Island Vacation Ch. 03

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Jen and Tim learn about their new friends.
5.5k words
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Part 3 of the 19 part series

Updated 12/14/2023
Created 06/25/2023
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"So, tell me. Is that what I have to look forward to every morning?" smiled Jen as she sipped her second cup of coffee.

Tim shrugged and raised his eyebrows playfully. "Who knows? I've been a little more stimulated than usual for the last 24 hours. So, maybe... if the stimulation continues..."

There was a fair amount of truth in his playful words. Since they had arrived on the island yesterday afternoon he had cum 4 times. Hard. That was more sex than he had seen in any week of at least the last seven years. Frankly, he was a little surprised that he had been "up" for the task each time. And he was even more surprised that Jen had been that willing. Or that "stimulating". Even this morning she was dressed in a way that made him think twice about his golf date: a simple white blouse with buttons down the front, tied just under her breasts and open enough at the top to hint at her cleavage, red shorts that hugged her lean hips and those long, tanned legs that he hardly remembered ever seeing before.

As he took in the sight he heard a long, low whistle behind him. "Man, are you sure you want to turn her loose on this island looking like that?" It was Mickey, who was quickly scolded by his wife.

"Behave yourself! She looks amazing and Tim knows that she can certainly take care of herself."

"Amazing, indeed," agreed Mickey. "Tim, you are one lucky man!"

"I can't disagree with you."

Jen blushed as the threesome made a small fuss over her. She quickly tried to change the conversation. "So, where are you two off to this morning?"

"I thought I'd take your husband over to my favorite course," Mickey replied. "I've been playing it for years, so I hope to have an advantage over him there."

"I don't get to play that much these days," said Tim, "so I don't think I'm going to be much competition for you."

Mickey looked long at Jen before answering. "No, I don't suppose you can get out that much, with so many other things to do."

"Mickey!" There was a certain playfulness in Kate's voice as she tried to reign her husband in.

"Okay, Okay. Tim, kiss your wife -- and your money -- goodbye. Let's go play golf."

.......................................................

"I hope Mickey's teasing doesn't bother you, Jen. He's mostly harmless, but sometimes he pushes the boundaries of good taste. Especially when we're here."

"It's fine. I like a sense of humor. And, to be honest, I'm sort of pushing some boundaries myself this week," Jen confided.

The two climbed into the back seat of a taxi that had been summoned for them by a hotel porter.

"Times Square, please," said Kate. The driver smiled and pulled the car quickly away from the curb.

"Times Square?" Kate was confused.

"Yep. Believe it or not, it's a little shopping area just down the street. No neon signs or massive video screens. Just some fun little shops. So, tell me about those boundaries."

"I don't know. It's kind of silly, I guess. Our lives are just so... normal. When we're at home we're all about the kids, and work, and school stuff, and church and being responsible, you know?" Somehow, Jen found Kate to be easy to talk to. "So, for this trip, I decided to let my hair down a little and do some things I would never dare to do at home."

"Sounds fun! We have sort of developed the same habit when we come here. You know, 'what happens in Jamaica', and all that. Here, it's just about the two of us. We don't feel that we need to answer to anyone else. We just have fun and go where our whims take us. And they have taken us to some pretty nice places over the years," Kate laughed.

She paid the driver, tipping him generously, and they stepped onto the sidewalk, heading for the closest store. "So, exactly how do you plan on letting your hair down?"

"Honestly?" Jen wondered how much she should tell her new friend. "I was just hoping to enjoy a little more, um, intimacy with Tim. My wardrobe for the week is a lot more revealing than anything I would dare to wear at home. And, so far," she blushed, "it seems to be working."

Kate laughed again. "I thought I noticed a certain satisfied glow about you. Now," directing Jen to the nearest store, "let's go in here and work a little more on that wardrobe."

.......................................................

Mickey's first drive was long and straight, which meant the cart would be stopping for Tim first. Mickey followed him over to the edge of the rough for his second shot. He talked constantly, or so it seemed, but Tim didn't mind. He liked his new friend.

"Listen, Tim. I hope you didn't take offense to what I said about Jen. You're a very lucky man, as you know, and what woman doesn't like a compliment?"

