Part of a story trade with Quillsman from DeviantArt. He recommended a story about pirates being tickle interrogated over the location of cursed treasure.
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“Captain. Captain! Are you there?” A banging at the door accompanied the voice. Theresa stirred groggily underneath her covers. She knew she’d given orders to wake her up from her siesta if anything happened, but to actually do so was another thing entirely. She rolled over to turn her back to the door, pulled the covers over her head, and prayed to whatever gods would listen to someone like her that this was low enough priority that the knocker would take a hint and go away. It wasn’t. “Captain, we got a situation!” the voice continued to shout, accompanied by more forceful banging.
“I’m up! I’m up. Quit yer belly achin’ and gimme a moment to get decent,” Theresa shouted back. Throwing the covers off in resignation, the shapely Spaniard rolled out of bed. It took a bit of fumbling around through the darkened room before she remembered that she’d tossed her loose brown pants and button up white shirt onto the chair of her desk. It was only after a profanity-filled bout of struggling to figure out which end was which in the dark that it occurred to her sleep-addled brain that the entire process probably would’ve been easier if she’d bothered to open the curtains of her window first.
Theresa Martil liked to believe she wasn’t normally this scatterbrained. You didn’t make it as a successful pirate captain in the Caribbean without keeping your head on your shoulders, and you couldn’t manage that literally without doing so figuratively. That was especially true when you were trying to break into the criminal industry as a woman. It was one of those paradoxical things that had always stood out to Theresa, that being a beautiful 27-year-old Spanish woman with wavy brownish-black hair, a nice olive complexion, large chest, tight waist, and long legs somehow made it harder to get her fellow pirates to join up under her. If you then took that and projected it out to the fact that the entire crew of her ship, the God’s Fortune, were similarly all pretty young women, it meant they’d all needed to be cunning twice over to get by in this (often quite literally) cutthroat industry.
The issue of lighting was solved by whoever was knocking running out of patience. The door swung open to reveal a harried looking woman framed in the afternoon light. It was Theresa’s first mate Mary Roberts, dressed in her usual long sleeve lace up and a long red skirt. Theresa didn’t know if Mary was even her real name and preferred to keep it that way. Who you were before didn’t matter once you signed on with the God’s Fortune. What was important was that Mary was a pretty young woman with beautiful long blonde hair, shining blue eyes, and a pleasingly large chest her captain found easy on the eyes. She also was the only member of the crew who was literate and knew far more about the magical peril they encountered throughout the Caribbean than anyone Theresa had ever met. Her knowledge had proven invaluable time and again in keeping them all from falling prey to the occultic nonsense that had a bad habit of cropping up around the islands.
“Right, now what’re ye wakin’ me up fer?”
“There’s a ship on the horizon, Ma’am. Pirates from the looks of it and not any of the ones we’re friendly with. They aren’t flying the flag for parley nor will they stop approaching when we signal them to.”
“They’re lookin’ for a fight then?”
“We’re assuming so. All hands are on deck, just needed to fetch you.”
Theresa nodded. All annoyance at being disturbed was forgotten. If there was anything that warranted interrupting her beauty sleep, coming under attack was it. The captain followed her first mate out the door to the main deck. One of the benefits of being the captain was that her cabin directly overlooked everything from the stern of the ship. From where the two of them stood, they could see women running to and fro in preparation. Some were already kitted out with cutlasses and muskets while others were doing some last second maintenance on the cannons. Pretty much all of them were stealing glances off the starboard side as they went. The captain followed their gazes and grimaced.
“Ugh, the Golden Grin…” she groaned, recognizing the giant golden skull sporting a toothy grin painted on the ship’s mast.
“Who’re they, captain?”
“What do ye mean ‘Who are they’? Ye can’t grab a pint these days without…” Theresa began before something occurred to her. “I forgot, ye don’t come with us to the tavern whenever we dock, do ye Mary?”
“Nope! Alcohol is one of the roots of sin. It’s bad for both your mind and body!” the blonde proclaimed with a huff.
The Spanish captain had to hold herself back from pointing out that as pirates the two of them had gotten up to more sinning in the past year alone than most people did in their entire lives. Instead, she pressed on with her explanation. “They’re a new crew in these waters. Started flying the colors a couple months ago. Black Eye Lena and her merry band of sadistic ladettes. Ye can’t visit a port these days as a member of the God’s Fortune without all the locals yappin’ yer ear off about them. They’re held to be our rivals now, on account of Black Eye being the only other cap’n in these waters who has a crew of only ladies.”
The God’s Fortune had made a name for themselves in recent years for being a pirate crew consisting solely of women. After making the journey here from Spain, Theresa had been quick to notice that many ladies were being denied working on ships purely on the belief that a woman wouldn’t be able to handle the rough living conditions. As far as she was concerned, it was the other crews’ loss and her gain. Many of the girls she’d picked up over the years had proven just as capable as their male counterparts when it came to the important activities of finding buried treasure and keeping the ship from sailing into the side of a cliff. She’d had the pick of the litter selecting the best people she could find in every category, every one down to the last desperate to leave their jobs as seamstresses or barmaids behind for a life of adventure on the high seas. Word on the street was that the Golden Grin was crewed by all the women who’d been too uncontrollably psychopathic, sadistic, and greedy to make the cut on the God’s Fortune, which was all true as far as Theresa could tell from the stories about them.
Any further discussion on the approaching pirates was cut off by a thunderous sound followed soon after by a spray of water a few dozen meters away from their position. “They’re opening fire!” someone cried out.
“Man the cannons! Make them regret the day they crossed the God’s Fortune!”
“From the way they’re continuing to approach, they must mean to board us,” said Mary. Theresa nodded in agreement. That was the only reason she could think of for the other ship’s reckless charge through the cannon fire. “Were there any rumors pertaining as to why they might want to pick a fight with us?”
“None that matter. We’ll be wearing their guts for garters at the end of this either way,” Theresa growled. The captain rushed back into her room to grab her saber. If it was a hand to hand fight they wanted, by the gods she was going to give it to them.
She had just managed to return back to the deck when the ship lurched underneath her feet. A cannonball fired from the Golden Grin had managed to impact the side of the God’s Fortune right at the waterline. With nothing within arm’s reach to grab onto, Theresa lost her footing to the ship rolling violently from the force of the blow.
“Captain! Grab on!” She heard Mary cry out. Her first mate had one arm wrapped around the bannister and was holding out the other towards her. The captain lunged as best she could for the outstretched hand, but their efforts proved in vain. Her feet slid out from under her and the ship’s captain was sent plunging off the side of the ship into the churning waters below. Her world went black as her body crashed into the churning waters below.
—--
A rhythmic thumping right between her breasts stirred Theresa back awake. She was vaguely aware of shouting around her, but it was like listening to a conversation several rooms away. Everything felt so far removed. The thumping on her chest made her cough, causing her to spit out a torrent of sea water, and things began to swim back into focus.
“Captain! Stay with me, captain!”
She could hear a woman shouting. The Spanish scoundrel’s eyes cracked open briefly before realizing she needed to blink the water out of the way to see anything. It looked like Mary had placed her on her back in order to administer chest compressions.
“Captain Theresa! Thank goodness. I thought I’d lost you!” Mary cried with relief. The woman was completely soaked. Nearest Theresa could tell, her first mate must’ve dove in after her to fish her back onto the deck.
Theresa rolled over onto her front and coughed up the last of the sea water inside of her. “I won’t be going down that easily,” she muttered, as much to herself as to her friend. Unsteadily clambering to her feet, the captain took stock of the situation. It looked like Mary had dragged her into one of the nearby storerooms before attempting resuscitation. Her heart sank peering out the door leading out to the deck. The crew of the Golden Grin had successfully boarded the ship while she was out. It was easy to tell at a glance that they were getting overrun. Women wearing scarves and bandanas emblazoned with a smiling golden skull had the girls she recognized outnumbered nearly two to one. They weren’t using their weapons anymore, instead opting to leverage their numbers advantage to swarm over the defenders with fists and submission holds to non-lethally take their opponents down.
“Let’s go. The girls need us,” said Theresa. Glancing around the room, the only thing vaguely resembling a weapon at head was a nearby mop. It would have to do until they could salvage a better one. Mary looked like she wanted to say something, but kept her lips set in a grim line. A wooden bucket appeared to be her makeshift weapon of choice for now.
The pair shouldered through the door in an attempt to salvage the fray in front of them. Theresa swung the handle of her mop at the back of a nearby pirate’s head. At the same time, Mary had jammed her bucket over another unsuspecting foe’s head from behind before knocking her over with a kick.
Their joining in the fight didn’t turn the tides nearly as well as either of them wanted. Neither had enough time to pick up one of the discarded weapons littering the deck before cries of alarm sprung up from the Golden Grin crewmembers who had recognized them. Soon, enemies were swarming them from all sides, all eager to be the ones to claim the glory of being the ones to take down the God’s Fortune’s captain and first mate. Theresa swung her mop as frantically as her still unsteady body could manage while Mary swung fists and feet, but nothing could stop the press of bodies bearing down on them. Both were wrestled to the ground less than a minute after emerging onto the deck.
“Let me go, ye bastards!” Theresa shouted. Fighting off half a dozen women dogpiled on top of her would’ve been impossible under normal conditions, to say nothing of how out of it she still was from her dip in the ocean. The only thing the captain could do was helplessly crane her neck around in the hopes that one of her crewmates was able to come to their rescue. What she saw made her heart sink further. The fighting was dying down all around them. What last members of her crew were still standing were being subdued like she and Mary were as she watched.
“Are these the ones?” A sultry Puerto Rican woman sporting a frilled long sleeve shirt, light vest, tight pants, and a bandana around her neck sporting a golden grinning skull approached the pinned pair after the last member of the God’s Fortune was taken down. Tousled black hair fell down around her shoulders around a face stained with sweat. The first couple buttons of her shirt had been undone to show off a copious amount of her large chest and her pants hung low around her hips, like she was dressed more to attract attention at the pub than for a fight.
“Yep, this is them, Isabella. Stormrider and her first mate. Just like in the wanted posters.” One of the pirates holding Mary down extracted herself from the pile, pulled out several pieces of paper crumpled up in her pocket, and straightened them out for the woman to sea. Isabella glanced back and forth between the paper and the two captive women. With a nod, she gestured back towards the Golden Grin with her thumb.
“Looks like. Good job. Take them back to the ship. The cap’n would like to have a word with both of them.” Both Theresa and Mary were manhandled back to their feet. Their captors frogmarched them forward with hands firmly gripped on their shoulders and wrists to prevent any last ditch efforts at fighting back before they could begin.
Theresa glanced around as they were led onto the Golden Grin. All of the other captive members of her crew were being manhandled into position across the deck. Girls were being lined up against the railing along the sides where they had their hands bound behind their backs with lengths of rope to whatever was available. Some were brought over to rather prominent bondage devices that seemed to have been installed as part of the deck itself. Theresa didn’t know what they were for, but given the rumors she’d heard about Black Eye Lena’s crew torturing their prisoners, she highly doubted anyone placed in them was about to be pampered.
“Cap’n! We got ‘em!” one of the women escorting the pair shouted. A woman who was in the middle of tying the ropes around on the God’s Fortune member’s wrists raised up her hand in a gesture of acknowledgement. It was hard to tell how old she was with her back turned, but she was fairly small in comparison to the other pirates milling around her. Brownish-black hair hung just long enough to reach the back of her neck and Theresa could make out tanned, weathered skin in between her long sleeved t-shirt and long pants, both of which were soaked with sea spray and sweat. The buccaneer doubted she would’ve realized that the woman was the ship’s captain to begin with if she hadn’t reacted to her crewmate’s call.
That impression was blown away the moment she turned to face them. Theresa had always assumed that “Black Eye” Lena’s namesake was thanks to sporting an eyepatch. Either that or it was a joke about her coming out of a bar fight having acquired a bad eye injury. What became immediately apparent was that the name was far more literal than she could’ve expected. Lena’s entire right eye was pitch black as deep as the ocean during a cloudy night. The effect was so striking that both prisoners stopped to gawk at her in surprise, only resuming their walk forward after a few seconds of spirited prodding from their captors.
Instead of joining the rest of their crew on the deck, the two pirates were led up towards the captain’s quarters near the stern. They were jostled inside to the sight of several bondage devices taking up the space that normally would’ve been reserved for the navigation table. A trio of pirates wrestled Thersa into a padded chair that stretched out her arms to the side while spreading her legs out horizontally in front of her. Mary, despite her best attempts to struggle free, had a pair of girls stretch her out across a long table that bound her arms and legs together with rope. A few cranks of a pulley on the side left her stretched out tight just on the verge of discomfort.
“So this is the famous Stormrider and her first mate, eh? I was expecting more from the women who led their crew into the biggest storm in decades and returned with more treasure than her hold could contain,” Black Eye Lena commented as they were being bound.
Neither woman rose to her provocations, so Isabella spoke up for them. “Someone in our crew mentioned seeing Stormrider fall overboard after we started shelling them, Cap’n. A good number of their crew were more preoccupied fishing her out of the drink than with fightin’ us.”
“Lucky us then! Now they’re just two helpless women for us to play with. We know just how to treat a girl, don’t we Bella?” Lena’s smile took a nasty tinge to it as she reached over to lightly jostle Theresa’s boot.
“Yeah, yeah. You and every scalliwag between here and the mainland. I’m quaking in me boots just thinkin’ about it,” Theresa stated flatly. Lena’s face went blank.
“I… You…” the black-eyed captain spluttered incoherently. Of all the responses she’d expected, her captive being dismissive of her evidently wasn’t one of them. Theresa would be the first to admit she probably hadn’t chosen the best thing to say given their predicament, but she hadn’t been expecting the other woman to be so easily thrown off balance by a few words. After a few seconds, Lena seemed to regather enough bravado to fire back. “Oh, you will be. Every woman who ever set foot on the Golden Grin has learned to fear the name Black-Eye Lena!”
“Even your own crew? That sounds like some poor working conditions to me. I’d quit within a fortnight!” Mary joined in.
“Oh, look at her. She’s as bright as a ripe tomato! With the stories you hear at port, you’d think the Black-Eye would at least know how to intimidate a girl,” Theresa jeered. Lena’s face had gone scarlet with a mixture of rage and embarrassment.
Any further mockery was cut short by Mary letting out a strangled yelp. Isabella had taken advantage of nobody focusing on her to press her fingertips into the bound blonde’s stomach through her soaked shirt. An audible bang could be heard by everyone in the cabin from the busty pirate bucking her hips with surprise.
“Alright, alright. That’s enough, you two. Don’t go teasin’ our cap’n like that. She gets sensitive when captives don’t act proper terrified like they’re supposed to. It’s a confidence thing,” Isabella admonished. Lena gave her a look straddling between hurt and belligerent.
“Words like that’ll get you in the stocks, Bella.”
“Why do you think I said ‘em, Cap’n? Okay, you lot. Looks like we’re good here. How about givin’ us some alone time to get to know these ladies better?” That last bit was said to the rest of the crew. None of them seemed the slightest bit perturbed over being asked to leave. They proceeded to file out door chatting amiably with each other, the last out making certain to secure the double doors shut behind her.
“Down to business then.” Lena took the opportunity to get the conversation back on track. She assertively placed her foot on Theresa’s chair and leaned in close to glower at her. “Where’d ye hide the Tesoro de Suave Oscuridad?”
Theresa and Mary both stiffened up at the mention of the name.
“Ye don’t want that. Not that one,” Theresa warned, her face deadly serious.
“I was hoping you’d say that.” Lena’s glower transformed into an almost unnervingly happy smile. Rather than respond with words, she leaned in further, her hands reaching forward. Theresa was initially convinced the woman was reaching for her chest and was surprised when her hands passed by to grope at her rib cage instead. The tan-skinned captain stiffened, feeling the fingers gently, almost lovingly, stroke against the middle of her rib cage with just enough force for her to feel it.
“What do you think you’re doing?”
“I told ye we know how to treat a girl. Stroke a fair maiden’s skin juuuust right, and even the hardest gal in the Caribbean will be singing like a little bird for you before long.” Her touch was light. Maddeningly so. Theresa soon had to grit her teeth in order to prevent an errant giggle from escaping between her lips. Never before had the brave captain been so caught off guard. With all of the stories of the Black-Eye inflicting horrific torture on her captives, the idea that said torture could be tickling of all things had never once crossed her mind.
“Same question to you. Tell us where you hid the Tesoro de Suave Oscuridad. As the first mate, you should know just as well as your cap’n where it is.” Mary wasn’t being excluded from the interrogation. Isabella had rolled up her waterlogged shirt to expose her captive’s flat stomach. Slightly flexing her fingers caused her long nails to tease a centimeter of the taut skin presented to her with each stroke.
“I don’t know what you’re talking about.” In contrast to her captain’s visible struggles to hold back her laughter, Mary’s countenance was stone cold. It was like the light tickling didn’t register to her.
“Then let me jog your memory. By all accounts, the Stormrider and her God’s Fortune struck upon a score several months ago. The Tesoro de Suave Oscuridad, a legendary treasure horde said to be too vast for the largest galleon in the British navy to hold.” Isabella was distracted from her explanation briefly by experimenting with a new way to toy with Mary’s stomach. Her nails went from lightly scratching to tracing waving patterns from one side to the other. It proved to be just as ineffective as the earlier strategy at drawing out a reaction.
