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A Friendly Wager
By : Almister
Category: Pokemon > General
Views: 13438 -:- Recommendations : 2 -:- Currently Reading : 0
Disclaimer: I don't own Pokemon, I make no money from this story.
Chapter List
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                A few days passed and Liz and Sasha were finally at the Violet City, on their way to the Pokemon Gym. They had stopped the night before at the Pokemon Center, to rest and get cleaned up. Liz had to mentally beat up the small part of her that giggled at the memory of another fun time in the shower. She smiled at the thought anyways, if that was what awaited her at every Pokemon Center she was in for a good trip.

                The town was rather busy, groups of people trainer and otherwise wandered through the streets. The pair walked towards the Violet City Gym with no real hurry or urgency, often stopping to window shop, or poke around in interesting shops. Liz had made a good chunk of money on her way here, and Sasha wasn't charging interest.

                Soon enough the gym was in view, along with a rather sizable crowd in front of it. Drawing closer both trainers noticed the crowd was mainly young girls, with a rather handsome and well dressed boy in front. "Fangirls." Sasha commented with some distaste, picking up the sounds of squealing praise even from this distance. Liz was surprised to see that anything could cause the boy to lose even a small fraction of his endless patience.

                "Hey, I know that guy." Liz said, cringing at the thought of bumping into him. "His name is Darius, he's a rich guy from New Bark Town. His family is wealthy, and he always holds it over other people."

                "Well, this should be interesting then." Sasha merely replied, hurrying along towards the crowd.

                Once they were close enough Darius turned to look at them, distaste evident on his face. "Well well well, if it isn't little Elizabeth. It certainly took you long enough to get here."

                "It couldn't have been that long Darius, if you're only getting your badge now." Liz replied, trying to keep a cool head.

                "I've been training in Sprout Tower, some of us are trying to raise strong Pokemon after all. I'm actually more shocked that you're still training, I figured a poor girl like you would have run out of money by now. Or at least you would have found a rich boy to sleep with, to keep going." Darius said haughtily.

                Liz cringed, that was exactly what she had done, but she had more pride than the little whores that followed Darius around. Even now about a dozen skimpily dressed girls hung on his every word, acting as little more than cheerleaders for the boy.

                "Instead, it seems like you're following some country hick." He said, giving Sasha a once over. "Does he even speak? He looks rather simple."

                "Oh? Hey, you have a Larvitar? I didn't think you could catch them around here." Sasha said, ignoring the entire banter and crouching down to inspect the Pokemon. He reached out with his stick and tried to poke the creature, only to laugh as it tried to bite the stick in half.

                Darius twitched slightly and swatted the stick away. "Of course I didn't catch it. My family purchased it for me." he said, straightening his jacket.

                "Oh? Let me guess. You have a full team already, consisting of a Larvitar, Dratini, Bagon, Beldum, Gible and Deino." Sasha said, standing back up with that same simple smile on his face.

                "The best money can buy. Not that either of you would know much about money. Larvitar here just beat everyone in that gym, and he's not even winded. I can give you a demonstration if you like?" Darius said, giving a small grin.

                Liz opened her mouth to mention that Sasha didn't battle, but the boy cut her off. "Sure thing, how about a three on three?" Shocked, Liz looked over in surprise at the boy, who placed his backpack and guitar on the ground and drew out three Pokeballs.

                Darius grinned and tossed out two more Pokeballs, revaling his Metang and Deino. Sasha tossed his own casually, revealing his Mienfoo as well as a Duosion and Pawnard. Liz sat off to the side, ignoring the cheers of Darius's fangirls.

                "Well? What are you waiting for?" Darius called, seeing Sasha not really paying attention. "Fine, I'll start things off. Larvitar use screech on that Pawniard!"

                Sasha merely continued smiling. "Pawniard, use hone claws." The Dark/steel type stared down the Larvitar, content to sharpen its claws against each other.

                "Deino use Bite on that Duosion!" Daruis called, remaining calm.

                "Pawniard, intercept it." Sasha said, the little dark/steel type stepped into the way, catching the bite and easily tossing the Deino aside.

                "M-Metang! Hit that Mienfoo with a confusion!" he ordered, the Steel/Psychic finally getting in on the action.

                Sasha yawned. "Pawniard, again!" He ordered, the Dark type leaping into the way and soaking the damage easily. "You really picked poor choices for this battle. Have you fought team battles before?"

                "S-shut up! Larvitar use-" Darius began.

                "Enough of this, Meinfoo, U-turn on that Metang! Pawniard, follow it up with a Pursuit!" Sasha called, and the weasel Pokemon darted forward, kicking off the Metang's head. Before the Pokemon could recover Pawniard was in its face, slamming into it with several bladed limbs and sending it back in a heap.

                "Metang!" Darius called, trying to coax the Pokemon to its feet.

                "Pawniard, Fury Cutter on the Dieno, Mienfoo, Force Palm!" Sasha continued, and another vicious double team hit the little dragon.

