Author's Notes:

This chap contains mostly vanilla sex and a bit of TF/TG at the end.

Jolly cracked into another coconut and greedily drank at the milk inside. He was sick of coconuts, but he didn’t have much of a choice given his current predicament. He looked out at the waves and sighed. He couldn’t remember how long he had been on the island. Though judging by his beard, the answer was quite some time.

“I'm gonna die here... alone...” he groaned, looking up at the sun. He furrowed his brow and narrowed his eyes. “No, I’d rather die at sea than starve on this pile of sand.” He grabbed his knife and cut off a piece of his shirt, an idea forming in his head. He then grabbed a stone and a stick and started making a makeshift axe. When he was done he chopped at a tree and attempted to make a raft.

It took him through most of the day, but by sundown, he did indeed make a raft. He smiled for the first time in a long time and put the raft in the water. His smile grew when it floated and he pulled it back in. He then made a spear to fish with and grabbed several coconuts to keep him fed. He pushed it in again and started to flee his island prison.

“Freedom!” He cheered, throwing his hands into the air. He laid down on the raft, sighing in relief and staring at the stars for a little bit. “Truly a beautiful night to reclaim my life.”

A light giggle caught his ear, a splash filling the air. He looked towards the source of the noise and his eyes bugged out of his skull. Three all too familiar fins were circling his raft.

“I didn't even make it a day...” he lamented with a defeated groan. He grabbed his spear and knife and prepared to fend them off, or die trying. “If I’m going to die, it’s going to be as a stallion, not as a sniveling babe,” he said, gripping his weapons tightly.

The three fins sunk back into the water, and in their place, the heads of three mares breached the surface. Their muzzles seemed a little oddly shaped though. Jolly blinked, lowering his weapons slightly.

“It’s official, isolation has driven me mad.”

“Oh no, I assure you, you're very sane.” One assured, giving him a fanged smile. Her mane was a silvery color and her fur seemed to be a burnt orange with black stripes.

“We don't get to see a lot of land ponies out here,” another spoke up. Her mane was a navy blue that matched her eyes and her fur was a steel grey.

“Shark ponies?” Jolly asked, seeing their teeth. “I thought those were just stories.”

“Nope! We’re real!” The third smile, pulling herself up onto the raft. She had a silvery mane like the first one, though her eyes and fur were a light blue. Except for her chest and stomach which were white. Jolly blinked, seeing her breasts were totally exposed.

“Um… yes, I can see that,” he said, setting his spear and knife down.

“You are a handsome one.” The first pulled herself onto the raft, licking her lips.

“You’re too kind,” Jolly said with a chuckle. “I haven’t groomed myself in…” he tugged his beard. “Months.”

“You must have gotten... lonely.” The second one joined her friends on the raft, swishing her tail.

“Yes, I haven’t seen another pony in all that time,” he agreed. “My only company has been gulls and crabs.”

“I bet we could change that~” the third wrapped her arms around him, pressing her breasts into his back. He shuddered, the pleasant contact feeling foreign after so long without the touch of another.

“As if I’d deny the company of three lovely ladies.”

“Excellent.” The striped one smiled, pulling his shirt off. She let out a pleased sound, feeling his chest.

“Can I get your names?” Jolly asked, returning the favor to the striped one. “I am Jolly Roger.”

“You can call me Riff Raff.”

“I’m Rip Tide,” the blue and white mare chimed.

“I’m Driftwood,” the grey mare greeted. Riff Raff made short work of his pants, tossing them away. He watched them bob on the water.

“It’s a good thing I have you three to keep me warm,” Jolly commented, pulling Riff Raff close and squeezing her ass. “Otherwise I’d miss those.”

“You won't be needing them,” Riff Raff assured him. “Tell me Jolly, how do you feel about being a father?”

“I’d say as long as you help me get far away from that Faust forsaken island, I’ll put as many foals in you as you want,” he replied with a grin.

“Perfect!” She beamed, reaching down and giving his dick a squeeze.

“It’s been too long since I’ve been with a mare,” he groaned, running his hand along her back and taking in her foreign features.

“I’ll be sure to make this amazing,” she assured, straddling him.