“But ye scurvy dogs didn’t hold onto it for long. Spent a single night livin’ it up in a shanty town on the coast of Jamaica. Then the very next mornin’, for some reason, ye held up every fine establishment ye’d all visited that night for all yer money back. ‘The Stormrider’s Backstabbin’ Crawl’ the locals call it now. After that, ye disappeared with the loot not to show yer faces again until a couple weeks later, not a single coin o’ the treasure in sight since.”
Theresa wasn’t holding up quite as well as her first mate. Lena had been making steady progress up and down her ribs. The sadistic black-eyed woman had found a couple spots that caused her victim to tense up or squirm at the touch, but she was opting to keep exploring rather than sink her fingers in to abuse them. She was, however, revisiting them often enough to drill it into Theresa’s head that she knew exactly where they were if they were ever needed. Every time those fingers stroked one of those spots, the Spaniard had to grit her teeth to prevent herself from making a sound.
“We told ye. Ye don’t want that one,” the captured captain spat through gritted teeth. Her body tensed up every time the fingers traveled downward towards her sides and stomach. She couldn’t help it. She knew from errant tickling dispensed by family and friends growing up that her stomach was far more ticklish than her ribs. What she hated more was that Lena clearly knew that it was getting to her. The black-eyed she-devil wouldn’t be constantly going down to linger at the bottom of her rib cage only to travel back up again if she didn’t.
“Oh? And why wouldn’t a pirate want treasure?” While Mary had initially acted like the tickling didn’t affect her at all, an involuntary twitch of her cheek when the nails got too close to her belly button let her sadistic tormentor know that she had only been putting on a brave face. The Puerto Rican pirate began to drag her nails in lazy circles just a few centimeters outside her victim’s button and was delighted to watch the bound blonde squirm with discomfort.
“It’s cursed, ye daft broad! Why else would we give up such a haul?”
“Ha. Quite the tall tale! Everybody with half a brain knows that there’s no such thing as curses.” Lena snorted derisively. If Theresa or Mary had been paying attention to Isabella at that moment, they would’ve caught the Golden Grin’s first mate casting her eyes up towards the ceiling in annoyance. Isabella had never once been able to get her captain to realize that her fabled black eye was the consequence of a close call with a curse no matter how many times she’d explained it. She’d frankly just given up on trying by this point. Lena was still convinced to this day that it was caused by a bit of gunk staining her eyeball.
“It’s true,” said Mary. “Everything we could find in the old legends say that taking a single coin from its resting place will bring nothing but misery and misfortune to the thieves until every last piece has been returned. We had no choice but to return iiiiheeekhehehehe!” Mary’s explanation was cut short by her tormentor playfully slipping a finger into her exposed belly button. The surprised maiden let out a squeak, her hips briefly bouncing off the table, before sputtering out a few giggles. A smile had formed on Isabella’s face over having finally provoked a reaction out of her new plaything. Her nails returned to tracing circles after a few seconds of belly button teasing, the threat all the more pronounced now that she’d proven she was willing to make good on it.
“Yes, I’m certain you aren’t lying. Now how about you two tell us where you hid the treasure and we’ll be reeeeeal careful about this big, bad, scary curse…” Theresa wasn’t faring much better. Lena had decided she’d prefer listening to laughter than her first mate being insulted in front of her. Rather than briefly tease one of the bad spots she’d found on the Spanish woman’s rib cage, she’d settled on massaging the spot through the soaked shirt. Her fingers followed effortlessly no matter how the bound woman attempted to twist her upper body away
The black-eyed pirate focussed on Theresa’s ribs for just long enough to give her captive the idea that she had settled on focussing there before suddenly jumping her fingers down to the flat stomach below. The fingers then moved inwards to dig into the vulnerable, soft flesh of Theresa’s helpless tummy before shaking around. An audible bang could be heard from the Spaniard jumping in surprise, followed soon after by girlish tittering that did nothing for her image as a rough and tumble ship’s captain.
“That’s what I wanted to hear…” Lena cooed. “Feels good, doesn’t it? I bet you love it!”
“Fuhuck youhehehAHAHAHAHA!” Once she’d lost control of holding it back, Theresa’s tittering quickly grew into full blown laughter no matter how hard she tried to hold it back. Lena’s attack was relentless. Her fingers jumped all around the bound pirate’s stomach and sides, poking, stroking, wiggling, and fluttering unpredictably. Theresa quickly discovered she hated the feeling of helplessness that came from not knowing where or how the fingers would strike next.
“Now tell us where you hid the Tesoro de Suave Oscuridad or I’ll tickle your cute little tummy for forever and ever,” Lena taunted. A cruel smile played upon her lips. “Once you do, we can move on to working over the rest of you!”
“Is that what you consider motivating someone to talk here? Promises of more torture when we do? You lot need to learn how to incentivize people,” Mary griped. Isabella hadn’t found quite as much success with opening up her victim yet. Her fingers continued to steadily scratch away at Mary’s stomach, but she hadn’t gotten anything better than the errant gasp out of the busty first mate.
“We find that it doesn’t matter one way or the other in the long run. Tickle a girl’s worst spots in the right way for enough time and she’ll eventually be willing to do anything you want to make it stop. All we have to do is keep playing with you two until you’re so desperate for a break that you won’t care what you have to do to get it.”
Isabella pursed her lips. It was time for a change of tactics. More so than frustration at a lack of success, she was starting to get bored. There was nothing fun about tickling a girl if it didn’t cause a reaction. Her eyes roamed up and down the body of the woman stretched out before her. They naturally came to rest on the blonde’s rather substantial chest. The plunging neckline of Mary’s lace up advertised both her sizable melons and the fact that she didn’t have any underwear on at the moment to contain them. “You know, it’s been a while since I’ve gotten to play with such a nice chest. You wouldn’t mind if I had a little taste, would you?”
“Yes! Yes, I very much would. Get your hands off me, you pervert!” Mary cried. Isabella ignored her protests in favor of rolling up her captive’s shirt to reveal her breasts. Hopping onto the rack, she straddled Mary’s hips while menacingly hovering her fingers within inches of the milky white globes. More so than getting to ogle Mary’s bare chest, what brought a wicked glint to the sadistic pirate’s eye was seeing the look of fear in the girl’s eyes.
“Well then, don’t mind if I do!” The Puerto Rican’s fingers dove into flutter all over Mary’s breasts. After so many minutes of not getting a reaction, it was gratifying to the sadistic pirate to have her victim go wild the instant her fingers made contact.
“Oh Gohod! Oh GodhohohEHEHEHEHAHAHA!” Mary let out a loud shriek and began struggling with all her might to escape the fingers. Her hands futilely tugged at the cuffs around her wrists while her legs kicked against their restraints hard enough to make the rack rattle. Isabella didn’t know where to look. Watching the milky white skin of her new toy’s breasts jiggle every time her fingers made contact again was almost hypnotic, but she was also in love with the way the woman whipped her head from side to side as laughter poured from her lips.
“Ooooh! Found your spot! Found your spot!” Isabella teased. Keeping her fingers moving this fast for an extended period of time would be too tiring, so she changed methods of attack as much to preserve her own stamina as to explore further ways of causing Mary agony. She leaned forward to grab the jiggling breasts in her hands. Mary had a few seconds to fool herself into thinking that there was no way for the tickling to continue from that position only to once again be forced to shriek with laughter. Isabella had groped her for the purpose of holding her breasts still so she could use her forefingers to flick the nipples crowning her milky white globes. She changed between hitting both simultaneously and alternating from left to right and back again at random intervals to drive Mary wild with unwilling ticklish mirth.
“Looks like those two are hittin’ it off well. I usually like to take my time breakin’ the new girls in, but let’s try not to let ‘em beat us to the punch, eh, Stormrider?”
“Thihis isn’t a compehetitionhehehehe.” Lena had been content to toy with Theresa more slowly up until then. She’d interspersed lighter teasing that made her rival captain giggle like a little schoolgirl with more energetic tickling to make the Spaniard bounce around in her seat while laughing her head off. Seeing Isabella so gleefully push Mary as hard as she could reminded the black-eyed scourge of the seas that there was an actual purpose to this. A purpose besides having fun with a pair of beautiful womens’ bodies, that is.
“Oh yes it is! It’s a competition between ye and yer first mate. Whoever tells us where the treasure is hidden is going to get a nice break from the tickles, cause the bad girl who doesn’t talk has an extra special punishment waiting for her that’ll take aaaall our attention.” Lena’s proclamation made both of the bound womens’ blood run cold. Neither of them had expected to be pitted against the other like this. Theresa glanced fearfully at Mary. The last thing she wanted in the world was to stab her closest crew member in the back.
She didn’t get long to stare. Lena had taken a few seconds to undo some of the buttons near the bottom of her shirt, exposing her stomach to unimpeded questing fingers. The cruel pirate captain sunk the pads of her fingers into the bottom of her victim’s stomach right at the edge of her pants and rubbed her fingers back and forth. Howls of laughter poured from Theresa’s lips as she leaned forward in her chair as far as her bondage would let her in a desperate attempt to curl into a ball.
“Is that too much? Is that too much for the widdle baby?” Lena jeered with a cruel smile. “All you have to do to get me to stop is tell us where you hid the treasure. I’m certain yer first mate will do juuuust fine with our undivided attention on her precious, tickly, titties!”
“NeverhahaheHEHEHEHAHAHAHA!” Thersa cried, believing that Black-Eye Lena would never expect that the thought of Mary suffering more was the rock she clung onto for strength against the torture.
Except that was exactly why Lena had said it. There was no feeling more wonderful in the world for the sadistic Black-Eye than breaking a woman using nothing but the light application of her fingers on their bare skin. Already submissive girls were no fun for her. What was fun was slowly peeling her victims apart one layer at a time until they shattered like eggs dropped on cobblestone. The strong willed ones were her favorite. The feeling of satisfaction from successfully breaking a woman who’d held on for weeks was infinitely better than a victim who caved within the day. She’d long since gotten into the habit of giving the girls in her captivity reasons to resist solely to extend their lifespan as her playthings.
“You know, I can sympathize with having ticklish titties. The rest of the girls simply can’t get enough of mine,” said Isabella. The seductive Puerto Rican playfully jiggled her chest for emphasis, not that Mary was in a position to appreciate it. “Whenever I let them tie me up, they’re certain to keep working over my boobies until I’m in tears.”
“Bella is our first and longest lasting tickling slave,” Lena helpfully explained. “We picked her up as the sole captive of one of our very first raids. We’d meant to drop ‘er off back at her hometown after keeping her tied up on deck for a month-long voyage, but she’d loved it so much that she’d begged us to keep her on board. Hell, whenever we don’t have fresh toys to play with, Bella here will spend her days bound naked out on deck to give the rest of the crew some entertainment!” Isabella was the one woman Lena never grew tired of torturing. The sultry tan-skinned woman had a love of being tickled that bordered on unnatural. Never before had Lena met someone who could be gang tickled for hours on end and come out the other side begging for more. It’d proved to pair well with Lena’s unending sadism. Isabella was a woman she could tease and tickle for years but never successfully break.
“YOHOU’RE FREAKSHEHEHAHAHAHAHAHA!” Mary screamed.
“Awful kind of you to say,” responded Isabella with all sincerity. Her cruel smile became almost wistful as she continued to play with Mary’s tits. “That reminds me… The girls used to love breaking out the feathers when they were playing with me. Having them stroke my titties with both long stiff eagle feathers and soft downy plumes would drive me completely out of my mind. I could never figure out if I was supposed to be cumming or screaming at any given second. It’s been a while since they’ve done that to me…”
“We still have the feathers. Got a pair in me desk,” Lena chimed in. Isabella’s eyes lit up with excitement. Mary was given a brief reprieve to wheeze for breath. Isabella had stopped tickling in favor of rummaging around in her captain’s desk. It took less than a minute to find the drawer containing an unordained wooden box nearly as long as her forearm. The masochistic first mate brought it back to open it in front of her victim.
“Pick your poison. Which would you like me to try out first?” Isabella asked. Undoing the latch on the box and opening the lid revealed a variety of feathers nestled in felt. Mary’s eyes went wide with fear in spite of her best efforts to not betray any reaction. She couldn’t stop herself from skimming over the array of long, stiff turkey feathers, fluffy plumes, and tail feathers that ranged every size in between.
“D-dealer’s choice,” she tried to say glibly, but the quaver in her voice betrayed how frightened she was at even the thought of one of those touching her.
“Top to bottom it is!” Isabella grabbed a long, stiff looking brown pheasant feather off the top row before hopping back on the rack to straddle Mary again. Grabbing one of the bound woman’s breasts to hold it still, she began dragging the length of the feather across her rock hard nipple.
Mary’s eyes bugged out the moment the implement made contact with her bare skin. She let out an ear piercing shriek and bucked hard enough to almost unseat her tormentor off of her. The room was soon filled with screams and cackles loud enough to drown out Theresa’s own tormented laughter. Mary bucked and spasmed, shook and twisted as hard as she could in a desperate attempt to escape, all while letting out laughter louder than she had ever known her body was capable of producing. Nothing she did got her more than a second of reprieve from the skilled tickler and her tormenting feather.
“Looks like we have a winner! Capn’, you gotta give this a try. I can’t remember the last time we had a girl this tickly!”
“Oh, I gotta try this.” Lena reached over to grab a nearby piece of cloth. Efficiently tying it in a knot, she forced it into her rival captain’s mouth before securing it behind her head to serve as a cleave gag. More so than being glad for a break from her own torment, Theresa could do nothing but watch with horror as her tormentor went to help make her first mate’s suffering all the worse.
Lena’s hand reached towards the box containing the feathers before seemingly hesitating for a moment. Walking over to her desk, she rummaged around it briefly. A length of cloth similar to the one she’d used to gag Theresa was pulled out of one of its drawers. Repeating her process of tying a knot in the middle and forcing it into the cackling Mary’s wide open mouth left the curvaceous pirate gagged just like her captain.
“Don’t want her breaking on us too quickly, now would we?”
“Teehee! You always did enjoy taking your time gettin’ to know the girls, Cap’n.”
Only then did Lena’s hand return to the box to pull out a long black quail feather. Taking up position at Mary’s side, her free hand seized the busty blonde’s free breast to allow her feather to come into play.
A scream resounded through the cabin. Mary had been convinced she’d already reached the furthest depths of ticklish suffering. Those few minutes of nipple feathering had tickled so badly she was certain it was impossible for the torture to get any worse. Feeling the bristles of the second feather make contact with her achingly erect nipple blew those preconceptions away in an instant. She wasn’t even laughing anymore. Screams that would do a banshee proud ripped through her lungs one after another. Her body wildly thrashed in its bondage, putting everything she had in a last ditch effort to get away.
Theresa watched in despair as the two cruel pirates reacted to the display with pure, unbridled glee. Over the next several minutes they continued to dance the feathers against Mary’s nipples. They would lightly dust the tips of the feathers back and forth, slowly drag the lengths across the sides of her nipples, and swirl them around in circles all over her areola. Once or twice they would try to flip their implements around to attack Mary’s sensitive breasts with the quills, but quickly gave up after finding that it didn’t have as devastating an effect as the plumes did. Mary babbled garbled pleas for them to stop and Theresa begged into her gag for them to tickle her instead, but nothing could get the two sadists to let up for even a second.
Relief in the form of a short break didn’t come until after an entire hour of having her titties mercilessly toyed with. The sound of screams of laughter was replaced by hiccups and sobs of misery. Tears of agony had left tracks down her cheeks and she was so physically exhausted from her thrashing that she’d been reduced to feebly twitching in response to the torturous stimulus for at least the last 15 minutes. Lena reached behind Mary’s head to undo her gag.
“Are ye ready to talk, or do ye need a little more persuadin’?” She waved her feather within an inch of Mary’s nipples again for emphasis.
“Please! PLEASE! I’ll tell you everything. Anything if it means you won’t tickle me anymore!” Mary sobbed.
“Good. And once you’re done, I’ll show you how much more tickly a girl gets after you make her cum. We’ll see how much fun it is to play with your luscious melons after making you orgasm so hard you won’t be able to think!” Isabella sadistically taunted. She mimicked her captain’s threat by lazily wafting her feather in Mary’s direction, only to be caught by surprise from Lena holding up a hand to stop her. The glimmer in her captain’s eye was all she needed to know that a particularly evil idea had struck her.
“Would this ‘anything’ of yers happen to include helpin’ tickle yer cap’n?” Both Theresa and Mary’s blood ran cold. They shared a glance of fear. “Oy! Oy. No lookin’. Wouldn’t want ye sharin’ signals now. Yes? Or no?”
“I… I…”
“Looks like there’s still some fight in her, Cap’n. How ‘bout we gag her again and ask in the morning? I’m certain she’ll be more agreeable then.”
“Hrm… Sounds like we gotta. Don’t want a half-hearted helper, after all.” Both women let out a giggle at the stark look of terror that came over Mary’s face. They slowly began to lower their feathers back towards Mary’s melons, savoring the way the beautiful blonde shook her head in a panic.
“I’ll do it!” Mary screamed right before the torturous tools could touch her again.
“Do what now? We need you to say nice and loud for the lady in the back to hear,” Lena sadistically commanded. The two of them undid Mary’s bondage before manhandling her into a standing position. Mary was forcibly marched over to stand in front of Theresa.
“I’ll… I’ll tell you where we hid the treasure. And I”ll help you tickle the captain as much as you want. Anything… anything you want. Just… just please don’t tickle me anymore…” Tears of misery streamed down her cheeks. The threat of further torture had broken the last of her will to resist and being forced to announce her betrayal out loud like this shattered her remaining spirit.
