Three Mature Friends and a Week Without Rules in the Caribbean
Pilar, my sister-in-law, had divorced a few months earlier and couldn’t seem to get back on her feet. She was sad, irritable, and having very little luck meeting anyone new, and I, who had always considered her an attractive woman, couldn’t help looking at her with a hint of lust I preferred to keep to myself. One night, during one of those dinners they called “therapeutic,” she convinced my wife, Daniela, and Sonia, her lifelong friend, to do something crazy: the three of them would leave for a week in the Caribbean, taking advantage of a last-minute bargain.
Despite the rush, they booked it with barely five days’ notice. They packed for that specific kind of experience and, with almost no time to think about it, found themselves there. They didn’t have many goals beyond the obvious one. When I asked Daniela what they expected from the trip, she looked at me with half a smile and said:
—I’d probably better tell you when I get back.
And she told me when she got back. Almost everything.
***
They had no trouble getting started. They arrived on the first day just in time for dinner and, instead of going to bed early, went down to the beach bar for a walk. They were almost in costume: Daniela and Sonia in gauzy dresses that barely weighed anything, with delicate sandals that made their legs look longer; Pilar in short shorts and a top that left no doubt about the reason for the trip. It didn’t take long for them to be surrounded by local boys, young men who moved as if rhythm were built into their bodies, and among whom it was possible to make a calm first selection.
They were determined, but they needed two mojitos to shake off the embarrassment that still tied them to their real lives, their jobs, and their surnames. The alcohol did the rest. Within minutes, they were dancing from hand to hand with those fun, sturdy young men. The women were around forty-three; not one of the boys was over twenty-two.
They had never imagined it would be so easy. They danced, were caressed with a brazenness they permitted amid laughter, and in less than an hour each had picked out her first trophy. Sonia, curious and shameless, slipped her hand inside her boy’s swim trunks and pulled him out with her fist closed, laughing as she gauged the weight of his dark cock, without fully withdrawing her arm, squeezing it against her thigh while she kept dancing. Pilar had talked too much and ended up sitting on a stool with her legs apart, letting a boy kiss her neck while he had already slipped his hand inside her shorts and was rubbing her pussy through the fabric of her panties. Daniela, trying to maintain her composure, kept telling a broad-backed young man that she only wanted to dance, while he wrapped her in his arms and pressed his hard cock against her ass from behind.
That first night, my wife ended up in her room with that boy. As soon as they closed the door, he yanked her gauzy dress over her head and pushed her facedown onto the bed. Daniela didn’t even ask for a moment. She stayed on all fours, her panties around her knees, while the young man lowered his trunks and showed her for the first time the long, brown cock he had been promising her on the dance floor all night. He put it in her hand, and she sucked it for a few seconds without taking her eyes off him, until she left it glistening with saliva. Then he grabbed her by the hips and drove his cock all the way into her with a single thrust, without gentleness, and Daniela came almost a minute later, biting the pillow so she wouldn’t wake the entire hotel. He kept fucking her like that, on all fours, for more than half an hour, until he squeezed her buttocks against his groin and emptied his cum inside her with a hoarse moan. Sonia settled for less, as she herself explained to me afterward without the slightest embarrassment: she took her boy into a bathroom at the beach bar, opened his trunks, knelt on the wet tiles, and sucked his cock until he came in her mouth, swallowing all his semen without spitting out a drop. And Pilar, too loaded on rum, failed on her first attempt and made it to bed staggering and laughing her head off, alone.
***
They woke up late. The time change, the journey, and the mojitos had taken their toll, and they didn’t go down to the beach until nearly noon. Before that, Sonia gave them a gift with all the mischief in the world: two minuscule swimsuits, so tiny that they were forced to protest and laugh in equal measure before putting them on. They covered so little that they decided to go out anyway, delighted by the provocation.