                "Larvitar! Get in there and help him!" Darius panicked, seeing his Pokemon getting bullied.

                "Duosion, hit that Larvitar with an Energy Ball. Pawniard, Metal Claw, Meinfoo Rock Smash." Sasha ordered, and a vicious trio of attacks knocked the Larvitar clear out of the ring.

                "There's more to training than having strong Pokemon. Strategy is everything." Sasha said, recalling his Pokemon and picking up his bags.

                "How dare you do that to Darius's Pokemon! That was unfair, ganging up in a fight!" Came calls from the defeated trainer's fan club.

                "Any of you want to face me for revenge, beat Liz first. I'm going inside." Sasha called, leaving his 'slave' to handle the sudden onslaught of challenges.

O~O~O~O~O

                "Oi, Falkner!" Sasha called, looking around an empty gym.

                "I'm in the back! If you're here for the challenge you'll have to come back tomorrow, my gym challenge team is recovering." Came a voice from behind an open door near the back. Most gym leaders rotated their Pokemon, keeping their strongest in reserve and using weaker ones to challenge trainers. This helped the league circuit scale itself to the general level of travelling trainers, yet allowed the leaders to deal with threats with much stronger Pokemon.

                'Weaker' of course, was relative. All gym leader Pokemon were well trained and gym leader battle tactics made for tough battles.

                Eventually a familiar head poked out of the back, and brightened noticeably at seeing the travelling trainer. "Alexander? What the hell are you doing in my gym?" Falkner asked, coming out of the back room.

                "Eh, I'm on vacation." Sasha shrugged. "Training my latest member of my backup team." With that he tossed out his Mienfoo.

                Falkner let out a low whistle, sizing up the little weasel. "Is that?"

                "The son of Marshal's Mienshao? Yep, been working with him for a few months now. He's a real prodigy though." Sasha said.

                "So you finally got that trio huh? You are one heck of a gambler. A lot of trainers would kill to be raising the offspring of three of the Unova Elite Four's Pokemon." Falkner said.

                "Yeah, I've heard it before. But hey, I'm not the league champion in the Unova triple battle circuit for nothing." Sasha shrugged.

                "You're also a notorious slacker, apparently you haven't been doing your job in months." Falkner grimaced.

                "Like I said, I'm on vacation. There's a tournament once a year, as long as I show up and win I keep the title right? The rest of my time the underlings can take care of it." Sasha said, returning the Mienfoo. "I'm just travelling around training my reserve team, and Liz."

                "Liz huh? Only you would take up training trainers as a hobby. Is she any good?" Falkner asked, taking interest.

                "She's pretty good, probably better than the last guy you fought." Sasha commented.

                "Doubtless, that guy was a total jerk, and not very good as a trainer." Falkner said, sighing, "Sometimes I wish I could bring out my real team against guys like that."

                "See why I'm always wandering? I don't want to have to deal with the things you do." Sasha laughed. "Anyways, Liz should be done soon, I take it we'll have to delay our battle till tomorrow?"

                "Preferably, I take it she'll sweep my team anyways, but rules are rules." The flying trainer shrugged.

                "Alright, I'll take her to Sprout Tower then."

                "Oh, and call Skyla once in a while, she talks about you a lot you know." Falkner said, laughing at the blonde trainer as he left.

                "Don't they all?" Sasha laughed as well, causing Falkner to shake his head in exasperation.

O~O~O~O~O

                "Well? Anyone else have a problem?" Liz asked, her Teddiursa stood in front of her, claw in mouth and look about adorably. There were several grumbles of 'Stupid tomboy' and similar comments, but she let them pass over her. Like Sasha had said, they could insult her all they wanted, it changed nothing. They were just cheerleaders, not real trainers themselves. They weren't trying to win anything, just riding on coattails.

                It had been tough, there were at least ten girls present, and each had two or three Pokemon, poorly trained as they were.

                "Oi, Liz, done playing around yet?" Sasha asked, once more emerging from the Gym. "Falkner is busy, we've got a day before we fight him. Let's go shopping."

                Rolling her eyes she recalled the little cub and fell into step beside him, the two walking steadily into town. They stopped by a few more stores, picking out various items they required, food, medicine, camping supplies, until Sasha dragged her into a 'special' store.

                It was an adult store, that much was obvious walking into it, everything was so... pink. She cringed, never really appreciating the color. Sasha strode in nonchalantly and began perusing the shelves, Liz followed him in, looking about nervously. "You aren't going to make me wear a collar or leash or anything are you?" She asked, looking at a rack of them, next to some rather standard kinky outfits.

                "Ah, you're one of those couples hm?" came a voice from behind the counter, a young lady walked out from behind a curtain and glanced over each of them. "She isn't well trained is she?" She said, eyeing Liz closely.

