Realm of the Winter Prince: A Pirate’s Tale, Chapter 1: The Litleo’s First Steps

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#11 of The Realm of the Winter Prince

This is the latest roleplay chapter in the series by myself and Nate_the_Great1.

Join an young orphaned Litleo. The day begins like any other in his poor life, but it ends in a most unexpected way for him.


Realm of the Winter Prince:

A Pirate's Tale, Chapter 1:

The Litleo's First Steps

The salty wind of the ocean blew across the wooden peer of a port town. The shops of the bustling seaside market were busy as always. Fish, bread, and produce mongers vie for the attention of their daily customers. Many craftspeople try to sale their wears to all in attendance. Even the children of the village are dutifully helping their parents with their daily grind for earning a decent living. Except for one orphaned Litleo. The boy was dressed in clothing that he sewed together himself from many fabrics found in dumpsters around the city. The preteen lion looked around for a good target, which meant finding a proprietor or townsperson with their guard down. The boy was known locally as a pickpocket and thief, but he was speedy enough not to get caught...most of the time.

On this particular day, he was sneaking around the fruit cart and when the cart vendor's back to the Litleo, the boy quickly stuffed his shirt with some apples, oranges, and grapes.

Just as he was about to turn and sneak away, the fly tending to the cart spotted him and screamed, "You again!?" The boy immediately dashed away at top speed as the vendor called, "Constable! The street rat is at it again!"

The young teen was gaining speed, but he bumped into something hard, causing him to fall backwards onto his rear. He looked up and saw a stern, tall bloodhound in an officer's uniform. "Uh... Hi, Officer Bones," the young Litleo chuckled nervously.

"Pyrodin. Up to it again I see..." The canine leaned down and looked the lad in the eye. Despite the elder male's rough exterior, he was in fact the nicest person on the town's small police force. "This must be the third time this month."

"Please, I was starving," whined Pyrodin as the bloodhound dragged him away to prison.

"Yeah, yeah," the officer said rolling his eyes, "Like I've never heard that one before."

Well, not so much dragged as carried. The police dog hoisted the scrawny preteen over his shoulder as if the boy were a sack of potatoes. Despite the kid's struggling, he couldn't break free. "I told you that I can't turn a blind eye to your actions. The mayor wants to keep the town's image clean for tourism, meaning I get the displeasure of having to somehow correct your behavior in spite of your more than understandable circumstances. You'll only be in the cell until tomorrow. I'll talk with the commissioner and see what deal I can work out for you."

"Fine, but that doesn't stop me from getting free produce," the feline grumbled as they reached the jailhouse.

"Technically you are correct because tonight's dinner does include vegetables." Upon coming to the door of an open, empty cell, the bloodhound gently put the younger male on his feet. "I don't know what I can do, but I will make sure no older prisoners will be locked in the same cell with you. When the commissioner returns from patrol, I'll try to make some arrangements for your release."

All Pyrodin could do was cross his arms and walk into the cell turning his back to the old officer in a huff.

With a sigh, the aged thirty-something officer closed the cell and turned the key, causing the sound of the metal locking mechanism to echo in the cell. He then went to a nearby desk and took his usual seat before turning to a small filing cabinet behind him and searching for the boy's record.

"I wish I'd never had to be stuck in this stupid cell or be caught by the law again," pouted the young feline as he shot a glance at the bloodhound.

Officer Bones had looked after the boy as if he was a son even though the boy disliked the old hound, but the dog cared for Pyrodin nevertheless.

The cop himself was not so well off. Yes, he had a roof over his head and a vixen wife, but no children. In a decision that was almost unheard of in their time, they resolved not to have children for the time being. This was a poor village after all, the reason why tourism and image were so important. That is also why both of them worked to keep their barely standing house.

Pyrodin paced back and forth in his cell still fuming for being stuck in there. He had such a good plan to get those fruits if it hadn't been for that fly-on-the-wall vendor. The Litleo's fur began to glow bright yellow with fury. " Why can't I get things to happen the way I want them to?" he complained to himself.

