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Chubby Cheeks

A Pirate's Tale

By Steve LancePublished 4 months ago 9 min read
Top Story - September 2025

YouTube Video is the Audio Version.

Milwood Milford, also called Captain Peg Leg, although not to his face, sat under a large palm tree, sipping a banana daiquiri.

Fun fact: banana daiquiris were invented by Captain Peg Leg…I…I mean Captain Milford, when he ran into three ships off Jamaica’s coast, he literally ran into them. Crash, bang, oops, sorrrrry, and all that. One was carrying rum, the second bananas, and the third was filled with limes. The cargo mixed in the warm waters of the Caribbean, and the sailors tossed overboard were treated to a wonderful new beverage.

However, that is a story for another time, and has nothing to do with the raid on the Golden City. Except, of course, Captain Peg Leg….ah…ah Milford was enjoying this splendid drink when the plan to raid the city was hatched.

Where were we? Ah yes, there was a warm breeze flowing off the tropical bay. Captain Peg L...—editor’s note: Captain Milford will now be known simply as Captain—was leaning back, his feet resting on a chest full of gold, when his first mate Rupert approached. Rupert was a pirate’s pirate. He had it all: the eye patch, the handlebar mustache, the three-corner hat, and a puffy shirt.

“Captain, the crew is getting restless. We haven’t raided anything in over a month,” Rupert said, trying not to stare at the Captain’s left leg.

The Captain sipped his drink and sighed. “I’m bored with raiding and pillaging. We have all the gold we could ever want. We don’t even bury it anymore,” the Captain glanced around the small island; treasure was piled everywhere. The place was a mess.

“It’s about more than the treasure. We are pirates. It is our purpose in life. Let’s raid the Golden City. It will make us rich beyond our wildest dreams.” Rupert rubbed his hands together, stepped forward, tripped over a gold, diamond-encrusted candle stick, fell headfirst into a basket of emeralds, reached over, grabbed a silver walking stick, and pushed himself to his feet. “Rich, I tell you, rich.”

The Captain yawned and motioned for Rupert to come closer and lean down. He then picked several emeralds out of Rupert’s hair and tossed them aside. “Nah, it seems like too much trouble. We will have to get everyone onboard the ship, sail to the city, climb the walls, and haul all their stuff back to the island. Where would we put it? No thanks.” The Captain leaned back and closed his eyes.

Rupert picked up a golden back scratcher and paced back and forth, contemplating the situation while trying to satisfy an itch. Repeatedly, he exclaimed, “Ooh, yeah, that’s the spot. Right there, baby, right there.” Midway through an “Ooh,” it came to Rupert. What did the Captain want more than anything else? Well, yes, a leg, but that ain’t happening. The Captain was a lonely man; he didn’t even have a parrot. He needed a companion to make the long nights a little less lonely. Someone to share a sunrise and a cup of coffee. Someone who would constantly nag him until going on raids was his only relief.

“Did I tell you Queen Sabrina rules the city?” Rupert said with a twinkle in his eye. “She has chubby cheeks.”

The Captain opened one eye and looked at Rupert, “Chubby cheeks?” His mind drifted back to his one true love, the beautiful and fair Gwenifer of Pigeon Bay. Long flowing blond hair, luscious red lips, a cute little button nose, and chubby cheeks.

“With dimples,” Rupert added.

“Chubby cheeks and dimples. I do like chubby cheeks, especially with dimples.” The Captain stood up and scanned the island. His crew were lying around, not doing much. One member was trying to skip silver dollars across the lagoon. Another was seeing how high he could stack rare, fragile teacups. A third was cutting up fine silk into strips to be used in the latrine. “What are we waiting for? Everyone aboard the ship. We have a city to raid.”

The Captain looked at Rupert. “Chubby cheeks?

“With dimples.”

*

Five hundred miles away on the coast of Panama, Queen Sabrina sat on her throne, holding a mirror. She was wondering if her cheeks were too chubby. Perhaps she would cut back on the roasted pig, although they made it just the way she liked, with extra fat.

The door to her palace flew open, and her trusted servant and BFF, Rosy, rushed down the long aisle and stood before the Queen. “Permission to speak, Your Majesty.”

“Rosy, it is so hot and stuffy in this palace. I wish I could take a trip to the islands. I hear they have warm breezes and delicious drinks.”

Struggling to catch her breath, Rosy said, “I have frightening news, Your Majesty.”

“Is it about the cats? I’ve told the city manager he simply must do something about all the stray cats. Even if he has to use a bow and arrow on them.”

“No, far worse.” Rosy noticed the Queen seemed depressed, and her cheeks were chubbier than usual. She made a note to tell the cook to cut back on dessert.

“Worse, then, a thousand feral cats roaming the streets?”

“Captain [Censored] is headed our way. He plans to sack the city.” Rosy swallowed hard. “He is going to capture you and take you back to his top secret pirate hideaway, located on the fourth island, second lagoon to the right, just after you enter the Virgin Islands.”

Queen Sabrina blushed. “Silly man, I haven’t been a virgin since the Christmas party. That punch they served sure was potent.”

“My Queen, the Captain has a reputation with the ladies. If he captures you, he will lift you up in his strong, muscular arms, carry you out of the palace onto his ship, the Passionate Prince, and cruise through the crystal-clear Caribbean waters to his lush tropical island. Who knows how many hot, sweaty, lust-filled nights you will have to endure?”

