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 - 4
Rumors that the Tortuga was making ready for sea spread through Port Royal in no time.
Tom overheard a shopkeeper talking with Big John. The merchant said he knew for a fact orders had been placed with the gunsmith for powder, the sail maker for canvas, and the cooper for barrels.
"If that isn't proof enough," the man said, lifting his drink, "Captain Searle has called his crew back." He gave John a knowing look and took a long swig.
Big John seemed to take the news in stride. "Well, if it's true, we'll still have a few more nights of good business afore they sail," he said with a sigh. He poured a second round for the shopkeeper. "After that, I guess a bit of a slow spell would be all right, especially after the way them lads tore up the place in that brawl."
Tom glanced across the room at Chandler. By the look on the boy's face it was obvious he had heard the conversation as well, and he was clearly upset.
"You two, get another cask of rum from the storeroom," John said, tossing a shot of liquor down.
Tom dropped the rag he was using to clean the table and with a look at Chandler, headed for the back.
Chandler led the way, pausing to pull the heavy iron key off the peg under the corner of the bar.
"You're not happy `bout the news are ya'" Tom said softly.
"I hoped you'd be staying longer," Chandler replied.
"I don't belong here. I belong at sea," Tom offered as they turned the corner and walked down four short steps and ducked under the floor supports.
Chandler put the key in the lock and opened the storeroom door. The small space was barely five feet high from floor to ceiling. He turned to look at Tom. "You could stay, John would keep you on," He said hopefully.
Tom shook his head, `no', "You know as well as I do that he don't need another boy."
Chandler looked down, sadness on his face. In fact he looked as if he was about to cry.
"It'll take the better part of a week to get stores aboard, maybe even a day or two longer. We still have some time."
Chandler looked even sadder.
"I'll talk to the Captain. He'll find a place for you and we'll both go," Tom offered.
Chandler scuffed the floor with the toe of his boot, "I dunno about that."
"There's lots of boys would jump at the chance to sail the seas, have adventures, make a fortune."
Chandler didn't respond.
"Well, you think about it," Tom said gently.
Chandler turned back to the storeroom.
"Let me know by the end of the week," Tom said.
Chandler nodded, his back still turned.
Two days had passed and Tom had gone aboard in preparation for setting sail. He promised Chandler he'd be back soon. Night fell, and with the tavern quieter than usual, Big John sent Chandler to bed early.
Chandler stripped down, put on his nightshirt and lay down. He pulled his knees up to his chest and curled into a ball. He thought about how only a few days earlier he and Tom had shared the tiny bed. His eyes grew moist. He tried, but sleep wouldn't come.
Later, there was a knock at the door. Chandler jumped up and rushed to open it, hoping it was Tom. He was saddened to see Sara.
"Missing him are you?" she whispered.
A lone tear rolled down Chandler's cheek.
Sara reached for him and he fell into her arms. She hugged him gently.
"I didn't think it would hurt like this," Chandler whispered, the tears starting again.
"And why wouldn't it? You having feelings for him."
Chandler looked up in surprise.
"Oh, I've thought for a long time you liked boys." Sara laughed tenderly. "But, it wasn't until Tom showed up that I knew for sure."
Chandler didn't know what to think or say. Sara had just said something he had yet to admit even to himself. They walked to the bed and sat down. Sara wrapped an arm around the boy and pulled him close.
"Time I tell you a story," Sara said softly.
Chandler looked up.
"You never heard much talk about your mum, did you?"
Chandler shook his head, `no'.
"Well, first off, she was my mum, too!" Sara said with a playful grin.
Chandler's eyes grew wide and he blinked.
"You're me little brother, well, half-brother more like it."
"But...?"
"Shhh, let me tell it," Sara said, touching Chandler's lips with a finger. "Mum was ever so pretty, at least that's the way I remember it." Sara smiled tenderly. "They tell me the night you was born I threw a temper tantrum, `didn't want a brother' I hollered and stomped around.
Chandler shrank back. "Nobody's ever wanted me," he whispered.
Sara gave him a squeeze. "Not true, our mum loved us both. I never knew the man that fathered me, just like you never knew the one that fathered you. But we shared the same mum."
"What was she like?"
"I wasn't more than about four years old when you showed up, and I was barely six when she died. What little I do remember, was that she was caring, loving, and was always laughing."
"What happened to her?"
Sara brought her hands together in her lap and looked down, "It was the fever!"
Chandler knew a bit about that, but it was rarely spoken of.
"Some said it was God's way of punishing them souls what deserved it," Sara whispered.
"Not my mum!" Chandler said with determination.
Sara smiled at the loyalty Chandler showed to a person he never knew.
"It was only a few days and then she was gone." Sara twisted a small locket hanging from a gold chain around her neck. "She give me this as I stood by her bed. Told me to never take it off, and I never have." Sara carefully opened it and revealed a tiny curl of hair.