“I was about to promise the same thing,” he replied with a grin, grabbing her hips. She winked, lowering herself onto his erection. They both moaned, their voices forming a perverted harmony.

“Oh damn, you squeeze tighter than a virgin,” he groaned. She giggled, guiding his mouth to a nipple. He gladly took it, suckling and nipping on it as his length hilted inside of her.

“Good boy,” she cooed, reaching down and cupping his balls. He moaned a bit, taking a bit to note the new sensations. She was a bit cooler than other mares he had been with, but it was a pleasant coolness. And she was wet. She was leaking fluids like a broken faucet already and they’d only gotten started. She gave his balls a squeeze, rolling them around in her hand. He let out an appreciative moan around her nipple and started stroking and squeezing the base of her tail.

She moved her hips, starting to pick up a rather nice pace. He continued to suck and nibble her nipple while he let his hands roam her exotic body. He closed his eyes as her folds glided against his length with ease.

“Mmmm you’re so big...” she leaned up, nibbling on his ear. She gave it a tug, her teeth scraping along the skin.

“And you’re so tight,” he groaned, his green eyes gazing into her ruby orbs. She looked back into his, pulling him into a deep kiss. He didn’t even hesitate, letting his tongue meet hers like an old friend as their hips started to move in tandem.

“Look at em go,” Rip Tide purred, watching with gusto.

“Mhmm,” Driftwood agreed, stroking her lower lips. “Jolly’s a fine catch. I think he’s a keeper.”

“We’ll have to do the ritual you know,” Rip Tide pointed out.

“Would you rather find a shark pony stallion?” Drift asked with an incredulous look.

“Did you forget what the ritual actually does you idiot?”

“No, I didn’t. But a converted stallion doesn’t have the same instincts as a natural one. Like being a complete asshole,” Drift replied with an indignant huff.

“Oh so, you'd rather him die from exposure then?” Rip Tide asked, glaring at her.

“You kidding, I’d gladly take that,” she pointed at the intimate display in front of them, “over any of the jerk sharks that are all teeth and no heart.”

“Agreed.” Rip Tide nodded. “I get him next.”

“That’s fine by me,” Drift said with a nod. “But we should find somewhere else before you do. I don’t think this raft can take how crazy you get.”

“Where else are we gonna do it?” Rip Tide frowned.

“There’s that cave not far from here,” Drift said. “Jolly should be able to hold his breath long enough for us to get there.”

Riff Raff smiled, overhearing them. “Hold your breath dear.” She winked, rolling off into the water, pulling him with her. He held on, closing his eyes and letting the girls lead him wherever they wished to go.

They surfaced in an underwater cave, Riff dragging him back into dry land. “Enjoy the water?” She asked, kissing his cheek.

“Despite being an Earth pony, I’m a creature of the sea,” he commented, pecking her lips. “So yes, I enjoyed that a lot.”

“How would you like to become one of us?” She asked, staring into his eyes.

“I couldn’t turn down an offer like that,” he replied, staring back into hers. “I was never any good at growing crops like my family.”

“We’ll have our fun before your conversion, you might not be much of a stallion after the ritual.” She pulled him into another kiss, moving her hips again. He matched her movements, running his hands along her dorsal fin. She moaned into the kiss, rapidly picking up the pace. He moaned as well, his hands gripping her flesh as he fought off his orgasm. “Close already huh?” She asked, bouncing up and down along his shaft.

“It’s been ages since I was last with a mare,” he replied with a grunt. “I never masturbated on that island either.”

“That just means you’ll have more to give.” She smiled, giving his balls a squeeze.

“It’s all yours from now on,” he said, thrusting into her to match her motions. “Anything for my three saviors.”

“Such a flatterer.” Riff smiled, nipping at his neck. He moaned, kneading her ass as he bit his lip, fighting off the inevitable. She wriggled her ass for him, letting her teeth sink ever so slightly into his skin. He groaned loudly, his hip movements becoming jerky as his eyes screwed shut. “Cum for me...” she moaned it in his ear, hilting herself on his shaft. He buried his face in her neck and came, coating her insides in white. She tightened around him, milking him for all he was worth. Riff let out a satisfied sigh, rubbing her bloated stomach.

