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Captured By Pirates

"Katie's big birthday cruise with girlfriends changes course when Pirates capture them."

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Author's Notes

"This is the longest story I've written, so I've divided it into sections for easier reading."

Heading Out

Katie was about to celebrate her fifty-fifth birthday, and she wanted help from her circle of girlfriends to make it special. She decided to rent a party boat from her friend Captain Mike, so her gals and his crew could set sail for a late afternoon and evening of fun and games at sea. She invited her similarly aged friends who knew how to have a good time, and arranged things with Mike so sex would be among those good times. Katie only invited those girlfriends who were single, divorced, or in an open marriage, so they could enjoy the sexual activities that were planned. She asked them to dress in a skirt or shorts and a blouse, nothing fancy, and to leave their cell phones on shore at Mike's office to keep them from distractions.

Leaving port at four in the afternoon on a beautiful, warm day, the party boat 'Good Times' motored out to sea with Katie and her friends, Barbara, Dianne, Helen, and Sue. The crew consisted of Captain Mike, who was a tall, often mischievous white man with a scruffy beard, and his able seamen, Jim who was a tall, thin, fun-loving black man, and Jon who was a six-foot-two white guy with a beard who exuded classy sexiness. All three men were muscular, having gotten strong from working the boats for a living, and were wearing puffy long-sleeved shirts and odd, billowy pants rather like the pantaloons the pirates used to wear, though no one ever explained why.

The crew was ready to do whatever Katie needed to be sure her friends had a good time, and the boat was stocked with happy hour snacks, a fine seafood buffet for dinner, and plenty of wines which Katie knew they'd all enjoy. She ensured that the crew would serve them and monitor their drinking so no one drank too much and missed any of the fun.

Everything started just fine, with Jim and Jon serving the ladies a glass of wine and happy-hour snacks as they headed out. The well-muscled crew members were a welcome sight for the girls, which got them a bit pre-heated for the cruise's extra-curricular activities to come. Captain Mike had plotted a course that kept them a few miles from shore so they would always be in sight of land and hoping no one would get seasick, but also carried medicine in case anyone did. Unfortunately, fate struck a blow when the boat's engine started to act up and died when they were about two hours from port. Captain Mike, unable to restart the engine, left Jim and Jon on board to keep the ladies happy while he took the dingy and started back to port to arrange for a tow.

He expected to be gone for about four hours.

Story Time

The ladies were a little concerned about the ship's engine dying, but Katie was not, urging them to continue as if nothing had happened since she was sure they would be fine. They had more snacks and another glass of wine while they played sex-talk games that Jim and Jon directed. This was meant to pass the time while they waited for help, to take their minds off the dead-in-the-water ship, and to get them in the mood for sex.

One game had them tell of the most unusual sex they'd ever had, while another was to talk of the strangest place they'd ever had sex. But the game that proved the most interesting was a truth or dare sort of game, in which each woman in turn had to tell her name and the things she liked to do and have done to her when having sex. Katie had instructed Captain Mike to have the crew listen and take notes to remember what the ladies liked so they could have their desires fulfilled later, which Jim and Jon did.

Katie went first so the other girls would know how much detail to include.

"Well, I'm Katie, and I'm a pretty free-spirited woman, open to almost anything, but what I really like is when a guy strips me before sex. He can slip my shoes off and caress my feet, then slowly unbutton my blouse and take it off, slide my bra straps off my shoulders before removing my bra and touching my breasts, unzip and ease my skirt down and off, and finally hook his thumbs into my panties' waistband and pull them off me slowly. Nothing gets me aroused so quickly. Then I love it when they restrain me with cuffs or ropes and ravish my whole body with their hands and mouth, and maybe spank or flog my ass before fucking me while I'm still restrained and helpless."

The girls all cheered Katie for her honesty and her exotic taste in sex. Then they went around their circle of chairs.

Dianne was next.

"I'm Dianne, and I'm divorced but always up for a good time. I like it when a guy looks at my body with appreciation when he first meets me, long before any fooling around. I love to see the desire in his eyes while I'm still dressed, and see his interest, and erection, grow as I tease him with glimpses of my breasts and pussy as I slowly take my clothes off. I like pretty basic sex, and nothing painful, but I do enjoy different positions that expose me with my legs spread wide. I'm open to being restrained since the idea of feeling helpless appeals to me."

Barbara went next.

"I'm Barbara, and I'm also divorced, and I'm sure I'm the oldest of us, but I've always loved sex and still do. I'm glad Katie invited me to this cruise, and I'm looking forward to a good time. Like Dianne, I also like rather ordinary sex and am not into pain, but I've always wanted to feel what it would be like to be taken over some guy's knee and spanked. I've also fantasized about being tied down and rendered helpless as the guy would have his way with my body, and I'd like to try that one day... maybe even today."

Next up was Helen.

