Story Notes:
Standard Disclaimer: I own the character Jack as well as the plot of this story, Pokemon and other known characters are their respective owners. This story contains sexually explicit content. Go away if you're offended or too young to read such revolting literature.
Chapter 14
On the 9th day of their voyage Jack led everyone up onto the deck for the announcement.
"Five Island ahead. Please have all your belongings ready to depart upon arrival. Repeat..."
"Here we are girls," said Jack with a grand gesture with his arms. Five Island and... Resort Gorgeous."
They all stared at him through bleary, tired eyes for a moment as the words "resort" and "gorgeous" sank in and then their expressions changed dramatically. Save for Jill, who wore a stoic expression of "why should we bother?" the others were ecstatic, and leapt upon Jack with more verve and excitement than he had anticipated, landing solidly on his back with three extremely pleased Pokémon giggling like schoolgirls on top of him.
"Really? A resort? This was the surprise?" asked Maya, who seemed more excited at the prospect of rest and relaxation than anything else.
Jack could only smile, "This is it. I hope this means you like it."
"Do we?" asked Laura. "Jack I'm not even sure if I can put out enough to pay you back for this!"
"We'll all have to put out together then," said Sasha, hugging Jack around the neck despite him still being on the floor.
Jill just scoffed, "We shouldn't be wasting our time here, there's too much training to do. You haven't lost any weight at all have you?"
Her body belied her actual expression though, and Jack could tell by the way she crossed her arms over her breasts that she was pleased as well. If anything she had heard the rumors about the Lost Cave located beside the Resort, a famous site known for expeditions that trainers go on for training in the mastery of their Pokémon's use of their HMs. Jack didn't press her on the point but he smirked inwardly, knowing that there would be ample things for a bored Lucario to do at Resort Gorgeous no matter how vehemently she protested it.
"You're just jealous that we called him first," said Laura grinning with narrowed eyes at Jill and seemingly picking up the same signals that Jack was.
Jill looked down and for a moment dropped her hands to her sides in a protest. She was about to say something when the ship's horn blasted and cut her off.
"We'll be arriving soon. I'll see you all when I've checked in all right?"
They all agreed, even Jill, albeit reluctantly, though she managed a slight smirk Jack's way as he sent her back into her Pokéball, which only reconfirmed his initial decision that this was a good purchase.
"Can't train all the time. Sometimes, you just need a vacation." He said to himself as he made his way back to the room to get all their things packed. "Even if it does come after a nine day cruise."
The Island was twice as beautiful as the brochure made it out to be. As soon as he stepped off the ship he was showered with shouts of welcome from the locals and garnished with plastic flower necklaces. It was by far the friendliest place he had been in a long time, and he wasn't even away from the docks yet. There was another short ferry ride to the actual resort but in the meantime he took to admiring the sights of the main town of the island. It was small to be sure, and rustic, but it had a certain island quality he had kind of expected in the tropics where weather was often less pronounced but more severe. Luckily though the forecast called for nothing but sunshine; that's what he wanted to hear.
When he finally arrived an open building with tall marble pillars and gleaming marble floors greeted him. The concierge took his backpack, though he tried to insist he didn't need help, and he checked in without a hitch. Once he was in the room, sporting two beds and the standard hotel room suite layout he decided on the best place to introduce his Pokémon to the scenery. He decided on the balcony, despite only being on the second floor he had a perfect view of the wide open ocean and the beach not a two minute walk away. He called them all out at the same time and watched their reactions change from merely excited to stunned. With mouths hanging wide open, and no nausea coming from Jill, they were all enormously enjoying the prospects of staying here for a while. Instead of voicing her opinion, however, Laura merely took Jack by the collar of his shirt and drew him into a deep and passionate kiss. She would have dragged him all the way to the bedroom and disrobed him right there and then, but Jill cleared her throat audibly and broke them apart with a sideways glare that made it clear she wanted no part in watching such displays of adamant affection. Laura gave him a long pronounced lick from the nape of the neck to his lips then in defiant response, drawing a threatening full bodied glance from all of them but clung to him regardless.
"How long do we have the room for?" asked Maya, still captivated by the ocean and the beach.
"Six days and seven nights. The Anne will be in port until then and we take her back right to Cinnabar, where we switch onto a smaller ship and hustle our way to the docks south of Pallet Town."
"Let's not think of leaving yet. We only just got here," said Sasha, taking Jack's other arm before Laura could apprehend it, "I think I know what we all want right now." Laura got a huge smirk on her face.
Which soon vanished as Sasha led them all to a huge open buffet with some of the richest and prettiest and good looking foods they had ever seen. Sasha went first, then Maya, who seemed content with where they were at the moment and then Jill, who slapped Jack's hand whenever he tried to take something tasty looking and not up to her own healthy standards. No one begrudged her though because when they all sat down at one large round table with plates filled high with good food she was the most adamant speaker. She went on about rumors of the Lost Cave and how she had always wanted to see it for real and how Jack would be more of a trainer if he went with her, which she very quickly rectified as 'them' and described in detail the perilous adventures and ghost stories of all the trainers who had gotten themselves lost and perished inside. Maya, who hung on every word, was frightened and fidgeted in her seat and Jack only partially heard what she was saying beyond all the things Laura and Sasha were whispering in his ear.
When they had finished eating and stacked all their dishes neatly for the cleaning staff they were off to the beach. Evening was fast approaching and Maya especially wanted to get a glimpse of the beach under the sunset before it was gone for the night. Laura and Sasha didn't mind, and though it would be the perfect place to find a little cozy nook to hide away in and do unsavory but altogether enjoyable things to Jack. Jill went along as well, if for nothing else than to keep Maya company.
The two had become somewhat enamored with each other the past few days, which was not lost on Jack as he watched the two of them interact. Maya seemed to be the bridge between Jill and the other two, while Jill was the protective one, saving Maya from the prodding questions and fingers of the others as they tried to include her in one of their many schemes of sexual nature. The two went well together and he watched even when it wasn't arousing, noticing that they seemed to complement each other well, not just in a friendly sense, but in a practical one. Jill was always there to catch Maya as she stumbled and Maya was always there with a healing gout of water or icy mist when Jill overexerted herself. Despite being on holiday for so long Jack had been watching and thinking of ways that they may become even stronger together.
