A Winning Losing Vacation

Laying inside of you in our cabana in Jamaica, it hardly feels like we just arrived at our vacation site. It feels as if we were made to be right where we are. After talking about getting together for a special trip for what seems like years, we finally arranged an entire week alone. Knowing that our passions needed to be unleashed, we choose a hedonistic vacation package after spending months reviewing the web site and planning our get away. Promising unbridled meeting of all desires and that is just what we intend to do. Our people at home are on their own vacations with friends, so no one expects to hear from us until after the trip.

Lying there, we hatch a plan. I have brought along a deck of cards, which I reach for while still keeping myself inside of your soft walls. The deal we devise is rather simple. Every few hours we will draw for high card. The loser has to do whatever the winner decides; whatever the winner decides. We talk through what this may include and agree, because we know no one here and we will never see them again, that anything goes. We both swear on this as I set the cards aside for now. On top of you, I renew my deep penetration and fill you to your depths very slowly. You can feel my flesh passing through your walls as I slide deeply within you and then equally slowly slide my hard cock back out to the very edge of your lips before plunging back inside again. My solid chest rubs firmly against your breasts and a thin layer of sweat forms between us. My hands reach back to your cheeks and I part you wide to allow deeper access to your sweet pussy. While I continue to fuck you, I massage and grab your ass cheeks and kneed them in my hands causing you to explode repeatedly with earth shattering orgasms. Finally you feel me building inside of you and you can tell that you will soon feel my cum pouring inside of you, so you fuck me harder. I cry out like a caged beast as my orgasm takes me to the brink of passing out on top of you. Exhausted I crash down on top of you, once again staying deeply inside.

An hour later, we awake as a cool breeze blows in from the beach. Ours is a clothing optional beach and we can see from our cabana that many of the couples are taking advantage of it. We kiss and hold one another while looking at the beautiful bodies playing on the beach. I reach over for the cards and lay them on your chest. "Shall we draw?" nervously you agree and reach for a card drawing a 2 as I draw a 3; I win.

My first challenge is a simple of one, but with your natural shyness, that will be a test of your willingness to fulfill your promise. I challenge you to simply open the door, walk to the ocean, past the other couples, singles and staff, wearing nothing at all. Oh, and for a little extra challenge, on the way back from the ocean you have to stare at one couple, checking them out until you pass them by. Your nerves are instantly on edge knowing that this is just the first task.

Boldly, you rise naked from the bed. You realize that you cannot think about it for a second or you will be unable to go through with it. I am instantly in awe of your beautiful body and stare at you as you approach the door. I look loving and lustfully at your butt, legs, incredible hair and your delicious skin as you pull the sliding glass door open and leave the safety of the room. Walking slowly but confidently, you move down the long beach to the ocean, which seems miles away. You can feel the dozens of eyes on you. You can see the stud cabana boys looking you up and down and to your surprise, rather than being horrified, you are completely turned on. As you walk on, you can feel how wet you are becoming and this in turn increases the confidence of your walk until, by the time you reach the surf, every eye on the beach is on you. They all watch as you disappear into the crystal blue ocean. More than anyone, I am stunned by the vision I have just watched.

Moments later you emerge from the water your body glistening and your hair trailing down your spine. Looking ahead, you remember the last part of the bargain. However, to my surprise you decide to push the envelope. As you stroll back to me, you stare lustfully at every couple; every cabana worker, men and women. Your hand occasionally passes over your shaved pussy as you lightly touch yourself practically making people cum just by watching you. Finally, you return to the patio just outside of the room and like a servant to a Greek Goddess I can only bow at your feet. You sit in a high back bamboo chair and parting your legs give me the signal that demands my worship. While everyone can look on, I kneel between your legs and service your sweet pussy.

The first day shot by and we are astounded by the number of different things we have done. Your walk from the beach seemed to have permanently emboldened you. We have had sex in every imaginable way thus far and we have refused each other nothing. We went to bed that night exhausted from all we had done. When we arrived, I was afraid I might push you to hard, but that is clearly not the case. Just before bed we draw cards again, for who will start the next day, again you lose. Seconds, before we drift off to sleep you whisper in my ear, "push my limits tomorrow." We kiss and fall asleep in each other's arms.

In the morning, you awake and can feel that I am not in bed with you. You move to open your eyes, but quickly you feel a hand placed firmly over them. "Open your mouth and he gets it!" Says and angry voice. "Nod your head if you understand what I am saying!" You nod your head with fear. "You are going to do everything we say or things are going to get unpleasant, understand!" Again, you nod, not wanting to see me hurt.

