Carribean Sail

Like a wave approaching the shore, my inner sex suddenly gathered and swelled to a full peak. First broad and pervasive, the tension sharpened as the peak of my next orgasm rolled toward the shore of my pubic bone. With every stroke, I could hear the water slap against the hull just as I heard his groin and his balls slap the opening of my pussy. That orgasmic wave rolled forward, curling but holding off on its break- then slam! It hit me full force just as his entire weight slammed into me with one last thrust that lifted me forward as it drove me flat to the deck. His cock convulsed, my pussy tightened with wave after wave of contractions, and his flood of cum poured hot and flowed into every crevice of my opening.

As I came back to my senses, I could feel the cum spilling out of my pussy and knew it was puddling on the deck beneath my ass. He was groaning and sweating and obviously enjoying the results of his pillage. But he did not collapse on me, laying head to those huge tits that had enticed him into immediate fucking. No, he rocked back on his heels, and smiling slightly, made it obvious that he was saving some for later enjoyment.

Meanwhile, the men at the wheel and lines were torn between enjoying the show and wanting to play. Their eyes were burning, their dicks rigid, and their time was soon to come. Or cum.

The captain walked back to the wheel. His dick, dripping slightly with my pussy juices and his own cum, had receded into a half-erect conqueror. He took the wheel without a word, and began to bring the boat about, heading toward a lush, green island.

I could see that the other two were not going to be put off for long. They wanted their turn to enjoy my marvelous mams, and any other body parts they fancied.

As the wind dropped in the lee of the island, the boat slowed to a crawl. I could see the reefs below- 20 feet, 15 feet, 10. I stood at the side of the deck, first facing all three men so they could again enjoy the sway of my boobs. The nipples that had been bitten, teased, flicked and then became the source of my 1st orgasm, were still fully engorged. Even my shadow, splayed out on the deck at my feet, had visible nipples, so large were they still.

But none of the men had really seen and appreciated one of my other assets- ass, to be specific. Used to posing both nude and clothed, I slowly turned with one hand on a mast-stay. I held the turn, inviting them to closely inspect the way my ass swelled plumply from my thighs, then curved back in perfect moons of ass-flesh to dip gently back to my spine. Letting them enjoy the profile, I bent at the hips as I completed my turn away from them. My pussy was still wet, still had cum left by the captain dripping from it, as well as my own juices from the orgasm that had swept over me like a tsunami and it was all running down the insides of my thighs. Sometimes sloppy seconds was as sexy as a virgin- that was evident on the men's faces. But I had other ideas.

My pussy spread before them, my ass rose above it, and I held the pose long enough for them to appreciate exactly what they were going to get. Then smoothly I straightened, and dove into the sea.

As I surfaced, the boat lost way quickly as the captain dropped all the sails except the small jib. I rose high enough out of the water to again remind them that they were viewing world-class tits, and arched my back to float with those tits gloriously displayed. The warm water caressed my legs and flowed between my thighs, washing away the cum and sweat that lingered there. Although I knew that I'd be covered in both before our island adventure was played out, I wanted to begin the next scene refreshed in many ways. And the sea always did that for me.

I stroked along effortlessly, matching the slow progress of the boat into the sheltered cove. I could only imagine that the sight of my tits, ass and body displayed below them, and the momentary arrival at our destination with the promise of using those assets for their ultimate pleasure, was raising the crew's arousal to new heights. At least, I hoped so. I wanted to see them fully displayed, before offering my body as their toy.

My breasts bobbed just below the surface of the water as I rotated to an upright position and positioned myself parallel to the boat. The sails were being dropped, and the men moved quickly at the captain's orders, securing lines and getting ready to drop anchor. I could see that all three of them were not unaware of the nearness of my body and that they still had a small portion of their minds on what they were going to do to me, even as the boat occupied the majority of their consciousness. But the quick glances they continued to send in my direction told me that they had merely postponed the full enjoyment of sex with me.