That thought aside though, the beach was magnificent. Recently combed and swept by the park crew the sand was crisp and clean and bunched up between Jack's toes even as he put his first foot down. He sighed as the latent heat seeped into his feet and kept walking, calmly enough to be left behind by the other, more excited Pokémon, Maya, Laura, and Sasha, and slow enough to match his more reluctant one.
"Penny for your thoughts Jill?" he asked.
"I don't know what you were thinking when you brought us here," she said, "It seems like just another excuse."
"An excuse for what?" he asked.
"Like you're giving them an excuse," she answered, nodding her head in the direction of the others, who had already made it to the water and were splashing around. "And don't play dumb. You know what I mean."
"Well, you may be right. But consider that we've got six days here, and I've only caught four Pokémon, little Riolu not included." He looked at her as though she should take the hint. "I have a day or two planned just for you Jill. And whether you like it or not, we're going to take a trip to the Lost Caves together."
Jill looked away, slightly embarrassed that she had been read so easily. But she smiled, and felt a little warm in her heart place that he would think to do anything with her despite her attitude.
Riolu hopped down from Jack's arms and barked as she ran on her hind feet, arms trailing above and behind her head towards the water where the others were tackling each other beneath the waves or trying to ride on top of Maya as she darted about.
Jill whispered a silent thanks to Jack for bringing her here regardless though. Even if she didn't show it, she liked the view very much.
Sunset came all too quickly and before long the water and the beach was too dark to stay on any longer. Despite Lopunny's begging to skinny dip in the waves Jack managed to weasel his way out and up to the lit beach house where a small dance was going on for the patrons. It was mostly humans and what Pokémon were there were likely still inside their Pokeballs. It wasn't so much odd to Jack as it was a little rude, since they're here on vacation they may as well give their Pokémon one too, but he guessed that few trainers treated their Pokémon quite the way Jack did.
The only one who didn't immediately join in the dancing was Jill, who stuck to the sidelines and found herself a chair to sit on. Ever the self-imposed outcast, when the song ended Jack wandered over to her and bent down.
"Dance with me?"
She averted her eyes as the next song started and Jack repeated himself. "Maybe I shouldn't have phrased it as a question. "Dance with me Jill." And before she could argue she was yanked off the chair by her hands and onto the floor, into a dance with twirls and sidestepping motions and a dip. She found that Jack was a fair dancer, at least as far as she knew. She had never danced before and let him lead all the way, which was a bit of a shock to her because she never would have allowed it otherwise.
"Jack, I can't..." she said between twirls, blushing deeper than before, feeling like the world's eyes were upon her at that very moment. "It's embarrassing."
When they were back up again Jack held her close to him with a hand around her back. "People only watch you at a dance when you sit out of it. Look around." She did, and saw not a single eye on her at all. Everyone had paired up. Laura and Sasha were busily tearing up the dance floor in the middle, and Maya was bent down with the little Riolu as she giggled playfully and wanted to be dipped again and again.
She really wasn't being watched. But it was still gnawing at her and she felt like stopping. She gripped his hands tighter. "It's all right Jill, watch." He spun her into a twirl that released her hand from his and she stopped, skidding on her feet into a position where her arms were out to either side, one stretched out towards him inadvertently. When the other dancers continued she found that she couldn't help but mimic their motions and twirled back into Jack's arms, this time with her back to his chest.
"See? All you have to do is have fun," said Jack as the dance wound down again and they remained in a slow calm routine.
"But I don't know how to dance," she said.
"A little late. You're actually pretty good. Look at Laura." She did, and watched as the uncoordinated Lopunny bumped into another couple and disturbed an entire line of dancers only to laugh and bow her head before taking the Blaziken's hands again. "You're a natural." He wound her into a prolonged spin so that her one hand came up above her head and the other twisted around her back in a lightly flowing arc. She found that she even arced her back a bit as it happened and when she stopped spinning, out of breath, she was in a dip and had one leg up in the air that Jack's arm held up for her, and her arm was out behind her head gracefully. Her eyes seemed to light up a little and as the music wound down again she found herself a little disappointed.
When Sasha came up to him in the next song she quickly removed herself from the dance floor, escaping onto the beach again and standing still in the dark. Despite herself she raised her hands for an invisible partner and twirled herself. She found it more difficult but she kept doing it, raising her arm above her head and trying to dip as low as she could go, trying to retain that feeling of Jack's arm behind her, supporting her, and his hand on her leg, holding it up to keep her in the dip. And her mind began to wander. To the feeling of his breath on her neck when she dipped, and his voice in her ear, just above a whisper. She stopped and was out of breath, bleary eyed, and held a hand to her breast, just over her heart, feeling it thumping inside as though she had run a marathon.
"You make it so hard to hate..." but that was the wrong word, "You make it so hard to dislike you Jack." She took a long glance at the dance floor, where the music had changed once again and he was dancing calmly and serenely with Maya, Riolu perched on his shoulders.
It was late when they returned to the room, and before he had a chance to protest, Laura grabbed his collar again and dragged him into the shower, closing and locking the door behind them. For the next little while noises of many different volumes and pitches could be heard and when they emerged, a billowing cloud of steam rolling out after them, Jill was the next to shove herself inside, pushing Jack beyond the threshold and locking the door behind him.
Alone in the bathroom, with nothing but the vanities for company, she moved into the widest part of the room and performed another flawless twirl and a dip and for a moment she was back on the dance floor with Jack right above her, so close. But then her hand brushed the door and she was instantly brought back to the humid white washed bathroom of their hotel. And she was just balancing herself alone, chasing a feeling she could never duplicate. With that in mind she slid with her back up to the wall into a sitting position and tugged her hands up to her knees. In her mind she could hear all the noises that stupid Lopunny made and every single one seemed aimed at her. Spiting her and declaring that which she could not have. Jill could feel a tear well up in her eye as she looked at the ceiling. Her lips mouthed a few words, but they didn't make sense in her mind. They were things she would never ever say.
At least not out loud.