"I'm Helen, and I'm always up for these kinds of get-togethers and new sexual experiences that might come along, so I'm very glad that Katie invited me. I enjoy sex and get especially turned on by being with an alpha male who will dominate me, make me feel submissive, and fuck me deeply, especially black men with big cocks. I like many positions as well, from missionary to doggie style."

Sue was last.

"Hi, I'm Sue, and I'd also like to thank Katie for inviting me on this cruise. I learned some years ago that I like to have some pain with my pleasure during sex, and I recommend everyone try it at least once. Things like being spanked, and having my nipples pinched and pulled when I'm about to climax, always increase the intensity of my orgasms. And being taken from behind, including anal and double penetrations, feeling a big cock or two in me, are things I like, as well as giving blow jobs and sixty-nines."

Rescued ?

When the talking game was over, Katie thanked the girls for playing along and sharing what they liked sexually, and what turned them on, while Jim and Jon prepared to serve dinner. The buffet had salads, bread, a nice variety of seafood with sides, and desserts. Their servers also poured wine for them as they sat at a table for six on the deck. Everyone enjoyed their food and good conversation, but eventually, the talk turned to Captain Mike and when he'd be back. Katie told them not to worry and that he'd be back with help soon.

As if on cue, Barbara spotted a ship in the distance, and tracking it, the ship seemed to heading their way. She told the others, who all looked, but when Jon came by and saw them staring into the distance, he pulled out his "spyglass" and looked for himself.

"That's not the ship the Captain went to get. That's a two-masted sailing ship, motoring it would appear, and it does seem to be heading our way."

"So, they'll come and rescue us, right?" Dianne asked.

"Maybe, but I doubt it. Can't see how they'd even know we had any trouble," Jon continued. Then as the other ship drew closer, he continued. "I see some sort of flag flying on its main mast, but it's nothing I've seen around here before."

It soon became obvious that it was heading straight for them, so Jon used his spyglass again and announced "The flag is a Jolly Roger, a pirate flag!"

"But there are no pirates anymore, are there?" Helen asked.

"I wouldn't think so, yet here they come," Jon answered.

Soon the pirate ship, a fine-looking two-masted brig, came alongside. A man in pirate clothing hailed the 'Good Times', calling to Jim and Jon on the party boat.

"Ahoy mateys! Captain Horny 'ere. We'll cast our mooring lines for ya to lash to yer bow bitt and aft cleat, and we'll be pullin' these ships together."

"Aye, aye, Captain!" both Jim and Jon answered, rather enthusiastically. The women wondered what was happening, and how it was that the captain of a "pirate" ship was ordering their crew to tie the ships together. It seemed that rather than being rescued, their ship was being captured, and their crew was happy to help. In no time, the two ships were roped together, and with a few steps up or down it was possible to move between them, which is exactly what Captain Horny and his two crew members did. Now there were five sailors and five women on board the party boat, as Captain Horny addressed Jim and Jon.

"I am Captain Horny, and I invite you sailors to join me and the crew of our fine ship the 'Raging Cock'. We are pirate re-enactors, and you'd be joining my crew of Peter and Eddie to roam the seas, to rescue, and maybe ravage, ladies such as these fine lasses. What say ye?"

Jim and Jon looked at each other, and in near unison, they said enthusiastically "Aye, Captain. We'll join you."

Turning to the ladies, Captain Horny said "With these fine lads, there are five of us pirates, and we've come to rescue you, but not until we indulge our pirate ways and ravish you fine ladies first. We pirates will gather to discuss how to divvy you ladies up among us. When we return, we'll be in pirate mode, and you'll be our captured women, ready to do our will... or else."

Then Jon spoke up, saying "Captain, these ladies have told us just what they like to do sexually, and we can share that with you and your crew if that will help."

"Aye, it will. Ladies, stay here. Crew of the 'Raging Cock' to the captain's quarters."

So the pirates left to hear what Jon had to say about the ladies' sexual desires and discuss how to divvy them up among the pirates.

After the "pirates" left, the women sat together, and Katie spoke.

"Well, this is an exciting change of plans, girls, but since we were always going to make sex a theme of the party, I say we should all play along with these 'pirates' and enjoy being 'ravished'. I mean, we told them what we like and that's what they're going to give us, so it should be great... wouldn't you agree?"

There was an enthusiastic "Yes" from all of the girlfriends, who, after the talk they'd been sharing and the wine they'd been drinking, were pretty much pre-heated and ready for a sex-filled evening.

Meanwhile, the 'pirates' met in the Captain's quarters. In addition to Captain Horny, there were Jim and Jon from the 'Good Times' and the two new guys from the 'Raging Cock', Peter and Eddie. Peter was an older white man, strong and sexy, and ready to do whatever the captain needed. Eddie was a lean but powerful five-foot-ten black man, athletically built and clean-shaven, with a dominant air when it came to women. They went over the notes Jim and Jon took when the ladies had described their sexual likes, and with Captain Horny's approval, they each chose one of the ladies. When he returned to the deck, the Captain spoke.