Officer bones let the boy fume. This was the younger male's typical routine after getting caught. That night, the officer put the boy to bed, making sure that he ate all of his meal and nestled in bed, before dog traded shifts with another constable.

Suddenly, from outside, the nighttime silence was interrupted by the sound of cannon fire.

The constable rushed out to see the commotion as the cub sat up on the wooden bed before he stood on a crate to look outside. "That can't be what I think it is."

'CRASH!' A large explosion blew the other constable to the other side and knocked him out cold as bits of rock and rubble shot through the door to Pyrodin's cell. When the young cub waved some of the rising dust and coughed a little bit, in stepped a tiger wearing a bright red, glossy coat that was open and exposing his bare chiseled chest; black, leather boots with glistening golod buckles; and navy, knee torn trousers, at his side he had a sword; and he walked over to the cub in the cell.

"Well, now. What be dis? I come to find possible members for my crew, but the only person here bee a kit." The tiger declared as he looked down upon the loan preteen.

The young cub looked up at the older feline feeling frightened at first; then, the tiger offered him a warm gentle smile.

With that inviting visage, he reached out an upturned paw. The elder feline declared, "If ye be in here, then ye must like stirrin' thin's up. Would ye like to be part of me crew, boy'ou?"

"Really? Truly?" Pyrodin asked with apparent excitement coming towards the cell door. "Yes. Yes, anything to get out of this dump."

The tiger grinned and deeply chuckled before replying, "That didn't take ye long. That be good, for me crew is efficient and will be done plunderin' soon. If ye have resolved to join me, take me paw, and you'll be on the on me ship in short order."

As the tiger reached his paw through the bars, Pyrodin rushed eagerly to the captain and shook it vigorously.

"Good lad. Now, ye may want to stand back," he said as he let go of the smaller paw, pulled out his blunderbuss, and aimed the firearm at the lock of the cell. The cub had barely jumped back before a BANG and glaring flash ignited from the gun, blasting the cell door's mechanism to obliterate. The door slowly swung open on it's own as the cub quickly exited the cell.

Then through the door to the jail, out came Pyrodin joining the captain by his side. "So, where's your ship?" the Litleo said looking up at the tiger.

"It be just on the other side of the port. Ye should stick close to me, boy'ou. Ye may want to cover your eyes as well, for me crew tends to be a bit brutal on our raids."

Pyrodin hugged the tiger's side tightly, and the captain wrapped an arm around his shoulder to help shield his eyes from the mayhem going on in the little town.

Meanwhile, Officer Bones was making his way through the chaos. Many of the townspeople were gathered in a secure place deep in the woods. After seeing his wife was safe, the canine ventured back into the city to find Pyrodin. Fire was set to the village, causing smoke to blind his sight. In-between coughs, he called out, "Pyrodin! Where are you?!...Come to the sound of my voice!"

However, the Litleo was nowhere to be found, and it wasn't long till the young cub found himself aboard the tiger's ship.

Immediately after, the ship sailed away from the burning town. The lion looked at the dimming light of the flames as the vessel set course for its next destination. The captain placed a gentle paw upon the lad's head. "Take it in, boy'ou. This be the first moment of the rest of ye days." "Yes, Captain," said Pyrodin with a long sigh and gazed out onto the pyre that was the town growing in the distance. Then, he turned towards the for what would happen from then on.

The stripped feline placed a gentle paw under the boy's chin and brought the lion cub's gaze up to meet his own. With a gentle tone he asked, "I see a glimmer of something in ye eyes, boy'ou. What be that?"

"Well, I want adventure, and I hope to find it with you," said Pyrodin hoping that the captain would grant his request.

"If ye play ye cards right, boy'ou, ye will be here a long time," he said before motioning to a door under the steering platform, where a crow wearing a black vest and pants with a red and white stripped bandanna was stirring the ship. "Come with me to me quarters, and we will discuss yer duties from this night on."

Pyrodin nodded as he followed the captain through the doo,r and he saw the tiger taking off his coat.

The tiger was now completely bare-chested. His toned torso was covered with scars from being slashed and stabbed during the usual dangers of his work. Placing a paw to his chest, the big cat declared. "This is something ye have to look forward to, boy'ou. This life isn't all pillaging and spoils. Ye will get hurt but even worse if ye don't watch yeself."