As expected, it didn’t take long for them to make friends with the locals. Lying on their loungers, they were flanked by three golden-skinned, well-built men, clearly regulars on that shore and of that kind of tourist. Each of them was equally happy to play with any of the women: all three were European prey, explicit and pleasing to the eye. After the ceremony of the first cocktail came the predictable sunscreen stage, which provoked nervous laughter and knowing glances between them. Those men’s hands kneaded breasts over the swimsuits under the pretext of applying lotion, tugging at the triangles until the nipples were exposed for an instant before covering them again, and not one of the three women moved a single hand away.
They still hadn’t learned to synchronize the pace of their conquests. They didn’t know how long each man would last. They entered the warm water slowly, accompanied, and the boys managed to remain calm so as not to seem eager while deploying their full arsenal. A few yards apart, each couple began testing the waters among the waves.
Daniela had little trouble slipping off her bikini and letting him feel her body against his beneath the water. The boy buried his fingers in her pussy right there, with people passing by on floats ten yards away, and she clung to his neck as she let him fuck her first with two fingers and then with three, the warm water rocking them. When she felt his hard cock driving between her thighs, she moved her thong aside and let him slip it inside her like that, standing up, her legs wrapped around his waist, the sea concealing what they were doing. She came biting his shoulder, silently, her teeth clenched. Sonia tangled with the oldest of the three: she turned her back, grabbed a buoy, and let him penetrate her from behind while she laughed under her breath. And Pilar, one step behind her friends, began kissing the youngest boy right on the lounger; five minutes later, the two of them disappeared toward the room.
That afternoon, Daniela confessed to me between laughs, my sister-in-law more than made up for the ground she had lost on the first night. As soon as they entered the room, Pilar knelt in front of the boy, pulled down his trunks, and took his cock all the way into her mouth, coughing a little before getting used to it. She sucked him with a hunger she had been building up for months, without using her hands, burying his cock down her throat, spitting strands of saliva onto his balls and massaging them with her tongue. When the boy lifted her, he laid her on her back on the bed, spread her legs, and ate her pussy until he made her tremble twice. Then he fucked her first missionary-style, very deep, with her legs over his shoulders; afterward he put her astride him and let her ride until Pilar came, dripping all over him; and they finished on all fours, with him spanking her ass until it was red and finally unloading his semen onto her lower back, in a long, thick stream that ran down over her buttocks.
My wife and Sonia wanted to enjoy the sun a little longer. Three cocktails later, their skin glowing, they left the sand with their two companions and went up to the same room. They got into the large bathtub and there, first with their original partners, let the men take turns eating their pussies, sitting on the edge with their legs spread, and then, without much ceremony, they exchanged men. Daniela ended up riding Sonia’s boy while Sonia sucked hers a few inches away. They looked each other in the eyes amid laughter and moans, touching each other’s breasts as they were fucked at the same time. They came out onto the bed dripping with water and semen, spread their legs almost simultaneously, and received the two boys again, now at the same time, two couples on the same enormous bed, with the men’s cum landing minutes later on their breasts and bellies. At nightfall, exhausted, they called Pilar. The six of them had dinner together. And that night they went back to bed with the boys in a calmer, almost tender way, until they fell asleep with company.
The funniest part—I thought when she told me—was the photo.
Daniela had taken a photo of her lover asleep on his back, his cock still glistening as it rested against his thigh, and shared it in the three-woman group chat like a trophy of war. The next morning, Sonia, always the practical one, took charge of saying goodbye to the boys and thanking them for their services with one last quick blowjob for each of them in the hallway, holding back their laughter, before sending them to the elevator.
***
On the third day, I received a message. A photo of Daniela wrapped in a towel, smiling, and a brief sentence: “I’m having fun.” Nothing more. What she didn’t tell me until the end was what happened that afternoon.