The next day Jack left early with Maya. Laura and Sasha were still sleeping soundly on the bed, curling up against each other, likely imagining the other was Jack with squishy bits on his chest. He wondered what they would think when they woke up to find themselves entangled like that but then shoved it from his mind as it started to give him an erection. Riolu was sleeping on a billowy chair curled up and sucking its thumb. Jill was nowhere to be seen and the bathroom was empty, so he imagined she had found some place to amuse herself before everyone else awoke. She was the early bird after all.
Maya eagerly wanted to find the best place in all the resort to swim and Jack let her lead, figuring her sense of direction towards water was greater than his anyway. When she got them lost though he took over and managed to find his way to the resort's collection of hot springs. She was overjoyed and grabbed him by the hand to lead him there. She was a little cautious at first about getting in but the water was a comfortable temperature and she hopped in a moment later. Jack followed suit, though he stripped down first, much to the bemusement of Maya, who gave him a sultry look and a predatory wink. When he slipped under the water and came back up Maya was gone and only a moment later he knew where she was. Her mouth had his shaft completely trapped and was eagerly licking and teasing him to erection.
Though she couldn't hear his groans of pleasure she was aware of his hands gently stroking the fins at the side of her head and gently guiding her down deeper. She was skilled though, far more than he realized and before long she had taken his cock all the way to the hilt and suckled on it hard, swallowing around the length and massaging the head. She could taste the beginnings of his pre as she withdrew for a breath of the warm mountain water and was upon him again almost instantly. She drew him in with a great swallow and then backed away, bobbing her head faster and faster as she brought her master and lover to his peak. He arched his back and thrust his hips towards her mouth and she took it all in, swallowing every last bit of his seed as he found his release in her throat. When he was done she drew back, making one last long slow lick up the shaft and then surfaced, kissing him and rolling her hips against his, wishing him back to fullness so she could have him again.
The day went by too quickly for the two of them, who spent most of the day in and out of the hot springs performing one act or another to completion. And when evening came they all convened at the dining hall and the beach to cool down afterwards.
The next day it was Sasha's turn, who had found a secluded spot up on the rocks away from the shore where they could be alone and private. It was a bit slippery but they managed to find a relatively flat perch to roost on as the waves licked at their feet. For a long while Sasha only leaned against Jack's shoulder, wanting to enjoy the moment. But gradually her mind shifted and even as her hand slowly trailed up his leg, her head turned and she nipped at his ear, licking it playfully and whispering sweet nothings to him, which were returned in short order as his hands wandered over her body and tickled and excited and pleased her in ways they both knew they loved.
Soon they were disrobed and Sasha was poised on top of him. Her arms were above her head and she showed off her body to him. Jack, on his back and his hands on her hips, slowly guided her down so that her sweet feminine lips parted ever-so-gently for his shaft. She slowly sank downwards, grabbing her breasts as she did so and rolling them and mashing them together in the palms of her hands, tweaking the nipples as she hilted and sat for a moment to collect her thoughts as they swam around her pleasure filled mind. Then she began to grind her hips, gyrating them around and about but never lifting off of him.
His mind swam with all the sensations of his fire Pokémon's perfect motions, each driving him higher and higher. The way she had him pinned prevented him from thrusting but perhaps that was the way she wanted it right now. The way she moved he could feel her juices roll down and around his cock and lower body, mingling with the small puddle the waves had deposited on the rock over time. He groaned loudly but despite the perfectness of the moment and the erotic sight above him she was taking it so slow, driving them both up but taking her time with it. She took him by the hands and guided them both up to her breasts as she lowered her upper body to him, continuing with her soft grinding and gentle humping. Her eyes were closed tight shut and her breath came in ragged.
As they were both driven higher, sweat peeling down their brows she lowered herself completely onto him and bucked her hips, for the first time raising them off of his and then slamming them down, causing both of them to shudder and quake in pleasure. She repeated this and squealed, a plume of fire shooting from her mouth and singing the rock beside Jack's head. But he was too entranced by his Pokémon to notice. He tightened his legs and thrust up to meet her on the way down, slamming hard and grinding there for a moment before parting again. Every move they made was accompanied by a squelching sound as their mingled juices and soaking bodies slapped against each other in tandem. Faster and faster they moved together until finally, as they both reached their peak they groaned or squealed in blissful energy and the most intense orgasm either of them had had for a long while erupted between them, showering them and the rocks below with their juices.
Out of breath and panting hard they remained like that for a long time before Jack's softening length finally came loose from her still scorching hot body. They kissed then, and continued to do so even as the waves began to rise and the taste of salty sweat and ocean bit at their tongues.
On the third day it was Laura's turn, and she knew just where she wanted to go and what she wanted to do. With an excited gallop she took Jack to a secluded spot, sort of, where she had found something very interesting.
"Laura, why are we in the men's bathroom?"
"Because silly, I want to try this neat little thing I found yesterday." She stuck her tongue through a small round hole about waist high in one of the stalls, which thankfully had floor low walls to separate inside from out. Jack zoomed in on the glory hole immediately and almost passed out. Let alone why she knew about something like this, why would she know something like this existed in the men's restroom?
"Should I even ask?" he dared ask anyway.
"No. You just have to unzip and let me have it. I want to try it. It'll be fun."
Despite all the wires in his mind telling him not to, he unzipped his fly and placed himself against the rough surface of Laura's tongue, still poking through the hole in the wall. She retreated immediately and he followed, anxious now for the sensations she promised.
"As long as you promise me you'll brush your teeth afterwards okay?"
He heard no response and began to feel very awkward with his cock shoved through this hole in the wall. Then he felt her hands on him and was partially relieved. Though she was smearing something on his skin. It was slick and slippery but warm to the touch. Then there was more and he could feel her grip change a bit.
"Now just stay still. This is an experiment for me too."