"Yes, Captain," said Pyrodin as he walked up to the big tiger, and the captain caressed the cub's cheek in his paw.

He kneeled down to be eye level with the cub. Smiling gently, he cupped his free paw around the boy's rear and gently pulled him in. "Touch my chest, boy'ou."

Pyrodin nodded before slowly placing both paws on the tiger's chest. The snowy white fur felt so soft and warm to the touch that the cub felt like purring.

"Good kit," the white chest and bellied, orange with black striped feline declared as his paws began to slowly and lightly rub back and forth over the cub's head and derrière. "I like men who know how te follow orders." His piercing, electric blue eyes met the copper orbs of the Litleo, and a short but lingering moment of silence was shared between them. Pyrodin felt a strange mix of admiration with a small hint of fear for and from the tiger. The strange sensation caused him to knead his tan furred hindpaws in his old worn straw sandals. Then, his ears twitched when he heard a commanding suggestion from the captain. "Why don't ye take ye shirt off, boy'ou?"

"Ye.... Yes, sir," said the young cub as he slipped his sleeveless tunic off his top half to reveal a scrawny, yet slightly toned chest.

The elder male's paw traced over most of the youth's nude torso. "You're underdeveloped, boy'ou. Ye haven't been eatin' much have ye? You've got some muscle though, so ye will have a good body for our ventures when ye come of age if ye take care of it."

"I'll try, sir," Pyrodin said as he looked down at his own feet but then the captain's paw lifted his chin to gaze into the tiger's commanding eyes.

"Ye won't be alone, boy'ou. There are other lads around ye age on this ship. However, there be one thing that we need to discuss before ye meet them." He leaned closer to the boy until his face was merely inches away from the lion's.

"What is it?" the young Litleo asked, feeling uneasy at first.

"The boys on this ship have three duties: cleaning the ship, learning how to run it for when they are older, and keeping the crew...company during our long voyages. Do ye understand what I mean, boy'ou?" The older cat's warm breath gently caressed the muzzle of the kit.

"I understand the first two tasks, captain," said Pyrodin shyly, "but I don't know what you meant on the last one."

"In this case, to keep company means to help occupy the men when they be at sea, in much the same way as the lasses in the pier bars." He presents the boy a knowing smile.

"Y-Y-You mean..." The cub stammered understanding now what the captain meant.

The captain only nodded slightly before inching ever closer to the boy's muzzle. His eyes remained locked with the lion's.

"But... I don't know how it's done," stammered the shy Litleo as the tiger caressed his cheek.

"Ye will learn on the job, boy'ou. Now, look me in the eye, and I'll take things from here."

Pyrodin nodded as the captain drew his face closer and the cub closed his eyes as their lips finally met in a passionate kiss.

In a quick fluid motion of his strong arm, the striped feline brought the boy into his arms as he stood, holding the boy to his body in princess style. He held the kiss as he walked to his bed, which was big enough for two men of his size and flanked by candlelit lanterns hanging from the ceiling. As the lay the boy on the red, silk sheets and rested his tiny head on the fluffy white pillow, the pirate leader positioned himself over the younger male and slipped his tongue between the lad's unsuspecting lips.

Pyrodin had never before known such pleasure like this, and, so far, he loved the attention.

The tiger began to caress the boy's dark brown chest and stomach with his big, strong, white-padded paw. The elder male's free hand was rubbing the red tuft of fur atop the cub's head, proof of his puberty and emerging physical maturity. Then he broke this long kiss to allow the boy to breathe.

"Will...Will...it hurt much?" asked Pyrodin as he panted for fresh air to fill his younger, smaller, and heating body him.

Strategically sitting up so that the shadow of his towering body would cover the cub's frame, he replied, "It will at first, boy'ou. I'll go slowly to limit the pain. When ye get used to it," he produced a confident smile before adding, "ye won't want it to ever end."

With that thought entering into the child's mind, the tiger reached for his sash. "Have ye ever seen another man naked boy'ou?"

"I've never even been with one before," the young cub said shyly.