They arranged an excursion with a guide and ended up scuba diving in a reef area they called the Aquarium. When they came out of the water, they already had dinner plans with the instructor and two of his friends. The guide, Joost, was a Dutchman of about sixty, weathered by the sun, a genuine old sea dog. His friends were Théo, a Caribbean man, and a local boy everyone called Yago. They had dinner on Joost’s boat deck, where everything felt simple: they could spend the whole day in a sarong, bikini, and sandals and still feel like queens.
Daniela fell hard for Théo’s rough skin, which, by brushing her hand and thigh, had gradually drawn her toward his shoulder without her quite noticing. Sonia became infatuated with the local boy. Pilar, who openly admitted to her weakness, chose the tallest Caribbean man. The rum flowed without restraint, and everything accelerated.
Joost proposed a game to my wife that he called tantric. They sat facing each other, held hands, and very slowly began stroking each other’s forearms, necks, and earlobes, moving only barely toward the breasts. So slowly, so subtly, that Daniela swore to me she had nearly come from that almost invisible touch alone. When she opened her eyes, the Dutchman was still serene, calm, but he was looking at her in a way that left no room for doubt. She couldn’t stand it any longer and asked him to stop playing.
The Dutchman opened her legs right there on the deck, moved her bikini aside, and slowly licked her pussy, with the same patience he had shown while caressing her arms, while Théo untied her bra and sucked her breasts. Daniela came with Joost’s tongue inside her, gripping his head with both hands, and as soon as she recovered she got on all fours to suck the Caribbean man’s cock while the Dutchman positioned himself behind her and pushed his into her wet pussy. They fucked her like that for quite a while, taking turns, then putting her on her back so Théo could penetrate her while she kept eating Joost’s cock. They ended with both men emptying themselves on her face and breasts almost simultaneously, while she licked the semen from the corners of her mouth.
Meanwhile, Sonia, who was enjoying it more every day, gave herself to Yago with an intensity the boy would remember for months. She took him to the bow, yanked off his trunks, and rode him astride some coils of rope, moving her ass with hungry fury, whispering insults as she drove his cock all the way into her. Yago tried to turn her around so he could fuck her, but she wouldn’t let him stand up until she had come twice on top of him. Only then did she turn facedown and ask him to put it in her ass, and the boy obeyed, slowly at first and then deeply, until he unloaded his cum inside her and left her trembling on the deck. Laughing, and almost at dawn, they persuaded Joost to take them back to the hotel. The three women entered celebrating their personal tally: three days, three men each. The hunt was going wonderfully.
***
They decided to take the fourth day easy. Spa, massage, rest. Pilar and Daniela relaxed in the hands of two experienced female masseuses, but Sonia, with her usual mischief, chose a young male masseur. In barely fifteen minutes, and with all the encouragement she gave him—opening her legs every time he ran his hands over her thighs, letting the oil trickle down her shaved pussy until the boy couldn’t help caressing her there—the masseur was on the verge of certain dismissal, whispering to her not to make any noise while he buried three fingers inside her, making her press her lips against the back of the table so she wouldn’t scream. Sonia then invited him to her room, opened the door naked, pushed him onto the bed, lowered his trousers, and sat on his cock without preamble. She fucked him until he came inside the condom, gave him twenty dollars, and the two of them were, according to her, equally satisfied with the treatment.
When she returned to her friends, she found them already surrendered to the mojitos being served nonstop beside the pool. They started chatting with four Australian students who had no idea how lucky they were. Within a couple of hours, two of them were with Pilar, while Daniela and Sonia divided the other two between them, athletic and bewildered by so much frankness.
Pilar took the two Australians to her room and positioned herself between them on her knees, sucking their cocks in turn, moving from one mouth to the other until she left them hard as rocks. Then she lay on her back, one man eating her pussy while the other filled her mouth with his cock, and afterward they positioned themselves both at once: one beneath her, with her riding him, and the other behind her, taking her from the ass. Pilar came three times, screaming without restraint, and both boys ended by unloading their semen all over her, one on her breasts and the other on her belly.