"What do you mean an ex-ah!" he gasped suddenly as he felt something hot and tight and mostly dry slip around him. Laura gasped audibly as well and though he couldn't see it her tongue was hanging out of her mouth and she slowly continued pushing backwards onto his cock, the tight ring of her sphincter stretching around him and engulfing him in waves of tight, arousing heat. He could only breathe in gasps at the sensations winding through his body and though every bit of his mind screamed at him to remove himself immediately his body wouldn't obey. He found himself clinging to the wall and trying desperately to shove himself deeper. When she finally got as much of him inside her ass as the barrier between them would allow she reversed, pulling him with her for a moment before hearing a slick pop as she pulled off entirely.
"Let's try that again, shall we?" she asked, and hearing no reply smirked to herself and pushed back again, taking him inside her tight depths again and gasping as he struck a sensitive area. She reached down instinctively and began stroking her drooling pussy even while she began bucking her hips back and forth onto his slippery cock and taking him in quickly and harshly.
Pleasure blotted out his mind and he was breathing raggedly in moments, already nearing his peak. The tightness and the heat of her sphincter drove him to heights so quickly he almost couldn't control the volume of his masculine groan as he came. She felt it too, the splattering of his seed all over her insides and quickly withdrew, taking several long strands of white sticky seed all over her bottom and then turning quickly, to take the last few on her tongue. She smiled, swallowing all of it quickly and then exited the stall. Luckily there was no one else waiting for the stalls at the moment and she knocked on his door.
He stumbled out in a daze and she caught him by the arm. As they left she wiggled her tail excitedly, still wearing a few streaks of errant white across her bottom that she didn't care about cleaning right away.
"What's say we hit the shower next. I want to do that again but I want you to see me when we do."
He could barely respond, barely walk at all and only bleakly found himself pounding away at her tight little ass in their hotel room shower several minutes later and for an hour afterwards.
The fourth day seemed to come all too slowly for Jack. For out of everyone he had planned on seeing this week for some private time he had wanted to spend time with Jill very much. He found her on the balcony of their room as the sun rose and he quickly changed into some clean clothes and grabbed a few items for his backpack. When he met her outside she was sitting calmly and for a moment he thought she was meditating and that he should come back a little later. As he turned to leave though she turned her head and looked at him. They stared at each other for an awkward moment and he opened his mouth to speak.
"I'm ready to go," said Jill, in a resigned way. He was a little confused but followed her the long way down the winding trails towards the Lost Caves on the north eastern side of the island. When they finally got there Jack stood beside her with an almost queasy look on his face.
The caves were anything but inviting, the mouth of which loomed before them with jagged teeth of rock and echoes of dripping water resounding eerily off the many facetted ridges. "This is where you want to be is it?" he asked Jill.
"It's a place to train," she said, "And it's private enough that we won't be interrupted."
He wasn't sure why she said the last part but ignored it and brought up another point. "You know, I don't have any HMs to teach you or the others. We may not get very far."
She nodded but continued onward anyway, leaving him behind to catch up at his own pace.
Being a Pokémon of her build she seemed perfectly designed to move through the cave's intricate system of paths and ledges. Jack on the other hand lagged behind quite a ways before she stopped to regard him. She managed to balance and hop from one slippery rock to the next without so much of a pause, but he had to take the long way around. It had been hours by the time she stopped and let him catch up, and she suspected they still weren't very deep inside yet.
"I'm... not sure... why these caves are... so amusing to you..." he gasped, holding out a hand for her to help haul him up onto her ledge, "But they're giving me... a workout if ever... there was one." He was drenched from the knees down from when he had slipped into a shallow pond and his pants and shirt were torn on the legs and sleeves in a few places when he skidded around a corner to fast and brushed up against a few jagged rocks on the wall. The caves were getting cooler as the light of day faded away, only briefly illuminating choice areas of the caves through tiny peepholes in the ceiling and walls. They rested in one of those areas now and Jack could see his breath and sneezed. "Why are the caves so cold in a tropical area?" he asked to no one in particular, not expecting an answer.
"They likely lead into some subterranean cave systems farther in. Probably right under the sea," answered Jill, who looked at Jack with only mild concern. "You probably shouldn't have joined me here," she said.
"Nonsense. I'm here for you just like I'm here for the others," he said, raising his arm tiredly her way before it dropped. He shivered.
"Then I suppose we should just get it over with," she mentioned with a resigned sigh, taking a position above him with one leg on either side of his waist. She waited for a moment as she expected him to unbuckle himself but when he only looked at her dumbly she grimaced and gently rubbed her foot along his crotch, getting an instant jerk from him as he sat bolt upright and then stood in front of her.
"Whoa! What are you doing?"
"What's it look like?" she asked, averting her eyes, "You only came here with me to be with me like you were with all the others anyway. We should just get it over with so you can go back to the hotel." She felt her fist balling at her sides as she said it and resisted his gaze even more when he knelt down to her eye level.
"Is that what you think?" he asked honestly, "Really Jill? Jill, look at me, look! Jill!" he raised his voice and grabbed her by the shoulders, causing her to wince in shock and meet his gaze with sharp threatening but tender eyes.
"Why else would you come to such a desolate place with me? You just wanted to find some excuse to get me alone in a place supposed to be for training," her voice cracked unintentionally and she covered her mouth as she lowered her eyes again.
"Oh Jill," he said comfortingly moving forward to wrap his arms around her shoulders. He couldn't think of what else to say at that moment and so let the already spoken words hang there. When they had finally gathered themselves he parted with her again and found her in the same posture as before. "Jill, I wouldn't do that to you. I wanted this to be special, yes, but special to you. If that means you don't want to be with me like the others that's okay. I don't expect it to be the case. I want you to be happy with me Jill, but you don't have to be like them. Just be you. I thought you wanted to be here because it would be good training," and he chuckled then, "But it turns out I'm the only one being trained." She didn't share his mirth. When he smoothed over her cheek with his palm and turned her gaze to his he only nodded. "Do you want to be here Jill? Because if you do, I want to be right here with you. I don't know what we're supposed to achieve but maybe that's what people come here to find out."
She couldn't turn her eyes away with his grip on her chin but she bit the inside of her lip and nodded. "I want to be here," she said slowly, and added in her mind that she wouldn't want to have come here by herself.
"Good. Then let's keep going. Maybe we'll find something to light a fire ahead. It's getting really cold in here."