"Well, me fair ladies, we have decided which of me mates here will escort each of ya to a cabin to have his way with ya. Since Jon here knows ya by name, I'll let him announce the pairings."

Then Jon spoke. "Barbara, you'll be going with Peter. Dianne will be with Eddie. Helen will go with Jim, Sue will be with me, and Katie will join the Captain."

"Aye, and so it will be," Captain Horny continued. "And a warning to ya, me ladies: you'll be doing as yer told, or you'll taste the cat-o-nine fer sure. Now me matey's, take yer ladies to yer cabins and give 'em what they deserve! And if they give ya any trouble, you have yer Captain's permission to flog 'em.

And so the pirates took the ladies they were paired with and went to their various cabins on the two ships.

Barbara and Peter

Peter, being the oldest and paired with Barbara, the oldest of the ladies, took her to his cabin on the 'Raging Cock'. It was small but had a twin-sized bed with short corner posts on its frame, and Barbara noticed that they had padded cuffs attached to them.

"So, me lady, I'll be having ya over me knee afore we do anything else," Peter told her as he moved a chair over to an open area and sat down.

"Off with yer bottoms, me dear," he ordered.

Barbara knew a spanking was exactly what she'd said she wanted to try, so she pulled her shorts down.

"Yer panties too, me lass, and then over me knee!"

A bit reluctantly, Barbara pulled off her panties and stood beside him as he sat on the chair. He grabbed her arm and pulled her over his knee, easing her down so her rear was prominently displayed as she lay across his lap. Then he spanked her cheeks with his hand, lightly, as if he were teasing her, but soon the swats became stronger. Barbara squirmed with each swat, but then Peter stopped and ran his hands up and down her legs and over her slightly sore rear, calming and relaxing her before he put his hands between her thighs and pushed her legs apart, exposing her pussy to his intentions.

Barbara was happy with this turn of events, and Peter soon had his fingers on her snatch. He ran his fingers over her slit, gradually opening it to spend time caressing her tender folds, getting her excited and very wet. She moaned with pleasure as he traced his fingers up and down her slit until he settled on her clitoris and began to swirl her tender nub into a frenzy. Barbara was so aroused by his play at her clit that she began rocking on his lap and moaning loudly, but before she could get too close to a climax, Peter stopped.

"Up and off with the rest of yer clothes, then to the bed with ya," he commanded.

So, Barbara got up and walked toward the bed, with Peter behind, swatting her rear teasingly to keep her moving. At the bed, she removed her shoes, blouse, and bra, and he helped her lay down on her back. Then he took her arms and, one by one, moved them over her head to the corners where he cuffed them to the bedposts. He repeated that with her legs, opening them and cuffing her ankles to the bottom posts. Barbara was now naked and helpless, spread eagle on the bed.

She watched as Peter took his pirate clothes off, revealing his good-sized penis, before he moved between her legs where he knelt. He ran his hands over her body, starting with her breasts which he cupped and fondled. He played with her nipples, rolling them between his fingers until she squirmed and squealed in delight, laughing. Then he moved lower, caressing her abdomen as he headed toward her crotch. He traced his fingers over her exposed pussy, then ran them in the crevice between her labia and hips before returning to her slit. He fingered her and assailed her clit, making Barbara gasp and squirm as much as she could while restrained, as she moaned in helpless pleasure at his touch.

When he used his other hand to insert a finger into her, she sighed loudly, so he inserted a second and started to finger-fuck her as she lay helpless, moaning, wiggling her hips in time with his fingers. After a few minutes of his fingers swirling her clit and finger-fucking her, Barbara was nearing a climax, so Peter stopped.

He moved closer and slapped her pussy a few times with his erect cock, making sure it hit her clit each time and making her jerk with each slap, her clit on fire and fueling her entire body with desire. Peter pressed his penis' head to her opening and pushed in. Barbara moaned in ecstasy as he pressed into her, backed out, and then drove deeper. She bucked with his thrusts, their bodies meeting when he drove into her, his balls slapping against her ass with each push. Soon she was soaking him with her juices and they were both at the end of their control. Peter jerked hard and shot the first of his loads into her, the warmth triggering her to start spasming as her orgasm hit her with untold pleasure. He continued to fuck her, spurting his semen into her, and she continued her orgasm with spasms and squirts until they were both spent a few minutes later. Peter pulled out of her, got off the bed and stood, then undid the cuffs that held her down.

Barbara lay there, happy with the great orgasm Peter had given her while letting her have the spanking and tied-down, helpless sex she wanted to try. She loved it and knew she'd always remember the kind but controlling way this "pirate" treated her.

Helen and Jim

Jim, the black seaman from the 'Good Times' crew, was Helen's escort. Jim was a good six-foot-five tall, built like a basketball player, but with a certain "in-charge" air about him that suited Helen, and she was happy to be paired with him. He put her arm in his and walked her to his cabin on the 'Good Times'. On entering the small space, she saw a twin-bed in one corner and a desk with a chair in the other.