“Good to have you on board, ‘swabbie’.” Mary winced at the friendly way Lena clasped her hand on her shoulder. “Now, since this is yer first day helpin’ out on the Golden Grin, you should dress more appropriately. Nothin’ says ‘First Day’ like yer birthday suit, don’t ye think?”
Mary hesitated, but a single glance at her two tormentors standing by her side cowed her into submission. Shaking hands reached up to finish pulling off her lace-up before reaching down to undo the button keeping her skirt around her waist. Her underwear hit the ground soon after to leave her standing in the buff right in front of her bound captain. She kept her eyes averted off to the side in embarrassment and her hands reached to cover her privates in an attempt at modesty, only for Isabella’s hand to gently tug them away.
“You’re too beautiful to hide yourself like this,” Isabella crooned in her ear.
“Now for ye. I told ye there would be punishment if ye didn’t talk. Bella, go get some girls to help keep her under control.” Lena turned to Mary once she was done. Theresa glared back with as much hatred as she could muster. Having been forced to watch the woman closest to her be tortured for over an hour then forced to humiliate herself like this had left her angrier than she’d ever been before in her life.
Unfortunately, that rage wasn’t enough to allow her to fight back when Isabella returned with half a dozen members of the Golden Grin in tow. Theresa found herself unceremoniously stripped naked no matter how much she kicked or bit at the people around her. Once she was completely disrobed, Lena directed the crowd to frog-march their captive out onto the deck.
A terrified inkling of what Lena had in mind occurred to Theresa as she was half-dragged half-pushed out of the cabin. The remaining members of her crew had all been left bound to whatever was available out on the deck. They formed a rough circle around the bondage devices she’d first noticed when they’d first been brought on board, which were conspicuously the only things nobody had been restrained to at the moment.
Her fears were proven correct when Lena pointed to one of the bondage devices. She was forced to kneel on a well-padded stool near the center of the deck. A pair of stocks were locked around her ankles to hold her feet in place while a rope was looped around the back of her knees to secure her to her perch. A pair of manacles hanging above the stool shackled her wrists where a full cranks on the pulley they were attached to ratcheted her up until she was left kneeling up straight with barely any slack to pull her arms down. Theresa didn’t know where to look. Everywhere around her were the despair-filled faces of her crew members. The humiliation of being forced into such a compromising position in front of the people who relied on her burned her cheeks.
“Don’t they have just the loveliest looks on their faces right now?” Lena leaned in close to whisper so only Theresa could hear. “How do you think they’ll all be after they watch their precious cap’n beg like a dog right in front of them?”
“I-... You-...” Theresa spluttered. Her anger was petering out to be replaced with horror. It was impossible for her to think of a decent response to the taunt with how hopeless the situation was.
Not that her captors were interested in hearing any rejoinder to begin with. Theresa nearly lept out of her skin with surprise feeling a pair of slim fingers poke her sides from behind. “Now, now. That won’t do,” Isabella’s sultry voice purred in her ear. “It wouldn’t do for one of our guests to look so upset. Let’s put a smile on that face…”
Theresa flinched and squirmed away from the fingers. The stool she was kneeling on proved to be bolted to the deck, reducing her to only being able to lean her upper body a little in any given direction and twisting around. None of it was anywhere near what was needed to escape Isabella’s probing fingers. The sadistic Puerto Rican was taking advantage of her position behind her victim by giving quick tickles interspersed at unpredictable intervals. She would goose Theresa’s sides, ribs, and hips just enough to make the bound captain shy away, then pull away her hands to wait before striking again.
Theresa’s face flushed with embarrassment from her own squirming. With all the eyes boring into her from every direction, she was keenly aware of how flinching away too hard would cause her chest to bounce a little. Never before would she have given it a second thought, but her current predicament was making her far more self-conscious than normal. It led to this paradoxical feeling that she needed to hold still for the tickling to avoid humiliating herself even further.
“Come on! Ye ain’t gonna entertain our guests with dancin’ like that!” Not helping matters was Lena stepping forward to join in. After roughly a minute of watching the teasing with amusement, the infamous Black-Eye could no longer hold herself back. Her fingers reached forward to skitter the tips of her nails all over Theresa’s olive globes.
A strangled gasp almost escaped from between Theresa’s lips before she managed to bite it off by gritting her teeth. The teasing was unbearable. She hated how clear it was that Lena and Isabella were used to ganging up on a girl like this. Lena kept up a steady attack of light tickles with her nails all over her breasts to contrast Isabella’s fingers coming in suddenly at random locations. At first she thought that the Dutch pirate captain was ramping up her tickles to coincide with when her first mate came in for another pass, but the pair proved her wrong the moment she started bracing herself for it.
“Eehehehe!” The dam finally broke after nearly a minute of getting double teamed. Theresa had let her guard down for a second, having convinced herself that because Lena was going light again meant that Isabella wasn’t about to strike. She was proven wrong when the slim, tanned fingers not only stroked her bare buttocks, but stayed to scrabble around. Theresa let out a squeal that was equal parts ticklish surprise and indignation at having her bottom handled like this before breaking down tittering.
A blush spread across her face. This was easily the most humiliating treatment she’d ever had to suffer in her life. Not only was she forced to endure a pair of women she hated running their fingers over her bare breasts and butt in front of a crowd, she was reduced to giggling like an empty-headed village lass from it.
“Oy, swabbie. Are you just gonna stand there or are you gonna join in the fun?” Isabella called out. Mary had spent the entire time standing with her arms folded behind her back off to the side. Her eyes had been averted from the display in front of her in shame, though she hadn’t been able to keep herself from flinching with guilt after hearing Theresa break down giggling. She jumped with surprise when a calloused hand suddenly clasped her shoulder. Isabella had stopped tickling Theresa’s butt just long enough to walk over to her. Her voice was positively dripping with gleeful malice. “You said you’d help, didn’t you? Or would you rather join in the show? We have plenty of spots left, if that’s what you want.”
One glance at her captain twisting this way and that in a fruitless attempt to shake Lena’s fingers off her melons was all it took to cow Mary into submission. Lena scooched over a little to make room in front of Theresa while Isabella guided her to kneel. “Now that we’re workin’ over her chest and booty, there’s only one place where it makes sense for ye to help out. How about ye get started on her womanhood to complete the set?”
“I… I…” Mary gulped. Being pressured into saying she would help torture her captain was one thing. Having do it, in front of her crew members no less, was something else entirely. She subconsciously looked up at Theresa’s face for guidance, but all that got her was a close up view of the woman’s distressed expression past a pair of hands going to town on her jiggling melons.
That was the final push Mary needed. Anything was better than having to suffer that for herself again. Her hands raised up towards Theresa’s naked groin, but hesitated before she could make contact. Instead, she reached down to stroke her captain’s thighs as a more “safe” target. Her nails gently scratched up and down the fronts of Theresa’s thighs in an effort to look like she was tickling without contributing much to the Spanish pirate’s suffering and was unpleasantly surprised to hear the giggling ratchet up a notch in intensity.
“Nice find! Try working over her inner thighs next. It isn’t uncommon for girls to get tickly there.” Hearing Isabella’s words of encouragement only made Mary feel worse. Nevertheless, she attempted to worm her fingers in between Theresa’s legs, only to find that her captain was squeezing her legs together as tightly as she could to keep her out. No amount of pushing, poking, and prodding could get the Spaniard to part her legs enough to allow her hands inside.
Panicking that she was about to be punished for failing to follow orders, Mary’s fingers returned to scrabbling all over what sections of Theresa’s thighs she could reach. Theresa’s heavy giggling graduated to peals of unrestrainable laughter under the assault. Mary wasn’t paying much attention to where she was tickling. Her fingers were moving everywhere on Theresa’s legs she could reach, tickling without much thought or intent behind it past trying to look busy.
A loud shriek sounded across the Golden Grin’s deck a few seconds later. Mary’s fingers had been moving up Theresa’s thighs and, without thinking about it much, traveled up to the bound buccaneer’s exposed groin. Theresa’s entire body spasmed as she let out a scream of laughter loud enough to make the onlooking crowds’ ears ring. Mary’s long nails gently scratching all over her groin and pussy was sending jolts of ticklish agony ripping up through her body to squeeze every last particle of air out of her lungs in the form of wild peals of laughter.
The reaction was strong enough to cause all three surprised ticklers to pause briefly. Mary pulled her hands back out of a mixture of shock and guilt, but Lena and Isabella shared an evil smile. Lena reached down to snag both of Mary’s wrists and pull them up over her head before the busty blonde knew what was happening.
“When ye find a spot that sensitive on a girl, yer supposed to tickle it for all it’s worth.”
“You need to really work it over. Make her regret she was born with a ticklish body. You know, like this!”
“HEheheHAHAHAH! STOOOHOP! STOP! I’ll tickle herHEHEHAHAHAHAHA!” Mary screamed. Isabella was illustrating her captain’s point by stroking her nails all over Mary’s hyper sensitive breasts. The naked blonde was left screaming in a mixture of ticklish agony and terror from how the sultry Puerto Rican would teasingly dance her nails down towards her nipples only to teasingly draw them away centimeters before making contact. Mary managed to get her legs out in front of her in an attempt to kick Isabella away, but all that resulted in was her tormentor sitting on her legs to render her completely helpless. No amount of begging or promises of compliance could get the evil pair to let her go for the next several minutes.
“Ye want yer playthings to feel nice and helpless just like this, like the tickles will never end no matter how much they beg. If yer havin’ trouble rememberin’ what yer supposed to do, just recall how this felt and ye’ll be fine.” By the time Lena released Mary’s hands several minutes of agonizing torture later, the busty blonde didn’t have a single doubt left in her head what fate was in store for her if her hands stopped again. With Lena’s barely concealed threat ringing in her ears, she shakily got back on her knees. Theresa’s panicked expression seeing her hands reach towards the helpless Spaniard’s groin again didn’t even register at this point. All that mattered to Mary at that point was doing whatever she could to keep from getting tickled again.
“How do ye think yer crew think of Mary now? Bet it makes ‘em feel all good inside to watch their first mate torture her cap’n just ‘cause another girl played with her breasts a little,” Lena whispered in Theresa’s ear. Theresa shuddered. That was horribly twisting the situation and they both knew it, but any response she could muster was cut short. Her entire body convulsed feeling the tips of Mary’s long nails stroke up the length of her womanhood. She didn’t have the strength in her anymore to prevent herself from breaking out in peals of laughter again.
To make matters worse, Lena and Isabella had kicked things up in intensity themselves. Lena had retaken her position behind Theresa’s back. Her nails were dancing unpredictably all over Theresa’s round butt and the back of her legs. Occasionally, she would reach around to squeeze the broad hips in front of her, causing them to adorably wiggle, or all the way to scrabble her nails across the olive skin of her tummy in a ticklish bear hug.
Lena’s assault was even worse. The sadistic black-eyed woman was taking advantage of having her victim’s upper body more-or-less all to herself. She would tap her nails all over Theresa’s jiggling breasts, randomly jumping between poking at the tops, flicking nails against the painfully stiffened nipples, and gently stroking the undersides. Nails were raked down the lengths of her armpits from her biceps all the way down before squeezing in between her ribs at random intervals. When Lena noticed Isabella working over Theresa’s stomach, she joined in to double down on extracting deep belly laughs out of their victim.
Theresa was completely beside herself. She’d woken up from nightmares about being tortured by other pirates before. None of them could hold a candle to the sheer ticklish agony she was in now. Compounding that was an overwhelming feeling of humiliation. She’d harbored a complex over the past couple years over how ticklish her erogenous zones were. What few efforts at physical intimacy she’d made with both men and women alike had all ended in her would-be lovers walking away hurt when she’d burst out laughing the moment they’d touched her, misinterpreting her ticklish laughter for mockery. Having those specific places targeted to force her to laugh herself silly was akin to having an old wound kicked.
The only thing keeping the suffering Spaniard from cracking was feeling the eyes of her crew boring into her. She knew that Lena’s goal was to break the spirits of every member of the God’s Fortune by forcing them to watch their captain break in front of them. Her refusal to let the rest of the girls down was what kept her desperately holding on no matter how badly she was tortured.
Unfortunately for Theresa, she failed to realize that that was the real purpose behind Lena’s cruel game. Rumors all over the Caribbean were that Theresa cared about her crew above all else. Breaking her in front of them wasn’t just for the fun of humiliating the woman in front of the people she cared about, the insatiable sadist had the inkling that her fellow captain would dig down into the deepest parts of herself to resist the torture for as long as possible if that’s what it took to give her girls hope. Just the thought of how broken the woman would be when the endless tickling took even that away from her was enough to get evil Dutch wet between the legs.
Theresa’s laughter filled the air around the ship for the next hour. At some point Mary had been handed a set of feathers to use. Feeling the soft plumes and stiff bristles stroking all over her sopping wet folds had proven more ticklish than when her first mate brought her nails into play. The assault on the rest of her body was so random and varied that her head was a mess trying to predict what they would do to her next. The once-proud captain had been reduced to purely reacting with screams of laughter as the women sadistically toyed with her body.
“PLEAHASEHEHEHEAHAHAHA! PLEASEHEHEHE STOHOP!” No matter how much the captain tried to hold on, it eventually became too much for her to bear any longer. Lena and Isabella had settled on tag teaming Theresa’s stomach for the past couple minutes. Theresa wasn’t even laughing by the time they decided to move onto something else. One scream ripped out of her throat after another. The last of her willpower crumbled away when Lena leaned in to pop one of the Spaniard’s erect nipples into her mouth, nibbling and licking at the sensitive nub at the same time her free hand tickled around the rest of the breast, while Isabella’s nails danced all over her jiggling rump. It didn’t matter that her crew was watching anymore. The only thing left in her mind was doing whatever it took to get it to stop.
“If all it took for us to stop tickling was a simple ‘please’, then we would never have any fun!”
“And we wouldn’t want to stop havin’ fun, would we? If we stop ticklin’ ye, then who are we supposed to play with?”
“MAHARY! Ticklehehe MaRYHEHEHAHAHAHA!” Thersea screamed at the top of her lungs. “MY CREHEHEW! TIHICKLE ONE of thehem. Pleahase! PleAHASEHEHEHA! TAKE ANYHEONE you waNTHEHE! JUST PLEASEHE STOHOHOPHOHOHOHAHAHAHAHA!”
Her words were music to Lena’s ears. A wide smile spread across her lips seeing the faces of the women tied up around them fall into the furthest pits of despair. “Ye lot heard her! Take anyone ye want. Ye all know how to treat a girl right!” she crowed loudly enough to be heard over Theresa’s screams of laughter.
A cheer rose like a swell from one end of the ship to the other. The rest of the Golden Grin’s crew had been watching the entire affair with amusement. Watching their leaders so thoroughly destroy a woman was getting them all wound up tight as a spring with the need to get a girl under their fingers for themselves. There was a general commotion as the pirates untied the captured members of the God’s Fortune from the spots on the deck in favor of dragging them over to the various bondage devices strewn throughout the ship. Some were rebound out on deck while others were dragged into private rooms or the ship’s hold. Regardless of where they were taken, laughter could be heard emerging from all corners of the ship minutes later.
Mary wasn’t exempt from the fun. Her single-minded focus on tickling Theresa’s pussy was interrupted feeling a multitude of hands grab her limbs. The naked blonde was dragged kicking and screaming over to a horizontal X-frame right next to Theresa. Soon the curvaceous blonde was left gibbering with fear up at the quartet of women leering down at her.
“We told you, didn’t we? We’d be right back to playing with you the moment we were done with your Cap’n,” Isabella taunted. She gently dragged a single nail down Mary’s taut stomach. “Now, the cap’n was doin’ something real naughty with her titties at the end there. It looked like a world of fun with me, so how about we start with that? After that, we can find how much you like havin’ your titties feathered after I give you the biggest orgasm of your life!”
Mary’s scream of terror instantly transformed into howls of laughter. Isabella and one of the other pirates had leaned in to wrap their lips around her rock hard nipples. At the same time, the other pair of pirates had lathered up her soles with oil before laying into them with hairbrushes. Mary was in hysterics within an instant. Her strict bondage denied her the relief of struggling away from the tickles being inflicted on her. Straps just below her breasts, around her hips, and above both knees prevented her from struggling any part of her body more than a centimeter or two. Lengths of twine served as toe ties that kept her from wiggling her feet under the harsh scrubbing. The only part of her body she could move freely was her head, which she whipped back and forth in a frenzy wildly enough to make her hair fly around her.
“Please… Please, I gave you my crew. Please don’t tickle me anymore…” Theresa sobbed. Just like Mary before her, being forced to betray those dear to her to save herself had shattered what was left of her spirit. The once proud captain had been reduced to pathetically bawling her eyes out in her bondage. The crowd of pirates standing around watched the display with every hint of enjoyment.
“Oh, don’t worry. The Cap’n and Bella are done with you for now.” One of them jeered.
“We just thought ye’d be lonely. What with bein’ the only one not bein’ tickled now ‘n’ all.”
“We’z got a policy here on the Golden Grin. Every guest o’ ours needs a smile on ‘er face. We’re just here to uphold that.”
Theresa screamed. Hands were converging on her from every direction at once, scraping, scrabbling, and stroking every bit of exposed flesh they could get their hands on. Within moments, the sound of Theresa’s screams of laughter joined in with her crews’.
—--
Weeks had passed since the crew of the God’s Fortune had been brought aboard the Golden Grin. Theresa would’ve described the experience as nothing short of a living tickle hell. Every last woman in the crew had proven to be just as cruel as their leaders. The members of the God’s Fortune had been reduced to little more than their playthings to tease and toy with as a way of passing the time, and there was plenty of free time to be had while sailing across the open seas. Not a single woman had the good fortune to not be ticklish enough to amuse their captors. Those who’d had the misfortune to catch one of the pirate’s fancy were kept bound in their cabin to serve as personal tickle toys while the rest were rotated throughout the ship to serve as free objects of entertainment.
