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  • Writer's pictureDrasayer

Oh Captain, My Captain

Original dA post: https://www.deviantart.com/drasayer/art/Clusterfuck-tober-Week-1-Oh-Captain-My-Captain-766525566

Seaman claim that booty.

Jarin stood on the deck of the mighty boat, “Little Pinky”. A smaller vessel but one he was proud of, regardless! He was going to brave the ocean waves all on his own! A dumb idea, he was told but he wasn’t in search of anything smart. He was out to find the elusive treasure island! He knew how to get there and didn’t need help! He was going to bring it back and be a hero for the crew!

He sailed for many hours on his own. It was tiresome to see the same old blue horizon and constant lull of the ocean. He nodded off occasionally, racked with the boredom of the journey. He just wanted to be on the island already!

Jarin jerked awake, feeling the ship lurch and a loud grinding noise. He got to the island, alright! He crashed right into its beach! He hopped from the deck to inspect how bad it was. Pretty bad… No way it was budging with just Jarin’s strength. He’d have to hope the tide would rise enough that he could get it pushed back to sea. But for now…treasure!

Jarin smiled and turned around to survey the island. He wasn’t ready to see a human skull right in his face! He screamed and jumped backwards, crashing into the side of his boat! “What are you!?”

The skull creature took a step closer, smiling and Jarin’s mind was putting together that it wasn’t an actual human skull looking back at him. Rather, it was a very beautiful woman with a painted face. Jarin looked her up and down. His face turned redder than the setting sun over the sea. Her gown was undone, and she wore nothing else under it. She didn’t even seem to mind! He gasped and covered his eyes with his hands, “Sorry, miss!”

The woman turned her head and smiled sweetly, “Sorry?”

Jarin shook his head, “I didn’t mean to look upon your body in an inappropriate manner! I meant nothing by it! Sorry!” To disgrace such a beautiful woman! But she shouldn’t be dressed so… wait… Jarin cracked his fingers open slightly, “Wait, do you live on this island, by chance?”

The woman stepped towards Jarin, sliding up to him, looking him up and down, feasting her eyes on him like he was her next meal, “You could say that. My…look how sweet you look…” She brushed a hand up to his cheek, pushing some of his dark hair behind his ear. Such pale skin. He would cook within a day.

Jarin flinched away from her hand, painfully aware of how naked she was, “I-I thought this island had been deserted long ago. Are…you one of the crew members of the pirate ship that crashed here?”

“He’s onto us,” a deep voice chuckled, coming from around the other side of the boat. Jarin looked over, not expecting another person so soon. He gasped and covered his eyes again at the sight of another face painted like a human skull and he was even more naked than the woman!!

The man leaned over the woman, pressing her body up against Jarin’s. He grinned, “If you know that much, you must be looking to find our treasure, no?”

Jarin cracked his fingers up, perking up at the sound of ‘treasure’, “Well, I…I didn’t think anyone would still be here so…”

The man leaned over the woman’s shoulder, “Shaliegha, I do believe, we have a pirate on our hands.” He brushed his beard whiskers against Jarin’s cheek, giving him a hard gaze, piercing blue eyes against the black painted eyes.

Shaleigha feigned a gasp. She slid a clawed finger up Jarin’s throat, leaning in to take a nibble, “Why, Justin, I think you’re right. Came to steal from us.”

Jarin whimpered and swallowed hard. “N-no, no! I thought it was up for taking! No one said anybody was still here! I-I won’t take it,” he laughed nervously, ducking under Justin’s arm and peeling away from Shaleigha.

Shaleigha laughed and caught Jarin by his waist before he ran. She turned him around and pulled him back to the boat, holding him against her chest. “Now, that’s not how a pirate would behave. Running?”

Justin stayed close, boasting his own ripped body. “You do want treasure, don’t ya? We could show you. You could be up to your eyes in treasure. Think of the adventures out on the sea. The freedom of the water. Take what you want and never look back.” He smiled, tipping Jarin’s chin up.

Jarin was enamored by his words. It brought a little sparkle to his eyes. Yes, that sounded like a very fun life! Maybe he could be a good pirate. Less pillaging and murdering, just harmless adventure and parrots for pets. The simple pirate necessities! He nodded like he was in a trance, “Well…maybe that does sound like fun…”

Justin smiled over to Shaleigha. They had him now. He looked back at Jarin, “Well, first thing’s first. Dress code. Ya can’t be strikin’ fear into the heart of men with that nun outfit. You look like you own a bread shop in the country side.”

Shaleigha helped to relieve him of his trousers while Justin pulled his shirt off over his head. Jarin pinched his knees together and cupped himself, blushing hard. Justin pushed his hands back, “Ah, no pirate would ever be ashamed of their firearms.”