Tim paused long enough to line up his second stroke, landing his ball fairly close to Mickey's drive. "No offense taken. And I don't think she minded either. You want to know the truth? It's probably been a long time since anyone has ever said anything like that to her."

"Seriously?" Tim was genuinely surprised. "I would think you would be knocking guys away from her all the time."

"Well, how can I put this? You caught her on an unusual week," Tim laughed.

"How so?"

"Jen's very conservative. She wears very little makeup. She dresses like a mom. I know that she's beautiful, but she does nothing to enhance it or to be sexy in public. Apparently, she's bought an entire wardrobe just for this trip. In fact, she told me her suitcases are going to be empty going home since she can never wear any of this stuff again."

"Really?" Mickey's second shot landed a few feet shy of the green. "Well, I think I understand, actually. This annual trip to Jamaica is our one chance to just enjoy ourselves, without the usual restrictions of everyday life and responsibilities. Our first trip here changed us in ways we would have never dreamt of."

"That good, eh?" Tim's next shot was well to the left of the green, rolling down a hill toward a sand trap.

"Unbelievably good." Mickey seemed to drift away for a bit as they climbed back into the cart.

.......................................................

They were already in their third store. Kate seemed to be looking for something in particular as she led her new friend from place to place.

"What, exactly, are you looking for?" Jen finally asked.

Kate smiled and raised her eyes mischievously. "Something for you. Something perfect!"

"Why do I feel like I should be nervous?"

Kate laughed. "No need to be nervous. We're on vacation. This is Jamaica. There's no stress here. That's why I love coming down every year. It's our annual escape from life."

"Really? How bad is life that you need to escape from it?"

"No. Don't misunderstand, our life is great. This is just different. And important. We've learned how valuable this time is to us as a couple. We get to rekindle the things that get lost in the routines and stresses of our normal schedules and responsibilities. Those things aren't bad. In fact, most of them are good. They just get in the way of us sometimes, you know?"

Jen nodded. She knew all too well.

"It seems like every year we learn a little more about ourselves and about each other. So we decided a long time ago that this trip was only about us. Our relationship. Our fun! Nothing else matters. We have fun and then we get to remember it for a year and think about what might be coming next year."

Jen was about to ask why they couldn't have "fun" at home, but before she had the chance Kate was pulling her toward a rack of bathing suits in the corner of the store.

"What kind of suits did you bring. Or did you even bother?"

Jen's mind immediately flashed the image of what they had seen on the beach the day before. "No! I mean, yes, of course, I brought suits. I didn't even know that the hotel was... um... you know... until yesterday."

Kate studied her younger friend for a brief second before smiling. "You remind me of me on our first trip here. You were shocked by what you saw, right? Worried that Tim saw, too. Worried that he might have liked it. Even worse, worried -- just a little -- that you like it, too. At least on some deep, hidden almost scary level."

Jen bit her lip.

"I get it. All our lives we good girls are told to be careful, to cover up, to protect, to deny, to ignore what we might be feeling. As we grow up we surround ourselves with others who say and believe the same thing. Then one day, it's like we get run over by reality. Something we didn't expect is suddenly staring us in the face and it triggers a response that we don't quite know how to handle."

"So here you are this week. Dressed in a -- what did you call it? -- a more revealing way than normal. And you find out that you are not even close to the most daring person here. You find out that your husband likes it. And that you like the extra attention that you get from him, and other men."

"No. No other men. I just wanted to do something for Tim."

"And you mean to tell me that you haven't noticed the effect you are having on others? What about Mickey's comments this morning?"

Jen suddenly felt terrible. "Kate, I am so sorry. I didn't mean..."

Kate laughed again, looking through the selection of bikinis on the rack. "No silly. I know you didn't mean anything. My point is that men notice. Mickey noticed. The guys at the counter are noticing right now."

Jen's head snapped to her right where she caught the admiring gaze of two young men, who quickly tried to look away as she turned to face them.

"See. Guys notice. And we like it when they do. Am I right?"

"I don't know. Honestly. It's been a while since anyone has noticed. I mean, I'm fine with that. I have Tim and we love each other. And we're happy. And that's enough."

