two pillows. Quan smiled, the room seeming to light up. The boy's eagerness was evident.
The Captain dropped his britches and stroked his member. The slightly more than average length was enhanced by an impressive girth.
Quan stared in fascination.
The Captain climbed on to the rack and straddled the boy's chest. Rising to his knees he crawled closer, his cock jutting out firm and throbbing.
Quan reached for it as it came near and guided it to his waiting mouth. The Captain eased the fat head between the boy's lips. Quan licked the surface and stroked the thick shaft.
Tom rubbed his own cock as he watched the Captain slowly fuck his dick in and out of the boy's mouth. The twinkle in Quan's eyes never faded. He was clearly enjoying himself. The Captain ran his hands over the boy's head and urged him on with an occasional pull forward. The sound of sucking was filling the room.
Tom stepped closer. Tom's arms were becoming nicely muscled, climbing the rigging and doing hard deck work was adding to his lean but strong build. His legs were especially strong and his ass rock hard.
The Captain reached out his hand and Tom slipped his cock between the man's fingers. The Captain slowly stroked him, rubbing his palm over the knob from time to time.
The sucking continued for a few minutes longer and then the Captain eased out of Quan's mouth. The Captain crawled backwards and then got up. He took the lad by the ankles and pulled him to the edge of the rack and then rolled him over onto his stomach. He pulled the boy off the bed just enough that his chest stayed on and the rest hung over the edge. He pulled Quan up so that the boy stood on the deck, his chest still on the mattress, his ass open and inviting.
"Get him ready," the Captain said softly and stepped back.
Tom got on his knees behind the boy and spread his tender cheeks. Without a moment's hesitation Tom licked Quan's crack on one side and then the other.
"Oooohhh," Quan whimpered and wiggled his bum. "Lick my hole," he begged in a needy voice.
Tom washed the young boy's crack a bit more and then focused on the tight ring in the middle. He licked around the rim and pushed his pointed tongue in and out. Quan swayed happily from side to side as Tom ate him out. Tom could taste a slightly earthy flavor, but it wasn't objectionable. It was all boy. Tom dug his tongue into the lad's entrance and coated it with spit.
The Captain watched for a few minutes more and then reached for a small clay jug with cork stopper sitting on the table. It held olive oil. He put the end of his cock over a bowl, pulled the stopper, and poured oil over the tip. Then he rubbed a generous amount more over the entire length.
When he was ready, the Captain put a hand on Tom's shoulder and pulled him away. Quan looked back as the Captain slowly pushed his oily finger into the boy.
"Uggghhh" Quan grunted.
He spread his legs wider apart as the Captain twisted and turned, widening the opening. He raised his ass up apparently eager for more.
Then, hands on the boy's waist, the Captain centered his tool. Quan grunted, pushed his ass back and ever so slowly impaled himself on the stiff rod. The Captain didn't move an inch. Quan wiggled, bent, and fucked himself until the head of the Captain's cock was well up his ass. Then the boy stopped. The Captain took Quan by the waist, pushed forward, and eased the rest home.
Quan rose up higher on his toes as the thick stalk pressed deeper. To Tom, it looked like the boy's hole was way too small for such a sizable endowment. Nonetheless, it was now securely planted. The Captain seemed to enjoy the moment, and then pulled back and started a regular rhythm.
"Yes, Sir," the boy whimpered, "bugger me," he moaned.
The Captain fucked a little faster.
"That's it," Quan grunted, "bugger me good!"
Tom's cock was throbbing. He watched as the Captain took his pleasure, speeding up and then slowing down as he stuffed the lad. Quan wiggled on the thing in his ass like he was very happy for it to be there.
Tom stepped to the clay jug and oiled his dick. His hand made a slurping sound as he rubbed it up and down the shaft. He watched as Quan begged to be fucked.
He scooped up a small amount of oil in his palm and stepped behind the Captain. He ever so lightly touched the man's ass. He waited for permission. The Captain kept at his work for another couple of minutes and then bent at the waist. It was time.
Tom spread oil in the man's crack and then eased a finger into his hole. The Captain didn't say a word. Tom pulled back and added a second finger. He twisted and turned them until he was satisfied his Captain was ready.