The efforts to drop anchor were distracting them from putting their full attention on my body, their cocks and the plans they were forming to point those cocks directly at their target and follow them into the depths of my body. No longer as rigid and engorged as when they watched the captain fuck me, their dicks were still obviously ready to be re-stimulated from their semi-erect status. And I was enjoying the fact that, as I bobbed in the shallow water, the physical exertion that the boat demanded meant that both captain and crew were putting on a display of muscled flesh that I appreciated. Broad shoulders strained under the efforts of pulling in lines. Long arms showed a surprising amount of muscle as the sails were dropped to the deck and secured. And the chest that had spread above me just a short time ago as he plunged his dick into me was now rippling as he maneuvered the wheel to set the anchor and come into the wind. I appreciated the moments of being able to concentrate on these three strong and well-built bodies, without the distraction of their full-blown hard-ons.

With a smile, I lay back and floated, my tits making islands afloat in the sea. The shore-break just ahead moved my body in gentle up and down rhythm, bouncing and jiggling my boobs as they reached for the sky. Enjoying the sensation for myself, regardless of whether it was being watched and enjoyed, I could feel the lovely warmth of the sun spreading from my exposed tits and shoulders to the inner reaches of my sex. I began to move with more purpose, without conscious thought but moving by instinct towards the lovely beach that beckoned me. The warmth of sun, sand and rock... that was the next sensation I craved.

Still face up in the very gentle surf, I opened my legs and stretched them for a few frog kicks. I was barely aware of the men at this point, and they were still busy with the necessary precautions required for leaving a boat at anchor. But at some level of consciousness, both I and they were aware that their eyes had traveled to the split between my legs. I was showing a great deal of my shaved pussy, and they were enjoying it. But for the next few minutes, at least, they were required to stay with the boat and complete its secure mooring, while I was free to indulge in sun-worship.

I could feel the sand rising up, and lowering my legs, I stood in the knee-deep surf. Gravity took over from the support of the sea, and the weight of my tits caused them to sag a bit, swaying and bouncing as I took a few steps toward the beach. Again, I could feel how much of a distraction my big titties were causing on the deck. So rather than confound the crew with the need to fuck me NOW, I swiveled and let them view my tight ass and long legs as I found my footing and looked around.

The light sand curved around the cove, and sloped gently upward to the line of tropical trees. But off to my left about 20 feet, the smooth and flattened top of a rock reef joined the sand. I could see it was well-worn, not only by the sea but by eons of sea winds and it looked to be a perfect spot to lay back and soak up sun.

On close examination, the rock was indeed smoothed, gently curving and cupped gently to form a sun-filled hollow. Although tide pools were scattered across its base, the upper section of the rock formation obviously was no longer submerged at normal high tides, and therefore held no water pockets. I lowered my ass to its warmth, finding a spot where I could lay almost flat. It wasn't a place I could sunbathe all day, but there was no way I'd be left for mere sunbathing for very long. And it made a perfect place to absorb heat that would make me as flexible as those horny seamen were going to expect in a very short time.

As I lay back onto the warm rock, I thought about what had brought me here. This wasn't the way I spent most days of the year- actually being fucked by the many men who crossed my path and wondered just what it would be like to engulf the nipples they were examining through my clothes with their mouths, or fantasizing just how deep they would drive their dicks into the ass I was hinting at with the tight skirt of my cocktail uniform. I'd been hired to serve drinks to tourists when I arrived last year. Hired because my tits were huge and I didn't mind showing those tourists most of my real estate, especially since the tips were usually right in line with the size of my tits. Hired because when I walked, my hips would swivel and sway, entrancing any straight man in the area with thoughts of conquering that ass with his lance of a dick. And hired because I could flash a 1000-watt smile that promised at least the remote possibility that this might happen, while always knowing that they saw only the outside of this body and hadn't a thought that there might be more within it than a receptacle for their cum. And for the ability to live here, to bring in this kind of money- I could disappear into their fantasies.

