Captain Chuck's Bondage Cruise

[Chuckdom19]

The next morning, I thought it best to allow the ladies, once finished with breakfast, a little time to enjoy the beautiful morning. The wind had come up in the night, so my First Mate had spread all canvas, and "Sailing Master" was flying before the wind. Jenny was working some of the controls on the sheets, and learning proper control of the rudder while sail-powered. Although she wore only deck shoes, a hat, and sunblock, it was obvious I had chosen well to add her as a temporary Third Mate under instruction. I borrowed her for just a few minutes, as it was time for exercise.

We all started laps around the deck, just to loosen up. Plain running was awfully nice to observe in this case, as all our fair crewladies were blessed, figure-wise. None-the-less, I wished to make it a little more sporting.

"Ladies, over here, please. Since we're running today, I want to make the run more exciting. The first to finish the race is done for today. No chores! The LAST one to finish the race gets to spend several hours in an appointment with me, a feather, and a belt. Special prizes for 2nd, 3rd, and 4th place.

"Now for the exciting part. The race will be 8 times around the deck, and I'll be handicapping the race a little. On the scale, ladies, one at a time!" Each got on the scale, and a couple had put on a little weight over the holidays.

"Each will have a weight carrier placed between your ankles. The one closest to her ideal weight will only have a handicap of 5 pounds. It will progress by five pounds, lowest to highest. However, I will be 'encouraging' a little faster running in reverse order. The one closest to their ideal weight will be encouraged the most. And here's the whip I'll be using to encourage with. Just a plain old buggy whip.

"Help each other with the weight carriers and the weights, then get to the head of the stairs, and I'll get you started." (And no, naughty readers, I am not going to expose or hint at the order of the individuals. All ladies are beautiful: some are just more beautiful than others. So don't ask and I won't have to cuss you out.) "Ready, set, go!"

"Well-done, ladies! A five-way tie, in spite of several pretty sore backs and fannies. Next race will have only four participants, as it requires teams of two. Jenny, you're out of this one so you can continue your sailor lessons.

"Two teams. WB and BabySub, Bisarah and yellowrose. This will be a wheelbarrow race with a twist. The front person's legs will be tied to the back person's arms, so if you fall down, it'll be a little hard to get back up. Oh, I forgot; there'll be thumbtacks here and there, so you want to be real careful as you run and where you fall, and the person in front will be blindfolded, so communications will be important.

"Get into position, and I'll get things fastened up, and the tacks spread out. Ready, set, go!" The ladies took off pretty fast, which will be a mistake. They'll find out at the first turn. Aha! One down, one swings wide to avoid them, and runs straight through the tacks. Now they're down too, pulling out tacks. Since the driver's hands are bound to the feet of their front, who is blindfolded, pulling out those tacks can be really hard. Guiding to a tack on the other person turned out to create some really wicked contortions. And some couldn't be reached at all.

The eighth lap showed how tired the four were getting, so I decided to end the race a couple laps early. WB and BabySub crossed the finish line first. I untied the teams, and all four got to clear the tacks from the deck. I didn't let the losers use their hands or feet, though. I gave them each a bra to wear, and they had to use those. No longer was the race 'pointless'.

About an hour later the track was clear, and the losers had VERY sensitive breasts. Ah, well. It was getting to lunchtime, so yellowrose and WB went down to prepare some cold sandwiches and soda. BabySub and bisarah had the priviledge of being my furniture for lunch, and I soon had them bound in position. With the ladies all busy, I dashed to the head to have a refreshing shower. I'd just finished and slipped into a 'lava-lava', which is the Tahitian form of lower garment now adapted by lots of islanders. A single piece of cloth, wound around, usually in bright color patterns.

After all had had lunch, I decided to take the afternoon watch and told Nick to let 4 of the ladies relax as they wished, but they needed to have at least an hour of sleep. And of course he could invite/order one to his bunk. He did.