Tom slid the head of his cock up and down the Captain's hairy crack. Quan's whimpers and squeals of delight were building.
"Now, Captain?" Tom whispered.
The Captain nodded and spread his legs a fraction more.
Tom centered the head of his dick and rammed it in brutally hard. "Fuck a boy will you?" Tom grunted and fucked deeper. "How's it feel up YOUR ass?" Tom slammed in harder and harder.
The Captain grunted and pounded away at Quan. Tom put his legs into the next thrust and slammed in deep, rooted around, and pulled back only to do it again.
"So buggering boys gets you off, does it?" Tom goaded as he reamed the Captain hard. The man just groaned and took the assault. Tom pounded away as the Captain drilled Quan. "Here's how you bugger a hole!" Tom grunted and fucked in as hard as he could, making no effort to go gently. He kept at it, with single minded determination.
Tom used every inch he had to good advantage twisting and turning the head to probe deeply. This would be a fuck that the Captain would well remember. The boy's youth, enthusiasm, and staying power were all coming into play. His hips became a blur as he thrust into the man again and again and again.
From the sounds coming from the other boy, Quan was having a good time as well. "Permission, Sir?" Quan squeaked.
The Captain grunted, slammed in tight, lifted the boy off his feet, and balanced him on the end of his dick.
"Thank you, Sir" Quan coughed, wiggling on the stalk and reaching for his own cock. He started to stroke. The Captain set him down and bent him over again.
Meanwhile, Tom was still giving the fuck everything he had, fast, hard, and deep. "Like my cock in you?" he grunted, and pulled back to slam in again.
The Captain groaned.
"Love to get fucked up the ass, don't you?" Tom grunted under his breath.
Again the Captain just made a sound.
"You're getting buggered by a boy on your own ship!"
The Captain moaned.
"There's a good mate, give me your hole!" Tom grunted.
The coupling went on for several more minutes. The action grew even more intense as each neared completion. Grunts, groans, and heavy breathing filled the room.
It wasn't surprising that Quan was first. The Captain's dick deep in his ass gave him the perfect motivation. He stroked, grunted, and then shot four long strings of cream out over the blankets.
"Oh fuck, oh fuck, oh fuck!" he whimpered as his balls emptied. The white spurts arched up and fell in splatters.
The Captain must have felt the boy's sphincter tighten as he reached orgasm, because with a grunt of his own, he slammed in and held himself deep inside the boy.
"Take it," he groaned, holding one long breath.
Tom knew the Captain wanted to feel cum in his own ass at that very moment, so he rabbit fucked him until he too shot his load. He could feel his cock throb and jerk as he squirted three long streams up the man's bum.
"There!" Tom groaned as his cock twitched, no doubt spitting the last. "You got it, Sir," he said softly, holding on to the man's shoulders for support and slowly pumping the slippery stuff deeper.
The three grew calm and then held still, the man in the boy and the boy in the man. Finally the Captain slowly withdrew. Tom did the same.
The Captain turned and gave Tom a look.
Tom's eyes twinkled.
"Well done," the Captain's face slowly turned into a smile.
Tom blushed, "Knew you'd like that one," he smiled and laughed.
The Captain chuckled. "You always seem to know my moods,"
Tom smiled again.
"Well, what about me?" Quan giggled.
The Captain turned back to the boy who was now sitting crossed legged in the center of the mattress. "You were fine too!"
Quan smiled widely. "Liked my bum did you?"
The Captain nodded. He headed over to a cabinet and took out a bottle and three glasses. He poured a measure of rum into each.
"To a very long night," the Captain raised his glass in a toast.
The boys smiled and they all drank.
The fucking soon resumed and continued well into the early morning.
"You just getting back?" Chandler yawned as Tom crawled in next to him and snuggled under the blanket.
"Yeah," Tom sighed.
"So, was the Captain smiling when you left?" Chandler giggled.
Tom just laughed.
Comments? Suggestions? Write to me at Playbuddy123@yahoo.com
A special thank you to Jon B., Andrew, and Matt for help with this chapter. I'm eager to hear reader reaction, so please do send me a note. Thanks, Jon