As they continued, Jill didn't stray so far from Jack anymore, and let herself imagine that they were wandering into the darkness hand-in-hand.
Little did they know that two eyes watched them both very carefully and a toothy maw grinned widely as they passed.
"Five Island ahead. Please have all your belongings ready to depart upon arrival. Repeat..."
"Here we are girls," said Jack with a grand gesture with his arms. Five Island and... Resort Gorgeous."
They all stared at him through bleary, tired eyes for a moment as the words "resort" and "gorgeous" sank in and then their expressions changed dramatically. Save for Jill, who wore a stoic expression of "why should we bother?" the others were ecstatic, and leapt upon Jack with more verve and excitement than he had anticipated, landing solidly on his back with three extremely pleased Pokémon giggling like schoolgirls on top of him.
"Really? A resort? This was the surprise?" asked Maya, who seemed more excited at the prospect of rest and relaxation than anything else.
Jack could only smile, "This is it. I hope this means you like it."
"Do we?" asked Laura. "Jack I'm not even sure if I can put out enough to pay you back for this!"
"We'll all have to put out together then," said Sasha, hugging Jack around the neck despite him still being on the floor.
Jill just scoffed, "We shouldn't be wasting our time here, there's too much training to do. You haven't lost any weight at all have you?"
Her body belied her actual expression though, and Jack could tell by the way she crossed her arms over her breasts that she was pleased as well. If anything she had heard the rumors about the Lost Cave located beside the Resort, a famous site known for expeditions that trainers go on for training in the mastery of their Pokémon's use of their HMs. Jack didn't press her on the point but he smirked inwardly, knowing that there would be ample things for a bored Lucario to do at Resort Gorgeous no matter how vehemently she protested it.
"You're just jealous that we called him first," said Laura grinning with narrowed eyes at Jill and seemingly picking up the same signals that Jack was.
Jill looked down and for a moment dropped her hands to her sides in a protest. She was about to say something when the ship's horn blasted and cut her off.
"We'll be arriving soon. I'll see you all when I've checked in all right?"
They all agreed, even Jill, albeit reluctantly, though she managed a slight smirk Jack's way as he sent her back into her Pokéball, which only reconfirmed his initial decision that this was a good purchase.
"Can't train all the time. Sometimes, you just need a vacation." He said to himself as he made his way back to the room to get all their things packed. "Even if it does come after a nine day cruise."
The Island was twice as beautiful as the brochure made it out to be. As soon as he stepped off the ship he was showered with shouts of welcome from the locals and garnished with plastic flower necklaces. It was by far the friendliest place he had been in a long time, and he wasn't even away from the docks yet. There was another short ferry ride to the actual resort but in the meantime he took to admiring the sights of the main town of the island. It was small to be sure, and rustic, but it had a certain island quality he had kind of expected in the tropics where weather was often less pronounced but more severe. Luckily though the forecast called for nothing but sunshine; that's what he wanted to hear.
When he finally arrived an open building with tall marble pillars and gleaming marble floors greeted him. The concierge took his backpack, though he tried to insist he didn't need help, and he checked in without a hitch. Once he was in the room, sporting two beds and the standard hotel room suite layout he decided on the best place to introduce his Pokémon to the scenery. He decided on the balcony, despite only being on the second floor he had a perfect view of the wide open ocean and the beach not a two minute walk away. He called them all out at the same time and watched their reactions change from merely excited to stunned. With mouths hanging wide open, and no nausea coming from Jill, they were all enormously enjoying the prospects of staying here for a while. Instead of voicing her opinion, however, Laura merely took Jack by the collar of his shirt and drew him into a deep and passionate kiss. She would have dragged him all the way to the bedroom and disrobed him right there and then, but Jill cleared her throat audibly and broke them apart with a sideways glare that made it clear she wanted no part in watching such displays of adamant affection. Laura gave him a long pronounced lick from the nape of the neck to his lips then in defiant response, drawing a threatening full bodied glance from all of them but clung to him regardless.
"How long do we have the room for?" asked Maya, still captivated by the ocean and the beach.
"Six days and seven nights. The Anne will be in port until then and we take her back right to Cinnabar, where we switch onto a smaller ship and hustle our way to the docks south of Pallet Town."
"Let's not think of leaving yet. We only just got here," said Sasha, taking Jack's other arm before Laura could apprehend it, "I think I know what we all want right now." Laura got a huge smirk on her face.
Which soon vanished as Sasha led them all to a huge open buffet with some of the richest and prettiest and good looking foods they had ever seen. Sasha went first, then Maya, who seemed content with where they were at the moment and then Jill, who slapped Jack's hand whenever he tried to take something tasty looking and not up to her own healthy standards. No one begrudged her though because when they all sat down at one large round table with plates filled high with good food she was the most adamant speaker. She went on about rumors of the Lost Cave and how she had always wanted to see it for real and how Jack would be more of a trainer if he went with her, which she very quickly rectified as 'them' and described in detail the perilous adventures and ghost stories of all the trainers who had gotten themselves lost and perished inside. Maya, who hung on every word, was frightened and fidgeted in her seat and Jack only partially heard what she was saying beyond all the things Laura and Sasha were whispering in his ear.
When they had finished eating and stacked all their dishes neatly for the cleaning staff they were off to the beach. Evening was fast approaching and Maya especially wanted to get a glimpse of the beach under the sunset before it was gone for the night. Laura and Sasha didn't mind, and though it would be the perfect place to find a little cozy nook to hide away in and do unsavory but altogether enjoyable things to Jack. Jill went along as well, if for nothing else than to keep Maya company.
The two had become somewhat enamored with each other the past few days, which was not lost on Jack as he watched the two of them interact. Maya seemed to be the bridge between Jill and the other two, while Jill was the protective one, saving Maya from the prodding questions and fingers of the others as they tried to include her in one of their many schemes of sexual nature. The two went well together and he watched even when it wasn't arousing, noticing that they seemed to complement each other well, not just in a friendly sense, but in a practical one. Jill was always there to catch Maya as she stumbled and Maya was always there with a healing gout of water or icy mist when Jill overexerted herself. Despite being on holiday for so long Jack had been watching and thinking of ways that they may become even stronger together.