"Then, ye be in for a treat," the head of the ship declared as he pulled off his sash with just a simple and quick motion of his paw. His black pantaloons immediately dropped to the floor, exposing his full, white testicles and fleshy sheath. The lad's eyes were drawn to the black cock head, which was beginning to poke out of his natural housing.

"It looks so big," the boy said nervously as he watched the captain's member begin to grow from the preteen's attention.

The big cat smiled widely and asked, "Like what ye see, boy'ou?"

"To be honest, sir... Yes, I do," Pyrodin replied shyly as the cub still had his trousers on, "So... what happens now?"

He smiled and leaned toward the boy to lock eyes again. The captain new the boy was around his finger and would fit in well with the other boys on his ship. Now was the time for imprinting the desire for sex, preferably seeding the need as deep as the boy's one for adventure. "Well, boy'ou, ye can't do awfully much with ye panaloons still on."

Pyrodin nodded and began to undo his own trousers. The moment he was completely bare, his own member was hard and stiff, but his size was a lot smaller than the captain's in comparison. The Litleo thought this must've been the biggest step he had ever taken in his life. Yes, he was nervous, but he felt an attraction to the big tiger and wanted the captain to hold him close for a very long time.

In a murring voice, the elder male declared, "You are a sexy little kit, boy'ou. When ye are older we will have ta beat the lasses off of ye." He reached a paw out for the kit's face and began to stroke the youths muzzle with his thumb. The captain had done this many times before. The next step was to make the boy want it as much as he did.

"So... what happens now?" said Pyrodin as the tiger crawled above him.

The tiger's manhood was now fully erect, standing nine inches tall and as thick as a broadsword handle. He placed his veiny flesh staff over the boy's muzzle. "Now, boy'ou," he began in a gentle voice with dominant undertone, "inhale my scent, ye face can touch, but keep ye muzzle closed. Do ye understand?"

Pyrodin nodded his head, and he closed his eyes as his nose rubbed alongside the barbed limb. The Litleo took a deep breath to take in the tiger's musk, and the smell was more arousing than Pyrodin had thought it would be. He wanted to lick it but dare not disobey an order given to him by the captain.

The tiger let out an audible purr as he gently ran his cock over the boy's face and stopped when his full scrotum was at the boy's snout. "Another one, boy'ou."

Pyrodin looked up before he closed his eyes again to take another good sniff of the older feline's musk. The little cub's own pink member was starting to dribble the clear liquid of pubescent sexuality that all young men his age begin to develop.

Grinning, the captain asked, "Tell me how ye feel, boy'ou."

"To be honest... I really want to know what you taste like," said Pyrodin while he was taking even deeper breaths of the tiger's musk.

In a flash, the tiger sat up and re-positioned his ass over the cub's face. His gluteal globes were just centimeters away from the youth's snout. "Taste me tailhole first, boy'ou. Ye have to earn a go at me manhood."

Pyrodin sniffed at the puckered entrance to the tiger's chamber, and then he closed his eyes as he lightly licked it. The taste was somewhat sweet as though the tiger had lathered himself in scented oils before doing this.

"MMMMMMMM. That's it boy'ou," He declared with a purring undertone to his voice. "Lick me right there to your youthful heat's content." After he spoke he rested a single digit on the very tip of the cub's light pink pecker, which stood in great contrast to his bark brown sheath and testicles. As the boy continued to carry out his oral order, the tiger traced the pre slickened flesh rod of the preteen lion.

Pyrodin flinched and moaned at the sudden intrusion yet he kept on giving his captain pleasure. The rough, battle roughened pads of the elder male hurt his inexperienced cock a little, but he got used to it after while.

The elder male traced a circle around the tip of the feline cub's rod. "That's it, boy'ou. Get deeper inside of me. Me hole is more than ready for it." Extending his tongue further out of his mouth, Pyrodin managedto work his way into the tiger's chamber.

"OH YES, BOY!" he declared as he took a firm hold to stroke the tiny cub bone in his encompassing, toned paw and began stroking the boy's inexperienced cock.

Pyrodin began to moan and purr as he felt the captain's warm paw around his member while the boy's tongue dove deeper inside the tiger.