Theresa and Mary had spent the majority of their time serving as centerpieces out on the deck. Multiple scalliwags were working them over at any given time to prevent them from having a single moment’s rest from dawn till dusk. Isabella had backed down on her promise of making them cum their brains out in favor of a cruel game of seeing how long they could be kept on the edge of an orgasm. Both would be rubbed and licked to the verge of cumming in the morning and again periodically throughout the day. Neither had been allowed to orgasm a single time for the last several weeks. Their constant state of arousal had trapped them in a heightened state of sensitivity, pushing the already unbearable gang tickling into new heights of ticklish agony neither of them had known possible.
Twice a day, at breakfast and dinner, they would be brought into the mess hall for a “tickling feast”. Their naked bodies would be stretched out across the long tables inside so the entire crew could take turns eating food off of them in the most ticklish ways they could manage. They had to hold still as best they could under the threat of having their soles scrubbed with hairbrushes while their breasts and pussies were teased with feathers if even a single food item fell off of either of them. The single time they had both managed to go a round without being punished had incensed their tormentors into spending the rest of the evening hammering their entire bodies with feathers, fingers, and brushes as punishment for denying the girls a reason to tickle them.
By this point, every last member of the God’s Fortune had given up on begging for mercy. There was nothing anybody could say or do that would keep their naked bodies from being tickled all day long. This was torture for the fun of it, pure and simple. The only thing the sadistic pirates wanted out of the women in their captivity was to make them suffer as long and deeply as possible, and their fingers dug in at every given opportunity to drive that home.
Mercy didn’t come until the Golden Grin reached its destination: a small, unnamed cay situated in the Cayman Islands. Lena had taken Theresa and Mary aside to make them point out the location of the hidden Tesoro de Suave Oscuridad on a map, making certain to remind them that every extra day the ship spent searching for it was another day spent as toys for the crew. The ship was now anchored a short distance away.
Theresa gazed out at the isle. It was just as unimpressive as the day they’d found it. The landmass was small enough that you could stroll around the outer edge within half a day. There wasn’t much to explore past that. What could generously be called a small mountain jutted out of the middle surrounded by a smattering of palm trees.
“That should be the last ‘o it,” one of the pirates called out. Rowboats had been sent out to scout the location and come back loaded down by chests filled with treasure. The crew members had reported following Mary’s directions to a small cave entrance that led down into a room filled from floor to ceiling with treasure. It’d taken the better part of the day to make enough trips to transfer the piles of gold coins, gems sparkling in every color of the rainbow, jewel encrusted goblets, and every other knickknack from the cave back to the ship. The end result couldn’t be contained in the Golden Grin’s hold. Chests bursting the seams with treasure were left lashed to the deck with rope for lack of a better place to put them.
“There. It’s yers. I hope ye choke on it,” Theresa spat. She along with the rest of the crew were standing naked out on the deck in a row.
“Aw, I thought ye’d be happier. Trip’s over! Or did ye decide ye liked bein’ our tickle toy after all?” Lena grinned at her. The crew of the Golden Grin were standing lined up opposite their God’s Fortune counterpoints. Each was holding a long pole ending with a multitude of feathers. Lena waited for a bit to see if Thersea had any last parting shots to take. She shrugged after several seconds of silence before continuing. “Guess it’s time we did the good ol’ piratical tradition then: Walkin’ the plank!”
That was the signal for the rest of the crew to jab their poles forwards. Squeals of laughter echoed across the deck from the feathers at the end brushing up against the bare flesh of the women across from them. The girls of the God’s Fortune had all been so broken by the tickling that they didn’t try to put up a fight anymore.
“Come on! Come on! Get walkin’ unless you wanna spend the entire trip back being tickled too!”
There was a point behind the tickling and threats. Theresa and her crew were corralled towards a plank extending off the edge of the ship to avoid the feathers. Theresa looked out across the expanse of water. Lena’s one small bit of mercy was that she’d made certain the ship was anchored close enough to swim to shore.
Feeling a multitude of feathers brush up against her sides made Theresa squeal. She stumbled away from the ticklish implements and found that she’d been driven to the edge of the plank faster than expected. Suddenly, there was nothing under her feet followed soon after by the impact of hitting the water below.
Rushing water swept all around her. Theresa flailed her limbs frantically in an effort to get herself under control. The pirate captain was an experienced enough swimmer to right herself despite the disorientation. Her head broke the waterline gasping for air. She could hear her crewmates hitting the water behind her, but there was nothing she could do to help them in this situation. Taking a moment to orient herself towards land, Theresa struck out towards the safety of the shoreline.
It was by no means an easy swim, but she managed to make it. The Spanish scalliwag walked up enough of the beach to put a buffer between herself and the waves lapping at her heels before collapsing to rest. The woman barely had time to close her eyes before she heard footsteps approaching. Cracking an eye open, she saw Mary walking hesitantly towards her.
“Captain… I…” Mary stuttered before falling silent.
“Apology accepted.”
“Wha-!? I haven’t said anything though!”
“Ye feel bad about backstabbin’ me back on the ship, but ye feel too guilty about it to think I should forgive ye.” A grin spread across Theresa’s lips over the look of bafflement on Mary’s face. “Come on, how long have we been together now? Ye’ve always had a bad habit of clammin’ up when ye feel bad about somethin’ ye did.”
“You can’t forgive me just like that. Thanks to me, they spent the last couple weeks tickling all of you! I should’ve just kept my trap shut…”
“No. No ye didn’t. If ye hadn’t cracked then, Lena and her bitches would’ve just kept ticklin’ until ye did. And even if ye hadn’t, there was nothin’ stoppin’ ‘em from ticklin’ the rest of us anyways. They just made us sell each other out for the fun o’ bein’ assholes about it.”
Mary didn’t have a response for that one. Silence stretched out between the two of them. Eventually, Theresa stretched out her hand towards her companion. Mary took it, thinking she was about to help her captain stand up, and was caught off guard when Theresa pulled her off her feet with a sharp yank. The first mate fell onto the sand to sprawl out on her back. A weight settled on her thighs from Theresa settling down to straddle her waist.
“Now, I don’t know about ye, but I’ve spent the last couple weeks needing to cum so bad I thought I was gonna go crazy. If ye ain’t willin’ to accept me forgivin’ ye with words, would ye listen if I said it with me body instead?”
Mary’s face flushed, but she wasn’t about to say ‘No’. The need had been burning away inside her too. Her hands reached up to interlace fingers with Theresa’s. It took a couple seconds of awkward fumbling from both of them, but they managed to get into position with their legs interlocked to allow their groins to come into contact.
Theresa began to move her hips, savoring the wonderful sensation of Mary’s pussy rubbing against her own, when she heard several footsteps behind her. She ignored them. The only people it could be would be their crewmates and they’d all taken advantage of her ship’s “Free Love” policy that they didn’t have room to complain. It wasn’t until she felt a hand grasp her shoulder that she bothered turning around to look.
The sight that greeted her made Theresa’s mind go blank. The face of the woman who’d grabbed her shoulder wasn’t a familiar one. Fish scales dotted her immaculate skin, which was a light shade of blue, from her face all the way down to feet. Both the woman and her companions were all just as naked as the two pirates. Every single one of them was so otherworldly beautiful that the pair stopped in their act of lovemaking to stare.
Their wonder didn’t last long. The scaled woman roughly pulled Theresa off of Mary. Another came forward to help hold her arms. Mary was similarly manhandled into a standing position by the other mermaids.
“Hey! What’s that for!?” Theresa cried.
“The curse of the Tesoro de Suave Oscuridad demands eternal suffering to thieves until it’s returned,” the scaled woman stated harshly.
“Hold on. We didn’t take it. The women on the ship did, we were just stranded here.”
“You were on the ship when it was stolen. You are as guilty of the curse as the rest,” chimed in another.
All further protests were summarily ignored. Theresa and Mary were pushed and shoved further inland towards cay’s mountain. Theresa glanced back towards the beach meaning to catch a glance of the Golden Grin. What she saw made her jaw drop. Scaled women were swarming everywhere. What members of the God’s Fortune crew had successfully made it onto land were being rounded up. More still were emerging out of the sea carrying the women who hadn’t yet made it to shore. Their legs appeared to merge together to form a large fin while they were swimming before splitting in two back to human legs for walking on land.
“Mermaids…” Mary gasped. Evidently she’d been watching too. The mermaids manhandled the both of them into the cave entrance that led down to where the Tesoro de Suave Oscuridad was originally held. They were led past through the treasure room to an unassuming wall where the leader of the group placed her hand against the bare rock face. A portion of the wall swung inward like it was on hinges revealing a staircase spiraling downward.
Theresa didn’t know how long they were led downward. The staircase constantly spiraled in on itself until she’d lost all sense of direction. What was most unsettling of all was that the path wasn’t lit by anything, but for some reason both pirates could still see without issue. This place was clearly supernatural in nature to the point even someone as unlearned as Theresa could tell at a glance. The room they were led to at the bottom was even worse. Everything about it was pure black. The walls, ceiling, and floor was the pitch blackness of nothingness stretching on forever.
A shove from behind sent the pirate sprawling forward. She screamed, fully expecting to fall into the void stretching out in front of her. Instead, she was overcome with a feeling of weightlessness. The pirate attempted to turn around only to find that she couldn’t move in the slightest. It was the most paradoxical of feelings, like she was simultaneously being pressed down on by a force too great for her to resist while feeling absolutely nothing at all. Her limbs slowly drifted apart until she was floating in the darkness in an X position.
The darkness slowly rotated Theresa around to face the group of mermaids. She watched as Mary was similarly shoved into the room, but she couldn’t turn her head to see if her first mate ended up in a similar position.
“W-what are you plannin’?” she asked the mermaids worriedly. The only portions of her body she had any control over were her eyes and mouth. A slight grin graced her captor’s beautiful features.
“As we said, eternal suffering awaits you until every last coin of the Tesoro de Suave Oscuridad returns.” The mermaid stepped forward into the room. Unlike the pirates, she was able to move freely, gracefully gliding around like she was swimming. “You will be kept in agony beyond mortal ken to endure. You will suffer in a way that pleases our master, never aging, never hungering. Never shall you find the escape of insanity from your torment or relief from sensation. You will be kept in full memory of the crime you have committed, so that you will be forced to endure the weight of your sins until another fixes your folly for you.” The mermaid swam up to Theresa to languidly place her fingers on the pirate’s biceps just above her armpits. Theresa’s eyes nearly bugged out of her head. She wanted to cry. This couldn’t be real. “But take heart, mortal. For our master enjoys the laughter of women above all else. Your torment shall be a merry one.”
Theresa squealed with laughter. The mermaid hadn’t moved her fingers in the slightest, but she’d felt something brush inside of them all the same. It was like the soft bristles of one of the fancy make up brushes the rich used perfectly fitted for the curvature of her armpits. The mermaid watched with a smile on her face as peals of laughter poured from between Theresa’s lips. The sensation was unbearable. The invisible brushes stroked up and down the length of her pits at the perfect intensity and pace to extract the maximum ticklish sensations.
The tickling stopped as soon as it’d started. The pirate captain found her head being guided down to look between her breasts towards her feet. Something down there was calling for her attention. She squinted into the unnatural gloom. If she focused hard enough, she could almost make out the form of a woman wearing a simple party dress seated at her feet.
The outline of a woman reached forward one of her hands to gently stroke Theresa’s foot. The pirate captain threw her head back to let out the loudest scream her lungs were capable of producing. Lena and Isabella combined had never managed to make it tickle as bad as that one light touch. It wasn’t so much like the woman had tickled her as she’d commanded the nerve endings in Theresa’s first to produce the maximum ticklish sensations possible.
Peals of laughter flowed freely from Theresa’s mouth as the woman’s fingers lightly danced all over Theresa’s feet. The helpless woman was so consumed by the ticklish sensations that she lost track of everything else. She didn’t notice the mermaid swimming away nor her crew members being brought into the room to share her fate. Not even Mary laughing her head off from a shadowy woman dancing her fingers all over her jiggling melons managed to draw the captain’s attention. The only thing that mattered was how much the woman’s fingers tickled.
Knowledge flowed into Theresa’s head as the woman continued to play with her feet. The being tormenting her was an incomprehensible entity akin to the gods of old. The woman in a dress wasn’t shrouded by the darkness, she was the darkness itself. She was a goddess formed from the very concept of torture from light, teasing touches exacting her very being on Theresa’s helpless flesh. Her tormentor wasn’t doing this because she got a kick out of it. Tickling women was its very purpose for existing.
The goddess gently lifted her hands from Theresa’s feet after what felt like an eternity. The ghostly outline stood up between Theresa’s legs to hover its hands right above Theresa’s helpless pussy.
“No… No, please. Anything but that. I won’t be able to take it. I’ll go crazy. Please. Please… Tickle me anywhere but there,” Theresa begged. Tears of terror were rolling down her cheeks. The crew of the Golden Grin had spent the last several weeks thoroughly teaching her how unbearable pussy tickling was when she was kept on the verge of orgasm. She and Mary being interrupted before they could help each other finish had left her the most sexually frustrated she’d ever been in her life. At this exact moment, there was nothing that terrified her more than the idea of experiencing that inhuman ticklish technique on her worst spot in her current state.
The shadowy outline of a woman didn’t have an expression normally. Hearing Theresa’s fearful begging, a thin line formed where her mouth would be to resemble a wide smile. Theresa was forced to watch as the woman’s fingers lowered down to scratch its nails against her wet, unwilling pussy.
A scream ripped its way through her throat. The mermaid hadn’t been kidding when she’d said it would be agony beyond a mortal’s ability to endure. The ticklish sensations coming from her pussy were far beyond anything she had experienced before. She desperately wanted to buck her hips or kick her legs, anything to express with her body just how horribly it tickled. Her bladder was cramping in an attempt to pee from how badly it tickled, but even that was denied her. The only thing she could do was descend into shrieks of maddened laughter.
Theresa didn’t know how long the shadow continued to play with her pussy. There was no way to tell time here. The only thing she was aware of anymore was the tickling. To make matters worse, terrible knowledge was flowing into her again. She knew beyond the shadow of doubt that the goddess was just getting started with her. Soon her stomach would be coming under attack. Following that her breasts. The goddess of tickling would continue to explore every last centimeter of her sensitive skin. It would take its time getting to know every part of her and the best ways to make her suffer in intimate detail.
As the pirate captain howled and screamed with laughter, she silently prayed for it all to end. She prayed with all her might that someone would return the Tesoro de Suave Oscuridad to its resting place and save her from this eternity of torment.
—--
“And to women well tickled, a cheer!”
“Hoorah!”
Lena shouted along with the crowd. Tipping her flagon back, she downed her ale in a single go.
“Everybody’s really cutting loose, Cap’n,” commented Isabella.
“Of course they are. We got us the haul of a lifetime by ticklin’ a bunch of girls out of their minds. Things couldn’ta gone more perfect in me dreams!” Lena looked down at her first mate. They were currently sitting in the mess hall together. Or to be more specific, Lena was sitting at the long table while Isabella was bound stretched out across it in the nude. “How’re ye fairin’, Bella? Did I tie the ropes right?”
Isabella tugged at the ropes keeping her hands overhead. They held firm. She gave an encouraging nod to her captain. “I’m feelin’ a little pent up. I love givin’ another girl a good tickle, but nothin’ beats feelin’ the feathers on my own skin.”
“That’s the Bella I know and love.” Lena leaned forward to give Isabella a quick peck on the lips. “So what’re ye feelin’ up for? I imagine yer in the mood for us to play a little rough with ye.”
“I think I’ve been due for some extra punishment. Remember when I made fun of you in front of Stormrider and her first mate for getting flustered? I think you owe me back for that with several weeks of interest.”
“Thanks for remindin’ me. Several weeks of debt, eh? It’s gonna take a couple days for ye to work that one off, plus ye’ll be accruing interest as we go.” Lena grinned wickedly. The sadistic captain snatched up one of the bottles of oil lying next to Isabella and began slathering a hefty amount on the Puerto Rican’s helpless soles. Isabella licked her lips in anticipation. Her feet were easily her worst spot and she loved nothing more than when Lena would dive in to hammer her there first. She didn’t even try to hold back her laughter when the hairbrush came in to furiously scrub all over her oiled soles.
“HAHAHARDER! TICKLE HARDERHEHEHAHAHAHAHA! MAKE MEHE BEGHEHEHEHAHAHAHA!” she screamed in between bouts of laughter. Heads turned from her peals of laughter echoing throughout the hall. Girls were getting up out of their seats to join in. There wasn’t a self-respecting member of the Golden Grin who wouldn’t want to join in after hearing a woman’s tortured laughter.
A swell caused the Golden Grin to jump a little under their feet. The crew barely noticed. It was normal for them. With them all in the mess hall helping tickle Isabella, they especially didn’t notice the lid of one of their treasure chests jump up a little. A few of the cursed coins belonging to the Tesoro de Suave Oscuridad spilled out of the crack onto the deck. There they slid and rolled around with the rocking of the ship until they all fell off the side into the ocean.
The mermaid treading water just underneath the Golden Grin’s keel watched the coins float past her on their way down to the bottom of the ocean depths. She didn’t have enough companions to complete the assault on the ship yet, but more were arriving by the minute. In roughly an hour there would be enough of them to wash over the ship like a wave and drag the thieves back for their divine punishment.