Last night, I'd been singled out for private table service by the man I now know as Captain, the man who'd fucked me as we sailed the azure waters of the Caribbean. He'd been to the bar before, always tracking me with his eyes and doing the same mental x-ray vision as all the other men as he watched me walk, bend and serve. I knew he was a tit-man, who appreciated the size, shape and bouncy natural firmness of my jugs. He had always tipped me well, often tucking his bills into the deep-v neckline of my uniform shirt. Just like countless other men, he had the audacity to swipe a finger the last inch under the scoop of thin, tight tee-shirt, that inch that just barely covered the brown aureola of my nipples. As always, whether I wanted it to or not, my nipples would react to a touch by becoming even more prominent and engorged. So not only did the man who tipped me get a thrill from seeing my nipples react to his touch, the rest of my customers were treated to buds the size of bottle caps poking from above the shelf-bra I wore to support my boobs, threatening to break through the tissue-thin material. The tips were self-sustaining!

The captain came into the bar last night with something obviously on his mind. I was a little worried as he first checked me out with obvious enjoyment and design, then moved to talk to my manager. I was afraid he was trying to arrange a "date" through my manager- and I was not a whore. My every move through the night might suggest that any man in that bar had the ability to fuck me silly if the situation was right. That was my livelihood- generating tips from hopes. And indeed, there were men from every walk of life that had tripped that certain something within me, and I had let them buy me a last drink at closing time, and then taken them on the trip of their fantasies. But that was my choice, not my occupation.

But I didn't need to worry. My manager quickly approached me, pulling me aside to explain. This man had rented the upstairs Sky Room, a private space that was open to the sky and overlooked the crowd below. We all knew it was heavily monitored by cameras, required by law and frequently checked by the local police, so while a lot of teasing and touching was common there between both customers and the waitresses, no actual fucking was going to happen on site. And as part of the "rental", the man was required to cover my nightly tip average, so I'd be taking on a single customer for the next hour or so, giving him my every attention short of swallowing his dick or spreading my pussy for him. And I'd be well-paid, maybe even earning a bonus.

Knowing he was a big admirer of my boobs, I ducked into the bathroom and adjusted my bra to make sure my nipples were completely free from any fabric except the tee-shirt. I pinched them repeatedly to bring them up to full and hard points then pulled the scooped neck of the tee-shirt down so it exposed the tops of the brown circles. I turned on my biggest smile, in case he looked above the level of my chest, and adjusted my Lycra skirt so it stretched tightly across my ass and hips, ending just below the curve where my ass met my thighs.

Emerging from the bathroom, I picked up a special tray of finger-food that was complementary to the Sky Room. I didn't have to worry about drinks- the Sky Room had a full bar within it. Balancing the tray meant lifting my arms, pointing my barely-covered boobs to the sky and bouncing them as I walked. I could see many eyes following me, but most intense was the gaze of the captain.

He had not preceded me- no, he was going to follow me up the stairs. Smart man- he knew he'd get the best view of my rounded ass cheeks straining the stretch of the skirt. I smiled knowingly, and started the show- walking with hips swaying, boobs bouncing and the shadow below the curve of my ass enticingly peeking out as I climbed.

I reached the top of the stairs, placed the tray on the table, and turned to reach out and pull him my way by the belt atop his tight jeans. I pulled him close alongside me, brushing my tits across his nice chest as I guided him to the sofa. I'd done this before, so I knew just how much to tease to elicit the best tips without winding up under his hips with his dick grinding into one of my holes. I pushed him gently to the sofa, straddled him and hovered a few inches above the growing lump in his jeans. Bending down to almost display my boobs, giving him a huge view down the slopes of my cleavage, I asked what he'd like to drink.

To my surprise, he told me he had a business proposition for me, not a sexual one, or at least not a sexual one NOW.

I fixed him a drink, and again bent deeply in front of him to deliver it. He swiped a finger into the barely-there cup of my uplifting bra, immediately finding and teasing the nipple. I expected that he'd delve further into the flesh displayed for him, but instead, he gave me a slightly rueful grin, and pulled me down onto his lap. So perched on his lap, a few inches from the bulge in his jeans, he proceeded to lay out his business proposal.