WB and I wandered up onto the deck and unlocked the controls, hoist anchor, and raised sail. We were less than 50 miles from out first destination, and I planned to cover that by nightfall. A tropical storm was coming, and I wished to be in a wind-protected harbor by the time it hit. Point "b" had such a natural harbor inside some high ridges; perfect protection.

I had looked forward to spending some quality time with WB. She sit on my lap while I put up sail and got us underweigh, behaving until I got the autopilot programmed and operating. Then I got to pay a little attention to my little Loonie Tune lady (WB. Warner Brothers? Home of Bugs Bunny, Porky Pig? If you're not native to the US, you may not have seen them. If you ARE native to the US and don't know them, you grew up under a rock somewhere. Culturally deprived.)

We both had the chance to explore and play with this and that; shortly we were both ready for more. More was very nice, all three times.

Supper was brought on deck, and I let WB get me a plate of it and feed me while I was still nominally on watch. After the meal, Nick relieved me. This would be a short leg on today's reach, as we were only about an hour from the harbor, and less than two from sunset. I decided the sunset would go on even if I didn't watch it, and went to my cabin to sleep. I was awoken three times that night, first by bisarah, next by BabySub, and finally by Jenny. It was a very pleasant day.

[yellowrose]

Chuckling softly to herself as she watches as Master Chuck heads off to bed. Poor man has to balance the needs of five women, to do so without causing jealously and still run the ship.

Despite all that he seemed to be more relaxed then she could remember seeing him. The sea air must agree with him, with all of them.

Turning she watches the sunset. The colors so vivid and alive as if the sky and water danced together for a brief moment. Shifting to feel a twinge where several tacks had found their mark she smiles, Ah yes, it was a good day.

[BabySub]

Babysub, it is so nice that you could join us, doesn't yellowrose look wonderful in here all natural tan!!

Mmm, yes, I have to agree WB. YellowRose does look so appealing right now.

I also have to agree with YellowRose, it was a good day. Very.. energetic. I'm most surprised that I didn't come last in the race however, as I'm not as fit as I could be. Perhaps a little personal training could be in order..?

Captain Chuck, Sir, you looked most handsome in that 'lava-lava' if I may say. Was that a batik pattern? The cloth was very nice. (a little sucking up never hurts, eh?) The evening entertainment even nicer.

::coughs gently:: WB... please, no scrambled eggs with grape jam. I beg you. :help:

[wannabeXopsed]

OH thank you Captian Chuck Sir, we did enjoy the fun all 3x's and the power you hold over me, it is so much fun, and all torture you gave me, you know how much i love that, standing in front of you exposing myself for your pleasure, and delighting in your full arousal and such stamina, it is amazing.

It is a pleasure to serve you as you take each morsel and lick my fingers, i'm ready for more Sir, lets make it 4x's

Ok, babysub, how about some ketchup with those eggs :Tasty: I know some GREEN eggs and HAM. :rofl:

T

[Chuckdom19]

I had picked this island for several reasons. First, no residents, and no predators. No snakes. Nothing poisonous.

Next, plenty of water, some pretty hills and trees. A 'jungle paradise'. Easy access from a safe harbor. And a deep-water anchorage which served well for transporting some of the things I'd had shipped here.

Thus first thing in the morning, I woke the ladies from well-deserved slumber. The two on breakfast detail got busy, while the rest of us took a morning shower and got ready for the day. I issued the ladies long-sleeved denim shirts, jeans, and ankle-high walking boots, and Nick and I followed suit.

We ate a huge breakfast while watching the beautiful sunrise. Gathering the goodies we'd need for the day, we locked up the ship, set the alarms, and used the lifeboat to head for the beach. I had all the ladies follow Nick and me as we broke trail through the jungle.

Our first stop was a small clearing, next to a little brook. A sturdy set of stocks were in this clearing, with a twist, of course. Picking two ladies at random, I fastened them together, back to back, with a single rope around their waists. The knot was between their backs, and their feet were padlocked into the leg-parts of the stocks. I fastened their hands in front of them with rope, using a knot they would eventually open; likely after chipping some nail polish. The keys for the leg locks were hanging over their heads, frozen in a block of ice. Each was warned not to do anything until signalled, and had a butterfly vibe fastened in place.