That thought aside though, the beach was magnificent. Recently combed and swept by the park crew the sand was crisp and clean and bunched up between Jack's toes even as he put his first foot down. He sighed as the latent heat seeped into his feet and kept walking, calmly enough to be left behind by the other, more excited Pokémon, Maya, Laura, and Sasha, and slow enough to match his more reluctant one.
"Penny for your thoughts Jill?" he asked.
"I don't know what you were thinking when you brought us here," she said, "It seems like just another excuse."
"An excuse for what?" he asked.
"Like you're giving them an excuse," she answered, nodding her head in the direction of the others, who had already made it to the water and were splashing around. "And don't play dumb. You know what I mean."
"Well, you may be right. But consider that we've got six days here, and I've only caught four Pokémon, little Riolu not included." He looked at her as though she should take the hint. "I have a day or two planned just for you Jill. And whether you like it or not, we're going to take a trip to the Lost Caves together."
Jill looked away, slightly embarrassed that she had been read so easily. But she smiled, and felt a little warm in her heart place that he would think to do anything with her despite her attitude.
Riolu hopped down from Jack's arms and barked as she ran on her hind feet, arms trailing above and behind her head towards the water where the others were tackling each other beneath the waves or trying to ride on top of Maya as she darted about.
Jill whispered a silent thanks to Jack for bringing her here regardless though. Even if she didn't show it, she liked the view very much.
Sunset came all too quickly and before long the water and the beach was too dark to stay on any longer. Despite Lopunny's begging to skinny dip in the waves Jack managed to weasel his way out and up to the lit beach house where a small dance was going on for the patrons. It was mostly humans and what Pokémon were there were likely still inside their Pokeballs. It wasn't so much odd to Jack as it was a little rude, since they're here on vacation they may as well give their Pokémon one too, but he guessed that few trainers treated their Pokémon quite the way Jack did.
The only one who didn't immediately join in the dancing was Jill, who stuck to the sidelines and found herself a chair to sit on. Ever the self-imposed outcast, when the song ended Jack wandered over to her and bent down.
"Dance with me?"
She averted her eyes as the next song started and Jack repeated himself. "Maybe I shouldn't have phrased it as a question. "Dance with me Jill." And before she could argue she was yanked off the chair by her hands and onto the floor, into a dance with twirls and sidestepping motions and a dip. She found that Jack was a fair dancer, at least as far as she knew. She had never danced before and let him lead all the way, which was a bit of a shock to her because she never would have allowed it otherwise.
"Jack, I can't..." she said between twirls, blushing deeper than before, feeling like the world's eyes were upon her at that very moment. "It's embarrassing."
When they were back up again Jack held her close to him with a hand around her back. "People only watch you at a dance when you sit out of it. Look around." She did, and saw not a single eye on her at all. Everyone had paired up. Laura and Sasha were busily tearing up the dance floor in the middle, and Maya was bent down with the little Riolu as she giggled playfully and wanted to be dipped again and again.
She really wasn't being watched. But it was still gnawing at her and she felt like stopping. She gripped his hands tighter. "It's all right Jill, watch." He spun her into a twirl that released her hand from his and she stopped, skidding on her feet into a position where her arms were out to either side, one stretched out towards him inadvertently. When the other dancers continued she found that she couldn't help but mimic their motions and twirled back into Jack's arms, this time with her back to his chest.
"See? All you have to do is have fun," said Jack as the dance wound down again and they remained in a slow calm routine.
"But I don't know how to dance," she said.
"A little late. You're actually pretty good. Look at Laura." She did, and watched as the uncoordinated Lopunny bumped into another couple and disturbed an entire line of dancers only to laugh and bow her head before taking the Blaziken's hands again. "You're a natural." He wound her into a prolonged spin so that her one hand came up above her head and the other twisted around her back in a lightly flowing arc. She found that she even arced her back a bit as it happened and when she stopped spinning, out of breath, she was in a dip and had one leg up in the air that Jack's arm held up for her, and her arm was out behind her head gracefully. Her eyes seemed to light up a little and as the music wound down again she found herself a little disappointed.
When Sasha came up to him in the next song she quickly removed herself from the dance floor, escaping onto the beach again and standing still in the dark. Despite herself she raised her hands for an invisible partner and twirled herself. She found it more difficult but she kept doing it, raising her arm above her head and trying to dip as low as she could go, trying to retain that feeling of Jack's arm behind her, supporting her, and his hand on her leg, holding it up to keep her in the dip. And her mind began to wander. To the feeling of his breath on her neck when she dipped, and his voice in her ear, just above a whisper. She stopped and was out of breath, bleary eyed, and held a hand to her breast, just over her heart, feeling it thumping inside as though she had run a marathon.
"You make it so hard to hate..." but that was the wrong word, "You make it so hard to dislike you Jack." She took a long glance at the dance floor, where the music had changed once again and he was dancing calmly and serenely with Maya, Riolu perched on his shoulders.
It was late when they returned to the room, and before he had a chance to protest, Laura grabbed his collar again and dragged him into the shower, closing and locking the door behind them. For the next little while noises of many different volumes and pitches could be heard and when they emerged, a billowing cloud of steam rolling out after them, Jill was the next to shove herself inside, pushing Jack beyond the threshold and locking the door behind him.
Alone in the bathroom, with nothing but the vanities for company, she moved into the widest part of the room and performed another flawless twirl and a dip and for a moment she was back on the dance floor with Jack right above her, so close. But then her hand brushed the door and she was instantly brought back to the humid white washed bathroom of their hotel. And she was just balancing herself alone, chasing a feeling she could never duplicate. With that in mind she slid with her back up to the wall into a sitting position and tugged her hands up to her knees. In her mind she could hear all the noises that stupid Lopunny made and every single one seemed aimed at her. Spiting her and declaring that which she could not have. Jill could feel a tear well up in her eye as she looked at the ceiling. Her lips mouthed a few words, but they didn't make sense in her mind. They were things she would never ever say.
At least not out loud.
