Island Vacation - Ch. 01

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Jen gets brave with a sexy vacation wardrobe.
3.7k words
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Part 1 of the 19 part series

Updated 12/14/2023
Created 06/25/2023
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She took one last deep breath, holding it as though it were the last of her resolve. When she finally let it go, the decision was made. After all, she reasoned, who would ever know? They were on vacation, alone, far from home. Besides, it wasn't as though the dress was that scandalous. They sold them by the thousands at the mall; just not to women like her. It was short, tight, and revealed the cleft between her soft breasts. Not exactly cleavage, mind you, but enough to let you know she had something there. The two tiny straps that draped over her shoulders did nothing to hold it in place -- While Mother Nature hadn't been generous with her in that department, she gave her all she needed for that task -- but they prevented her from wearing any sort of a bra underneath. Compared to what she normally wore, Jen felt very exposed.

But she wasn't going to turn back now. They had been planning this trip for over a year, and she had been making her own plans for the trip for months. Between the extra workouts at the gym and the trips to a mall an hour and a half from home to buy her wardrobe, she had too much invested to change her mind. She just hoped Tim would like it.

She gave herself one last glance in the mirror. Not bad for 35. Her large blue eyes were free of the wrinkles that some of her friends were starting to show. Her auburn hair, styled short for the trip, was still all natural. She was toned and energetic. As she turned sideways, she could see that her backside seemed especially obvious. Maybe those squats were working after all. She quickly shoved the clothes she has worn to the airport in the bag, along with her sneakers, slipped her feet into the strapless three-inch heels that matched the print of the dress, and opened the door.

There was a man waiting to use the room as she exited. They did their best to give way to one another, though the man seemed more interested in looking at her than in finding the bathroom. Eventually, she made her way up the aisle toward her husband, dropping into the seat next to him, her heart nearly pounding through her chest.

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

"I'm sorry. This is my wife's..." Tim started to say, then fell dumb at the sight of his wife. He had never seen her look like this. She had kept herself in great shape, even after two kids. She had her mom's good looks and she tried to stay stylish. But this was completely out of the ordinary. Her firm breasts pushed at the thin fabric of her dress. He was almost certain he could see the outline of her nipples. Her legs seemed longer than normal; a result, he knew, of the short hemline. In fact, it appeared that the dress was so short that her bare bottom was now on directly on the seat.

When he finally pulled his eyes up her body to her face, she was looking directly at him, a question nervously posed on her face.

"Do you like it?"

All he could do was nod.

"I wasn't sure if... I mean, I didn't if... well, you know."

He nodded again. Even though he didn't know.

"It's just kind of..." she struggled for the word, "um, different. You know. For me. I mean, I wouldn't wear it at home, of course."

"Of course," he nodded, wishing with all of his might that she would, but not daring to say it.

"So, you're OK with it?"

He gently kissed her on the cheek, taking her hand and pulling it into his lap, letting her feel his hardness. "Oh, yeah. I'm more than OK, as you can see."

She jerked her hand away, immediately turning to see if anyone had seen them. The other passengers seemed lost in their own worlds. She snuggled into him, whispering, "Well, then I think I may just have a few other things that you're going to like this week." His dick got even harder when he heard that.

Her gentle perfume added to his disorientation. Even when she dressed for bed she never looked this sexy. It's not that he wasn't attracted to her. It was just that the passing of time, the arrival of the kids, and the stress of life had left them in a rut. Add to that her conservative, religious sensibilities and you were left with a wardrobe best defined as "modest and sensible".

While this wasn't immodest, exactly, it was a departure from the norm. A serious -- but pleasant -- departure. Even as she cuddled into his side, he could glance down and see the curve of her breasts, both that part that was snugly caressed by the fabric and that which was exposed to his view. As he let his gaze drop further, her firm thighs seem to smile up at him. Almost without thinking, his left hand gently brushed her lap, and she responded by snuggling in even tighter to him. Her skin was smooth and warm, and whatever he had been daydreaming about when she was in the restroom was now far from his mind as he found himself completely consumed with his wife's semi-exposed body.