Chandler's eyes grew wet again.
Sara sniffed and wiped at her nose with the back of her hand. She reached into her pocket and drew something out. She reached for Chandler's hand and pressed two small coins into his palm and closed his fingers around them.
"She gave me those to give to you someday," Sara whispered, "She said it was all she had left."
Chandler opened his hand. The coins weren't worth much at all, barely enough to buy a loaf of bread. But to him they were precious.
Sara wiped her eyes with both hands and straightened her dress. She smiled and pulled Chandler closer. She gave him a quick kiss on the forehead. "There, you know it all," she said with another sniff.
Chandler sat for a moment, taking it all in. "Why wait until now to tell me?"
"Folks don't like talk about the fever. When I was little, Big John made me swear to keep the secret, said it would be bad for business."
Chandler nodded. It didn't make much sense, but then nothing much did.
"He's asked you if you want to go to sea with him hasn't he?" Sara asked gently, wrapping her arm around the boy once again.
"How did you know?"
"Just a hunch," Sara smiled.
Chandler looked up, unsure if he should talk about it.
Sara gave him an encouraging look.
"I've been thinking about it," Chandler whispered, "But I wouldn't know how to tell Big John."
Sara chuckled. "Silly boy, he knows already!"
"What?" Chandler asked in surprise.
"Tom told him he was going to speak to the captain."
"What did John say?"
"It would be your choice; he wouldn't stand in your way."
Chandler was stunned.
"Oh, one more thing, he knows you probably fancy boys, and he definitely knows you fancy Tom!"
"But? How?" Chandler stuttered.
"Let's just say John knows a bit about the world. Nothing gets passed him, I can vouch for that!"
Chandler shifted uncomfortably. There was still one more thing on his mind.
"I'm your very own big sister," Sara teased, "You can ask me anything."
Chandler shifted again, a blush growing on his cheeks.
"If I was to go to sea," he whispered, "there'd most likely be things expected of me." He gave Sara a worried look.
Sara seemed puzzled at first, but then her eyes twinkled; she nodded, and gave him another soft squeeze. "Well, I'm not exactly sure what you're worried about, but I'm guessing some of those things might be things you'd enjoy!" She chuckled, "I've heard some of what goes on when men are at sea for a long time."
Chandler looked to the floor in embarrassment, "Yeah, that's what I'm worried about."
Nothing was said for a moment. Finally, Chandler plucked up his courage and turned to Sara.
"Will you tell me what its like to get it up the bum?" He whispered.
Sara got wide eyed, and then laughed. "Now, that's something you best ask Tom!" she giggled.
Chandler's face grew red.
Sara reached over and gave Chandler a tender hug. "Now, off to sleep with you," she said standing up.
Chandler pulled his legs up onto the bed and wrapped his arms around his knees. He sat curled up tight.
"Thanks, Sara," he said softly as she stepped to the door.
She smiled and nodded.
Chandler drifted in and out of sleep. The house was quiet but he was restless.
The knock at the door was tentative. When there was no response, there was a second knock. Chandler opened his eyes, and climbed out of bed. "I'm coming," he yawned and padded barefoot across the room.
"`Bout time," Tom smiled when Chandler opened the door.
"I thought you had to stay on the ship?" Chandler grinned, happy to see his friend.
"Captain said it was all right," Tom smiled and walked inside.
Chandler closed the door as Tom climbed onto the bed and sat cross-legged.
"How's the outfitting going?" Chandler asked, sitting down next to him.
"Moving along, stuff keeps coming and the crew is busy putting everything in its proper place."
"You'll be leaving soon then?" Chandler asked softly.
Tom nodded, "in a few more days."
Neither boy spoke for a moment, but then Chandler grinned. "I have to tell you about Sara," he smiled and snuggled closer, "you'll never believe it!"
Tom shook his head after hearing the story. "You shouldn't have told me," Tom teased, "now all I can think about is what she and I done in her room! And she, your sister!"
Chandler laughed, "I won't get mad!"
Tom bit his lip as if in thought, "I've got news, too."
"What's that?"
"The cook's boy run off. He didn't come back after going to his mum's for shore leave." Tom shrugged, "Captain says that makes a place for you if you want to come aboard."
Chandler gave Tom a long look.
"It wouldn't be much different than what you're doing here," Tom offered.
Chandler sat back and laid his head against the wall. "But there's more to it though, ain't there!" he gave Tom a look.
Tom nodded, "Worried about your bum?" Tom laughed gently.
Chandler blushed. "I've never done stuff like that."
"I'll show you the way," Tom said softly.
"I just wish you wasn't so big..." Chandler muttered, glancing at Tom's crotch.