It seemed that he was about to develop a very special resort on a nearby, currently deserted island. This resort would cater exclusively to gentlemen who could pay handsomely for their every wish to be fulfilled, in a setting both beautiful and completely private. He would be providing the finest in food and drink, prepared on the island by talented chefs and bartenders who were never seen. The accommodations would be simple but luxurious, calming and relaxing the clients with sensuous textures and colors. Service would be silent and invisible. But of course, some pleasures and wishes would only be satisfied by women who were beautiful, sexually inviting and available, and tantalizingly real.

The man had been watching me, he said. He understood that my presence in the bar and on the beaches was a persona, but that was exactly what he wanted. Women who would disappear into personas, not attached to their own personality but who would enthusiastically entice his clients and fulfill their wishes. Those wishes might be very simple: Sex. Often. Hard or soft. The client was the boss. Or the wishes might be complex: multiple women to service him, or one who he and his associates would use together, scenarios to enact that heightened the sexual tension and awareness.

He felt I could provide this personally, and more important, identify other women who met his standards and needs. No, he was not asking me to be a madam for a whorehouse- quite the contrary. He was asking me to partner with him in making this resort the most closely held secret success, the place where the most wealthy and exclusive clients would enjoy their oddest or most basic fantasies, and would pay us beyond imagining to make that happen.

The women would need my personal stamp of approval, ensuring that they met the highest standards of beauty and body. They would not be "professionals". Instead, they could come and go at their pleasure, but they would never know just where this resort was. No cameras, recordings, internet connections- they would be encapsulated from the outside world. It would be as imaginary as their personas and the men's fantasies. No one would ever prove it was more than a daydream or a wet dream.

Our agreement would be put on paper as a completely different venture, since secrecy was necessary at every level. However, the real agreement would be between the two of us. Tipping me backwards to thrust my tits into the air, he pulled me back against his swollen cock. Knowing that we were being watched without any sound being recorded, he rubbed my hip against his jeans-clad dick, just as many customers in this situation did. Admiring my tits almost spilling out of the sheer tee-shirt and shelf bra that did not contain my darkened areolas, he held me arched on his lap with one hand while the other dipped into the overflowing boob-flesh. Easily, he scooped a tit free of its support and covering, rubbing the hardened nub between his fingers. Sharply, he pinched my nipple, making me yelp and groan at the same time, as pain shot down my boob and excitement swelled in my pussy. Twisting, pinching, pulling, just hard enough, he pressed the limits of what was allowed in the private room. But out of ear-shot of the security force (who were probably getting off on watching my tits and the action he was getting out of them), he was describing exactly what he was going to do after hours, to seal our bargain.

"I know you're the right one to partner with. You'll be the star, the one every man who sets foot on the island will want to fuck every way he can think of. He can have his fill of any of the girls you bring out. But only you will choose who you'll fuck, and how many you'll fuck together, and how often, and where you'll do it. If you want, you can fuck 5 guys on a stage at midnight. If you want, you can fuck me while they all watch you take it up your ass. But if you want, you can tease them from the moment they set eyes on you, and never let them touch you. You can choose, and the more exclusive you are, the better they pay us."

"You are agreeing to become a very rich woman, and to help make me a very rich man. The only fucking that I will require from you in this whole venture is that tonight, when you choose to leave this bar, you will fuck me until neither of us can give one more orgasm. You will fuck me however I choose to put it in you. You will prove to me that you are my equal in business and in sex, but that you will choose to be my slave. We will fuck until morning and beyond, and when we're done, we're partners. And future fucking- well, that is up to you."

He didn't even finish the bottle of Reposado that I'd served him. Not much more was said that night, and the private room merely became our foreplay. He was a benevolent master, but he was my sexual master that night and since.

The sun was warming my entire body as the heat from the rock seeped through me, and as the heat in my pussy built just thinking about that night. He proved to be better than his word. I have no idea how many orgasms I had before we were both completely spent. I know his cum slathered my pussy, my tits, my mouth and my ass, and he fucked me both hard and gently. My ass was his for penetrating with his big dick, and for slapping with those calloused hands that worked the lines and tiller. My tits were covered with his teeth marks, and my nipples were bright red from being sucked, slapped and pulled. All this I remembered as I lay there on the beach. And my pussy flowed with juices at the memories.