“Oh, my.” The Queen fanned herself. “Does anyone else think it is hot in here?”

“Should I alert the palace guards, lock the city gates, and have boiling oil ready in case they try to scale the walls?”

“This Captain sounds like a naughty boy.” Queen Sabrina smiled. “A lush tropical island, you say?” She hummed softly and swayed back and forth. “You are right; we must prepare.”

“I’ll have them start boiling oil.”

“Wait, we can do all that later. Right now, I need you to draw me a bath, lay out my red dress; I think it brings out the blush in my cheeks, and call the hairdresser. Chop, chop, we don’t have much time.”

*

The Captain gazed at the high city walls, cursing this stone monolith that stood between him and happiness. He feared that the Queen’s chubby cheeks would never grace his pillow. To come all this way, only to be foiled by a pile of rocks. The Captain gathered his strength and vowed the Queen would be his, or he wasn’t Captain [Censored].

“I need a volunteer to scale the walls and open the gate. They will probably pour hot boiling oil on you. You will most likely die of your burns. It will be a horrible, painful death. But on the bright side, we will sing songs about your bravery and toast you with ale as we get drunk in the after-raid party.”

A young sailor stepped forward and said, “Captain [Censored], maybe the gates are open. I hear country folks don’t lock their doors.”

“What did you call me?” The Captain narrowed his eyes. “I think we found our volunteer.”

Rupert pulled on the gate, and it let out a long, slow squeak as it opened. “Hey, the kid is right.”

“You’re lucky,” the Captain said to the young sailor.

Inside the gates, cats were running around. There were a few run-down huts and a couple of broken pots.

“Are we in the right place?” the Captain asked as he scratched his head. “It was turn south at the Cayman Islands, correct? Or should we have gone west?”

Rupert grabbed one of the citizens and asked, “Is this the Golden City?”

“Yep. Don’t feel bad. They suckered me, too. It’s all a marketing ploy. I guess nobody would move here if they called it the Shithole City.”

The Captain pushed Rupert aside and shook the man. “Do you have a Queen?”

“Yes, yes, we have a Queen. We may be a shithole, but that doesn’t mean we can’t have royalty.”

“Does she have chubby cheeks?”

“Chubby cheeks?”

The Captain terrified that his dream was slipping away, shook the man harder. “Think, man, think. Are her cheeks chubby?”

“Yes, I suppose they are chubby.”

“With dimples? For the love of all that is holy, does she have dimples?”

The man nodded and glanced down at the Captain’s leg. “Where did you get the [Censored]?”

The Captain’s face turned red. “I will have you flogged. Nobody says [Censored] in my presence.”

Rupert tapped the Captain on the shoulder. “Captain, I left your best whip back on the island.”

“The one made of imported Italian leather, with a ruby sewn into the handle?” Rupert nodded, and the Captain sighed. “Just point to where she is.”

The man pointed down a rut-filled road. At the end was a dilapidated palace, where several cats darted in and out.

*

Queen Sabrina sat on her throne, fixing her hair. She held a cat on her lap and two more sat at her feet. The Captain’s [Censored] echoed throughout the large cavernous room. The smell of cat urine engulfed them. Rupert put his hand over his nose.

The Queen blushed and smiled at Rosy, who ran her tongue over her teeth, hinting to the Queen that her lipstick had smudged.

Rupert elbowed the Captain in the side. “You’re about to meet the woman of your dreams.”

“I’m as excited as when we raided our first ship. Remember, it was a little schooner off Nantucket.”

“Those were the days,” Rupert gave the Captain a light punch in the shoulder and straightened his lapels.

“Hey, does my breath smell okay?” The Captain opened his mouth and exhaled into Rupert’s face.

Rupert drew back. “Whoa, will we have been eating dried cod for a month? Just don’t say any word that starts with the letter H.”

“I have to say, Hello. I can’t just grab her and haul her to the ship without introducing myself.”

“Say greetings instead. You’ll do fine. Ready tiger?”

The Captain gave Rupert a thumbs up, turned, and saw the Queen for the first time. “Man, them are some chubby cheeks.”

“Wow, they sure are.” Rupert swallowed hard.

“Do you think they may be a little too chubby?”

“Hard to say. I’m more a leg man myself.” Rosy glared at the two men, and Rupert gave her a forced smile. “Don’t forget about the dimples.”

“Are you sure they are dimples? And what is with all the cats?” The Captain stared wide-eyed at Rupert. “How far away is the ship?”

“Are you thinking we should go to Plan B?”

“Yep.” The Captain slowly backed away.

“Rosy’s on to us; it’s now or never.”

The Captain turned and shouted, “Run like hell.”

As Rupert and the Captain were running out of the palace, Queen Sabrina stood and shouted, “You’re no catch either with that stupid PEG LEG!”

Short Story

About the Creator

Steve Lance

My long search continues.

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Comments (3)

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  • Alice Garry3 months ago

    I just went through your story, and I really enjoyed it. It inspired a few ideas I’d like to tell you about.

  • Was sure I had read this, great fun, I have now

  • Julie Lacksonen4 months ago

    Fun story!! I can always count on you for entertainment. I'm still a little lost about the censored word though. 💜🤭

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