----------
“Captain. Captain! Are you there?” A banging at the door accompanied the voice. Theresa stirred groggily underneath her covers. She knew she’d given orders to wake her up from her siesta if anything happened, but to actually do so was another thing entirely. She rolled over to turn her back to the door, pulled the covers over her head, and prayed to whatever gods would listen to someone like her that this was low enough priority that the knocker would take a hint and go away. It wasn’t. “Captain, we got a situation!” the voice continued to shout, accompanied by more forceful banging.
“I’m up! I’m up. Quit yer belly achin’ and gimme a moment to get decent,” Theresa shouted back. Throwing the covers off in resignation, the shapely Spaniard rolled out of bed. It took a bit of fumbling around through the darkened room before she remembered that she’d tossed her loose brown pants and button up white shirt onto the chair of her desk. It was only after a profanity-filled bout of struggling to figure out which end was which in the dark that it occurred to her sleep-addled brain that the entire process probably would’ve been easier if she’d bothered to open the curtains of her window first.
Theresa Martil liked to believe she wasn’t normally this scatterbrained. You didn’t make it as a successful pirate captain in the Caribbean without keeping your head on your shoulders, and you couldn’t manage that literally without doing so figuratively. That was especially true when you were trying to break into the criminal industry as a woman. It was one of those paradoxical things that had always stood out to Theresa, that being a beautiful 27-year-old Spanish woman with wavy brownish-black hair, a nice olive complexion, large chest, tight waist, and long legs somehow made it harder to get her fellow pirates to join up under her. If you then took that and projected it out to the fact that the entire crew of her ship, the God’s Fortune, were similarly all pretty young women, it meant they’d all needed to be cunning twice over to get by in this (often quite literally) cutthroat industry.
The issue of lighting was solved by whoever was knocking running out of patience. The door swung open to reveal a harried looking woman framed in the afternoon light. It was Theresa’s first mate Mary Roberts, dressed in her usual long sleeve lace up and a long red skirt. Theresa didn’t know if Mary was even her real name and preferred to keep it that way. Who you were before didn’t matter once you signed on with the God’s Fortune. What was important was that Mary was a pretty young woman with beautiful long blonde hair, shining blue eyes, and a pleasingly large chest her captain found easy on the eyes. She also was the only member of the crew who was literate and knew far more about the magical peril they encountered throughout the Caribbean than anyone Theresa had ever met. Her knowledge had proven invaluable time and again in keeping them all from falling prey to the occultic nonsense that had a bad habit of cropping up around the islands.
“Right, now what’re ye wakin’ me up fer?”
“There’s a ship on the horizon, Ma’am. Pirates from the looks of it and not any of the ones we’re friendly with. They aren’t flying the flag for parley nor will they stop approaching when we signal them to.”
“They’re lookin’ for a fight then?”
“We’re assuming so. All hands are on deck, just needed to fetch you.”
Theresa nodded. All annoyance at being disturbed was forgotten. If there was anything that warranted interrupting her beauty sleep, coming under attack was it. The captain followed her first mate out the door to the main deck. One of the benefits of being the captain was that her cabin directly overlooked everything from the stern of the ship. From where the two of them stood, they could see women running to and fro in preparation. Some were already kitted out with cutlasses and muskets while others were doing some last second maintenance on the cannons. Pretty much all of them were stealing glances off the starboard side as they went. The captain followed their gazes and grimaced.
“Ugh, the Golden Grin…” she groaned, recognizing the giant golden skull sporting a toothy grin painted on the ship’s mast.
“Who’re they, captain?”
“What do ye mean ‘Who are they’? Ye can’t grab a pint these days without…” Theresa began before something occurred to her. “I forgot, ye don’t come with us to the tavern whenever we dock, do ye Mary?”
“Nope! Alcohol is one of the roots of sin. It’s bad for both your mind and body!” the blonde proclaimed with a huff.
The Spanish captain had to hold herself back from pointing out that as pirates the two of them had gotten up to more sinning in the past year alone than most people did in their entire lives. Instead, she pressed on with her explanation. “They’re a new crew in these waters. Started flying the colors a couple months ago. Black Eye Lena and her merry band of sadistic ladettes. Ye can’t visit a port these days as a member of the God’s Fortune without all the locals yappin’ yer ear off about them. They’re held to be our rivals now, on account of Black Eye being the only other cap’n in these waters who has a crew of only ladies.”
The God’s Fortune had made a name for themselves in recent years for being a pirate crew consisting solely of women. After making the journey here from Spain, Theresa had been quick to notice that many ladies were being denied working on ships purely on the belief that a woman wouldn’t be able to handle the rough living conditions. As far as she was concerned, it was the other crews’ loss and her gain. Many of the girls she’d picked up over the years had proven just as capable as their male counterparts when it came to the important activities of finding buried treasure and keeping the ship from sailing into the side of a cliff. She’d had the pick of the litter selecting the best people she could find in every category, every one down to the last desperate to leave their jobs as seamstresses or barmaids behind for a life of adventure on the high seas. Word on the street was that the Golden Grin was crewed by all the women who’d been too uncontrollably psychopathic, sadistic, and greedy to make the cut on the God’s Fortune, which was all true as far as Theresa could tell from the stories about them.
Any further discussion on the approaching pirates was cut off by a thunderous sound followed soon after by a spray of water a few dozen meters away from their position. “They’re opening fire!” someone cried out.
“Man the cannons! Make them regret the day they crossed the God’s Fortune!”
“From the way they’re continuing to approach, they must mean to board us,” said Mary. Theresa nodded in agreement. That was the only reason she could think of for the other ship’s reckless charge through the cannon fire. “Were there any rumors pertaining as to why they might want to pick a fight with us?”
“None that matter. We’ll be wearing their guts for garters at the end of this either way,” Theresa growled. The captain rushed back into her room to grab her saber. If it was a hand to hand fight they wanted, by the gods she was going to give it to them.
She had just managed to return back to the deck when the ship lurched underneath her feet. A cannonball fired from the Golden Grin had managed to impact the side of the God’s Fortune right at the waterline. With nothing within arm’s reach to grab onto, Theresa lost her footing to the ship rolling violently from the force of the blow.
“Captain! Grab on!” She heard Mary cry out. Her first mate had one arm wrapped around the bannister and was holding out the other towards her. The captain lunged as best she could for the outstretched hand, but their efforts proved in vain. Her feet slid out from under her and the ship’s captain was sent plunging off the side of the ship into the churning waters below. Her world went black as her body crashed into the churning waters below.
—--
A rhythmic thumping right between her breasts stirred Theresa back awake. She was vaguely aware of shouting around her, but it was like listening to a conversation several rooms away. Everything felt so far removed. The thumping on her chest made her cough, causing her to spit out a torrent of sea water, and things began to swim back into focus.
“Captain! Stay with me, captain!”
She could hear a woman shouting. The Spanish scoundrel’s eyes cracked open briefly before realizing she needed to blink the water out of the way to see anything. It looked like Mary had placed her on her back in order to administer chest compressions.
“Captain Theresa! Thank goodness. I thought I’d lost you!” Mary cried with relief. The woman was completely soaked. Nearest Theresa could tell, her first mate must’ve dove in after her to fish her back onto the deck.
Theresa rolled over onto her front and coughed up the last of the sea water inside of her. “I won’t be going down that easily,” she muttered, as much to herself as to her friend. Unsteadily clambering to her feet, the captain took stock of the situation. It looked like Mary had dragged her into one of the nearby storerooms before attempting resuscitation. Her heart sank peering out the door leading out to the deck. The crew of the Golden Grin had successfully boarded the ship while she was out. It was easy to tell at a glance that they were getting overrun. Women wearing scarves and bandanas emblazoned with a smiling golden skull had the girls she recognized outnumbered nearly two to one. They weren’t using their weapons anymore, instead opting to leverage their numbers advantage to swarm over the defenders with fists and submission holds to non-lethally take their opponents down.
“Let’s go. The girls need us,” said Theresa. Glancing around the room, the only thing vaguely resembling a weapon at head was a nearby mop. It would have to do until they could salvage a better one. Mary looked like she wanted to say something, but kept her lips set in a grim line. A wooden bucket appeared to be her makeshift weapon of choice for now.
The pair shouldered through the door in an attempt to salvage the fray in front of them. Theresa swung the handle of her mop at the back of a nearby pirate’s head. At the same time, Mary had jammed her bucket over another unsuspecting foe’s head from behind before knocking her over with a kick.
Their joining in the fight didn’t turn the tides nearly as well as either of them wanted. Neither had enough time to pick up one of the discarded weapons littering the deck before cries of alarm sprung up from the Golden Grin crewmembers who had recognized them. Soon, enemies were swarming them from all sides, all eager to be the ones to claim the glory of being the ones to take down the God’s Fortune’s captain and first mate. Theresa swung her mop as frantically as her still unsteady body could manage while Mary swung fists and feet, but nothing could stop the press of bodies bearing down on them. Both were wrestled to the ground less than a minute after emerging onto the deck.
“Let me go, ye bastards!” Theresa shouted. Fighting off half a dozen women dogpiled on top of her would’ve been impossible under normal conditions, to say nothing of how out of it she still was from her dip in the ocean. The only thing the captain could do was helplessly crane her neck around in the hopes that one of her crewmates was able to come to their rescue. What she saw made her heart sink further. The fighting was dying down all around them. What last members of her crew were still standing were being subdued like she and Mary were as she watched.
“Are these the ones?” A sultry Puerto Rican woman sporting a frilled long sleeve shirt, light vest, tight pants, and a bandana around her neck sporting a golden grinning skull approached the pinned pair after the last member of the God’s Fortune was taken down. Tousled black hair fell down around her shoulders around a face stained with sweat. The first couple buttons of her shirt had been undone to show off a copious amount of her large chest and her pants hung low around her hips, like she was dressed more to attract attention at the pub than for a fight.
“Yep, this is them, Isabella. Stormrider and her first mate. Just like in the wanted posters.” One of the pirates holding Mary down extracted herself from the pile, pulled out several pieces of paper crumpled up in her pocket, and straightened them out for the woman to sea. Isabella glanced back and forth between the paper and the two captive women. With a nod, she gestured back towards the Golden Grin with her thumb.
“Looks like. Good job. Take them back to the ship. The cap’n would like to have a word with both of them.” Both Theresa and Mary were manhandled back to their feet. Their captors frogmarched them forward with hands firmly gripped on their shoulders and wrists to prevent any last ditch efforts at fighting back before they could begin.
Theresa glanced around as they were led onto the Golden Grin. All of the other captive members of her crew were being manhandled into position across the deck. Girls were being lined up against the railing along the sides where they had their hands bound behind their backs with lengths of rope to whatever was available. Some were brought over to rather prominent bondage devices that seemed to have been installed as part of the deck itself. Theresa didn’t know what they were for, but given the rumors she’d heard about Black Eye Lena’s crew torturing their prisoners, she highly doubted anyone placed in them was about to be pampered.
“Cap’n! We got ‘em!” one of the women escorting the pair shouted. A woman who was in the middle of tying the ropes around on the God’s Fortune member’s wrists raised up her hand in a gesture of acknowledgement. It was hard to tell how old she was with her back turned, but she was fairly small in comparison to the other pirates milling around her. Brownish-black hair hung just long enough to reach the back of her neck and Theresa could make out tanned, weathered skin in between her long sleeved t-shirt and long pants, both of which were soaked with sea spray and sweat. The buccaneer doubted she would’ve realized that the woman was the ship’s captain to begin with if she hadn’t reacted to her crewmate’s call.
That impression was blown away the moment she turned to face them. Theresa had always assumed that “Black Eye” Lena’s namesake was thanks to sporting an eyepatch. Either that or it was a joke about her coming out of a bar fight having acquired a bad eye injury. What became immediately apparent was that the name was far more literal than she could’ve expected. Lena’s entire right eye was pitch black as deep as the ocean during a cloudy night. The effect was so striking that both prisoners stopped to gawk at her in surprise, only resuming their walk forward after a few seconds of spirited prodding from their captors.
Instead of joining the rest of their crew on the deck, the two pirates were led up towards the captain’s quarters near the stern. They were jostled inside to the sight of several bondage devices taking up the space that normally would’ve been reserved for the navigation table. A trio of pirates wrestled Thersa into a padded chair that stretched out her arms to the side while spreading her legs out horizontally in front of her. Mary, despite her best attempts to struggle free, had a pair of girls stretch her out across a long table that bound her arms and legs together with rope. A few cranks of a pulley on the side left her stretched out tight just on the verge of discomfort.
“So this is the famous Stormrider and her first mate, eh? I was expecting more from the women who led their crew into the biggest storm in decades and returned with more treasure than her hold could contain,” Black Eye Lena commented as they were being bound.
Neither woman rose to her provocations, so Isabella spoke up for them. “Someone in our crew mentioned seeing Stormrider fall overboard after we started shelling them, Cap’n. A good number of their crew were more preoccupied fishing her out of the drink than with fightin’ us.”
“Lucky us then! Now they’re just two helpless women for us to play with. We know just how to treat a girl, don’t we Bella?” Lena’s smile took a nasty tinge to it as she reached over to lightly jostle Theresa’s boot.
“Yeah, yeah. You and every scalliwag between here and the mainland. I’m quaking in me boots just thinkin’ about it,” Theresa stated flatly. Lena’s face went blank.
“I… You…” the black-eyed captain spluttered incoherently. Of all the responses she’d expected, her captive being dismissive of her evidently wasn’t one of them. Theresa would be the first to admit she probably hadn’t chosen the best thing to say given their predicament, but she hadn’t been expecting the other woman to be so easily thrown off balance by a few words. After a few seconds, Lena seemed to regather enough bravado to fire back. “Oh, you will be. Every woman who ever set foot on the Golden Grin has learned to fear the name Black-Eye Lena!”
“Even your own crew? That sounds like some poor working conditions to me. I’d quit within a fortnight!” Mary joined in.
“Oh, look at her. She’s as bright as a ripe tomato! With the stories you hear at port, you’d think the Black-Eye would at least know how to intimidate a girl,” Theresa jeered. Lena’s face had gone scarlet with a mixture of rage and embarrassment.
Any further mockery was cut short by Mary letting out a strangled yelp. Isabella had taken advantage of nobody focusing on her to press her fingertips into the bound blonde’s stomach through her soaked shirt. An audible bang could be heard by everyone in the cabin from the busty pirate bucking her hips with surprise.
“Alright, alright. That’s enough, you two. Don’t go teasin’ our cap’n like that. She gets sensitive when captives don’t act proper terrified like they’re supposed to. It’s a confidence thing,” Isabella admonished. Lena gave her a look straddling between hurt and belligerent.
“Words like that’ll get you in the stocks, Bella.”
“Why do you think I said ‘em, Cap’n? Okay, you lot. Looks like we’re good here. How about givin’ us some alone time to get to know these ladies better?” That last bit was said to the rest of the crew. None of them seemed the slightest bit perturbed over being asked to leave. They proceeded to file out door chatting amiably with each other, the last out making certain to secure the double doors shut behind her.
“Down to business then.” Lena took the opportunity to get the conversation back on track. She assertively placed her foot on Theresa’s chair and leaned in close to glower at her. “Where’d ye hide the Tesoro de Suave Oscuridad?”
Theresa and Mary both stiffened up at the mention of the name.
“Ye don’t want that. Not that one,” Theresa warned, her face deadly serious.
“I was hoping you’d say that.” Lena’s glower transformed into an almost unnervingly happy smile. Rather than respond with words, she leaned in further, her hands reaching forward. Theresa was initially convinced the woman was reaching for her chest and was surprised when her hands passed by to grope at her rib cage instead. The tan-skinned captain stiffened, feeling the fingers gently, almost lovingly, stroke against the middle of her rib cage with just enough force for her to feel it.
“What do you think you’re doing?”
“I told ye we know how to treat a girl. Stroke a fair maiden’s skin juuuust right, and even the hardest gal in the Caribbean will be singing like a little bird for you before long.” Her touch was light. Maddeningly so. Theresa soon had to grit her teeth in order to prevent an errant giggle from escaping between her lips. Never before had the brave captain been so caught off guard. With all of the stories of the Black-Eye inflicting horrific torture on her captives, the idea that said torture could be tickling of all things had never once crossed her mind.
“Same question to you. Tell us where you hid the Tesoro de Suave Oscuridad. As the first mate, you should know just as well as your cap’n where it is.” Mary wasn’t being excluded from the interrogation. Isabella had rolled up her waterlogged shirt to expose her captive’s flat stomach. Slightly flexing her fingers caused her long nails to tease a centimeter of the taut skin presented to her with each stroke.
“I don’t know what you’re talking about.” In contrast to her captain’s visible struggles to hold back her laughter, Mary’s countenance was stone cold. It was like the light tickling didn’t register to her.
“Then let me jog your memory. By all accounts, the Stormrider and her God’s Fortune struck upon a score several months ago. The Tesoro de Suave Oscuridad, a legendary treasure horde said to be too vast for the largest galleon in the British navy to hold.” Isabella was distracted from her explanation briefly by experimenting with a new way to toy with Mary’s stomach. Her nails went from lightly scratching to tracing waving patterns from one side to the other. It proved to be just as ineffective as the earlier strategy at drawing out a reaction.
“But ye scurvy dogs didn’t hold onto it for long. Spent a single night livin’ it up in a shanty town on the coast of Jamaica. Then the very next mornin’, for some reason, ye held up every fine establishment ye’d all visited that night for all yer money back. ‘The Stormrider’s Backstabbin’ Crawl’ the locals call it now. After that, ye disappeared with the loot not to show yer faces again until a couple weeks later, not a single coin o’ the treasure in sight since.”