"There's bigger than me on board," Tom snickered.
"That's what I'm afraid of," Chandler whispered.
"Look at it this way. Here's your chance to get away from here. Make your fortune."
Chandler turned to him, "Is the Captain really going after gold?"
"He says he'll tell the whole story once we're at sea, but he promises if it goes well, we'll all be rich!"
Chandler seemed deep in thought. Finally he looked at Tom with pleading, puppy dog eyes. "You'll show me the way?"
Tom nodded.
Chandler thought a moment longer, sighed, and then got to his feet. He pulled his nightshirt over his head and dropped it to the floor.
"Best we get started then," he said with a worried look.
Tom looked at the nude boy and smiled. "Are you sure?"
Chandler nodded, "As long as there'll be gold."
Tom got up. "Put your shirt back on, first there's a trip to the kitchen."
"Why?"
"You'll see," Tom chuckled and headed for the door.
Chandler closed his eyes and spread his legs a little further apart at Tom's instruction. He was on his knees, face flat against the mattress with his bum sticking up. He was beginning to have second thoughts about this whole thing.
Tom pushed down on Chandler's back.
"What are you doing?" Chandler asked.
"Need to get the angle just right."
"Is it going to hurt?" Chandler whimpered.
Chandler felt Tom poke his finger at the tight slit in the middle of Chandler's bum cheeks.
"You got a tight one," he mumbled, "Yeah, most likely it's gonna hurt."
"I knew it," Chandler whined, becoming increasingly uneasy.
The trip to the kitchen had yielded a large wooden spoon and a generous glob of bacon grease. Both were now resting on the floor beside the bed. Tom pulled his shirt over his head, shucked off his britches, and then ran his hands over the soft globes of Chandler's ass.
"First thing is, you need to relax," he whispered as he gently played with Chandler's rear end. His hands roamed up and down the smooth crack, over the plump mounds, and brushed against the puckered opening.
"Easy for you to say," Chandler thought, flinching when Tom's hand accidentally brushed against his nut sack.
"Sorry," Tom offered. He paused, reached down, and gave his own firm shaft a couple of strokes and then got back to the business at hand.
"Second thing is to make sure things is ready," Tom instructed, reaching for the spoon of grease. He dipped his middle finger in the lard and then painted Chandler's opening. Then he touched the end of his finger to the center. "Now take a deep breath."
Chandler did so and waited. A moment later, Tom's finger pushed forward. It was stopped solid by the tight ring. Tom added a little added pressure and a twist, and managed to get inside.
"Ooooh," Chandler sucked in a breath as he felt himself being penetrated.
Tom held his finger steady a moment, and then withdrew it. He dipped the tip into the bacon grease again and repeated the procedure. "How are you doing?"
"Okay," Chandler mumbled, his eyes still tightly closed. He shifted his ass as Tom made his way back inside.
Tom worked his finger in and out of the boy a dozen times, each time twisting and turning until Chandler could feel Tom's knuckles graze against his bum cheeks.
"Still tight," Tom pronounced after perhaps ten minutes of play.
"When are you going to put it?"
"In a bit, you're not ready yet," Tom sighed, pulling his finger out. He climbed off the bed. Where do you keep the new candles?"
Chandler looked up. "In there," he nodded toward the wash stand.
Tom opened the cupboard under the bowl and pitcher. He retrieved a candle and climbed back onto the bed.
"You're gonna use that?"
Tom spread a bit of the grease on the taper. Easy in and easy out," he chuckled. "Besides, it's sort of fitting, the first thing that should go up your bum is something made by a chandler."
Chandler felt the pointed end of the candle at his rear. "I don't know about this," he mumbled, finally saying what he'd been thinking for some time.
"You'll be thanking me in a minute," Tom chuckled, slowly pushing the thing forward. "Do you like the feel of it?" he whispered as he worked it in and out.
"It feels strange."
"Spread your legs more."
Chandler did as Tom suggested. "It's better, you can put more of it in," he offered.
Tom played with Chandler's dick as he pushed the thing in a little further.
"That feels kind of good."
"A bit more then," Tom giggled and slid the waxy tube deeper.
"It's hurting a little," Chandler squeaked.
Tom pulled it back, paused, and then thrust in again. "Relax your hole."
Chandler grunted. That was easier said than done.
The process went on until the boy finally had all six inches in his ass.
"Now jerk your dick," Tom instructed as he pushed and pulled the candle.
Chandler moaned and stroked himself as Tom diddled his rear end. The feelings were growing and the moment was getting closer.
"Yeah, that feels really good now," Chandler grunted as his hand became a blur.
Tom stopped the pushing and pulling motion, but Chandler kept right at his jerking.
Just as Chandler felt he was almost there, Tom abruptly pulled the candle out.