His hand became more intent on its task. Somehow, he found himself trying to arouse her, delicately finding those places along her thigh that he knew would heighten her excitement. He was vaguely aware that a crowded commercial airliner wasn't the appropriate place, but he didn't really care. Something seemed to be driving him on.

He could feel her relaxing, and she slowly began to allow her legs to part ever so slightly. He, of course, dipped his fingers into that narrow opening, silently hoping that she would somehow give him more access.

They both saw it at the same time. The gentleman across the aisle, one row ahead of them, moved suddenly. He was looking directly at Tim's hand, trying to see if perhaps he could get a better view up her skirt. Jen immediately pulled her legs tightly together, and Tim's hand retreated to his own seat. Like scolded schoolchildren, they sat in relative silence for the rest of the flight.

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

The arrival process was quicker than she expected. Within minutes they had passed through immigration, gotten their luggage and were crossing the terminal of the airport, looking for their driver. He was easy to spot with the large, but tattered sign they were told to look for. His name was Richard. He was tall, lanky, and friendly and spoke with that accent that everyone tries to imitate, but never quite does. His smile seemed to linger a bit longer as he looked at her, Jen thought, but then dismissed the thought quickly, remembering that he worked for tips.

"You are a very lucky man, my friend," he said to Tim, as he looked at Jen. Tim was quick to agree, and his wife found that she liked the compliment and the subtle attention. Richard pointed them toward his van outside and waited for a few other passengers to arrive. 15 minutes later they were weaving through the streets of Montego Bay on their way to the western end of the island and the beaches.

Richard pointed out a few sites as he drove, speaking above the Reggae that was giving a pleasant vibe to the drive. As he spoke, he looked up into a mirror over his head that gave him a view of his eight passengers. Tim had led Jen to the back row, and they cuddled close like high schoolers in the back of a school bus. They held hands till they got to the edge of town, then Tim released her and began caressing her thigh again as he had been on the plane. She was surprised at how good it had felt. She was sure that her dress, and the fact that others could have seen him, heightened her response.

She quickly found herself becoming aroused again, and furtively glanced around the van. The other passengers were busy looking out the window, talking with one another, or asking questions of their genial driver. None of them were paying any attention to the couple in the back, so she allowed her legs to open just a bit wider. Tim wasted no time, immediately letting his right hand slide deeper between her warm limbs. She glanced toward the front of the bus and made eye contact with Richard in the mirror. He was talking about a music festival that had just concluded, so she nodded as though she were following him.

She was not. Her focus was now between her legs, where her husband kept pulling his hand higher, ever closer to her warm slit. She stared blankly out the window, opening her legs even wider. Again, Tim moved immediately, softly, and with a specific purpose. He now had access to her panties, such as they were. Not quite a G-string, they were cut high, leaving the cheeks of her bottom exposed and only barely covering her trimmed slit. That, too, was new for the vacation. She had never allowed her pubic hair to get "bushy", but since she only wore the most modest of bathing suits, there was never any need for trimming things more closely. Tim noticed immediately.

"Um, this is new," he said as he stroked along the edge of her razor-thin panty.

"I told you that I have a few surprises for you this week."

"I like surprises," he replied as he let a lone finger run the length of the fabric covering her slit.

Jen shuddered and looked back toward the front of the bus. Again, she made eye contact with Richard. She tried to look away, but just then Tim's finger found her swelling bud, and he pressed it just lightly enough to send an electric pulse through the depths of her groin to her sensitive nipples. She actually heard herself gasp. Richard never looked away. Was it possible that he knew what they were doing? Could he somehow see her lap? She knew that he couldn't but the fact that he continued to stare at her as her husband teased her just out of view made her feel flush. She knew her cheeks were reddening and there was nothing that she could do about it.

By now Tim had worked a finger under the tight fabric of the panty. She was surprised at how wet she was when it breached her warm slit. Now, with his palm facing down, he was teasing her opening with two or three fingers, as though he were plucking a guitar. Jen felt every bump and rattle of the van; its vibrations adding to her arousal. Her breath was deeper and she felt the dress squeezing her breasts harder with every gasp. She did her very best to maintain a calm expression, but her body seemed to have taken control of whatever discipline she had.