Grinding his firm musky ass into the cub underneath, the tiger began to stroke the boy faster. "Let loose, boy'ou."

Pyrodin winced as he bucked his hips upward. In the next moment, small strings of seed erupted from his tender boy bone, and the cub pulled his tongue out of the tiger's rear to catch his breath as he moaned and shook in the pleasure.

The elder male pulled his seed covered paw away from the sensitive organ. Re-positioning himself upon the bed to sit in front of the prostrate cub, the tiger sits upon his rear as he asked, "Did ye enjoy that boy'ou?"

Pyrodin, still out of breath, looked up at the captain and nodded his head as he lay on his back facing upwards with his arms and legs spread out.

The big cat smiled at the panting boy. "Are ye out of it already, boy'ou? It's a shame, and just when I was about to let ye get to feel the pleasures of manhood."

"I.... can go a little further," Pyrodin replied showing that he could take it.

"Good te hear. Now turn yeself round so I can get acquainted with ye more intimate parts."

Pyrodin nodded and he turned over onto his chest and looked back at the captain wondering what he was planning to do.

After placing his big paws gently on the tiny rump of the orphan, the tiger leaned in until his snout was at the boy's crevice. He inhaled the boy's scent in a long, deep, audible breath and declared in a purring undertone, "Ye smell quite ripe, boy'ou. It be really appealing to me."

Pyrodin looked back at the tiger and blushed at the compliment. Then, he gasped as he felt something intruding his back virgin chamber.

The boy saw the tiger, snout deep in-between his young gluteal globes. The male decided to go easy on the boy and begin by teasingly tracing his unused pucker with his sandpapery tongue as he gently spread the lad's cheeks in his manly paws.

Balling up his fists around the fabric of the red sheets, Pyrodin let out a purring moan as the tiger thoroughly licked the youth's insides.

He was very slow, carefully and purposefully tonguing at the boy's wanting entrance. The captain steadily, almost dominantly, lapped his way into the cub's tunnel one centimeter at a time. Soon, he had worked through both of the boy's anal rings. The lad's sounds of pleasure only drove him to go slower as he wanted to saver the preteen's pleasure. Suddenly, the boy felt the wide, rough tongue hit his prostate.

Pyrodin flinched with his eyes wincing at the feel of the sandpapery tongue knocking around inside of him. He panted and clinched the sheets again as he let out a high-pitched whimper.

"Did ye like how that felt, boy'ou?" The captain asked as he suddenly stopped and pulled his muzzle away.

"It's... It's a whole new thing," said Pyrodin with a shaky breath as he turned his trembling head to the tiger. "I've never felt this way before."

"Just ye wait, boy'ou," the tiger traced the boy's love tunnel entrance with a digit as he declared, "Ye haven't felt anythin' yet."

Pyrodin gulped, fearing the worst. "I hope it's not going to be too painful," he thought to himself.

Smiling, the tiger said, "Just stay relaxed." Then, he pressed his digit against the loosened pucker.

Pyrodin gasped and moaned softly. He covered his mouth with his hand as he gasped and whimpered at the intrusion.

The boy felt the elder male's free paw rub over his red mane tuft atop his head. "Breathe and relax yeself, boy'ou," the captain advised gently as he gently works his digit in and out of the youth's tight entrance.

However, no matter how hard he tried, the boy just couldn't help but feel the mix of pain under the current pleasure.

"Ye are havin' trouble...turn onto ye back again, boy'ou." He gently withdrew his digit and backed away to allow the kit movement.

Pyrodin was heaving as he turned around and small tears appeared in his eyes. The tiger leaned his head down to lick the tears and gently kiss the boy's muzzle.

The striped feline took the boy's muzzle against his own and caressed the lad's lips with his bigger tongue. Soon, he gently forced his way into the lion cub's mouth and was slowly and gently exploring the preteen's maw, all the while he left his finger in to slowly wiggle into the lion's love tunnel. The boy took a sharp inhale and wrapped his arms around the captain's neck.