Jim spoke, saying "I'm so happy to have been paired with you, Helen. Your sexual preferences match mine well, you wanting a dominating alpha male, and my wanting a submissive woman. I'm always kind to my ladies, but I will expect you to do as I ask. I had to laugh at the captain saying we could give you the cat-o-nine if you were trouble... as if I'd ever do that to you. But I will take you over my knee, and that may be a good place to start."

"I'm happy you chose me, Jim, and I look forward to whatever a considerate man like you wants to do with me."

As she spoke, Jim pulled the chair from the desk to the middle of the small cabin. He sat and said, "Okay, Helen, let's be off with your clothes and over my knee."

"Aye, Aye, sir," she replied with a smile and started to undress. She kicked her shoes off, then, opening her blouse she slipped out of its arms and took it off, followed by her bra. Jim watched closely, and Helen noticed the bulge at the crotch of his pantaloons grow, encouraging her to continue. She slid her skirt down and off, and then her panties. Standing naked, Jim pulled her over to him and helped her ease onto his lap.

He swatted her cheeks rather gently at first, but increased his intensity as Helen jerked and wiggled a bit with each swat. Putting her over his knee and spanking her was his way of dominating, she figured. The spanking only lasted a couple of minutes, and then he massaged her cheeks to soothe her. She liked the feel of his big hands on her while she wondered what he would do next. Then he helped Helen get up. He stood and took her to the bed.

"Get on the bed and lay on your back, m'dear," he told her as he undressed next to the bed. She liked how he ordered her on what to do. She also couldn't help but notice his large penis. While not huge in girth, it was still a big black cock, quite large and especially long, appearing to be about eight inches. She wondered how she'd accommodate its length.

"Aye, Aye, again, sir," Helen answered and hopped on the bed.

Jim got on the bed and opened Helen's legs, then knelt between them, forcing them to stay spread. She was enjoying Jim's doing what he wanted with her, exposing her to his desires. Now that her pussy was completely open to him, he wasted no time in putting his mouth on it. He grabbed her hips to hold her as used his tongue to slide between her pussy lips and open her up, then he began to lick her tender slit. Up and down he tongued her as she sighed with delight at his gentle yet arousing way, and how he flicked her clit with each passing. When he started to spend more time at clit, swirling and sucking it, she moaned in pleasure, her excitement building. Jim continued to eat her pussy, tongue her hole, and swirl her clit, causing Helen untold arousal, with little jerks each time he tweaked her clitoris. When she began to squirm at his tongue's agile movements and seemed close to climaxing, Jim took his mouth from her snatch.

"Time for something different," he said.

Jim remained on the bed right behind her and flipped Helen over, effortlessly it seemed due to his strength. With Helen on her stomach, he lifted her hips until she was in the position he wanted; on her knees, her rear up with her elbows on the sheets. Jim moved her knees apart, then ran his hands up her inner thighs and grazed her pussy. Up and down he played her tender inner legs, and she tensed just a bit each time he touched her pussy, still aroused from the clit play. Soon he stopped at her slit and trailed a finger up it, spreading her already wet pussy lips open again as he went. He let his fingers drift down and paused at her clit as she sighed in delight, swirling it for a moment before he let his fingers continue their path up and down her tender folds.

As he continued to caress Helen's pussy and tease her clit, she again became alive with desire, and she moaned louder. Jim pressed a finger to her opening and she jerked a bit, then he pushed it into her, and she writhed and began to rock back and forth. He added a second finger and finger-fucked her while she rocked, keeping his fingers pumping her all the time. After a minute, as her squirming intensified and told him she was ready, he took his fingers out of her and pressed his black cock against her vaginal opening. She flinched a little when he pressed its head into her, stretching her some, letting out a few choice words, but she soon adjusted and enjoyed his pushes as he drove its entire eight inches into her.

Jim grabbed her rear and they rocked opposite one another as he thrust deep, over and over, sending Helen to another level of sexual pleasure. She could feel his length and girth fill her like she may have never been filled, pressing against her cervix at his deepest penetration, and her body was reacting with energy as she met his every thrust with an opposite push of her own. Both of them were enjoying the doggie-style action when Jim reached under her and resumed playing with her clit.

Helen's reaction came quickly and beyond her control. She jerked and spasmed as her climax hit, her orgasm as strong as any she'd had.

Over and over she jerked and came as Jim continued to fuck her and finger her clit. Her juices flowed freely as Helen's pleasure reached new limits, her orgasms running one into the next as she squirmed with delight. When Jim's climax finally came and he jerked and shot his load into her, the warmth triggered Helen to a new level, and she screamed with a passion she didn't know she had in her. She squirted onto him and could not stop, her orgasms so strong she almost fainted from pleasure.

After they finished, exhausted from their dalliance, Jim and Helen relaxed in each other's arms for a few minutes, then cleaned up and got dressed. Helen knew she would fondly remember the great sex she had with a tall and kind black pirate.