“Okay,” Jarin whispered. He looked up at Justin through his dark bangs, waiting for his next pirate lesson. Though the lesson odd, he was still quivering with excitement. Real pirates! Real adventure! “What do I do next!?”

Shaleigha grabbed Jarin’s thighs, spreading his legs, “Such a good boy.” She ran a ran to the inside of his thigh, brushing her fingers over his “pistol”. Jarin jerked and grabbed onto Justin’s arms, gasping in surprise. He looked over his shoulder, confused about this portion of the lesson.

Shaleigha smiled, taking him into his hand and stroking his dick for him, “We all have to work together, no? Checking each other’s weapons is a good way to instill trust in each other. We wouldn’t want someone to be unprepared during a fight out on the sea, would we?”

Jarin moaned, leaning his forehead into Justin’s chest. Her hand was so warm! She had complete control over him! Justin raised a cocky brow and grin. It was clear the boy had no experience in the matter and that only made him all the more valuable. He wrapped and arm around his waist and dropped another hand behind him.

Shaleigha made her own quiet sigh, flicking her eyes in Justin’s direction. She opened up her own stance, letting him slide his fingers between her legs. He loved to tease her, never quite giving her what she wanted when she wanted it. She pushed his fingers harder into herself, panting over Jarin’s shoulders while squeezing harder on Jarin’s dick, working him up in rhythm with her. “Only a thorough inspection will do.”

Justin smiled like he knew what she wanted, but he still like to toy with her. He tipped Jarin’s chin up, and kissed him hard, breathing him in, pushing his fingers into Shaleigha, so hot and wet. Jarin was completely wrapped up in the heatwave coming from front and back. Shaleigha’s pants and how she had him worked up, Justin’s lips and broad muscles pressed against him. It all had Jarin panting for more. He looked up to Justin again, “Is it my turn then?” He bit his lip, getting the memo, Justin was his responsibility now.

Justin and Shaleigha both grabbed Justin’s cannon and slicked him right up. “Of course, we all have our duties on the poopdeck” He chuckled at his own nasty joke. Jarin didn’t seem to get it but he didn’t have to as Justin reached down and picked him up by his ass. He shoved him up against Shaleigha who held him under his thigh.

Jarin squealed and held onto Justin, wrapping his legs around his waist. He flinched and tightened his abs, looking into the dark sockets for those brilliant blue eyes. He felt the cannons pointed right for his poopdeck. Was this friendly fire?

Justin smirked, pushing his dick into Jarin’s ass. “Most important rule about being a pirate. We always look for the biggest booty.” He clapped a hand onto Jarin’s asscheek, making his whole leg shake.

Jarin gasped and threw his head back, feeling Justin push his way into him. He moaned and clawed at his shoulders, bracing against Shaleigha’s chest. She chuckled away at how sensitive his was, groping his thighs. She lifted a leg of his up over Justin’s shoulder, making him moan loudly again as Justin could thrust deeper and harder into him. “Just being thorough,” she teased.

Jarin was sailing the high seas, wave after wave crashing into his vessel. “I’m gonna be the best pirate! Your seaman! You can have all of my booty! Oh, Captain, my Captain! Ravage my sail-“..


 

Shaleigha opened her eyes, feeling her horse nudge her elbow. She looked down to see the stud had decided to lay next to her and was wanting to use her lap as a pillow. She smiled gently and straightened her legs out from the position she had been in. She patted her lap and let him rest his massive head on her lap. She patted his cheek and looked out to the calm ocean before her.

What a meditation session that had been.

It left tingles in her toes just thinking about it. Pirates, huh? She did love reading about their tales and she always had a love for the ocean. It made sense to her. The guests in it…well, that was a bit odd. She had only seen Justin the one time she had gone to West RidgeRunner and he was jumping onto his tall friend’s shoulders like he was a rodeo bull. And Jarin, well…

She looked over to him, doing his own stretches on the beach. He was visiting to experience some culture in her yoga methods while trying to figure out how to be a racehorse jockey at the same time. “Jarin?”

Jarin hiked his butt up to the sky like he had been shown before. He deep a deep breath, letting his muscles relax and stretch. He looked over to Shaleigha with a sleeping horse next to her, “Yea?”

“Would you ever want to be a pirate?” she asked with a smile.

Jarin raised a brow, confused about the question with no context. “Uh…no I don’t think I would. They have really bad hygiene and I don’t think I’d enjoy all of the cannons. Not to mention, they're criminals...”

“No?” She snorted, remembering in her meditative dream-state, that had not been the case. Maybe she’d tease him about pirates a little more but the golden memory was hers to enjoy. Also, she needed to meet this Justin guy again…

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