“That… made the time on that island all worthwhile,” he said with a dopey smile.

“I bet.” Riff nuzzled him, proceeding to roll off him.

“So how would turning me into a shark pony work?” Jolly asked. “And what did you mean I wouldn’t be much of a stallion?”

“No I said you might not be much of one, there's a difference.”

“Okay, but that didn’t answer my question,” he said, looking into her eyes.

“Well, there is a chance you’ll lose your friend during the process.”

“Considering my choices are to take my chances on the raft, or join you three and possibly be a mare. I think I’ll stick with you three,” he said.

“Are you sure?” She asked, looking into his eyes. “There won't be any going back.”

“I was alone too long,” he said, stroking her cheek. “I don’t want to go back to that. Besides, I’ve got good luck.”

She giggled, kissing his cheek. “Just in case, you have fun with Drift and Rip, I’ll get what we need.”

“I believe it’s Rip’s turn,” Jolly said with a grin, standing up.

“I’m waiting.” Rip smirked, posing for him. He licked his lips and pulled her into his arms.

“The three of you make the princesses look like mules,” he said, kissing Rip deeply. She kissed him back, pinning him to the wall. He let her keep him against the wall while he took hold of her plentiful chest and kneaded her breasts.

“Ooh that's a good boy,” she praised, squeezing his balls.

“Well, normally I’m more into being in charge in and out of the bedroom,” he said, tugging on her nipples. “But I can live with following for a bit.”

“Good.” She wasted no time, impaling herself on his dick, thrusting her hips like a jackhammer. Jolly moaned and squeezed her breasts tight on reflex.

“Oh Faust, you girls are ruining normal mares for me,” he commented, trying to match Rip’s hip movements.

“Why would you want one anyway?” Rip asked, lightly biting into his neck.

“I don’t anymore,” he said with a groan. “You three are all I need now.”

“Good boy.” She smirked, running her hands over his chest. He ran his hands along her body as well, finally able to match the pace of her hips. She nicked his neck, lapping up the small trickle of blood.

“Mmm... you taste delicious.”

“I probably taste like coconut,” he noted with a chuckle. She moved her hips, reaching a hand down to rub his balls.

“I hope you got enough left in here.”

“Your belly’ll match Riff’s,” he assured her, nipping her own neck and grabbing her chest again. She shuddered, thrusting her chest into his hands. He smiled before nipping and kissing her neck and shoulder. He started thrusting into her even faster, reversing their positions so she was pinned to the wall. She panted, her chest heaving. He kept it up, his hands kneading her breasts, tugging and twisting her nipples while his lips kept kissing and biting her neck and shoulder. His hips moved in a blur, nearly pushing Rip up the cave wall.

“Yes! Show me how much of a stallion you are!” Rip cried, grabbing his mane. He obliged and nipped her neck hard enough to leave a mark as he jackhammered into her constricting depths. She let out a cry of pleasure, pressing against him.

“I told ya I preferred being in charge,” he said, smirking up at her pleasure contorted face. “And it looks like there’s a submissive streak in you.” She panted in reply, her tongue rolling out of her mouth. He bit her shoulder again, twisting her nipples.

“I've never seen anyone get her like that,” Drift commented, watching intently.

“Then it looks like we hit the jackpot with Jolly,” Riff replied with a smile as she pulled open a clam and removed the meat.

“I thought you went to get the stuff?” Drift asked curiously.

“I’m almost done,” Riff assured. “I just wanted to pop in to see how Jolly’s doing.”

“Aw okay.” Drift nodded, returning her gaze to the show.

Jolly let out a groan, feeling a familiar churning in his loins. He leaned in and whispered in Rip’s ear, “Who’s your stallion?”

“I dunno... think you can step up?” She asked, smirking weakly. He smirked back and tugged her ear with his teeth, rolling the sensitive flesh around.

“You won’t be able to walk or swim properly with me around,” he promised, pulling her nipples.

“Why don't you prove it?’ she asked, looking into his eyes. He smirked, taking his hands away from her breasts and hooking them under her legs. He hefted her up, letting out a feral grunt as he somehow thrusted into her depths faster. She cried in pleasure, her eyes rolling up into her head.