Dianne and Eddie

Eddie, a black man rather like an American football running back, short but strong, took Dianne to a cabin on the 'Raging Cock' where Dianne entered a small room with a twin bed. She noticed the bed was rather old-fashioned and had bedposts, and that there were handcuffs attached to all four corners. Were they there for her?

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"Yer a fine looking woman, me dear, and I'll have ya put on a strip show for me. And no funny business either, or I'll give ya a taste of the flogger," Eddie told her.

"The flogger won't be necessary, sir. Just sit yourself down and I'll put on a show for you," Dianne replied with a smile.

Then Dianne moved to the small open area of the room and started to sway while unbuttoning her blouse. She imagined stripper music in her head while she continued to unbutton it until it was open, then teasingly turned away from Eddie as she took the blouse off. She looked back at him and saw him licking his lips with desire in his eyes. Still turned, she slipped the bra straps off her shoulders, then turned toward Eddie as she unhooked her bra and slowly slid it off each breast, finally letting it fall to the floor. His face gave away his arousal as he was enjoying Dianne's show and now seeing her ample breasts exposed. She continued by unzipping and slowly sliding her skirt down her legs, pulling down one side and then the other, shimmying it off her little by little. as Eddie stared with growing excitement.

On seeing her thighs and upper legs come into view, Eddie was becoming agitated and anxious to see more of her skin, so, when the skirt was off and kicked away, Dianne smiled at him as she hooked her thumbs into the waist of her panties and started pulling them down. Eddie watched intently, admiring her body as it was revealed, and now trying to get a glimpse of her snatch as she worked her panties down her thighs. Dianne was enjoying this teasing, knowing he was desiring her and would be making love to her soon.

In a minute she had removed the panties and stood naked before Eddie, who got up and put his arms around her, kissing her neck before moving lower to kiss her breasts. He put his lips on her nipples and suckled her while he cupped her full mounds. Eddie moved his hand to her crotch and felt her pussy, then finding her slit damp, he ran his finger up and down to open it. Dianne sighed and opened her legs to give Eddie space to maneuver, and he took advantage as he traced her slit, feeling her juices grow with each up-and-down move.

Eddie took his hand away from Dianne's pussy and put his arms around her, then guided her toward the bed. There was a large, very puffy pillow in the middle of the bed, and he helped her to lay on her stomach across it. This raised her rear, and after Eddie opened her legs and cuffed them to the bedposts, her pussy was exposed and open to his intentions. He quickly secured her wrists to the top bedposts, leaving Dianne spread out with the large pillow under her, raising her rear and exposing her pussy to Eddie's desires.

Eddie wasted no time in assailing Dianne, kneeling behind her on the bed and grabbing her ass cheeks, kneading them, spreading them, massaging them. She loved the feel of his strong hands on her, especially with the helplessness of her position, knowing he could do whatever he wanted, and she could do nothing to stop him. After Eddie spent a few minutes warming her desires at her rear, he moved to her snatch, running his fingers along her slit until he had opened her and was caressing her sensitive skin beneath. He rubbed her up and down as she sighed with satisfaction, and more so each time he passed over her clitoris.

Soon Eddie was focused on Dianne's aroused clit, swirling around it and rubbing it. Dianne was moaning loudly now and squirming under his touch, and her wetness was prominent and leaking down her thighs to the pillow. Eddie was relentless in his assault on her clit, but now moved his free hand to her suspended breasts and began to roll, squeeze and pull on her nipples. The combination put Dianne at the edge of her climax, and sensing this, Eddie got up and pulled his pantaloons and briefs off, then quickly returned to his position behind her. Dianne noted how well-endowed Eddie was, with his penis larger than any she'd seen in a long time, especially in its girth. He pressed his erection against her pussy, then slapped upward at her clit several times to Dianne's added excitement, before pressing into her waiting vagina from his kneeling position behind her.

Eddie started slowly, pushing his big black cock deep into her, stretching her, then pulled back and almost out before pressing into her again. As Dianne got used to the size of his member, her juices flowed readily making his intrusion more comfortable, and she began to squirm under its pressure and pleasure. She moaned more loudly as Eddie drove deeper and harder, and when he began to fuck her faster, she writhed under him with wild abandon. He continued to pummel her pussy with his large cock, driving her toward her climax with his size and its added friction; his pulling on her nipples added an extra jolt of intensity.

When Eddie began to jerk and spasm, and started ejaculating his load into her, its heat and volume took Dianne over the top, and she joined him in coming. She jerked and came, her orgasm overtaking her as she began to squirt her feminine juices onto him and the pillow. They fucked like animals, and she screamed in her ecstasy as they continued until both of them were spent, exhausted, and he collapsed on her as they lay on the large pillow.

Thay rested for a minute before Eddie pulled out of her and got off the bed, then quickly undid the cuffs, freeing Dianne. She relaxed in the afterglow of great sex, having gotten exactly the kind of experience she had hoped for from her "pirate".