"Wha..." Chandler managed before he felt the blunt knob of Tom's cock where the candle had been. "AAAAAHHHH!!!!" Chandler yelped when Tom pushed the fat head through the gaping hole and into his rectum.
"Here comes the rest," Tom announced, and pushed the full length of his cock up Chandler's ass in one stroke.
"Take it out, take it out!" Chandler whined, squirming and trying to pull away. It hurts!
Tom leaned forward and used his weight to push Chandler flat against the mattress. With his cock now buried deep in Chandler's rear end, he paused. "I told you to relax," he grunted.
Chandler continued to whine. Tom resisted his pleas. He thrust a fraction deeper, withdrew, and then thrust in again. Chandler felt trapped. He didn't like this! He was being held down and a hard cock was being pushed up his ass.
"Now you're a bum boy," Tom panted, continuing to fuck. He went slowly, but made sure to give Chandler every inch, pushing in until his boy hairs rubbed against Chandler's bum. Then he pulled back.
Slowly the initial shock wore off. Chandler found the hard shaft in his ass uncomfortable, but he had to admit it was getting better. His own dick was now throbbing and in need of release. Tom was using long full strokes and Chandler's feelings were growing once again.
"Your bum was made for this," Tom whispered in Chandler's ear as he steadily thrust away. "Best one I ever did," he grunted, "So tight and warm!"
The ache in Chandler's ass was slowly giving way to pleasure. He even found there were moments when the head of Tom's dick hit a certain place and he saw stars. Those were the times he wiggled with happiness. He grunted, groaned, and even started to raise his ass up a bit.
"That's it," Tom encouraged. "Give me that sweet bum."
The feelings were becoming too much for Chandler. The head of his dick rubbed the mattress as Tom pounded his rear end with ever more enthusiasm. Those times when Tom's knob rubbed that special spot were the best. He raised his ass up higher offering Tom more.
A few moments later, Tom was there. "Here it is," he groaned and then shuddered.
Chandler felt the dick in his ass jerk several times, and then a warmth spread the length of Tom's cock ending in a spot deep inside him.
"Feel it?" Tom grunted as he slammed in again. "I'm shooting my seed up your bum!"
"Yeah," Chandler groaned. The slippery feeling of Tom's dick squishing in and out of him was what did it for Chandler, and he too started to squirt. Four long pulses overtook him, and volley after volley of cream spilled out.
Tom pulled back one last time and rammed it in hard. Spent, he collapsed onto Chandler's back.
The heavy breathing and gasps told the whole story.
Several long minutes passed. Tom stayed buried as deep as he could reach in Chandler's back passage. Finally his shaft wilted. He withdrew and rolled off Chandler's back.
"That was amazing, that was!" Tom groaned.
Chandler rolled over, onto his back. "You could have warned me," he pouted.
Tom rose up and looked into Chandler's face. "Would you have let me done it?" he teased.
"No!" Chandler grumped, but then slowly smiled.
"I think you liked it at the end," Tom smirked.
"Maybe," Chandler blushed.
Tom giggled. "So, do we have a new cook's boy?"
Chandler gave Tom a shy look, "there's some bigger than you?"
Tom snickered. "A few, but I wouldn't worry."
"Still," Chandler said playfully, "I think I'd need a bit more practice."
Tom laughed. "Give me ten minutes and we'll give it another go."
Chandler rolled his eyes, "I didn't mean now!" he giggled.
The next morning, Sara poured water into a glass and set it down in front of Chandler. The boys had come down from upstairs rather late.
"Have a good sleep did you?" Sara asked as Chandler reached for some bread.
"Uh huh," Chandler mumbled, looking away.
Tom slid lower in his chair.
"Thought I heard a bit of a ruckus coming from your room last night," Sara chuckled.
Tom shot Chandler a worried look.
"Bad dream," Chandler said softly.
"Uh huh," Sara smirked.
Several of John's girls made their way down the stairs, looked at Chandler and Tom, and broke into a fit of giggles.
"Bad dream!" Sara said in way of explanation and nodded at Chandler. She tried to hold back but couldn't and all the girls laughed.
"Uh, I'll be back in a few hours," Tom stammered, giving Chandler an apologetic look as he stood up and moved away from the table. "Captain will want me on board," he mumbled, and practically ran out the door.
Chandler squirmed under the gaze of the women.
"I have a home remedy," Sara smiled, "good for things what's sore!"
Chandler practically turned purple.
The girls all laughed again.
"It really works," Sara giggled. "I've even used it on a few bums," she winked.
Chandler sank lower in his chair, wishing he was anywhere but here.
That's all for this chapter. I hope you are enjoying the story. My thanks to Andrew for help editing, and John B. for brainstorming with me. Comments? Suggestions? Write me at Playbuddy123@yahoo.com Thanks, Jon