Theresa wasn’t holding up quite as well as her first mate. Lena had been making steady progress up and down her ribs. The sadistic black-eyed woman had found a couple spots that caused her victim to tense up or squirm at the touch, but she was opting to keep exploring rather than sink her fingers in to abuse them. She was, however, revisiting them often enough to drill it into Theresa’s head that she knew exactly where they were if they were ever needed. Every time those fingers stroked one of those spots, the Spaniard had to grit her teeth to prevent herself from making a sound.
“We told ye. Ye don’t want that one,” the captured captain spat through gritted teeth. Her body tensed up every time the fingers traveled downward towards her sides and stomach. She couldn’t help it. She knew from errant tickling dispensed by family and friends growing up that her stomach was far more ticklish than her ribs. What she hated more was that Lena clearly knew that it was getting to her. The black-eyed she-devil wouldn’t be constantly going down to linger at the bottom of her rib cage only to travel back up again if she didn’t.
“Oh? And why wouldn’t a pirate want treasure?” While Mary had initially acted like the tickling didn’t affect her at all, an involuntary twitch of her cheek when the nails got too close to her belly button let her sadistic tormentor know that she had only been putting on a brave face. The Puerto Rican pirate began to drag her nails in lazy circles just a few centimeters outside her victim’s button and was delighted to watch the bound blonde squirm with discomfort.
“It’s cursed, ye daft broad! Why else would we give up such a haul?”
“Ha. Quite the tall tale! Everybody with half a brain knows that there’s no such thing as curses.” Lena snorted derisively. If Theresa or Mary had been paying attention to Isabella at that moment, they would’ve caught the Golden Grin’s first mate casting her eyes up towards the ceiling in annoyance. Isabella had never once been able to get her captain to realize that her fabled black eye was the consequence of a close call with a curse no matter how many times she’d explained it. She’d frankly just given up on trying by this point. Lena was still convinced to this day that it was caused by a bit of gunk staining her eyeball.
“It’s true,” said Mary. “Everything we could find in the old legends say that taking a single coin from its resting place will bring nothing but misery and misfortune to the thieves until every last piece has been returned. We had no choice but to return iiiiheeekhehehehe!” Mary’s explanation was cut short by her tormentor playfully slipping a finger into her exposed belly button. The surprised maiden let out a squeak, her hips briefly bouncing off the table, before sputtering out a few giggles. A smile had formed on Isabella’s face over having finally provoked a reaction out of her new plaything. Her nails returned to tracing circles after a few seconds of belly button teasing, the threat all the more pronounced now that she’d proven she was willing to make good on it.
“Yes, I’m certain you aren’t lying. Now how about you two tell us where you hid the treasure and we’ll be reeeeeal careful about this big, bad, scary curse…” Theresa wasn’t faring much better. Lena had decided she’d prefer listening to laughter than her first mate being insulted in front of her. Rather than briefly tease one of the bad spots she’d found on the Spanish woman’s rib cage, she’d settled on massaging the spot through the soaked shirt. Her fingers followed effortlessly no matter how the bound woman attempted to twist her upper body away
The black-eyed pirate focussed on Theresa’s ribs for just long enough to give her captive the idea that she had settled on focussing there before suddenly jumping her fingers down to the flat stomach below. The fingers then moved inwards to dig into the vulnerable, soft flesh of Theresa’s helpless tummy before shaking around. An audible bang could be heard from the Spaniard jumping in surprise, followed soon after by girlish tittering that did nothing for her image as a rough and tumble ship’s captain.
“That’s what I wanted to hear…” Lena cooed. “Feels good, doesn’t it? I bet you love it!”
“Fuhuck youhehehAHAHAHAHA!” Once she’d lost control of holding it back, Theresa’s tittering quickly grew into full blown laughter no matter how hard she tried to hold it back. Lena’s attack was relentless. Her fingers jumped all around the bound pirate’s stomach and sides, poking, stroking, wiggling, and fluttering unpredictably. Theresa quickly discovered she hated the feeling of helplessness that came from not knowing where or how the fingers would strike next.
“Now tell us where you hid the Tesoro de Suave Oscuridad or I’ll tickle your cute little tummy for forever and ever,” Lena taunted. A cruel smile played upon her lips. “Once you do, we can move on to working over the rest of you!”
“Is that what you consider motivating someone to talk here? Promises of more torture when we do? You lot need to learn how to incentivize people,” Mary griped. Isabella hadn’t found quite as much success with opening up her victim yet. Her fingers continued to steadily scratch away at Mary’s stomach, but she hadn’t gotten anything better than the errant gasp out of the busty first mate.
“We find that it doesn’t matter one way or the other in the long run. Tickle a girl’s worst spots in the right way for enough time and she’ll eventually be willing to do anything you want to make it stop. All we have to do is keep playing with you two until you’re so desperate for a break that you won’t care what you have to do to get it.”
Isabella pursed her lips. It was time for a change of tactics. More so than frustration at a lack of success, she was starting to get bored. There was nothing fun about tickling a girl if it didn’t cause a reaction. Her eyes roamed up and down the body of the woman stretched out before her. They naturally came to rest on the blonde’s rather substantial chest. The plunging neckline of Mary’s lace up advertised both her sizable melons and the fact that she didn’t have any underwear on at the moment to contain them. “You know, it’s been a while since I’ve gotten to play with such a nice chest. You wouldn’t mind if I had a little taste, would you?”
“Yes! Yes, I very much would. Get your hands off me, you pervert!” Mary cried. Isabella ignored her protests in favor of rolling up her captive’s shirt to reveal her breasts. Hopping onto the rack, she straddled Mary’s hips while menacingly hovering her fingers within inches of the milky white globes. More so than getting to ogle Mary’s bare chest, what brought a wicked glint to the sadistic pirate’s eye was seeing the look of fear in the girl’s eyes.
“Well then, don’t mind if I do!” The Puerto Rican’s fingers dove into flutter all over Mary’s breasts. After so many minutes of not getting a reaction, it was gratifying to the sadistic pirate to have her victim go wild the instant her fingers made contact.
“Oh Gohod! Oh GodhohohEHEHEHEHAHAHA!” Mary let out a loud shriek and began struggling with all her might to escape the fingers. Her hands futilely tugged at the cuffs around her wrists while her legs kicked against their restraints hard enough to make the rack rattle. Isabella didn’t know where to look. Watching the milky white skin of her new toy’s breasts jiggle every time her fingers made contact again was almost hypnotic, but she was also in love with the way the woman whipped her head from side to side as laughter poured from her lips.
“Ooooh! Found your spot! Found your spot!” Isabella teased. Keeping her fingers moving this fast for an extended period of time would be too tiring, so she changed methods of attack as much to preserve her own stamina as to explore further ways of causing Mary agony. She leaned forward to grab the jiggling breasts in her hands. Mary had a few seconds to fool herself into thinking that there was no way for the tickling to continue from that position only to once again be forced to shriek with laughter. Isabella had groped her for the purpose of holding her breasts still so she could use her forefingers to flick the nipples crowning her milky white globes. She changed between hitting both simultaneously and alternating from left to right and back again at random intervals to drive Mary wild with unwilling ticklish mirth.
“Looks like those two are hittin’ it off well. I usually like to take my time breakin’ the new girls in, but let’s try not to let ‘em beat us to the punch, eh, Stormrider?”
“Thihis isn’t a compehetitionhehehehe.” Lena had been content to toy with Theresa more slowly up until then. She’d interspersed lighter teasing that made her rival captain giggle like a little schoolgirl with more energetic tickling to make the Spaniard bounce around in her seat while laughing her head off. Seeing Isabella so gleefully push Mary as hard as she could reminded the black-eyed scourge of the seas that there was an actual purpose to this. A purpose besides having fun with a pair of beautiful womens’ bodies, that is.
“Oh yes it is! It’s a competition between ye and yer first mate. Whoever tells us where the treasure is hidden is going to get a nice break from the tickles, cause the bad girl who doesn’t talk has an extra special punishment waiting for her that’ll take aaaall our attention.” Lena’s proclamation made both of the bound womens’ blood run cold. Neither of them had expected to be pitted against the other like this. Theresa glanced fearfully at Mary. The last thing she wanted in the world was to stab her closest crew member in the back.
She didn’t get long to stare. Lena had taken a few seconds to undo some of the buttons near the bottom of her shirt, exposing her stomach to unimpeded questing fingers. The cruel pirate captain sunk the pads of her fingers into the bottom of her victim’s stomach right at the edge of her pants and rubbed her fingers back and forth. Howls of laughter poured from Theresa’s lips as she leaned forward in her chair as far as her bondage would let her in a desperate attempt to curl into a ball.
“Is that too much? Is that too much for the widdle baby?” Lena jeered with a cruel smile. “All you have to do to get me to stop is tell us where you hid the treasure. I’m certain yer first mate will do juuuust fine with our undivided attention on her precious, tickly, titties!”
“NeverhahaheHEHEHEHAHAHAHA!” Thersa cried, believing that Black-Eye Lena would never expect that the thought of Mary suffering more was the rock she clung onto for strength against the torture.
Except that was exactly why Lena had said it. There was no feeling more wonderful in the world for the sadistic Black-Eye than breaking a woman using nothing but the light application of her fingers on their bare skin. Already submissive girls were no fun for her. What was fun was slowly peeling her victims apart one layer at a time until they shattered like eggs dropped on cobblestone. The strong willed ones were her favorite. The feeling of satisfaction from successfully breaking a woman who’d held on for weeks was infinitely better than a victim who caved within the day. She’d long since gotten into the habit of giving the girls in her captivity reasons to resist solely to extend their lifespan as her playthings.
“You know, I can sympathize with having ticklish titties. The rest of the girls simply can’t get enough of mine,” said Isabella. The seductive Puerto Rican playfully jiggled her chest for emphasis, not that Mary was in a position to appreciate it. “Whenever I let them tie me up, they’re certain to keep working over my boobies until I’m in tears.”
“Bella is our first and longest lasting tickling slave,” Lena helpfully explained. “We picked her up as the sole captive of one of our very first raids. We’d meant to drop ‘er off back at her hometown after keeping her tied up on deck for a month-long voyage, but she’d loved it so much that she’d begged us to keep her on board. Hell, whenever we don’t have fresh toys to play with, Bella here will spend her days bound naked out on deck to give the rest of the crew some entertainment!” Isabella was the one woman Lena never grew tired of torturing. The sultry tan-skinned woman had a love of being tickled that bordered on unnatural. Never before had Lena met someone who could be gang tickled for hours on end and come out the other side begging for more. It’d proved to pair well with Lena’s unending sadism. Isabella was a woman she could tease and tickle for years but never successfully break.
“YOHOU’RE FREAKSHEHEHAHAHAHAHAHA!” Mary screamed.
“Awful kind of you to say,” responded Isabella with all sincerity. Her cruel smile became almost wistful as she continued to play with Mary’s tits. “That reminds me… The girls used to love breaking out the feathers when they were playing with me. Having them stroke my titties with both long stiff eagle feathers and soft downy plumes would drive me completely out of my mind. I could never figure out if I was supposed to be cumming or screaming at any given second. It’s been a while since they’ve done that to me…”
“We still have the feathers. Got a pair in me desk,” Lena chimed in. Isabella’s eyes lit up with excitement. Mary was given a brief reprieve to wheeze for breath. Isabella had stopped tickling in favor of rummaging around in her captain’s desk. It took less than a minute to find the drawer containing an unordained wooden box nearly as long as her forearm. The masochistic first mate brought it back to open it in front of her victim.
“Pick your poison. Which would you like me to try out first?” Isabella asked. Undoing the latch on the box and opening the lid revealed a variety of feathers nestled in felt. Mary’s eyes went wide with fear in spite of her best efforts to not betray any reaction. She couldn’t stop herself from skimming over the array of long, stiff turkey feathers, fluffy plumes, and tail feathers that ranged every size in between.
“D-dealer’s choice,” she tried to say glibly, but the quaver in her voice betrayed how frightened she was at even the thought of one of those touching her.
“Top to bottom it is!” Isabella grabbed a long, stiff looking brown pheasant feather off the top row before hopping back on the rack to straddle Mary again. Grabbing one of the bound woman’s breasts to hold it still, she began dragging the length of the feather across her rock hard nipple.
Mary’s eyes bugged out the moment the implement made contact with her bare skin. She let out an ear piercing shriek and bucked hard enough to almost unseat her tormentor off of her. The room was soon filled with screams and cackles loud enough to drown out Theresa’s own tormented laughter. Mary bucked and spasmed, shook and twisted as hard as she could in a desperate attempt to escape, all while letting out laughter louder than she had ever known her body was capable of producing. Nothing she did got her more than a second of reprieve from the skilled tickler and her tormenting feather.
“Looks like we have a winner! Capn’, you gotta give this a try. I can’t remember the last time we had a girl this tickly!”
“Oh, I gotta try this.” Lena reached over to grab a nearby piece of cloth. Efficiently tying it in a knot, she forced it into her rival captain’s mouth before securing it behind her head to serve as a cleave gag. More so than being glad for a break from her own torment, Theresa could do nothing but watch with horror as her tormentor went to help make her first mate’s suffering all the worse.
Lena’s hand reached towards the box containing the feathers before seemingly hesitating for a moment. Walking over to her desk, she rummaged around it briefly. A length of cloth similar to the one she’d used to gag Theresa was pulled out of one of its drawers. Repeating her process of tying a knot in the middle and forcing it into the cackling Mary’s wide open mouth left the curvaceous pirate gagged just like her captain.
“Don’t want her breaking on us too quickly, now would we?”
“Teehee! You always did enjoy taking your time gettin’ to know the girls, Cap’n.”
Only then did Lena’s hand return to the box to pull out a long black quail feather. Taking up position at Mary’s side, her free hand seized the busty blonde’s free breast to allow her feather to come into play.
A scream resounded through the cabin. Mary had been convinced she’d already reached the furthest depths of ticklish suffering. Those few minutes of nipple feathering had tickled so badly she was certain it was impossible for the torture to get any worse. Feeling the bristles of the second feather make contact with her achingly erect nipple blew those preconceptions away in an instant. She wasn’t even laughing anymore. Screams that would do a banshee proud ripped through her lungs one after another. Her body wildly thrashed in its bondage, putting everything she had in a last ditch effort to get away.
Theresa watched in despair as the two cruel pirates reacted to the display with pure, unbridled glee. Over the next several minutes they continued to dance the feathers against Mary’s nipples. They would lightly dust the tips of the feathers back and forth, slowly drag the lengths across the sides of her nipples, and swirl them around in circles all over her areola. Once or twice they would try to flip their implements around to attack Mary’s sensitive breasts with the quills, but quickly gave up after finding that it didn’t have as devastating an effect as the plumes did. Mary babbled garbled pleas for them to stop and Theresa begged into her gag for them to tickle her instead, but nothing could get the two sadists to let up for even a second.
Relief in the form of a short break didn’t come until after an entire hour of having her titties mercilessly toyed with. The sound of screams of laughter was replaced by hiccups and sobs of misery. Tears of agony had left tracks down her cheeks and she was so physically exhausted from her thrashing that she’d been reduced to feebly twitching in response to the torturous stimulus for at least the last 15 minutes. Lena reached behind Mary’s head to undo her gag.
“Are ye ready to talk, or do ye need a little more persuadin’?” She waved her feather within an inch of Mary’s nipples again for emphasis.
“Please! PLEASE! I’ll tell you everything. Anything if it means you won’t tickle me anymore!” Mary sobbed.
“Good. And once you’re done, I’ll show you how much more tickly a girl gets after you make her cum. We’ll see how much fun it is to play with your luscious melons after making you orgasm so hard you won’t be able to think!” Isabella sadistically taunted. She mimicked her captain’s threat by lazily wafting her feather in Mary’s direction, only to be caught by surprise from Lena holding up a hand to stop her. The glimmer in her captain’s eye was all she needed to know that a particularly evil idea had struck her.
“Would this ‘anything’ of yers happen to include helpin’ tickle yer cap’n?” Both Theresa and Mary’s blood ran cold. They shared a glance of fear. “Oy! Oy. No lookin’. Wouldn’t want ye sharin’ signals now. Yes? Or no?”
“I… I…”
“Looks like there’s still some fight in her, Cap’n. How ‘bout we gag her again and ask in the morning? I’m certain she’ll be more agreeable then.”
“Hrm… Sounds like we gotta. Don’t want a half-hearted helper, after all.” Both women let out a giggle at the stark look of terror that came over Mary’s face. They slowly began to lower their feathers back towards Mary’s melons, savoring the way the beautiful blonde shook her head in a panic.
“I’ll do it!” Mary screamed right before the torturous tools could touch her again.
“Do what now? We need you to say nice and loud for the lady in the back to hear,” Lena sadistically commanded. The two of them undid Mary’s bondage before manhandling her into a standing position. Mary was forcibly marched over to stand in front of Theresa.
“I’ll… I’ll tell you where we hid the treasure. And I”ll help you tickle the captain as much as you want. Anything… anything you want. Just… just please don’t tickle me anymore…” Tears of misery streamed down her cheeks. The threat of further torture had broken the last of her will to resist and being forced to announce her betrayal out loud like this shattered her remaining spirit.
“Good to have you on board, ‘swabbie’.” Mary winced at the friendly way Lena clasped her hand on her shoulder. “Now, since this is yer first day helpin’ out on the Golden Grin, you should dress more appropriately. Nothin’ says ‘First Day’ like yer birthday suit, don’t ye think?”