Katie and Jon

While the others moved off to their cabins, Jon grabbed Katie around her waist and escorted her to a cabin on the 'Good Times' where Katie was to celebrate her birthday with great sex! She was excited to be with Jon, a strapping younger man with a fine smile and a great body under his pirate clothes.

On entering, he said, "I'm so glad to be paired with you, birthday girl, since I was hoping to be the one who would get to strip you, as you said you liked, and give you your birthday spanking. Go ahead and sit on the edge of the bed."

With that proclamation, Katie sat on the bed and Jon knelt before her, then took the sandals from her feet. He pulled her foot up to his mouth, where he kissed her toes before rubbing them. Giving both feet equal treatment, he played with her toes, and tickled the bottoms of her slender feet, eliciting squirms and complaints from Katie.

"Ah, that tickles. Please stop," as she wiggled to get her foot away from Jon.

"Well, then I'll just have to do it harder," he replied.

"No, please stop. I'm just so ticklish, I can't stand it," she said as she continued to try to pull her foot away from him.

"Okay, I'll be kind this time, but you better not give me any more trouble or I'll flog you like the Captain said I should."

"You wouldn't dare!" Katie said defiantly, hiding her secret desire to find out how it felt to be flogged.

"Oh, you think not, eh? Just try me and you'll see, pretty lady!"

Then Jon continued to strip Katie, undoing her blouse and sliding it off her shoulders and arms. He reached behind her, unhooked her bra, and took it off. Then he looked at her fine breasts and went after them with his hands, cupping and surrounding them while he pinched and rolled her nipples. Katie loved the feel of his big hands on her and sighed in delight. He continued to play with her nipples for a moment more, then had Katie stand. He unzipped her skirt and pulled it off her, revealing a thong pantie that barely covered her pussy.

"Well, isn't this inviting?" he said with desire in his voice.

"It's all yours, you nasty pirate, you," Katie replied encouragingly.

So Jon hooked his thumbs into the waist of the thong and pulled it down, with Katie stepping out of it. As she stood naked, Jon admired her, from her fine breasts to her hips and rear, and her beautiful, shaved pussy. He stood before her.

"Now on your knees, so you can give me a blow job," he said.

"Oh no, I'm not into that. You can do what you want with me but I'm not giving you a blow job," Katie said, intentionally trying to goad Jon into flogging her.

"Really, well then we'll just have to give you the cat, won't we?" Jon announced, having sensed from the way she was acting that Katie wanted it.

Jon grabbed Katie around her waist and pulled her out of the cabin and over to the deck of the 'Raging Cock', where he guided her to the main mast. There he took a rope and skillfully tied her arms around the mast, her naked breasts against the large pole and her rear exposed. Next, he tied her legs so they were wrapped around the mast but still held her weight. With Katie secured and helpless, he retrieved the cat-o-nine-tails flogger, a handle with nine strands of leather, each with a knot near the end. It was used in the old days by the British Navy to discipline or punish sailors and was a frequently used flogger in modern BDSM situations.

"I'll be giving ya ten strokes o' the cat for your obstinance, dear lady."

And then Jon flicked the flogger at her rear. striking both cheeks with the tails, and eliciting a loud "Ouch" from Katie, reflecting her desire to make Jon think it hurt more than it actually did. The next strikes were harder, and Katie screamed, again exaggerating the pain she felt, though it did hurt. The following swats were a bit lower, hitting her just below her cheeks on her upper legs. These hurt more, and she screamed again, though she wasn't acting much this time. He continued with strikes against the back of her legs which hurt a lot, her screams reflecting it. Jon paused before the last strikes, letting Katie wait in fear before he stuck her on her cheeks again. These were the hardest strikes of all, and Katie let out a fearful scream of actual pain. She was sure the others heard her as she wondered what they thought was happening.

With her flogging over, Jon vanished for a minute, but when he returned, he applied some aloe lotion to the red marks on her rear and the backs of her legs to ease the pain. Katie appreciated his kind attention to her discomfort, and knew that if this situation ever arose in the future she would not opt for such a flogging again. The aloe helped a lot with the pain, and soon Jon was untying her from the mast.

"As long as we're her, let's go ahead and have you like the pirates of old would have," he told her.

Then he turned her around so she was facing him, and he re-tied her to the mast, her arms over her head and her legs open and wrapped to the sides, secured. Her sore welts from the flogging were not directly touching the mast, for which she was thankful.

After tying her to the mast Jon reached his hands to her inner thighs and caressed her as he slid them up toward her crotch. He found her pussy and traced his fingers up her slit, opening her as he went, then began caressing her up and down, which felt so good to Katie compared to the pain of the flogging, and she sighed in relief. With one hand busy at her pussy, he moved his other hand to her breasts and fondled her tits, pinching each nipple in turn and rolling them between his finger and thumb. Katie loved his nipple play, while Jon continued caressing her slit, grazing her clit at the top of each pass, with Katie moaning a little each time his fingers touched her there.