Returning to the trail, we continued along. The next clearing had a most unusual, not readily recognizable device. The ladies walked up to it and tried to figure it out. Nick pulled out the goodie bag, and we got busy.

A chain which terminated in a y-shaped yoke hung from an overhead branch. Bamboo formed the bottom of the device, which looked a little like a standard bondage horse. The legs were wide-set, and went into the ground. A set of cables went from the footrest to a couple pipes set in front. Nick was threading a 6" dildo on an upright which rose from the base.

I picked another lady, and lifted her aboard. After fastening her hands to the yoke overhead, I impaled her on the dildo through the crotch hole in her slacks and allowed her feet to rest on the footrest. It spread her quite a bit. The chains from the pipe were fastened to two strong clips, fastened to the back of her areolae through small holes in her shirt. Pushing down with her feet allowed her a little more freedom for her hands, but pulled badly on her breasts. Her wrist keys were laying on the top of the yoke, but she would need to get a few inches more play in her wrist chains by pushing down on the footrest. The wrists would then be loose enough to, just barely, reach the ice cubes containing the keys. A butterfly vibe would keep her interested.

The last two ladies followed Nick and me to the second last clearing. Here we had just a small log, mounted four feet above the ground horizontally. We used some rope to fasten their arms, and cuffs to fasten their legs around the log. Here the keys were in two ice blocks laying right in front of the ladies on the wood, inches from their eyes. We attached another butterfly vibe on these two. I turned on the walkie-talkies which were strapped to each lady's upper arm.

"Hello, ladies. Each of the traps is escapable; just wait for the block of ice to melt. Oh, yes; it's clean ice, so you can drink the drippings. The keys might be a little hard to get at, but it is possible. You may start when your butterflies start vibrating. Just one small problem: you may not help each other, or hinder them either. You will then follow the trail back to the beach. There will be prizes for the first, second, and third to return. The last two will be in for some punishment. Ready, set, go!"

I flipped the remote for the vibes on, and joined Nick on a restful hike through the jungle further along the trail, which wound itself gradually back to the beach.

The ladies had a few surprises waiting for them. I could watch their progress through small cameras at each site. And I had speakers hidden here and there with jungle animal sounds which would advance and retreat.

We worked our way back to the beach, and set up 7 beach chairs. I motored back out to the Sailing Master and got a cooler loaded with chilled juices and GatorAde, along with a few select beers and wine coolers. I slid back onto the beach, and joined Nick in the shady place we had picked, right near the waterfall.

It was time to wait.

[BabySub]

The 'scene' I liked the best..

I picked another lady, and lifted her aboard. After fastening her hands to the yoke overhead, I impaled her on the dildo through the crotch hole in her slacks and allowed her feet to rest on the footrest. It spread her quite a bit. The chains from the pipe were fastened to two strong clips, fastened to the back of her areolae through small holes in her shirt. Pushing down with her feet allowed her a little more freedom for her hands, but pulled badly on her breasts. Her wrist keys were laying on the top of the yoke, but she would need to get a few inches more play in her wrist chains by pushing down on the footrest. The wrists would then be loose enough to, just barely, reach the ice cubes containing the keys. A butterfly vibe would keep her interested.

The walk through the wilderness was nice, it had been a while since BabySub had been out and about like that. She appreciated the semi-freedom, and the scenery as well as the brisk walk. Always curious, her mind was trying to figure out where they were going, and why.

It became obvious when they reached the first clearing, and she pondered the situation her friends were in. Interesting, what was next? Her eyes widened as they reached their next destination, and she saw the 'aparatus' waiting to be used. Her heart hammered, and her cunt twitched as she was grabbed and placed on the dildo, mewing quietly as it slid inside. Legs wide spread, BabySub gasped as the clips were attached, and pinched at her nipples; her breathing hard and laboured. The vibe was put in place, and she saw the keys ontop of the yoke. Blinking, she watched the others as they left, moving onto the next clearing.