The next day Jack left early with Maya. Laura and Sasha were still sleeping soundly on the bed, curling up against each other, likely imagining the other was Jack with squishy bits on his chest. He wondered what they would think when they woke up to find themselves entangled like that but then shoved it from his mind as it started to give him an erection. Riolu was sleeping on a billowy chair curled up and sucking its thumb. Jill was nowhere to be seen and the bathroom was empty, so he imagined she had found some place to amuse herself before everyone else awoke. She was the early bird after all.
Maya eagerly wanted to find the best place in all the resort to swim and Jack let her lead, figuring her sense of direction towards water was greater than his anyway. When she got them lost though he took over and managed to find his way to the resort's collection of hot springs. She was overjoyed and grabbed him by the hand to lead him there. She was a little cautious at first about getting in but the water was a comfortable temperature and she hopped in a moment later. Jack followed suit, though he stripped down first, much to the bemusement of Maya, who gave him a sultry look and a predatory wink. When he slipped under the water and came back up Maya was gone and only a moment later he knew where she was. Her mouth had his shaft completely trapped and was eagerly licking and teasing him to erection.
Though she couldn't hear his groans of pleasure she was aware of his hands gently stroking the fins at the side of her head and gently guiding her down deeper. She was skilled though, far more than he realized and before long she had taken his cock all the way to the hilt and suckled on it hard, swallowing around the length and massaging the head. She could taste the beginnings of his pre as she withdrew for a breath of the warm mountain water and was upon him again almost instantly. She drew him in with a great swallow and then backed away, bobbing her head faster and faster as she brought her master and lover to his peak. He arched his back and thrust his hips towards her mouth and she took it all in, swallowing every last bit of his seed as he found his release in her throat. When he was done she drew back, making one last long slow lick up the shaft and then surfaced, kissing him and rolling her hips against his, wishing him back to fullness so she could have him again.
The day went by too quickly for the two of them, who spent most of the day in and out of the hot springs performing one act or another to completion. And when evening came they all convened at the dining hall and the beach to cool down afterwards.
The next day it was Sasha's turn, who had found a secluded spot up on the rocks away from the shore where they could be alone and private. It was a bit slippery but they managed to find a relatively flat perch to roost on as the waves licked at their feet. For a long while Sasha only leaned against Jack's shoulder, wanting to enjoy the moment. But gradually her mind shifted and even as her hand slowly trailed up his leg, her head turned and she nipped at his ear, licking it playfully and whispering sweet nothings to him, which were returned in short order as his hands wandered over her body and tickled and excited and pleased her in ways they both knew they loved.
Soon they were disrobed and Sasha was poised on top of him. Her arms were above her head and she showed off her body to him. Jack, on his back and his hands on her hips, slowly guided her down so that her sweet feminine lips parted ever-so-gently for his shaft. She slowly sank downwards, grabbing her breasts as she did so and rolling them and mashing them together in the palms of her hands, tweaking the nipples as she hilted and sat for a moment to collect her thoughts as they swam around her pleasure filled mind. Then she began to grind her hips, gyrating them around and about but never lifting off of him.
His mind swam with all the sensations of his fire Pokémon's perfect motions, each driving him higher and higher. The way she had him pinned prevented him from thrusting but perhaps that was the way she wanted it right now. The way she moved he could feel her juices roll down and around his cock and lower body, mingling with the small puddle the waves had deposited on the rock over time. He groaned loudly but despite the perfectness of the moment and the erotic sight above him she was taking it so slow, driving them both up but taking her time with it. She took him by the hands and guided them both up to her breasts as she lowered her upper body to him, continuing with her soft grinding and gentle humping. Her eyes were closed tight shut and her breath came in ragged.
As they were both driven higher, sweat peeling down their brows she lowered herself completely onto him and bucked her hips, for the first time raising them off of his and then slamming them down, causing both of them to shudder and quake in pleasure. She repeated this and squealed, a plume of fire shooting from her mouth and singing the rock beside Jack's head. But he was too entranced by his Pokémon to notice. He tightened his legs and thrust up to meet her on the way down, slamming hard and grinding there for a moment before parting again. Every move they made was accompanied by a squelching sound as their mingled juices and soaking bodies slapped against each other in tandem. Faster and faster they moved together until finally, as they both reached their peak they groaned or squealed in blissful energy and the most intense orgasm either of them had had for a long while erupted between them, showering them and the rocks below with their juices.
Out of breath and panting hard they remained like that for a long time before Jack's softening length finally came loose from her still scorching hot body. They kissed then, and continued to do so even as the waves began to rise and the taste of salty sweat and ocean bit at their tongues.
On the third day it was Laura's turn, and she knew just where she wanted to go and what she wanted to do. With an excited gallop she took Jack to a secluded spot, sort of, where she had found something very interesting.
"Laura, why are we in the men's bathroom?"
"Because silly, I want to try this neat little thing I found yesterday." She stuck her tongue through a small round hole about waist high in one of the stalls, which thankfully had floor low walls to separate inside from out. Jack zoomed in on the glory hole immediately and almost passed out. Let alone why she knew about something like this, why would she know something like this existed in the men's restroom?
"Should I even ask?" he dared ask anyway.
"No. You just have to unzip and let me have it. I want to try it. It'll be fun."
Despite all the wires in his mind telling him not to, he unzipped his fly and placed himself against the rough surface of Laura's tongue, still poking through the hole in the wall. She retreated immediately and he followed, anxious now for the sensations she promised.
"As long as you promise me you'll brush your teeth afterwards okay?"
He heard no response and began to feel very awkward with his cock shoved through this hole in the wall. Then he felt her hands on him and was partially relieved. Though she was smearing something on his skin. It was slick and slippery but warm to the touch. Then there was more and he could feel her grip change a bit.
"Now just stay still. This is an experiment for me too."
"What do you mean an ex-ah!" he gasped suddenly as he felt something hot and tight and mostly dry slip around him. Laura gasped audibly as well and though he couldn't see it her tongue was hanging out of her mouth and she slowly continued pushing backwards onto his cock, the tight ring of her sphincter stretching around him and engulfing him in waves of tight, arousing heat. He could only breathe in gasps at the sensations winding through his body and though every bit of his mind screamed at him to remove himself immediately his body wouldn't obey. He found himself clinging to the wall and trying desperately to shove himself deeper. When she finally got as much of him inside her ass as the barrier between them would allow she reversed, pulling him with her for a moment before hearing a slick pop as she pulled off entirely.