"Of course it is. I'm not suggesting anything else. Except this bikini. And maybe this one."

Jen looked at the two small bathing suits that Kate was pushing into her hands. They had half as much material as the suits that she brought with her. "I could never wear these!"

"Why not? Let's face it, you'll be far more covered up than the people you saw yesterday." Kate opened a dressing room door. "And Tim will love it!"

.......................................................

As they left the second tee, Mickey continued. "We splurged for a room with an outdoor hot tub that first year. You've seen them, over in the buildings on the other side of the main pool?"

Tim had seen them. Each patio was surrounded by a tall, white fence, where the occupants could enjoy privacy or open a wide gate facing the ocean.

"It was our second night; the sun had set, and we were relaxing in the tub." Mickey laughed, "Of course, when I say relaxing you know what I mean right?"

"I think I have a pretty good idea." Tim tried to push the image of Kate's large breasts bouncing up and down, splashing in the water, out of his mind.

"Well, we had just finished 'relaxing' and were about ready to head back to the room when we heard the door in the patio next to our slide open. You can't see anything from one patio to the next, but you can certainly hear. At first, I thought it was two couples since I distinctly heard the voice of two men and a woman."

Tim was suddenly anxious to hear where this story was heading.

"The conversation was pretty general. Weather, the resort, and stuff like that. It didn't take too long to work out that there were, in fact, just the three of them: an American couple and a Jamaican man. They were a little awkward at first. The lady stayed mostly quiet. Then the Jamaican asked if they were sure about this. The husband said they were, and the man repeated the question to the lady. She said they would not have invited him if she wasn't sure."

Tim felt a lump growing in his throat. There was no pretense of golfing now. They sat in the cart, in the shade of a tree, watching others play through.

"After that, there wasn't much conversation, but what was happening was unmistakable. With each shuffling sound I imagined what part of clothing someone was losing. Eventually the lady's soft moans began to make their way over the fence. I could only imagine how their new friend was touching her. He was taking his time and she was enjoying every moment of it. Eventually, he let out a low groan. In my mind I could almost see her, on her knees taking him into her mouth. Or maybe sucking both of them. Her moans were muffled then as she serviced him, or them. Suddenly a piece of furniture scraped across the patio and after some hushed words between the men, she let out a little shriek. I can still hear it clearly. I suspected the Jamaican was penetrating her. Soon the rhythmic slapping of his hips against hers confirmed what I thought.

Kate and I sat as quietly as we could, listening to the sounds of them having sex. For the most part, it seems, the husband enjoyed watching his wife, coaxing her and telling her how good she looked and how much he loved her. She responded with the squeals and muffled shrieks of one orgasm after another."

"When they finally finished, we sat absolutely still, waiting for them to finally leave. Kate reached into my lap and found my hard-on. I was as hard as I've ever been. She quietly stroked me to orgasm as they chatted. As soon as they stepped back into the room, closing the door behind them, we went inside and fucked like teenagers for nearly another hour. I was still hard, and she was wetter than I remember her being in years."

"Ready for the next hole?" Mickey hit the accelerator and the cart lurched toward their next stop.

.......................................................

"Well, are you going to let me see?" Kate was pulling at the dressing room door as Jen stood staring at herself in the mirror. The suit was scandalous. Everything was covered, but just barely.

"I'm going to try on the other one first. Then maybe," she lied. There was no way she was going to let anyone see her in a bikini this small.

"Oh, come on. I want to see it. I bet it looks great on you. Just crack the door a bit."

Jen saw her hand reaching for the door. Against her better judgment, she turned the handle, never letting go as the older woman took a long look.

"Jen! You look amazing in that! The color is perfect for your skin, and it fits you like it was designed to fit. I could never wear it, but it really flatters you."

Jen turned again to the mirror. Kate wasn't wrong. It did fit well and the turquoise color against her tanned skin looked nice. Still, it was small. When she turned back toward Kate she noticed that one of the salesmen was directly behind Kate, well across the room but still trying to look through the opening. He smiled nervously and stepped away when Jen caught his eye. She was sure he couldn't see much since Kate was in the way, so she didn't give him much more thought.