Twisting occasionally, BabySub clenched her cunt around the dildo, letting out small cries of anticipation and by then need. She jumped as she heard the voice over the walkie talkie, and listened. The ice by then was starting to melt a little, and BabySub reached out with her tongue and caught a drip. How long would it take to melt completely..? "OOooohhhhh......" as the butterfly started, humming away at her clit. She pressed down slightly on her feet, "Oooouch..!" as her nipples were pulled painfully by the chains, but she realised she got closer to the keys... hmmmm....

[BabySub]

:goldcup: Yay! Heroine BabySub wins!

Tired and dirty, BabySub makes her way back to the lifeboat, and then back to the cruiser itself, looking forward to a hot shower. She still had quicksand in places best not mentioned. Very pleased with herself, she grinned the entire way back, giggling now and then. Back on the cruiser, she helped unpack the things from the lifeboat and stretched on deck. Her crotch and nipples hurt like hell, but it was worth it. She'd been a bit of a naughty sub until then, and it felt good to please her Sirs and Masters for a change.

Falling to her knees, placing her hands in her lap, she looked up and smiled sweetly. "I know you say I won Sirs, but please use this sub however you wish tonight. Once cleaned of course." Bowing her head slightly in respect, she then stood and proceeded to take the chairs and things back where they belonged.

Wow, Chksng, you had fun in that post, eh? lol.

[Chuckdom19]

BabySub had paid the appropriate homage, and I dismissed her to get cleaned up, then to relax until supper. None the less, she hefted the seven chairs and still mostly full cooler and rushed to put them away first. What the sea air (and distance from civilization, no doubt) did for some people. BabySub a model sub? Who'd have thought it possible?

Shortly all the rest were aboard, had accepted their "placing" in the contest, and had headed down for a shower and chores. BabySub was back on deck, learning controls and the rudiments of sailing a wind-powered craft.

We hadn't lifted the hook, although we were already a day behind schedule, as we had a few matters to take care of, and the cove was very safe. Some higher winds, upwards of 35 knots, were bringing us a small tropical storm. I judged staying at anchor to be safer, but we'd keep watch through the night to make sure. And as I was on watch tonight, I set my head down in a shady hammock to get a little sleep anticipating a long night.

Surprisingly, the losers had managed to lay out a fine feast for dinner, and we all had a fine meal. All five ladies dashed around cleaning up, as we had playtime scheduled afterwards.

The fun began when the ladies had the opportunity to collect on my bet with Nick. They all laughed and joked with him as they bound him, pretty much marrying him to one of the punishment/play columns in the main lounge. I noticed that before binding him, they had mounted a standard thin dildo/vibe to the post, and he had been penetrated as he was being bound. They made quick work of it; he was nearly mummified in rope and leather.

Their final pleasure was in a little cbt, having found a "gates of hell" device in the toy closet. Any stirrings of his libido, and some small, dull plastic spines would encourage avoiding an erection at all costs. Unfortunately his equipment was somewhat larger than average, so he dare not have so much as a twinge or the suffering would start.

Unfortunately for him, the ladies had other ideas. First of all, they activated the dildo, which had it's strongest effect at prostate depth. His proud penis raised and lowered more in the next hour than the flag caretaker at the United Nations. There was almost a breeze!

Then the ladies got busy. One of the ladies was an exotic dancer for parties in her earlier life; she went to work on him as though she expected a $300 tip. A couple of the other girls worked on him with lips, feathers, and fingers; his frustration level grew higher by the second.

Being a merciful Skipper, and truly worried that some day I might lose a bet myself, I called them off after about an hour. His face reflected the level of arousal, so I told them to remove most of the cbt, but to add some clothes pins here and there for a bit.