She knew that if Tim kept teasing her as he was for just a few more minutes, she would have an orgasm right there, on the van, two feet behind the elderly couple in the row ahead of them, while the driver watched. She had just begun to push Tim's arm away when the van suddenly slowed and then pulled off the road. For just a minute she thought perhaps he was stopping in order to scold them for their behavior, even though she was convinced that neither he nor anyone else could really see anything.

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

The change in speed and the driver's voice brought Tim out of his erotic fog.

"All right, ladies and gents, here's where we're gonna stop for a minute. Get yourself a Red Stripe and relax. Have a snack. Enjoy some music. We be goin' again in 20 minutes." With that, Richard opened the side door and allowed his passengers to step outside in front of a small stand that sold cold drinks and a variety of snacks and souvenirs. Tim grabbed a beer and a Coke for Jen.

As they stepped away from the counter Richard told him, "If you follow that little path, you might see some birds or something'". Then he walked away. Walking down the path sounded like a good idea. If nothing else, it might allow him to walk off the erection that had been forming for the last half hour on the van. Actually, it had started when he saw Jen's dress on the plane.

Taking his wife by the hand they slipped into the small stand of trees just behind the picnic tables that ran along the side of the small building. As it turned out, there were more trees than it appeared from the front, and within 5 minutes they felt like they were deep into a tropical jungle. They could still hear the chattering of the other passengers, but they were completely out of sight.

At a small clearing, Tim stopped, turned, and took his wife into his arms, kissing her deeply.

"Oh my! I guess you do like my dress," Jen teased.

"I like more than that," he said, reaching down to squeeze her ass cheek. As he kissed her again, she ground herself into him, and he could feel the stiffness under his shorts press against her lower belly. Now both of his hands were on her ass and he quickly pulled the fabric up so that he could feel her bare skin.

"Not here!" she whispered as she tried to pull away.

"Why not? We're alone, and from here I can see a bit up the trail. No one is coming. Besides, I can't go back to the van like this." He pointed toward his crotch. He needed relief and she was just the person to give it to him. He turned her around, pulling her ass into him.

"Tim!" Her voice was urgent and pleading. So was his dick. He pulled it from his shorts and bent her forward just a bit. They were almost the same height, and with her heels he only needed to squat the slightest bit to line himself up with her warm, wet hole. He pulled the tiny strip of fabric out of the way and nudged his head toward her opening. He was surprised again at how wet she was. In fact, he couldn't remember her ever being this slick. With only the slightest pressure, her pussy swallowed his cock. He paused just for a second to gain his composure, then started a slow, steady rhythm, sliding his member in and out of his sweet wife.

He knew they didn't have long. And he knew he wouldn't need much time! His dick was so hard that it almost ached. He wanted to pound her hard -- something he never did -- but was afraid of the noise he might make. So he just thrust deep and steady, listening to his wife's breathing getting deeper and faster.

Something suddenly caught his eye. Back toward his left -- not on the path but in the trees -- there was Richard, standing silently and watching them. He knew that he should stop, but he couldn't, almost as quickly as he recognized the presence of the voyeur he felt the first spurts of his orgasm. Jen felt it, too, breaking away from him and spinning around to catch most of his load in her mouth. Tim closed his eyes as he came, pulse after pulse, heart pounding and mind reeling. As he finished, he opened his eyes and looked to his left. His audience was gone.

A minute later he heard him calling from the parking lot. "OK, people. Now we go!"

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

By the time they got back to the van, everyone else had already climbed aboard. Except for Richard. He smiled broadly at Jen, extending his arm to help her up the step.

"Hello again, pretty lady! It is always nice to see you!"

Jen was just glad that he couldn't see her 5 minutes ago. She wasn't sure what had gotten into Tim. He had never been that... assertive. She knew they were taking an incredible risk but, somehow, she really hadn't cared. She was horny, and so was he. They were married -- and hidden -- so why not?