Mary hesitated, but a single glance at her two tormentors standing by her side cowed her into submission. Shaking hands reached up to finish pulling off her lace-up before reaching down to undo the button keeping her skirt around her waist. Her underwear hit the ground soon after to leave her standing in the buff right in front of her bound captain. She kept her eyes averted off to the side in embarrassment and her hands reached to cover her privates in an attempt at modesty, only for Isabella’s hand to gently tug them away.
“You’re too beautiful to hide yourself like this,” Isabella crooned in her ear.
“Now for ye. I told ye there would be punishment if ye didn’t talk. Bella, go get some girls to help keep her under control.” Lena turned to Mary once she was done. Theresa glared back with as much hatred as she could muster. Having been forced to watch the woman closest to her be tortured for over an hour then forced to humiliate herself like this had left her angrier than she’d ever been before in her life.
Unfortunately, that rage wasn’t enough to allow her to fight back when Isabella returned with half a dozen members of the Golden Grin in tow. Theresa found herself unceremoniously stripped naked no matter how much she kicked or bit at the people around her. Once she was completely disrobed, Lena directed the crowd to frog-march their captive out onto the deck.
A terrified inkling of what Lena had in mind occurred to Theresa as she was half-dragged half-pushed out of the cabin. The remaining members of her crew had all been left bound to whatever was available out on the deck. They formed a rough circle around the bondage devices she’d first noticed when they’d first been brought on board, which were conspicuously the only things nobody had been restrained to at the moment.
Her fears were proven correct when Lena pointed to one of the bondage devices. She was forced to kneel on a well-padded stool near the center of the deck. A pair of stocks were locked around her ankles to hold her feet in place while a rope was looped around the back of her knees to secure her to her perch. A pair of manacles hanging above the stool shackled her wrists where a full cranks on the pulley they were attached to ratcheted her up until she was left kneeling up straight with barely any slack to pull her arms down. Theresa didn’t know where to look. Everywhere around her were the despair-filled faces of her crew members. The humiliation of being forced into such a compromising position in front of the people who relied on her burned her cheeks.
“Don’t they have just the loveliest looks on their faces right now?” Lena leaned in close to whisper so only Theresa could hear. “How do you think they’ll all be after they watch their precious cap’n beg like a dog right in front of them?”
“I-... You-...” Theresa spluttered. Her anger was petering out to be replaced with horror. It was impossible for her to think of a decent response to the taunt with how hopeless the situation was.
Not that her captors were interested in hearing any rejoinder to begin with. Theresa nearly lept out of her skin with surprise feeling a pair of slim fingers poke her sides from behind. “Now, now. That won’t do,” Isabella’s sultry voice purred in her ear. “It wouldn’t do for one of our guests to look so upset. Let’s put a smile on that face…”
Theresa flinched and squirmed away from the fingers. The stool she was kneeling on proved to be bolted to the deck, reducing her to only being able to lean her upper body a little in any given direction and twisting around. None of it was anywhere near what was needed to escape Isabella’s probing fingers. The sadistic Puerto Rican was taking advantage of her position behind her victim by giving quick tickles interspersed at unpredictable intervals. She would goose Theresa’s sides, ribs, and hips just enough to make the bound captain shy away, then pull away her hands to wait before striking again.
Theresa’s face flushed with embarrassment from her own squirming. With all the eyes boring into her from every direction, she was keenly aware of how flinching away too hard would cause her chest to bounce a little. Never before would she have given it a second thought, but her current predicament was making her far more self-conscious than normal. It led to this paradoxical feeling that she needed to hold still for the tickling to avoid humiliating herself even further.
“Come on! Ye ain’t gonna entertain our guests with dancin’ like that!” Not helping matters was Lena stepping forward to join in. After roughly a minute of watching the teasing with amusement, the infamous Black-Eye could no longer hold herself back. Her fingers reached forward to skitter the tips of her nails all over Theresa’s olive globes.
A strangled gasp almost escaped from between Theresa’s lips before she managed to bite it off by gritting her teeth. The teasing was unbearable. She hated how clear it was that Lena and Isabella were used to ganging up on a girl like this. Lena kept up a steady attack of light tickles with her nails all over her breasts to contrast Isabella’s fingers coming in suddenly at random locations. At first she thought that the Dutch pirate captain was ramping up her tickles to coincide with when her first mate came in for another pass, but the pair proved her wrong the moment she started bracing herself for it.
“Eehehehe!” The dam finally broke after nearly a minute of getting double teamed. Theresa had let her guard down for a second, having convinced herself that because Lena was going light again meant that Isabella wasn’t about to strike. She was proven wrong when the slim, tanned fingers not only stroked her bare buttocks, but stayed to scrabble around. Theresa let out a squeal that was equal parts ticklish surprise and indignation at having her bottom handled like this before breaking down tittering.
A blush spread across her face. This was easily the most humiliating treatment she’d ever had to suffer in her life. Not only was she forced to endure a pair of women she hated running their fingers over her bare breasts and butt in front of a crowd, she was reduced to giggling like an empty-headed village lass from it.
“Oy, swabbie. Are you just gonna stand there or are you gonna join in the fun?” Isabella called out. Mary had spent the entire time standing with her arms folded behind her back off to the side. Her eyes had been averted from the display in front of her in shame, though she hadn’t been able to keep herself from flinching with guilt after hearing Theresa break down giggling. She jumped with surprise when a calloused hand suddenly clasped her shoulder. Isabella had stopped tickling Theresa’s butt just long enough to walk over to her. Her voice was positively dripping with gleeful malice. “You said you’d help, didn’t you? Or would you rather join in the show? We have plenty of spots left, if that’s what you want.”
One glance at her captain twisting this way and that in a fruitless attempt to shake Lena’s fingers off her melons was all it took to cow Mary into submission. Lena scooched over a little to make room in front of Theresa while Isabella guided her to kneel. “Now that we’re workin’ over her chest and booty, there’s only one place where it makes sense for ye to help out. How about ye get started on her womanhood to complete the set?”
“I… I…” Mary gulped. Being pressured into saying she would help torture her captain was one thing. Having do it, in front of her crew members no less, was something else entirely. She subconsciously looked up at Theresa’s face for guidance, but all that got her was a close up view of the woman’s distressed expression past a pair of hands going to town on her jiggling melons.
That was the final push Mary needed. Anything was better than having to suffer that for herself again. Her hands raised up towards Theresa’s naked groin, but hesitated before she could make contact. Instead, she reached down to stroke her captain’s thighs as a more “safe” target. Her nails gently scratched up and down the fronts of Theresa’s thighs in an effort to look like she was tickling without contributing much to the Spanish pirate’s suffering and was unpleasantly surprised to hear the giggling ratchet up a notch in intensity.
“Nice find! Try working over her inner thighs next. It isn’t uncommon for girls to get tickly there.” Hearing Isabella’s words of encouragement only made Mary feel worse. Nevertheless, she attempted to worm her fingers in between Theresa’s legs, only to find that her captain was squeezing her legs together as tightly as she could to keep her out. No amount of pushing, poking, and prodding could get the Spaniard to part her legs enough to allow her hands inside.
Panicking that she was about to be punished for failing to follow orders, Mary’s fingers returned to scrabbling all over what sections of Theresa’s thighs she could reach. Theresa’s heavy giggling graduated to peals of unrestrainable laughter under the assault. Mary wasn’t paying much attention to where she was tickling. Her fingers were moving everywhere on Theresa’s legs she could reach, tickling without much thought or intent behind it past trying to look busy.
A loud shriek sounded across the Golden Grin’s deck a few seconds later. Mary’s fingers had been moving up Theresa’s thighs and, without thinking about it much, traveled up to the bound buccaneer’s exposed groin. Theresa’s entire body spasmed as she let out a scream of laughter loud enough to make the onlooking crowds’ ears ring. Mary’s long nails gently scratching all over her groin and pussy was sending jolts of ticklish agony ripping up through her body to squeeze every last particle of air out of her lungs in the form of wild peals of laughter.
The reaction was strong enough to cause all three surprised ticklers to pause briefly. Mary pulled her hands back out of a mixture of shock and guilt, but Lena and Isabella shared an evil smile. Lena reached down to snag both of Mary’s wrists and pull them up over her head before the busty blonde knew what was happening.
“When ye find a spot that sensitive on a girl, yer supposed to tickle it for all it’s worth.”
“You need to really work it over. Make her regret she was born with a ticklish body. You know, like this!”
“HEheheHAHAHAH! STOOOHOP! STOP! I’ll tickle herHEHEHAHAHAHAHA!” Mary screamed. Isabella was illustrating her captain’s point by stroking her nails all over Mary’s hyper sensitive breasts. The naked blonde was left screaming in a mixture of ticklish agony and terror from how the sultry Puerto Rican would teasingly dance her nails down towards her nipples only to teasingly draw them away centimeters before making contact. Mary managed to get her legs out in front of her in an attempt to kick Isabella away, but all that resulted in was her tormentor sitting on her legs to render her completely helpless. No amount of begging or promises of compliance could get the evil pair to let her go for the next several minutes.
“Ye want yer playthings to feel nice and helpless just like this, like the tickles will never end no matter how much they beg. If yer havin’ trouble rememberin’ what yer supposed to do, just recall how this felt and ye’ll be fine.” By the time Lena released Mary’s hands several minutes of agonizing torture later, the busty blonde didn’t have a single doubt left in her head what fate was in store for her if her hands stopped again. With Lena’s barely concealed threat ringing in her ears, she shakily got back on her knees. Theresa’s panicked expression seeing her hands reach towards the helpless Spaniard’s groin again didn’t even register at this point. All that mattered to Mary at that point was doing whatever she could to keep from getting tickled again.
“How do ye think yer crew think of Mary now? Bet it makes ‘em feel all good inside to watch their first mate torture her cap’n just ‘cause another girl played with her breasts a little,” Lena whispered in Theresa’s ear. Theresa shuddered. That was horribly twisting the situation and they both knew it, but any response she could muster was cut short. Her entire body convulsed feeling the tips of Mary’s long nails stroke up the length of her womanhood. She didn’t have the strength in her anymore to prevent herself from breaking out in peals of laughter again.
To make matters worse, Lena and Isabella had kicked things up in intensity themselves. Lena had retaken her position behind Theresa’s back. Her nails were dancing unpredictably all over Theresa’s round butt and the back of her legs. Occasionally, she would reach around to squeeze the broad hips in front of her, causing them to adorably wiggle, or all the way to scrabble her nails across the olive skin of her tummy in a ticklish bear hug.
Lena’s assault was even worse. The sadistic black-eyed woman was taking advantage of having her victim’s upper body more-or-less all to herself. She would tap her nails all over Theresa’s jiggling breasts, randomly jumping between poking at the tops, flicking nails against the painfully stiffened nipples, and gently stroking the undersides. Nails were raked down the lengths of her armpits from her biceps all the way down before squeezing in between her ribs at random intervals. When Lena noticed Isabella working over Theresa’s stomach, she joined in to double down on extracting deep belly laughs out of their victim.
Theresa was completely beside herself. She’d woken up from nightmares about being tortured by other pirates before. None of them could hold a candle to the sheer ticklish agony she was in now. Compounding that was an overwhelming feeling of humiliation. She’d harbored a complex over the past couple years over how ticklish her erogenous zones were. What few efforts at physical intimacy she’d made with both men and women alike had all ended in her would-be lovers walking away hurt when she’d burst out laughing the moment they’d touched her, misinterpreting her ticklish laughter for mockery. Having those specific places targeted to force her to laugh herself silly was akin to having an old wound kicked.
The only thing keeping the suffering Spaniard from cracking was feeling the eyes of her crew boring into her. She knew that Lena’s goal was to break the spirits of every member of the God’s Fortune by forcing them to watch their captain break in front of them. Her refusal to let the rest of the girls down was what kept her desperately holding on no matter how badly she was tortured.
Unfortunately for Theresa, she failed to realize that that was the real purpose behind Lena’s cruel game. Rumors all over the Caribbean were that Theresa cared about her crew above all else. Breaking her in front of them wasn’t just for the fun of humiliating the woman in front of the people she cared about, the insatiable sadist had the inkling that her fellow captain would dig down into the deepest parts of herself to resist the torture for as long as possible if that’s what it took to give her girls hope. Just the thought of how broken the woman would be when the endless tickling took even that away from her was enough to get evil Dutch wet between the legs.
Theresa’s laughter filled the air around the ship for the next hour. At some point Mary had been handed a set of feathers to use. Feeling the soft plumes and stiff bristles stroking all over her sopping wet folds had proven more ticklish than when her first mate brought her nails into play. The assault on the rest of her body was so random and varied that her head was a mess trying to predict what they would do to her next. The once-proud captain had been reduced to purely reacting with screams of laughter as the women sadistically toyed with her body.
“PLEAHASEHEHEHEAHAHAHA! PLEASEHEHEHE STOHOP!” No matter how much the captain tried to hold on, it eventually became too much for her to bear any longer. Lena and Isabella had settled on tag teaming Theresa’s stomach for the past couple minutes. Theresa wasn’t even laughing by the time they decided to move onto something else. One scream ripped out of her throat after another. The last of her willpower crumbled away when Lena leaned in to pop one of the Spaniard’s erect nipples into her mouth, nibbling and licking at the sensitive nub at the same time her free hand tickled around the rest of the breast, while Isabella’s nails danced all over her jiggling rump. It didn’t matter that her crew was watching anymore. The only thing left in her mind was doing whatever it took to get it to stop.
“If all it took for us to stop tickling was a simple ‘please’, then we would never have any fun!”
“And we wouldn’t want to stop havin’ fun, would we? If we stop ticklin’ ye, then who are we supposed to play with?”
“MAHARY! Ticklehehe MaRYHEHEHAHAHAHA!” Thersea screamed at the top of her lungs. “MY CREHEHEW! TIHICKLE ONE of thehem. Pleahase! PleAHASEHEHEHA! TAKE ANYHEONE you waNTHEHE! JUST PLEASEHE STOHOHOPHOHOHOHAHAHAHAHA!”
Her words were music to Lena’s ears. A wide smile spread across her lips seeing the faces of the women tied up around them fall into the furthest pits of despair. “Ye lot heard her! Take anyone ye want. Ye all know how to treat a girl right!” she crowed loudly enough to be heard over Theresa’s screams of laughter.
A cheer rose like a swell from one end of the ship to the other. The rest of the Golden Grin’s crew had been watching the entire affair with amusement. Watching their leaders so thoroughly destroy a woman was getting them all wound up tight as a spring with the need to get a girl under their fingers for themselves. There was a general commotion as the pirates untied the captured members of the God’s Fortune from the spots on the deck in favor of dragging them over to the various bondage devices strewn throughout the ship. Some were rebound out on deck while others were dragged into private rooms or the ship’s hold. Regardless of where they were taken, laughter could be heard emerging from all corners of the ship minutes later.
Mary wasn’t exempt from the fun. Her single-minded focus on tickling Theresa’s pussy was interrupted feeling a multitude of hands grab her limbs. The naked blonde was dragged kicking and screaming over to a horizontal X-frame right next to Theresa. Soon the curvaceous blonde was left gibbering with fear up at the quartet of women leering down at her.
“We told you, didn’t we? We’d be right back to playing with you the moment we were done with your Cap’n,” Isabella taunted. She gently dragged a single nail down Mary’s taut stomach. “Now, the cap’n was doin’ something real naughty with her titties at the end there. It looked like a world of fun with me, so how about we start with that? After that, we can find how much you like havin’ your titties feathered after I give you the biggest orgasm of your life!”
Mary’s scream of terror instantly transformed into howls of laughter. Isabella and one of the other pirates had leaned in to wrap their lips around her rock hard nipples. At the same time, the other pair of pirates had lathered up her soles with oil before laying into them with hairbrushes. Mary was in hysterics within an instant. Her strict bondage denied her the relief of struggling away from the tickles being inflicted on her. Straps just below her breasts, around her hips, and above both knees prevented her from struggling any part of her body more than a centimeter or two. Lengths of twine served as toe ties that kept her from wiggling her feet under the harsh scrubbing. The only part of her body she could move freely was her head, which she whipped back and forth in a frenzy wildly enough to make her hair fly around her.
“Please… Please, I gave you my crew. Please don’t tickle me anymore…” Theresa sobbed. Just like Mary before her, being forced to betray those dear to her to save herself had shattered what was left of her spirit. The once proud captain had been reduced to pathetically bawling her eyes out in her bondage. The crowd of pirates standing around watched the display with every hint of enjoyment.
“Oh, don’t worry. The Cap’n and Bella are done with you for now.” One of them jeered.
“We just thought ye’d be lonely. What with bein’ the only one not bein’ tickled now ‘n’ all.”
“We’z got a policy here on the Golden Grin. Every guest o’ ours needs a smile on ‘er face. We’re just here to uphold that.”
Theresa screamed. Hands were converging on her from every direction at once, scraping, scrabbling, and stroking every bit of exposed flesh they could get their hands on. Within moments, the sound of Theresa’s screams of laughter joined in with her crews’.
—--
Weeks had passed since the crew of the God’s Fortune had been brought aboard the Golden Grin. Theresa would’ve described the experience as nothing short of a living tickle hell. Every last woman in the crew had proven to be just as cruel as their leaders. The members of the God’s Fortune had been reduced to little more than their playthings to tease and toy with as a way of passing the time, and there was plenty of free time to be had while sailing across the open seas. Not a single woman had the good fortune to not be ticklish enough to amuse their captors. Those who’d had the misfortune to catch one of the pirate’s fancy were kept bound in their cabin to serve as personal tickle toys while the rest were rotated throughout the ship to serve as free objects of entertainment.