The four losers of the competition put their names in a hat, and I drew out slips for each to get their punishments. I asked BabySub to attend to Nick's arousal, and for a minute I saw a devilish grin pass over her face before it returned to 'slave neutral'. Seeing that, the other four had to wait a minute. I unbound Nick's ankles and spread his legs, putting BabySub's legs through the gap and tying her so she was as close to the post as could be, then tied his ankles to her legs for support. An agony bra followed; I picked one 2 sizes too small and filled it with kitchen green scouring pads, brand new and stiff.I wanted her arms free, so I left them alone, but pushed her forward and bound her with a wide leather strap, over her bra closure in back. This put her face right into the action, so I swung his erection around and slid it into her mouth, then tying a noose around his balls. The line from the noose ran behind her neck, so any movement away from her attention would tighten the noose. I informed her that her task was to make him climax.... twice. Once he announced that completed (he was noisy when he came) she would be allowed to join the fun. She set at her work with a will.

(no thirty, more to come)

[Chuckdom19]

Twisting off the lid of a fine Guiness Dark Ale, I take a deep draught and smile as the rich nutty flavor rolls over my tongue. Very cold, ahhh. How can they drink beer warm? Must be an acquired taste.

"Well, Nick, who do you think will be first?"

My First Mate was also enjoying his cold drink, but it was a root beer instead. No drinking and Mate-ing! (pun very intentional).
"I think BabySub will be first."

"How can you say that? She has the hardest predicament to overcome!"

"As the feistiest woman of the five, I really think she can overcome her bondage quicker."

"Perhaps, perhaps. But can she get past the secondary traps? Being first, in this case, does not necessarily mean to win."

He looked at me, puzzled. I hadn't told him about those; what a man does not know, he cannot tell. You never know what might come up in pillowtalk. He would see. I bent down to my haversack and pulled out a small monitor. It was connected to hidden cameras all over the island. We flicked from one to another, and followed the progress of the five women.

The two at the first trap had both gotten their hands free, and had gotten out of the rope binding them together. The keys weren't in their hands yet; the ice hadn't melted enough. They sat and talked to each other rather than cooperating, and likely would lose because of it.

BabySub had figured out her trap; obvious as she grasped at the ice containing the keys. She was suffering tremendously by pushing down on the footrest, her breasts deformed by the mean clips on them. Every now and then, she stopped everything to shudder with another orgasm thanks to the butterfly vibe and the dildo inside her. She frequently unclenched those pussy muscles and would almost crash down; yet she would rise again, punishing herself to get free. Her tanned body ran with rivulets of perspiration, testaments to her struggle. A few small drops of blood stained her top as well, due to the harsh clips there.

The last two ladies were still looking at the ice. They had not yet figured out that their knots could be gotten at by simple cooperation, as they would be accessable to their partners. Here, too, the vibes had done their work; several insects were attracted by their girl-honey on the log.

Suddenly, BabySub's wrists came free! She had gotten the ice melted sufficiently to release the key. A few seconds later she had figured how to dismount the dildo, though her first few steps appeared painful. She was walking a little bow-legged.

Now came an interesting part. Nick and I had laid (ahem) a small bet. I said that BabySub would stop to help her sisters, while Nick had bet against that. The winner got a lead part in the punishments for the contest's loser. And for some of the winners, perhaps, as well.

We watched closely as BabySub looked up and down the trail, trying to figure which way to go. She made up her mind, and returned to the first clearing to assist those two in getting free. Seeing the two chatting, she told them to cooperate on melting the ice or they'd be last to return to the beach! Turning, she dashed uptrail past her tormenting place and on, in search of her other two friends.

Looking at Nick, I smiled and offered him double or nothing that BabySub would still get back first. He stared back at me, ("foolish man!) and nodded.

BabySub located the third clearing, and told the two to untie each other's ropes, then to use their hands or mouths to melt the ice. She made another smart decision then; she continued on the trail, as we had done, figuring (I later learned) that we would have taken the safest way.

Following through on that judgement,she ran along the trail and found the fourth clearing. Scanning the area and finding nothing, she turned to continue along the trail. And ran straight into the quicksand pit I'd had placed there.