My wife, who had completely let herself go, directed the scene in Sonia’s room with a new authority, sitting on her man’s face and making him pleasure her for quite a while while she leaned over to suck Sonia’s boy’s cock. She rubbed her pussy over the Australian’s mouth until she came twice on his tongue, without letting him breathe. Then she turned around, drove his cock all the way inside her, and rode him while looking him in the eyes, as Sonia did the same with the other man a yard away. They finished by swapping again, sucking each other’s cum from the men over the bed, semen running down their chins, laughing without the slightest shame. That night the three women slept like angels, exhausted and completely satisfied.
***
On the fifth day, eating breakfast at their leisure, they laughed as they reviewed their exploits and promised each other a gentler day at the beach. The good intention didn’t last long. Joost reappeared after dropping off some clients and invited Daniela for a ride in his jeep. She hesitated, but her friends literally pushed her out the door. She put on a pair of Bermuda shorts and a T-shirt with nothing underneath and climbed into the vehicle.
The ride didn’t go very far. A couple of hours later, after traveling along lush roads, my wife was with the Dutchman beside an idyllic river, in the back seat of the jeep. She didn’t care; she wasn’t ashamed. There she was a free woman, almost a character in someone else’s fantasy. As soon as Joost stopped the engine, she took off her T-shirt and Bermuda shorts and lay naked on the hot leather, legs spread, waiting. He ate her pussy first, for a long time, until he made her come once with his mouth. Then he lowered his trousers and showed her the thick cock she remembered from the boat deck. She sucked him on her knees, biting the edge of the seat to keep her balance, taking almost the entire shaft into her mouth until she gagged. She held on to the front seats while he held her from behind and whispered words in Dutch that she couldn’t understand but that aroused her. He entered her deeply, without a condom, fucking her wet pussy for quite a while, and then asked for her ass. Daniela spread her buttocks with her own hands, without hesitation. It hurt for a moment, and then she relaxed and came again, twice, with the Dutchman’s cock buried deep in her asshole. She didn’t want him to stop.
Pilar, for her part, had run into the boy from the first night, the one whose attempt had been cut short, and bluntly asked him to suggest something she had never done before. The young man called two friends, and in less than an hour Pilar was on the floor of the room with three cocks around her face, sucking them in turn, letting six hands paw her at once, her torn panties lying beside the door. All three fucked her one after another without a break, and she begged for more and more. They ended by coming all over her, on her face and breasts, and Pilar began to laugh with semen running down her chest, whispering that she had never done anything like that and wanted to do it again. Sonia, left alone, returned to the spa and easily reclaimed her masseur, who earned another twenty dollars with the same enthusiasm as the day before, this time fucking her against the locker-room tiles, with her gripping the towel rail while he drove his cock into her from behind.
When Daniela had coverage again, she called her friends to tell them not to worry, that Joost was a gentleman and a great lover. What she didn’t tell them—and told me almost in a whisper—was that Théo, the Caribbean man, appeared shortly afterward as well, and that the two men kept her entertained until well into the afternoon. They bent her over the jeep’s hood, one taking her from the front and the other sucking her breasts; afterward they sat her on Théo, the Caribbean man’s cock buried in her pussy, while Joost positioned himself behind her and put his into her ass. Double-penetrated, biting the Dutchman’s shoulder, with sweat and semen mingling on her skin while the river flowed a few yards away and she no longer cared who might see her, Daniela came again and again, screaming in a language none of the three men could understand.
***
They woke on the last day almost sadly. They packed for the airport, trying to review everything that had happened, even calculating whether they still had time for something else. Pilar, of course, felt like a different woman; she had left the sadness of her divorce on that island. Daniela had opened doors she no longer intended to close. And Sonia, true to herself, was thinking only about the next trip.
Just before boarding, I received my wife’s final message:
—I don’t think I can tell you everything. But it’s been very, very intense.
She told me. Not everything, I suppose, but enough for that week to change, without either of us saying it aloud, the way we looked at each other from then on.