Soon Jon was pausing to swirl and rub her sensitive nub, and Kaite was becoming very aroused despite some lingering pain from her flogging. He maintained his attention on her nipples while he assailed her clit, and had Katie squirming at his touch. She moaned more loudly as he deftly played her swelling clit, until she could hardly stand the pleasure and yearned for a release. Jon could sense her desperation, so he stopped and moved back, took off his pantaloons and the black briefs beneath, then moved closer to Katie's exposed pussy and pressed the head of his penis to her opening. Finding her wet and ready, he pressed upward to enter her and enjoyed the moans of pleasure his entry elicited.

He pushed further in, his length sliding easily along her soaking tunnel until his body was touching hers. He paused, letting her feel his full manhood inside her, then pulled back and almost out before thrusting deep again. Jon fucked Katie relentlessly as she writhed in pleasure while still roped to the mast. When Katie was almost at her climax, Jon sped up his thrusts and helped her get over the top as she started to jerk and spasm when her orgasm hit. She came repeatedly, squirting Jon's balls and legs with her juices, moaning in the ecstasy of the moment as he climaxed and jerked, repeatedly squirting his semen into her.

After Jon and Katie finished, he untied her from the mast and walked her back to his cabin on the 'Good Times', where he gave her a towel to clean up. She was still in the afterglow of the unusual and rewarding sex, and was glad to have tried a taste of the cat-o-nine while being tied to the ship's mast. Katie would definitely remember her fifty-fifth birthday.

Sue and Captain Horny

Captain Horny presented himself as a rather gruff old pirate, and he tried to came off as something of a dirty old man of about fifty who loved his women, but Sue could tell he would actually be a good and tender lover as well. He took Sue back to his captain's cabin on the 'Raging Cock' and when she entered it, Sue found a crowded room, larger than the crew's cabins she'd peeked into, and with a larger bed. The room looked like one from a pirate movie.

"Well, me lass, we'll be having yer clothes off now, if ya don't mind... and I know ya won't or ya'll get the lash."

"Yes, sir," Sue replied, and she started to undress. Captain Horny sat on a chair and watched her, admiring her body as she revealed it while she stripped. When she removed her blouse, he looked with interest at her fine breasts since she wore no bra. And when she pulled her skirt down and off, revealing her sexy black panties and shapely ass, she noticed the bulge in his pantaloons grow. He was licking his lips when she took the panties off and stood before him.

"Let's be having ya over me knee for a little spanking, me lass," he said as he scooted a chair to the middle of the room.

Sue walked to him and he helped her to lay across his lap, her smooth rear now prominently available to his intentions. He smacked her cheek with his hand, and she jumped a little at the contact. He spanked harder than she was used to, and it hurt a little more than usual, but Sue enjoyed such spankings as a prelude to sex.

After many swats and what Sue was sure would be a reddish rear, the Captain stopped spanking and spoke.

"Yer'll be spreading yer legs for me now, lassie, so I can have at that fine pussy o' yours."

Sue did as he asked and spread her legs open, since the spanking put her in the mood for it, and she was getting wet already. The Captain wasted no time in putting his hands on her snatch, finding her pussy shaved smooth and inviting as he explored her labia. He ran a finger up her slit to open her, then traced his fingers up and down to arouse the sensitive folds beneath. Sue sighed as the Captain played with her pussy, getting her wetter as he aroused her tender places, and when he rubbed over her clit, she moaned loudly with desire. Just as she was getting into what he was doing to her, he stopped.

"We'll be having ya give me a blow job now, me lass. Let's have ya on yer knees, then."

Sue was surprised by his sudden change of plans, but loved giving blow jobs so she got off his lap. He stood and she knelt before him, then she undid his pantaloons and pulled them down, followed by his underwear. Just as she grabbed his already erect penis and prepared to begin, the cabin door opened and someone entered. They both looked and saw another pirate standing at the doorway.

"Well, shiver me timbers, if it isn't Captain Mike!" Captain Horny exclaimed in his best pirate parlance.

"Yes, and I see you and the crew are having a fine time with these ladies. Mind if I join you?"

"Not at all, Captain. Let's have this lass hop on the bed and we'll take her together. I'll let her continue with me blow job and you can take 'er rear."

"Sounds good, Captain!"

With that exchange, they helped Sue onto the bed and had her rest on her hands and knees. Captain Horny stood before her at the edge of the bed, his dick about the same height as her mouth, while Captain Mike took his bottoms off, got on the bed, and kneeled behind her. Mike put his hands on her pussy and found Sue very wet from what Horny was doing before he arrived, and he continued to play with her, getting her juices on his fingers and transferring them to her anus. When she was well-lubed, he pressed the head of his dick against her entrance, grabbed her hips to steady her, and pushed in. Sue moaned loudly, not from the little pain she felt, but rather from the delightful anticipation of being taken from both ends.