“Who’s your stallion?” he growled, biting her neck and squeezing her ass possessively.

“Y-you...” she panted, her body trembling.

“And what do you want from your stallion?” he asked, holding the floodgates back.

“Make me a mommy!” Jolly captured her lips in a kiss, hilted himself inside her and came, his seed blasting into her womb. She went limp, her stomach bloating out. When his orgasm ended he gently placed Rip on the ground and slid out of her, not even a drop of his cum escaping her lower lips.

“Top notch!” Drift declared, giving him two thumbs up.

“I agree,” Riff said, pulling herself onto dry land. “I’d be jealous if I didn’t know you were my stallion too.”

“Anyway, my turn!” Drift grinned, walking over to him. She threw her arms around his neck, kissing him. He deepened the kiss, wrapping his arms around her and holding her close. She closed her eyes, pressing her breasts into his chest. He ran his hands up and down her back as he added tongue into the mix. His hands paid particular attention to the base of her tail and her fin.

She shuddered, becoming putty in his hands, her body shuddering at his touch. He gently lowered her to the ground, their lips never separating as he positioned himself above her.

“Take me hard.” She pulled away, wriggling her hips.

“Well, if it’s hard you want,” he grabbed her and put her on her hands and knees. “Then it’s hard you’ll get.” He slapped her ass as he lined up his dick with her folds.

“Oh yeah, more like that!” She thrust back against him, already wet. He grinned wildly, spanking her as hard as he could as he hilted himself in one thrust. She gasped, her body arching up from the sudden surge of pleasure.

“Mmm, I think you might be the tightest of the three, Drifty,” Jolly said, spanking her again as he started to buck his hips against her, holding her by the base of the tail.

Riff watched closely, starting to mix up some type of potion. She watched it change color to a soft blue. She tapped her chin and turned back to Jolly, waiting for a crucial ingredient.

“H-harder!” Drift cried, her breasts swinging wildly from the force of his thrusts.

“Ask nicely, Drifty,” he growled, swatting her ass and slowing his thrusts slowly. She whined, speeding up her own thrusts. He growled again, spanking her hard and pulling her tail to halt her movements. “I said,” he punctuated each word with a spank, “ask nicely.”

“P-please go faster...” she whined, wriggling her ass.

“That’s better,” he started to grope her ass affectionately and started thrusting even harder than before. The sounds of their hips colliding echoed through the cave. “See what happens when you ask not order?” She moaned, dripping onto the floor, a puddle forming under her. He spanked and groped her again, picking up the pace even further, her inner walls trying desperately to keep him inside, but the fluids she was leaking made her grip useless.

“Yes...” she moaned weakly, her tongue flopping out of her muzzle. Jolly squeezed her tail and draped himself over her back.

“You make such adorable noises~” he purred in her ear, nipping it. She squeaked in reply, looking up at him. He nipped her ear again, squeezing her tail as his speed plateaued. Drift let out a cry, an orgasm coursing through her body.

“Cumming already?” he teased. “Looks like somepony has a hair trigger.” She gave him a weak glare, trying to catch her breath. He spanked her again and gave her a sudden thrust to take her breath away. She gasped, squeezing her eyes shut. He resumed his high speed thrusts and started kissing and nipping her neck. She whimpered and mewled, submitting completely. He spanked her more and gave her a smouldering smirk. “I’m getting close, so tell me, how much do you want to be a mommy?”

“I-I want it bad Jolly...” she muttered, looking into his eyes.

“What would you do for it?” He teased, kissing the back of her neck.

“A-anything...” He nodded and threw his head back, moaning loudly as he hilted inside her and came. She let out a cry, rocked by a second orgasm. She collapsed, mumbling incoherently. He pulled out of her and stood up with a satisfied sigh.

“Alright, I guess it’s time for me to change,” he said, turning to Riff.

“I have the potion ready.” She smiled, standing up. She offered it to him, swishing her tail as he downed it. “Now, hold your breath.” She grabbed him, diving back into the water. He held onto her tightly and closed his eyes. He wondered where they were going as he felt them speed through the water.