The captain happily embraced the boy, for he knew it was a natural part of his first time bonding ritual with younger men. Everything he did was to cement himself as a fatherly figure and lover to the youth, and it was working. He delved deeper into the boy's rectum. The next moment, the boy tightened his hold and jerked his body at the feel of the thick digit upon his prostate.

"Sir... I think I'm gonna... gonna cum again," moaned the boy as he felt his member pulse into hardness again.

The captain pulled his muzzle off the boy's member and his finger slowly out of the boy's loosened hole. Before laying down and cuddling with the cub. "Not just yet boy'ou. I still want te play with ye a bit more."

"Ye... Yes sir," whimpered the cub softly as the tiger lovingly licked the boy's forehead.

To give the boy a feeling of trust and confidence, the elder male said, "If ye like, we can stop."

"It's alright, sir," declared Pyrodin hugging the tiger. "I can still take it."

"Then, how about ye climb on top of me and work yeself at ye own pace?"

Pyrodin nodded his head and he crawled up onto the broad muscular body of the elder male and got into a crouching position over the captain's member.

The boy hesitated when he felt the head of the elder feline's flesh mast. In response, the captain kept silent and gently placed his thick, white-padded paw on the boy's cheek. When the preteen orphan felt the rough brush of the captain's gentle thumb along his muzzle, he instinctively took the digit into his maw and suckled upon it out of anticipatory need.

Then Pyrodin slowly lowered himself further till the head was inside his tailhole, causing him to give he gave a whimpering mewl.

"That be very cute, boy'ou," the captain declared as he chortled from the muffled sound of pain and pleasure. "Take ye time. After all, ye chores don't start until the morrow."

"Can... can I kiss you, sir?" moaned the cub as he slowly continued to push himself down and upon the tiger's thick, black, barbed manhood.

Smiling at the rosy blushing kit, the Tiger declared, "As long as ye don't pull ye tight rear off of me mast, boy'ou."

The boy nodded as the tiger sat up, wrapped his arms around Pyrodin's waist and brought his lips to the Litleo's.

The captain held the kiss with the lad as his young body adjusted to the massive manhood inside of him. The preteen's youthful paws knead upon the bare, firm shoulders of the elder male as he relaxed and his love canal began to accommodate the tiger dick entering him. Before long he began pumping the girthy schlong in his rear and resounding purring moans from his muzzle.

The young cub began to purr strongly as he was soon working himself up and down the elder man's pole, with the mass never completely leaving his heated body.

Grunting in a deep, manly tone, the tiger declared, "I'm close, boy'ou. Ye should prepare yeself."

Pyrodin nodded as the tiger flipped him onto his back and started impaling the boy. His thrusts were strong and dominant as he gave away to the lust he had been holding back for the lad. However, his inner floodgates had broken, and the lust rushed through him as he showed the boy what he was in for as part of his new life at sea.

The cub whimpered and hugged the tiger's neck as the big cat began to make hilting impalements further inside of his deflowered body.

Resisting his natural urge to chomp on the lad's neck, the captain screamed in a deep manly, "AAAAAAAAAAAAAAAAAAAAH!" as his dick began to spasm hard. While the elder male continued his tough assault on his rear, the Litleo could feel a hot sensation cascade in and over his body.

Pyrodin closed his eyes and cried out as his own seed shot out onto the tiger's chest.

Quickly moving his paws, the panting tiger sat himself up by straddling himself over the boy and keeping himself balanced upon the mattress.

"That felt.... good," panted Pyrodin as he rested his head on the tiger's shoulders, and the captain gently rubbed the boy's chest with his manly paws.

Remaining inside the boy, the tiger reclined until his back touched the bed. After straightening out his legs, he pulled the boy's chest to his own torso, sandwiching the fresh cub cum puddle between the two of them.

Pyrodin looked up and smiled as the tiger caressed his cheek, and they both kissed.

The tiger slowly stroked the boy's head and back with one paw as they both catch their breath. "That was very good boy'ou. Ye will be a great addition to me crew."

"Thank you, sir," Pyrodin responded in panting breaths.

"Do ye understand ye main duties now, boy'ou?"

"Yes, I do, captain," said the little Litleo as he nestled into the tiger's chest fur.