Still, the smile that Richard gave her made her feel awkward somehow. As she took that step, she felt his hand brush her bottom as he "helped" her into the van. It made the lingering tingle between her legs jump a level. Since they were the last on, they wound up in the seat immediately behind Richard. If she had thought that he had been watching her on the first part of the trip, it seemed as though he never took his dancing eyes off her for the remainder of the ride.

Fortunately, it was over soon enough. As they reached Negril Richard began pulling into one hotel driveway after the next, letting off passengers at every stop. They finally reached their home for the next week and retrieved their bags from the back of the van. Jen was surprised when Richard refused Tim's tip.

"No, mon. I don't need that from you today. I got all I need already, you know!"

Tim stammered, then shook his hand and turned back toward his wife. Jen was already dealing with two porters from the hotel who were taking their bags and pointing the way to the front desk. Check-in was fast and within minutes they were being ushered into their ground floor, ocean view "Junior Suite". It was essentially one large room, divided by a small railing that ran parallel to the entry door and two sliding glass doors that looked directly onto the beach. At the railing, there was a small step down from the "bedroom" area into a comfortable space with a sofa, a large upholstered chair, and a small table set.

The door had barely closed when Jen felt Tim wrapping his arms around her again. She giggled at his enthusiasm and started to say something but he kissed her. It was hard, urgent, and filled with passion. She felt herself falling back onto the bed with him nearly tumbling right on top of her. As her back hit the soft mattress he released his grip, sliding down her belly and pulling her legs apart. His head ducked between her legs and his hot tongue went straight to her clit. She gasped and felt her lower extremities convulse at the sensation.

"Tim! What has gotten into you?" She wasn't complaining, just a little confused.

"I need to finish. I've been hard since before we got back in the van."

She had to admit that she was still aroused, too. The dress, the ride, the sex at the stand - all of it played a part. Now his tongue was pushing her over the edge again. She could do little but lay her head back and enjoy the sensation. It didn't last long. Within two minutes Tim was moving again, this time shoving his shorts down around his knees before lunging toward her, burying his shaft in her wetness. Again, she surprised herself by climaxing almost as quickly as he entered her. It was just a small orgasm, but sufficient to pull her to another level of arousal. Tim was like an animal. Passionate. Eager. Determined. He thrust deep and fast, grunting as he did. He almost sounded angry as he pounded her hard. This was sex like they never had it, and it drove her to two other orgasms in sequence, one harder than the other.

As the wave of the second washed over her, she was feeling another wave deep inside. Tim was coming, filling her with his warm seed, collapsing onto her chest, his face buried in the mattress to the left of her head. As the waves subsided, Jen opened her eyes, taking in the room around her. She exhaled deeply, letting her head roll to the right.

"Oh my God! Tim! Get up!" She pushed him off of her and pulled her dress down from around her waist all at the same time. "There's someone looking in the window!"

"I don't see anyone."

"He's gone. He moved as soon as I realized he was there. My God! What were we thinking?"

The sliding doors were covered only with a sheer panel of fabric. There was a heavier curtain, of course, but it was pulled to the side, allowing the occupants of the room a full view of the beach and the Caribbean. There was no one on the beach in front of the room. In fact, the amount of scrub brush (or whatever it was) at that particular spot wouldn't have allowed anyone to use the beach right there anyhow. The doors opened onto a small patio, which was adjacent to a walkway that led to a manicured beach just a few yards away. Jen's admirer had been simply standing on the patio, watching them have sex.

Tim tried to reassure her. "Relax, hon. He couldn't have been there long. And besides, there wasn't much for him to see."

"He could see us having sex! That's what he could see." For reasons that she couldn't explain or understand, she felt overwhelmed with guilt and shame.

"But you were dressed so he couldn't see you. Sure, he saw me on top of you and he knew what we were doing. And we weren't doing anything wrong." As he pulled her close, Jen knew he was right. She liked what they did. She liked the way it felt, and she liked the fact that she had clearly turned her husband on. There was nothing wrong with any of that. And he was right when he said that the stranger could see nothing... really.

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