Theresa and Mary had spent the majority of their time serving as centerpieces out on the deck. Multiple scalliwags were working them over at any given time to prevent them from having a single moment’s rest from dawn till dusk. Isabella had backed down on her promise of making them cum their brains out in favor of a cruel game of seeing how long they could be kept on the edge of an orgasm. Both would be rubbed and licked to the verge of cumming in the morning and again periodically throughout the day. Neither had been allowed to orgasm a single time for the last several weeks. Their constant state of arousal had trapped them in a heightened state of sensitivity, pushing the already unbearable gang tickling into new heights of ticklish agony neither of them had known possible.
Twice a day, at breakfast and dinner, they would be brought into the mess hall for a “tickling feast”. Their naked bodies would be stretched out across the long tables inside so the entire crew could take turns eating food off of them in the most ticklish ways they could manage. They had to hold still as best they could under the threat of having their soles scrubbed with hairbrushes while their breasts and pussies were teased with feathers if even a single food item fell off of either of them. The single time they had both managed to go a round without being punished had incensed their tormentors into spending the rest of the evening hammering their entire bodies with feathers, fingers, and brushes as punishment for denying the girls a reason to tickle them.
By this point, every last member of the God’s Fortune had given up on begging for mercy. There was nothing anybody could say or do that would keep their naked bodies from being tickled all day long. This was torture for the fun of it, pure and simple. The only thing the sadistic pirates wanted out of the women in their captivity was to make them suffer as long and deeply as possible, and their fingers dug in at every given opportunity to drive that home.
Mercy didn’t come until the Golden Grin reached its destination: a small, unnamed cay situated in the Cayman Islands. Lena had taken Theresa and Mary aside to make them point out the location of the hidden Tesoro de Suave Oscuridad on a map, making certain to remind them that every extra day the ship spent searching for it was another day spent as toys for the crew. The ship was now anchored a short distance away.
Theresa gazed out at the isle. It was just as unimpressive as the day they’d found it. The landmass was small enough that you could stroll around the outer edge within half a day. There wasn’t much to explore past that. What could generously be called a small mountain jutted out of the middle surrounded by a smattering of palm trees.
“That should be the last ‘o it,” one of the pirates called out. Rowboats had been sent out to scout the location and come back loaded down by chests filled with treasure. The crew members had reported following Mary’s directions to a small cave entrance that led down into a room filled from floor to ceiling with treasure. It’d taken the better part of the day to make enough trips to transfer the piles of gold coins, gems sparkling in every color of the rainbow, jewel encrusted goblets, and every other knickknack from the cave back to the ship. The end result couldn’t be contained in the Golden Grin’s hold. Chests bursting the seams with treasure were left lashed to the deck with rope for lack of a better place to put them.
“There. It’s yers. I hope ye choke on it,” Theresa spat. She along with the rest of the crew were standing naked out on the deck in a row.
“Aw, I thought ye’d be happier. Trip’s over! Or did ye decide ye liked bein’ our tickle toy after all?” Lena grinned at her. The crew of the Golden Grin were standing lined up opposite their God’s Fortune counterpoints. Each was holding a long pole ending with a multitude of feathers. Lena waited for a bit to see if Thersea had any last parting shots to take. She shrugged after several seconds of silence before continuing. “Guess it’s time we did the good ol’ piratical tradition then: Walkin’ the plank!”
That was the signal for the rest of the crew to jab their poles forwards. Squeals of laughter echoed across the deck from the feathers at the end brushing up against the bare flesh of the women across from them. The girls of the God’s Fortune had all been so broken by the tickling that they didn’t try to put up a fight anymore.
“Come on! Come on! Get walkin’ unless you wanna spend the entire trip back being tickled too!”
There was a point behind the tickling and threats. Theresa and her crew were corralled towards a plank extending off the edge of the ship to avoid the feathers. Theresa looked out across the expanse of water. Lena’s one small bit of mercy was that she’d made certain the ship was anchored close enough to swim to shore.
Feeling a multitude of feathers brush up against her sides made Theresa squeal. She stumbled away from the ticklish implements and found that she’d been driven to the edge of the plank faster than expected. Suddenly, there was nothing under her feet followed soon after by the impact of hitting the water below.
Rushing water swept all around her. Theresa flailed her limbs frantically in an effort to get herself under control. The pirate captain was an experienced enough swimmer to right herself despite the disorientation. Her head broke the waterline gasping for air. She could hear her crewmates hitting the water behind her, but there was nothing she could do to help them in this situation. Taking a moment to orient herself towards land, Theresa struck out towards the safety of the shoreline.
It was by no means an easy swim, but she managed to make it. The Spanish scalliwag walked up enough of the beach to put a buffer between herself and the waves lapping at her heels before collapsing to rest. The woman barely had time to close her eyes before she heard footsteps approaching. Cracking an eye open, she saw Mary walking hesitantly towards her.
“Captain… I…” Mary stuttered before falling silent.
“Apology accepted.”
“Wha-!? I haven’t said anything though!”
“Ye feel bad about backstabbin’ me back on the ship, but ye feel too guilty about it to think I should forgive ye.” A grin spread across Theresa’s lips over the look of bafflement on Mary’s face. “Come on, how long have we been together now? Ye’ve always had a bad habit of clammin’ up when ye feel bad about somethin’ ye did.”
“You can’t forgive me just like that. Thanks to me, they spent the last couple weeks tickling all of you! I should’ve just kept my trap shut…”
“No. No ye didn’t. If ye hadn’t cracked then, Lena and her bitches would’ve just kept ticklin’ until ye did. And even if ye hadn’t, there was nothin’ stoppin’ ‘em from ticklin’ the rest of us anyways. They just made us sell each other out for the fun o’ bein’ assholes about it.”
Mary didn’t have a response for that one. Silence stretched out between the two of them. Eventually, Theresa stretched out her hand towards her companion. Mary took it, thinking she was about to help her captain stand up, and was caught off guard when Theresa pulled her off her feet with a sharp yank. The first mate fell onto the sand to sprawl out on her back. A weight settled on her thighs from Theresa settling down to straddle her waist.
“Now, I don’t know about ye, but I’ve spent the last couple weeks needing to cum so bad I thought I was gonna go crazy. If ye ain’t willin’ to accept me forgivin’ ye with words, would ye listen if I said it with me body instead?”
Mary’s face flushed, but she wasn’t about to say ‘No’. The need had been burning away inside her too. Her hands reached up to interlace fingers with Theresa’s. It took a couple seconds of awkward fumbling from both of them, but they managed to get into position with their legs interlocked to allow their groins to come into contact.
Theresa began to move her hips, savoring the wonderful sensation of Mary’s pussy rubbing against her own, when she heard several footsteps behind her. She ignored them. The only people it could be would be their crewmates and they’d all taken advantage of her ship’s “Free Love” policy that they didn’t have room to complain. It wasn’t until she felt a hand grasp her shoulder that she bothered turning around to look.
The sight that greeted her made Theresa’s mind go blank. The face of the woman who’d grabbed her shoulder wasn’t a familiar one. Fish scales dotted her immaculate skin, which was a light shade of blue, from her face all the way down to feet. Both the woman and her companions were all just as naked as the two pirates. Every single one of them was so otherworldly beautiful that the pair stopped in their act of lovemaking to stare.
Their wonder didn’t last long. The scaled woman roughly pulled Theresa off of Mary. Another came forward to help hold her arms. Mary was similarly manhandled into a standing position by the other mermaids.
“Hey! What’s that for!?” Theresa cried.
“The curse of the Tesoro de Suave Oscuridad demands eternal suffering to thieves until it’s returned,” the scaled woman stated harshly.
“Hold on. We didn’t take it. The women on the ship did, we were just stranded here.”
“You were on the ship when it was stolen. You are as guilty of the curse as the rest,” chimed in another.
All further protests were summarily ignored. Theresa and Mary were pushed and shoved further inland towards cay’s mountain. Theresa glanced back towards the beach meaning to catch a glance of the Golden Grin. What she saw made her jaw drop. Scaled women were swarming everywhere. What members of the God’s Fortune crew had successfully made it onto land were being rounded up. More still were emerging out of the sea carrying the women who hadn’t yet made it to shore. Their legs appeared to merge together to form a large fin while they were swimming before splitting in two back to human legs for walking on land.
“Mermaids…” Mary gasped. Evidently she’d been watching too. The mermaids manhandled the both of them into the cave entrance that led down to where the Tesoro de Suave Oscuridad was originally held. They were led past through the treasure room to an unassuming wall where the leader of the group placed her hand against the bare rock face. A portion of the wall swung inward like it was on hinges revealing a staircase spiraling downward.
Theresa didn’t know how long they were led downward. The staircase constantly spiraled in on itself until she’d lost all sense of direction. What was most unsettling of all was that the path wasn’t lit by anything, but for some reason both pirates could still see without issue. This place was clearly supernatural in nature to the point even someone as unlearned as Theresa could tell at a glance. The room they were led to at the bottom was even worse. Everything about it was pure black. The walls, ceiling, and floor was the pitch blackness of nothingness stretching on forever.
A shove from behind sent the pirate sprawling forward. She screamed, fully expecting to fall into the void stretching out in front of her. Instead, she was overcome with a feeling of weightlessness. The pirate attempted to turn around only to find that she couldn’t move in the slightest. It was the most paradoxical of feelings, like she was simultaneously being pressed down on by a force too great for her to resist while feeling absolutely nothing at all. Her limbs slowly drifted apart until she was floating in the darkness in an X position.
The darkness slowly rotated Theresa around to face the group of mermaids. She watched as Mary was similarly shoved into the room, but she couldn’t turn her head to see if her first mate ended up in a similar position.
“W-what are you plannin’?” she asked the mermaids worriedly. The only portions of her body she had any control over were her eyes and mouth. A slight grin graced her captor’s beautiful features.
“As we said, eternal suffering awaits you until every last coin of the Tesoro de Suave Oscuridad returns.” The mermaid stepped forward into the room. Unlike the pirates, she was able to move freely, gracefully gliding around like she was swimming. “You will be kept in agony beyond mortal ken to endure. You will suffer in a way that pleases our master, never aging, never hungering. Never shall you find the escape of insanity from your torment or relief from sensation. You will be kept in full memory of the crime you have committed, so that you will be forced to endure the weight of your sins until another fixes your folly for you.” The mermaid swam up to Theresa to languidly place her fingers on the pirate’s biceps just above her armpits. Theresa’s eyes nearly bugged out of her head. She wanted to cry. This couldn’t be real. “But take heart, mortal. For our master enjoys the laughter of women above all else. Your torment shall be a merry one.”
Theresa squealed with laughter. The mermaid hadn’t moved her fingers in the slightest, but she’d felt something brush inside of them all the same. It was like the soft bristles of one of the fancy make up brushes the rich used perfectly fitted for the curvature of her armpits. The mermaid watched with a smile on her face as peals of laughter poured from between Theresa’s lips. The sensation was unbearable. The invisible brushes stroked up and down the length of her pits at the perfect intensity and pace to extract the maximum ticklish sensations.
The tickling stopped as soon as it’d started. The pirate captain found her head being guided down to look between her breasts towards her feet. Something down there was calling for her attention. She squinted into the unnatural gloom. If she focused hard enough, she could almost make out the form of a woman wearing a simple party dress seated at her feet.
The outline of a woman reached forward one of her hands to gently stroke Theresa’s foot. The pirate captain threw her head back to let out the loudest scream her lungs were capable of producing. Lena and Isabella combined had never managed to make it tickle as bad as that one light touch. It wasn’t so much like the woman had tickled her as she’d commanded the nerve endings in Theresa’s first to produce the maximum ticklish sensations possible.
Peals of laughter flowed freely from Theresa’s mouth as the woman’s fingers lightly danced all over Theresa’s feet. The helpless woman was so consumed by the ticklish sensations that she lost track of everything else. She didn’t notice the mermaid swimming away nor her crew members being brought into the room to share her fate. Not even Mary laughing her head off from a shadowy woman dancing her fingers all over her jiggling melons managed to draw the captain’s attention. The only thing that mattered was how much the woman’s fingers tickled.
Knowledge flowed into Theresa’s head as the woman continued to play with her feet. The being tormenting her was an incomprehensible entity akin to the gods of old. The woman in a dress wasn’t shrouded by the darkness, she was the darkness itself. She was a goddess formed from the very concept of torture from light, teasing touches exacting her very being on Theresa’s helpless flesh. Her tormentor wasn’t doing this because she got a kick out of it. Tickling women was its very purpose for existing.
The goddess gently lifted her hands from Theresa’s feet after what felt like an eternity. The ghostly outline stood up between Theresa’s legs to hover its hands right above Theresa’s helpless pussy.
“No… No, please. Anything but that. I won’t be able to take it. I’ll go crazy. Please. Please… Tickle me anywhere but there,” Theresa begged. Tears of terror were rolling down her cheeks. The crew of the Golden Grin had spent the last several weeks thoroughly teaching her how unbearable pussy tickling was when she was kept on the verge of orgasm. She and Mary being interrupted before they could help each other finish had left her the most sexually frustrated she’d ever been in her life. At this exact moment, there was nothing that terrified her more than the idea of experiencing that inhuman ticklish technique on her worst spot in her current state.
The shadowy outline of a woman didn’t have an expression normally. Hearing Theresa’s fearful begging, a thin line formed where her mouth would be to resemble a wide smile. Theresa was forced to watch as the woman’s fingers lowered down to scratch its nails against her wet, unwilling pussy.
A scream ripped its way through her throat. The mermaid hadn’t been kidding when she’d said it would be agony beyond a mortal’s ability to endure. The ticklish sensations coming from her pussy were far beyond anything she had experienced before. She desperately wanted to buck her hips or kick her legs, anything to express with her body just how horribly it tickled. Her bladder was cramping in an attempt to pee from how badly it tickled, but even that was denied her. The only thing she could do was descend into shrieks of maddened laughter.
Theresa didn’t know how long the shadow continued to play with her pussy. There was no way to tell time here. The only thing she was aware of anymore was the tickling. To make matters worse, terrible knowledge was flowing into her again. She knew beyond the shadow of doubt that the goddess was just getting started with her. Soon her stomach would be coming under attack. Following that her breasts. The goddess of tickling would continue to explore every last centimeter of her sensitive skin. It would take its time getting to know every part of her and the best ways to make her suffer in intimate detail.
As the pirate captain howled and screamed with laughter, she silently prayed for it all to end. She prayed with all her might that someone would return the Tesoro de Suave Oscuridad to its resting place and save her from this eternity of torment.
—--
“And to women well tickled, a cheer!”
“Hoorah!”
Lena shouted along with the crowd. Tipping her flagon back, she downed her ale in a single go.
“Everybody’s really cutting loose, Cap’n,” commented Isabella.
“Of course they are. We got us the haul of a lifetime by ticklin’ a bunch of girls out of their minds. Things couldn’ta gone more perfect in me dreams!” Lena looked down at her first mate. They were currently sitting in the mess hall together. Or to be more specific, Lena was sitting at the long table while Isabella was bound stretched out across it in the nude. “How’re ye fairin’, Bella? Did I tie the ropes right?”
Isabella tugged at the ropes keeping her hands overhead. They held firm. She gave an encouraging nod to her captain. “I’m feelin’ a little pent up. I love givin’ another girl a good tickle, but nothin’ beats feelin’ the feathers on my own skin.”
“That’s the Bella I know and love.” Lena leaned forward to give Isabella a quick peck on the lips. “So what’re ye feelin’ up for? I imagine yer in the mood for us to play a little rough with ye.”
“I think I’ve been due for some extra punishment. Remember when I made fun of you in front of Stormrider and her first mate for getting flustered? I think you owe me back for that with several weeks of interest.”
“Thanks for remindin’ me. Several weeks of debt, eh? It’s gonna take a couple days for ye to work that one off, plus ye’ll be accruing interest as we go.” Lena grinned wickedly. The sadistic captain snatched up one of the bottles of oil lying next to Isabella and began slathering a hefty amount on the Puerto Rican’s helpless soles. Isabella licked her lips in anticipation. Her feet were easily her worst spot and she loved nothing more than when Lena would dive in to hammer her there first. She didn’t even try to hold back her laughter when the hairbrush came in to furiously scrub all over her oiled soles.
“HAHAHARDER! TICKLE HARDERHEHEHAHAHAHAHA! MAKE MEHE BEGHEHEHEHAHAHAHA!” she screamed in between bouts of laughter. Heads turned from her peals of laughter echoing throughout the hall. Girls were getting up out of their seats to join in. There wasn’t a self-respecting member of the Golden Grin who wouldn’t want to join in after hearing a woman’s tortured laughter.
A swell caused the Golden Grin to jump a little under their feet. The crew barely noticed. It was normal for them. With them all in the mess hall helping tickle Isabella, they especially didn’t notice the lid of one of their treasure chests jump up a little. A few of the cursed coins belonging to the Tesoro de Suave Oscuridad spilled out of the crack onto the deck. There they slid and rolled around with the rocking of the ship until they all fell off the side into the ocean.
The mermaid treading water just underneath the Golden Grin’s keel watched the coins float past her on their way down to the bottom of the ocean depths. She didn’t have enough companions to complete the assault on the ship yet, but more were arriving by the minute. In roughly an hour there would be enough of them to wash over the ship like a wave and drag the thieves back for their divine punishment.