Seeing this, Nick exclaimed, "Sneaky bastard, aren't you?" I smiled once again, and offered to add a night in bondage as an additional part of the bet. He gawked at me for a moment, his mouth hanging open in surprise. "Darn right, I'll take that bet!" he said, quickly as though I might withdraw the offer.

The first two ladies had, by this time, gotten completely free. 40 yards or so down the trail, following backwards the way they had come up from the beach, they sprung the second trap and fell through the false trail carpet, and fell down into the ten-foot-deep hole. Although the bottom was padded with soft grasses and thick plants, they were a little stunned and took a few minutes to shake off the shock. They immediately started to climb the sides of the hole, and found the ground there soft and crumbling. They had not learned from the exercise at all, as there were at least three ways to get out. They simply had not tried teamwork.

The final two, had gotten out of the ropes and melted the keys out of the ice blocks. Trying their keys on their leg entrapments, they found neither worked! Another case of poor judgement, as I had promised them they could get themselves back to the beach, and thus it was possible. As a matter of fact, two different ways were available to excape; rather, they laid on the log and cried.

Our heroine, BabySub, had stopped to consider how to get out. She knew not to struggle, as that was the reason most people who were killed in quicksand died. Rather, she gently reached down with the toes of one foot, and searched for the bottom. Her reasoning of the problem was clear; no WAY would I allow one of them to die. Sure enough, she found the bamboo ramp under the sand, swung her other foot down, and simply walked out. Ten yards further along, she found a five gallon water jug, with a pump sprayer. She sluiced herself down to wash off the remaining sand and mud, then grabbed one of the smaller bottles along side. Taking a deep drink to restore herself, she resumed jogging along the trail; eyes sharp for any other traps.

As such, she walked out of the jungle on the far side of the beach, swaggered to the cooler, and selected a tropical fruit wine cooler. Draining it in one swallow, she replaced the empty, turned and knelt in front of me.

Nick's jaw dropped. He *hated* bondage. Heh heh heh. Foolish man, eh?

The ladies from the third clearing were next to arrive. They had missed the quicksand and kept on the trail (which saved them being trapped again; I had six more out there). They too offered respect at my knees, and I allowed them to pick any non-alcoholic beverage from the cooler.

It was nearly two hours later that I sent Nick to rescue the first two. Working independently, they still had not figured how to get out. My First Mate crouched at the side of the hole and suggested that one get on the other's shoulders; she would than find the rope at the side of the hole to extricate the other lady. Or, he offered, just dig together in the same side of the pit; soon it would be a ramp up and out. They followed him back, dirty and disgusted.

"Aha!" I cried. "The prodigals return!" The other three laughed a little, but knew it could just as well have been them.

"What did we learn from this, ladies?"

Long silence, as I had told BabySub to keep still. Finally, one of the last two said, "Teamwork, Sir?"

I smiled at her, and took ten spanks off her punishment.

"Exactly, yellowrose. Teamwork. Both the first and the third traps required teamwork.... but ALL of them could be gotten out from because I TOLD you they were escapable. I know you all needed BabySub's help, as she was the only one to use teamwork to escape... along with her common sense.

"First two, you had already escaped using teamwork from BabySub. Yet you did not think of it when trapped again. Third two, again it took outside help. And it took an hour to figure you could trade keys and open the correct locks to go with the keys. Or, you could have simply slid your legs off the ends; they were outside the mounting posts for the log!

"Thus, to the victors go the spoils. BabySub, you will get to pack the chairs and cooler into the boat, and accompany Nick and me back to Sailing Master.
Second two finishers, I will return for you in the boat. You get to row us back to Sailing Master; no motors for you. Last two? You get to swim back to the ship, and no starting until the second two have reached the ship. You'll also get to wash the dirt off in the ocean, while the other three get onboard showers, and BabySub gets hot water. Oh, last two? You have kitchen duty tonight: I expect dinner on the table in 2 hours. Better swim fast!"

By this time, BabySub already had the cooler in the lifeboat, and was kidding the other four, kindly, about losing. We unceremoniously dumped the other four from the beach chairs, and carried them to the boat.

Another fun day. And what promises to be a fun night as well.