"Let's try that again, shall we?" she asked, and hearing no reply smirked to herself and pushed back again, taking him inside her tight depths again and gasping as he struck a sensitive area. She reached down instinctively and began stroking her drooling pussy even while she began bucking her hips back and forth onto his slippery cock and taking him in quickly and harshly.
Pleasure blotted out his mind and he was breathing raggedly in moments, already nearing his peak. The tightness and the heat of her sphincter drove him to heights so quickly he almost couldn't control the volume of his masculine groan as he came. She felt it too, the splattering of his seed all over her insides and quickly withdrew, taking several long strands of white sticky seed all over her bottom and then turning quickly, to take the last few on her tongue. She smiled, swallowing all of it quickly and then exited the stall. Luckily there was no one else waiting for the stalls at the moment and she knocked on his door.
He stumbled out in a daze and she caught him by the arm. As they left she wiggled her tail excitedly, still wearing a few streaks of errant white across her bottom that she didn't care about cleaning right away.
"What's say we hit the shower next. I want to do that again but I want you to see me when we do."
He could barely respond, barely walk at all and only bleakly found himself pounding away at her tight little ass in their hotel room shower several minutes later and for an hour afterwards.
The fourth day seemed to come all too slowly for Jack. For out of everyone he had planned on seeing this week for some private time he had wanted to spend time with Jill very much. He found her on the balcony of their room as the sun rose and he quickly changed into some clean clothes and grabbed a few items for his backpack. When he met her outside she was sitting calmly and for a moment he thought she was meditating and that he should come back a little later. As he turned to leave though she turned her head and looked at him. They stared at each other for an awkward moment and he opened his mouth to speak.
"I'm ready to go," said Jill, in a resigned way. He was a little confused but followed her the long way down the winding trails towards the Lost Caves on the north eastern side of the island. When they finally got there Jack stood beside her with an almost queasy look on his face.
The caves were anything but inviting, the mouth of which loomed before them with jagged teeth of rock and echoes of dripping water resounding eerily off the many facetted ridges. "This is where you want to be is it?" he asked Jill.
"It's a place to train," she said, "And it's private enough that we won't be interrupted."
He wasn't sure why she said the last part but ignored it and brought up another point. "You know, I don't have any HMs to teach you or the others. We may not get very far."
She nodded but continued onward anyway, leaving him behind to catch up at his own pace.
Being a Pokémon of her build she seemed perfectly designed to move through the cave's intricate system of paths and ledges. Jack on the other hand lagged behind quite a ways before she stopped to regard him. She managed to balance and hop from one slippery rock to the next without so much of a pause, but he had to take the long way around. It had been hours by the time she stopped and let him catch up, and she suspected they still weren't very deep inside yet.
"I'm... not sure... why these caves are... so amusing to you..." he gasped, holding out a hand for her to help haul him up onto her ledge, "But they're giving me... a workout if ever... there was one." He was drenched from the knees down from when he had slipped into a shallow pond and his pants and shirt were torn on the legs and sleeves in a few places when he skidded around a corner to fast and brushed up against a few jagged rocks on the wall. The caves were getting cooler as the light of day faded away, only briefly illuminating choice areas of the caves through tiny peepholes in the ceiling and walls. They rested in one of those areas now and Jack could see his breath and sneezed. "Why are the caves so cold in a tropical area?" he asked to no one in particular, not expecting an answer.
"They likely lead into some subterranean cave systems farther in. Probably right under the sea," answered Jill, who looked at Jack with only mild concern. "You probably shouldn't have joined me here," she said.
"Nonsense. I'm here for you just like I'm here for the others," he said, raising his arm tiredly her way before it dropped. He shivered.
"Then I suppose we should just get it over with," she mentioned with a resigned sigh, taking a position above him with one leg on either side of his waist. She waited for a moment as she expected him to unbuckle himself but when he only looked at her dumbly she grimaced and gently rubbed her foot along his crotch, getting an instant jerk from him as he sat bolt upright and then stood in front of her.
"Whoa! What are you doing?"
"What's it look like?" she asked, averting her eyes, "You only came here with me to be with me like you were with all the others anyway. We should just get it over with so you can go back to the hotel." She felt her fist balling at her sides as she said it and resisted his gaze even more when he knelt down to her eye level.
"Is that what you think?" he asked honestly, "Really Jill? Jill, look at me, look! Jill!" he raised his voice and grabbed her by the shoulders, causing her to wince in shock and meet his gaze with sharp threatening but tender eyes.
"Why else would you come to such a desolate place with me? You just wanted to find some excuse to get me alone in a place supposed to be for training," her voice cracked unintentionally and she covered her mouth as she lowered her eyes again.
"Oh Jill," he said comfortingly moving forward to wrap his arms around her shoulders. He couldn't think of what else to say at that moment and so let the already spoken words hang there. When they had finally gathered themselves he parted with her again and found her in the same posture as before. "Jill, I wouldn't do that to you. I wanted this to be special, yes, but special to you. If that means you don't want to be with me like the others that's okay. I don't expect it to be the case. I want you to be happy with me Jill, but you don't have to be like them. Just be you. I thought you wanted to be here because it would be good training," and he chuckled then, "But it turns out I'm the only one being trained." She didn't share his mirth. When he smoothed over her cheek with his palm and turned her gaze to his he only nodded. "Do you want to be here Jill? Because if you do, I want to be right here with you. I don't know what we're supposed to achieve but maybe that's what people come here to find out."
She couldn't turn her eyes away with his grip on her chin but she bit the inside of her lip and nodded. "I want to be here," she said slowly, and added in her mind that she wouldn't want to have come here by herself.
"Good. Then let's keep going. Maybe we'll find something to light a fire ahead. It's getting really cold in here."
As they continued, Jill didn't stray so far from Jack anymore, and let herself imagine that they were wandering into the darkness hand-in-hand.
Little did they know that two eyes watched them both very carefully and a toothy maw grinned widely as they passed.