"Tim's going to love seeing you in that, Jen. But I think he's going to like the other one ever better!" Kate backed through the door, closing it with a mischievous smile.

If the first suit was daring, the second was positively obscene. At first Jen was convinced that she was holding the wrong size, yet the strings were long enough to easily wrap around her slim frame. The top consisted of two narrow triangles, barely wide enough to conceal her nipples. The bottom had that same narrow cut of fabric which only covered her slit. It was cut low enough that any public hair could be seen. In fact, Jen was certain that if she were to walk far enough in it the tiny hint of thin material would undoubtedly slide out of the way, exposing her genitals. And besides that, the suit was white and the material was so thin that she knew it would be almost transparent when dry, and nearly invisible when wet.

She reached to pull the tie on the back to remove the top when suddenly the door flew open. She had forgotten to lock it when Kate stepped out a minute earlier.

"So what do you think?" asked Kate. Before she could even answer her new friend offered up her own assessment. "I don't know what you see, but from where I am the view is amazing!"

Jen realized that her entire bottom was exposed to the older woman. She instinctively turned around and looked at her naked backside in the mirror.

"Oh, there is no way!" Jen declared emphatically. "I would get arrested in this thing."

Kate laughed. "Have you already forgotten what you saw yesterday? You'd win the best dressed -- or least the most dressed -- award on that beach! Besides, you're on vacation. And what were you saying about 'more revealing'?"

It was more revealing. There was no doubt about that. She was basically naked. She turned again and faced the mirror. As she did, she saw the reflection of the clerk again. This time he was closer to the dressing room, and he was making little effort to hide his gaze. Jen reached for the door, but Kate was standing in the way, chatting on about how much attention Tim would be paying her in that suit.

"He's not the only one, Kate. Close the door."

Kate turned to see, still standing in front of the open door, yet not quite in the doorway. Jen realized that the other clerk was about 6 feet behind her. Both men were getting a long and generous view of her exposed skin.

Kate turned back to Jen with a conspiratorial smile and raised eyebrows. "It looks like the suit is a big hit. I say we buy it!"

"Please just close the door," Jen pleaded.

"Well, OK," sighed Kate. "If you want to ruin their fun."

Jen locked the door the instant it was closed. She turned to the mirror one last time before removing the suit. Her eyes were immediately drawn to her breasts. Her nipples were erect and pushing at the fabric. She was surprised at that, especially since the room wasn't particularly cold. Then she noticed that warm, familiar sensation between her legs. It was subtle but undeniable. Was it possible that the bikini had aroused her? Or maybe it was Kate's comments. Or maybe - she was almost afraid to think it -- just maybe it was the look on the face of her two admirers. Whatever it was, it was something very, very new to her.

.......................................................

After another futile attempt of trying to match Mickey stroke for stroke on four, Tim finally worked up the nerve to ask the question that seemed all too obvious to him.

"I get that you had a great night, and things like that don't happen back home. At least they don't happen to me. But I'm not sure how that would be a life-changing event. Unless you two have become peeping Toms since then."

Mickey smiled. "No, we aren't peeping Toms. But it did trigger something in us. We had never talked much about sex before then. We enjoyed it, of course, and Kate is beautiful and has always been an eager participant. The next day, though, it was all we talked about. We had sex when we woke up, a couple of times during the day, and again that night.

"It was more than just the sex though. We both admitted to each other how surprised we were to see how turned on the other was by what we had heard. We tried to figure out what it was that aroused us so much. Was it just knowing people were having sex so close by? Or the fact that we heard them? Or that they didn't know we were there? Or the idea of a threesome? Or a black guy?"

"And what did you determine?" Tim was thinking about his own arousal over the last 24 hours. Sure, his wife looked great, but was he more turned on because Richard and the stranger saw them, or that they were playing in semi-public places, or something else?

Mickey laughed again. "We determined we needed more research!"

Tim's mind began to run wild.

"The next night we got back to our room very early," Mickey continued, "just before the sun was setting. We left the lights out in our room and opened the patio door. Earlier in the day I had noticed that there was a small opening between the building and the fence. No more than an inch or so. It didn't let you see much, but you could see something: the doors next door, a few feet of the patio, a couple of chairs, and maybe a third of the hot tub."

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