Captain Mike pressed firmly into her, slowly but with determination, his penis filling her and feeling very large to Sue. As she relaxed and her canal opened for him, his pushes were easier, and after a couple of minutes of pushing ever deeper, he was finally up his hilt. He began to pull back until he was almost out, then pushed deep again. Sue loved the feel of him in her, and his deep pushes felt heavenly. He held her hips steady with his hands and was able to keep Sue from falling forward as he speeded up, driving deeply and soliciting delightful moans from her.

Meanwhile, Captain Horny was presenting his cock for Sue to begin his blow job, and she happily accommodated him. Holding herself up with one hand on the bed, she used the other hand to grasp his penis and pull him toward her mouth. She used her tongue to lick along the sides of his dick, which was of good size and straight as an arrow. She flicked its head several times, causing the captain to flinch, then took the head into her mouth, where she used her tongue to swirl around it, eliciting sighs of pleasure from the captain. She took him deeper, sucking him into her and wrapping her tongue and lips around his member, causing the captain to moan with anticipation. Putting her hand back on the bed, she began to move her head in and out over his cock, fucking it with her mouth, and the captain responded in kind, pressing himself into her. She felt him at the back of her throat, almost gagging her, but she continued her oral assault to the pleasure of both of them.

As she gave Captain Horny a superb blow job, Captain Mike continued fucking her ass, and Sue was enjoying it greatly. Anal always gave her rewarding orgasms, and she was fast approaching her climax when Mike reached around her leg and started to play with her clit. He rubbed and swirled her most sensitive nub, causing Sue to buck with electric shocks of pleasure as he pushed her toward her orgasm. Just as she could stand no more and was about to come, she felt Captain Horny reach under her and grasp her nipples and pull on them. She was being fucked in the mouth and the ass simultaneously, having her clit assailed with intense pleasure, and now her nipples and breasts were being pulled on painfully. Sue loved it all and it sent her into an intense orgasm, which took her with ferocity as she came violently, jerking and spasming, her juices squirting onto Mike at her rear.

One orgasm blended into the next as Sue felt waves of ecstasy wash over her, coming repeatedly as both captains seemed to be triggered by her climax to have their own, and both jerked and shot their loads into her almost simultaneously.

Sue felt the warmth of Mike's load in her, and tasted Horny's semen before swallowing it, as they sandwiched her with their pushes and ejaculations. With all three moaning in pleasure, they came together in a sexual trifecta, unleashing their pent-up desires until they were spent. Exhausted, the men pulled out of Sue and all three lay on the bed. After they recovered, the captains got Sue a towel to clean up, and they all got dressed. Sue enjoyed the three-way encounter and was glad for Mike's return.

Back to Port

After recovering and getting cleaned up and dressed, all the pirates and their ladies returned to the deck of the 'Good Times', gathering at the table. They drank wine and beer, chatted, and laughed about the encounters each had just had.

Captain Mike explained that the pirates arriving to ravish the women was his idea, and he easily talked his friend Nick, alias Captain Horny, into helping with a promise of sex. Knowing Katie wanted some sexual fun to be the main course on her birthday cruise, he concocted the pirate idea and clued the crew into what would take place, but intentionally didn't tell Katie. He staged the 'Good Times' engine failure by simply shutting off the fuel line and letting the engine die, unable to be restarted. Then he took the dingy and met the 'Raging Cock' when they were still out of sight of the 'Good Times'. He directed Nick to head for and capture their prize and have a good time with the ladies. Then Mike hid in Nick's cabin until the rest of the crew got together in that cabin to decide which of them would take each of the ladies.

"Well, you certainly fooled me, Mike, but I love what you did for me and my friends. I know I had a great time, and I think we all did," Katie said with a big smile.

This triggered a chorus of "Yes", "Definitely", and "Did we ever" from the ladies.

"I'm so glad you and your friends enjoyed your birthday, Katie," Mike added. "We have about a two-hour ride back to port, if any of you want seconds, or to meet a different crew member?"

"I do!" cheered Katie.

"Me too!" said all the other women.

"Alright then," Mike replied. "You ladies can get together and decide how to divvy us pirates up this time. Meanwhile, we'll prepare the ships for our return."

So the ladies sat and listened as each of them shared what their pirate had done with them, while the crew got the ships ready. The women laughed and were even a little shocked at some of what they heard, but they were able to agree on who would like which pirate to take them for their "seconds". Before they separated the ships, the captains and crew came to the table where the ladies were laughing and enjoying themselves and found out who they would be with. Then they each took their lady by the hand and went to their cabins on the two ships, asked the ladies to wait while they got the ships headed to port, and returned when the ships were unleashed and underway. Both ships had an auto-pilot navigation system, so all the pirates could participate for a good hour or more. Mike made an appearance at both of the cabins on the 'Good Times', so the ladies who went with Jim and Jon this time both got a little three-way action.

Thus Katie and her friends were treated to another round of great sex to wrap up her birthday celebration, as the two ships sailed together for the trip back to port.

All in all, it was an evening at sea that none of them would forget!

The End

Published 
Written by BobbieRotica
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