Your head is held down while a blindfold is stretched tightly across your eyes. Feeling the sheets and blanket being torn away and it is at this moment you realize that there is more than one of them. Hands roughly grab at your naked body. They pull on your breasts and despite your efforts to prevent it, the same hands' slip between your legs. They flip you over, and you feel fingers penetrating deeply into your pussy and ass as others tear at your body. "Bitch, I am going to feed you my dick and you are going to suck it like your life depends upon it, because it does!" With that your head is pulled up by your hair and a stiff cock is forced between your lips. You want to gag, you want to escape, but you realize that if you fuck things up it may cost me my life, so you suck him into your mouth. You soon feel another cock pressing against your tight ass and realize that your ass will be the first to be raped. Without hesitation, one of them slams his cock into your taut hole, which almost causes you to cry out, but for the cock in your mouth. Eventually they are moving rhythmically inside of you. One cock buried in the back of your throat and another pressed to the hilt up your ass. Despite fighting the feeling, you soon realize that you are loving the sensations and you move your body with them. "I think this bitch is cumming." Just then, you start to cum; both men pour their loads into your waiting mouth and butt.

Certain that is the end of your abuse, but it is then you realize there is more than two guys in the room. Several powerful arms lift you from the bed and then your ass is lowered onto another stiff dick. As the breath escapes you another mounts on top of you and pushing your legs apart shoves himself as far as possible. His fucking is hard and punishing. He moves so quickly and hard inside your pussy you cannot help but cum repeatedly. Using your arms, you raise and lower yourself onto the cock in your butt, while still keeping, your legs open for the full penetration in your front. Your head is pulled back and a stiff rod is once again pressing against your lips. Opening your mouth, you can feel it slip all the way down your throat. Holding your head he starts to fuck your mouth as if it was a pussy. Once again the momentum builds and cum is pouring in every hole. Your body is completely out of your control and you find yourself having climax after climax.

Again, you are raised from the bed, but this time you are forced onto the ground on all fours. There you find another cock eagerly awaiting you. You lower yourself onto this dick and you can feel that it is much larger than the others and it feels like it is tearing you apart. Once again, you are filled in all three areas, but the enormous tool between your legs captivates your mind. You pound your body up and down on it pushing it into recesses that have never felt this deep of penetration. As you cum repeatedly your pussy is increasingly wet and you are able to slide faster and harder on his big fat dick. His dick swells to an unbelievably larger size and soon it explodes inside you sending all four of you into a massive joint climax. You cry out at the top of your lungs and then pass out from pleasure.

You wake and hour later, your body still sore from the punishment. Opening your eyes you see an empty room except for me sitting in a chair. "Did I forget to mention that your challenge this morning was to satisfy six guys?" I smile warmly at you. For the rest of the morning we swam in the ocean, walked along the beach, and finally took a siesta in our hammock while a cool Jamaican breeze softly rocked us to sleep in each other's arms

When I wake up, you are standing there with the deck of cards in your hands and a naughty smile on your face. We both draw cards and again, I win. "I can't believe I lost again!" "Did you really lose?" I say with a grin. You respond with a blush.