She pulled him along to a strange set of standing stones gesturing for him to stand in the middle. He did as she wanted and looked at her curiously. She started to chant in a language he plainly didn't understand, the stones around him lighting up. He looked down and saw his stomach was glowing as well and slowly spreading to the rest of his body. Her chanting got louder and his body started to feel hot.

She gave him a reassuring smile, not pausing in her chants. He had to fight back a grunt, feeling his muzzle elongate to accommodate his sharpening teeth. He then felt the hair fall out of his tail as it morphed into a shark tail. He watched as his body streamlined, reducing drag. He felt a shifting in his neck and released his breath, adjusting to his gills. The changes seemed to end with an uncomfortable pinching in his back. Then, he groaned and felt a clutching pain in his chest. Before he knew it, his chest swelled, becoming almost as large as Rip’s prodigious bosom. Then, his beard fell out, the hairs floating up before his eyes. He looked down quickly, sighing in relief, his best friend still there.

“Well, I wasn’t expecting this,” Jolly said, hefting his new breasts and posing. He blinked for a moment, surprised by the sound of his own voice.

“I think you look great.” Riff swam over, giving him a kiss.

“I won’t miss the beard,” Jolly replied, returning the kiss. “As far as I’m concerned, I’ve only gained from this deal.”

“I'm glad you think so.” She smiled, squeezing his breasts.

“Mmm,” Jolly moaned, his tail swishing from the contact. “See? Those are much more fun to toy with than my pecs.”

“I agree.” Riff leaned down, biting at one of his nipples. Jolly moaned and wrapped his arms around her.

“Heh, I’ve gone from a captain that sailed the seven seas to a mare that swims through them,” Jolly noted with a small smile.

“Now you’re a part of it.” She pecked his lips, putting his hand on her stomach.

“I dunno, we could cause some terror for the ne'er do wells of the sea,” Jolly said with a grin. “It could be fun to ransack Griffin pirate ships together.”

“Mm... planning a harem are we?” She chuckled.

“Perhaps,” Jolly admitted. “What do you say? Want to become a pirate, First Mate Riff Raff?”

“I love that idea Captain Jolly Roger.” She smirked, nuzzling his neck.

“Then let’s show the others the new me and tell them our plans,” Jolly said, testing out his new tail. “Then the villains of the sea will be in for quite a surprise.” Riff took his hand, leading him back to the cave. The two surfaced and found the other two mares laying down and rubbing their stomachs idely. “Hello girls!” Jolly called. “Miss me?”

“Jolly?” Rip asked, sitting up.

“The one and only,” he replied, pulling himself out of the water and posing for them. “What do you think of the sharky me?”

“You got some bangin tits!” Drift grinned, licking her lips.

“And I kept my three friends,” Jolly said, cupping his male genitalia. “Which means we can keep making kids if you girls want.”

“He’s truly perfect.” Riff smirked, grabbing Jolly's ass.

“Looks more like a she to me,” Drift teased, pointing out Jolly’s hourglass figure.

“Semantics,” Riff dismissed.

“We had something else we wanted to to tell you,” Jolly said, putting an arm around Riff. “How would you girls feel about ransacking pirates and other baddies that travel the seas?”

“Sounds amazing!” Drift nodded, giving a toothy grin.

“That sounds way better than just catching fish, sleeping and masturbating the day away,” Rip agreed. “Will we get to dress up like pirates?”

“If you want.” Jolly nodded.

“Sweet!” Rip chirped, pumping her fist. “I can’t wait to get started, Captain.”

“Wanna start right now?” Jolly grinned.

“Maybe,” Rip replied, her tail swishing slowly behind her.

“Then let’s find a target.” Jolly said. The girls all nodded and hopped into the water. They swam near the surface, keeping an eye out for any large ships. They shared a smirked as a ship sailed into view, flying the crossbones.

“Oh, I know that skull and bones,” Jolly said with a devious grin. “That’s the griffin captain Deadeye Hilda. You name a crime and she’s done it.”

“Ooh, she’ll be fun to tame.” Rip rubbed her hands together.

Like the sharks they were, the quartet swam with purpose. They'd find their prey today. Good 'eats' for a long time coming.