Sitting on the beach not far from us is a beautiful Latino woman sitting all by herself. She has been there for some time and we have not seen whom she is with. She is however, naked on the beach. "Your challenge is simple, you just have to go over to her, sit down next to her so your bodies are touching and stay there for at least 10 minutes talking." Immediately you feel all of your old fears and inhibitions coming back, but realizing you have to be true to your promise you reluctantly walk to her. Approaching her, she looks deeply into your eyes with a knowing smile. "May I sit here?" you ask. She smiles and pats the beach next to her. You sit down next to her and feel your skin brush hers as you go down. You introduce yourself and try to make small talk, but your mind is completely enraptured by the sensation of your soft skin against hers. Despite yourself, both your nipples and your clit respond to this sensation. You suddenly come back to yourself and realize that you have been completely out of it and she is staring at you. Slowly she leans forward, presses her sensual lips to yours, and kisses you softly. It is a feeling you cannot describe, but it is completely intoxicating. Pulling away, she looks embarrassed, "I'm sorry. I've never done that before." Your eyes meet hers and you are drawn into her. Once again, your lips lock, but now much more passionately. You press her to the ground and slide your tongue inside of her mouth. Gently your tongues dance around each other as your hands pass over your bodies. You cannot believe how good this feels and you are hungry for more. You kiss passionately for several minutes. She runs her hand through your hair and rubs your back gently. Laying on top, kissing her with even more fire you press your breasts to hers. Unable to restrain yourself, your hand slides down her body to the soft folds of her silk. Having felt your own for so long you could not have imagined that another's would feels so good. Your fingers slide between her wanting lips as she raises her hips to meet your touch. The warmth between her legs and how sleek her walls are to your touch absorbs you . In a short time, you find yourself hungering even more and you slowly slide down her body. Taking a nipple in your lips you suck her eagerly into your mouth as she lets out and audible sigh. Your hand continues to penetrate inside her and she is now moving to fuck your hand. Having overcome your shyness you move to the next step. Sliding across her warm belly, kissing all the way, you finally slip between her soft, but firm legs. Using your hands to tenderly part her legs you place a soft warm kiss on her clit. The taste is wonderful and you can now understand why I enjoy going down on you so much. Your tongue explores every inch of her silk and you are completely lost in the experience. You flick her clit as your hands find their way to entering her. She too is burning with a new desire. She pulls away from you for a brief second to pull your pussy on top of her face in 69. You feel her tongue frantically diving into you and the gentle brush strokes across your clit. You are both lost in your magic world and before long you are both caught in a torrent of orgasmic bliss from each other's coaxing. There is no pause before you both immediately start again. Both of your hands are filling your pussies and asses and you are fucking each other with zest relishing the other's repeated orgasms and cries of pleasure. Finally, after what seems like hours, you are both too exhausted to continue. Rolling to her side you begin to kiss tenderly.

You are both oblivious to the number of people who have just watched you and frankly, you couldn't care less. Rising, you take her hand and lead her past the gaped mouth spectators to our room. We are introduced before you stride across the room to grab the cards. We draw, but this time I lose. You look to your new lover, "What would you like to see him do?"

She smiles, "I have always been curious to see what men do when they masturbate". You nod at me, and I realize this is now my obligation. I was sitting on the bed, but now I move to stand in front of the couch were you are sitting in each other's arms. I am wearing nothing but a towel. Both of your hands move between the folds of the cloth to my quickly stiffening member. Your soft strokes tantalize me and I lean back with my eyes closed. She reaches her hand out to mine and places it on my cock. I look down at the two of you as you lean back into the couch to watch me. Slowly, I start to stroke my stiff dick and run my hands from the top of the shaft to the base. My breathing gets deeper as I stroke my self firmly. You can see the muscle in my thighs and stomach tightening and beads of sweat form on my chest and forehead. I continue to pull on my dick, now with my hand on my back for balance. The sweat has made my strokes easier and more even. I am rubbing myself with passion. You can tell it will not be long now.

Meanwhile, her hand slips between your legs and she is rubbing your clit while absorbed with watching my dick. You can tell I am getting close to cumming, when suddenly you stop me. "I have a different idea."

You move her to the arm of the chair and spread her legs. Simultaneously, you spread your legs on the couch raising your butt in the air, inviting me to fuck you. Obliging, I slip my sensitized dick into your waiting hole. My movements form a pattern, which you quickly duplicate on her tasty pussy. As I stroke inside of you, you slide your tongue along her lips to her clit and then back again as I withdraw.

"What are you doing?" says a clearly shocked voice behind us. We all stop what we are doing and see a lean attractive man with a French accent standing by our open door with his hands on his hips. He is obviously upset and it looks as if the mood will be spoiled. However, much like you earlier, she is emboldened by her sex with you and she moves quickly across the room to her knees in front of him. Stunned by his wife's metamorphosis he doesn't even try to stop her as she rips his shorts off and hungrily takes his cock into her mouth. You slide off the couch and join her on the floor in front of his dick, where the two of you work together to suck him off. While she takes him in her mouth your tongue drags along his balls to his butt and all around. He is in heaven. Taking a break, you look to me. "I think you have a promise to fulfill, don't you?" I am embarrassed to do it with another guy in the room, but I did promise, so I go back to work on my own dick. The two of you take turns pulling him into your mouths and occasionally sharing him at the same time. It is a very short time before he is pouring his cum onto your lips as you kiss her. Turning around you can see I am struck by the entire action as I cum across my chest in a powerful orgasm. You rise and move back to me. You lay on top of my cum soaked body. Holding each other, we don't even notice when the other couple departs.

Eventually, we rise from couch to shower before bed. There we somehow are able to make love again. It is much different as we kiss and hold each other tight while feeling each other's orgasms. The passion between us is transcendent. Exhausted we pour ourselves into the bed. Just before lights out, we draw cards one more time for who starts tomorrow. I lose. We fall asleep with a kiss not believing this was only the second day.