                "Ah well, I find the best approach to training is to allow a rather free run of things, so long as they obey when it's important." Sasha shrugged, as if he was talking about training Pokemon. Liz had to wonder how many girls he had 'trained' in the past. "Do you have anything... interesting?" He asked, seeming to be bored with most of the shops stock of items.

                "Hmm, I'm not sure if we have much in the way of Master/slave items. Usually we get Pokephiles around here." The lady at the counter said, pulling up an inventory on her computer.

                "P-pokephiles?" Liz asked, it was such an abstract concept to her, people sleeping with their Pokemon. Blushing she turned her attention back to browsing the store. There was a rack of costumes in one corner, all stylized after various Pokemon, made out of various fabrics. She toyed with one of them, styled after a Furret, and noticed it came with a butt-plug tail.

                "Does that take your interest?" Sasha whispered, coming up behind her silently. Her ass clenched at the thought of wearing the entire ensemble, and she could picture bending over and being taken while wearing it.

                Shaking her head to clear it, she began perusing other things. There were dvds near the back, both regular porn and Pokephilia. She had to suppress a giggle at some of the absurd titles. Still, she took a few glances back at the rack of costumes.

                "I didn't take you for a Furret fan." Sasha commented, noticing her glances.

                "I'm not, really." She said absently, looking over at the rack.

                "They've got other ones, Luxray, Pikachu, any of the Eevee-lutions." He noted. "Even a six tailed Vulpix one."

                That one caught her attention, she had wanted to add a Vulpix to her team at some point, when she initially started her journey, finding them absolutely adorable. She moved over to inspect the costume, it was a rather simple piece. It had a headband with ears and three small red curls on top, a pair of gloves for her hands, a tube top that could easily be pulled down to expose her breasts, and a pair of shorts that could expose her ass and pussy when needed all covered in a rather nice skirt. It also came with cute little socks, along with the six part red tail/butt plug.

                "I didn't take you for the type." Sasha said, seeing her looking the costume over with more than just curiosity. "I figured you'd stick to ice types, or at least look for a bear-styled one."

                "I'm a sucker for cute Pokemon." She shrugged, turning away from the costume, it was far too expensive anyways.

                "We'll take three pair." Sasha said, causing her to nearly trip.

                "Three?" She stammered.

                "Well, not the tail of course, we only need one of those. But you can't travel the world with only one pair of clothing." Sasha said, Liz wasn't sure if he was joking.

                "Y-you're going to make me walk around in public wearing this?" She asked, nearly in tears.

                "Don't worry, it's not all that much different from your usual outfit is it? Aside from the overalls." Sasha shrugged.

                "And the butt plug? How am I going to pass that off?" She asked.

                "It's built so that when wearing the whole thing the tail looks like a belt, see? Nobody will know exactly where the tail connects to your body. We can modify other clothing later, if it starts to get too cold." Sasha waved off her concerns. Soon enough the lady behind the counter had their order ready, and the two returned to their room at the Pokemon center.

O~O~O~O~O

                "I can't do it!" Liz called from inside the bathroom.

                "You can't or you won't?" Sasha called back, walking over to the closed door.

                "I can't, there's just no way it'll fit." She called back. He opened the door and walked inside, seeing her dressed in the full costume, on her hands and knees. One of her hands held onto the tail, trying to force it into her.

                "Take it easy, you can't force it." Sasha said, kneeling down next to her. "I'll help you put it in."

                "It won't fit." She said, nearly in tears.

                "Come now, remember what I said about trusting me?" Sasha gave her a small smile, which she somehow managed to return before turning to look down and raising her ass into the air. "Suck on this for a bit, it'll help." He said, handing the tail to her.

                As she slipped the plug into her mouth he leaned forward, separating the overlapping slit in the fabric over her asshole and giving it a light lick. He continued, as she started to moan around the rubber object, pushing slightly harder until the tight ring of muscle began to give way and he managed to slip the tip of his tongue inside. Moving his hand up he slipped two fingers into her wet pussy, getting them soaked with her juices, and then replaced his tongue with one.

                It slipped in easily, and he moved it around a bit, loosening the girl up enough that he could fit in the second. With the second one inside he began stretching her, gradually opening her up enough that she could take the plug. When he decided she was ready he took the tail from her and positioned it at her entrance. "Are you ready? Don't clench, push like you're going to the bathroom." He instructed, seeing her asshole wink in response.

                He pushed, gently at first but gradually increasing the pressure until the narrow tip began pushing its way inside. She groaned and clenched her teeth against the intrusion, and Sasha stopped, rubbing her gently until she relaxed again. "I don't think I can do it." She panted out.

                "Of course you can, just relax." He instructed, once again pushing. They were halfway done, and he was rocking the plug back and forth, gradually loosening the incredibly tight ring further and further as she moaned with ever centimeter of distance. Eventually they got passed the thickets section and the rest slid in with a nearly audible pop.

                Liz gasped out as she felt the entire thing enter her, and began adjusting to the feeling. Moving around a bit caused her to moan as she felt the 'tail' shift inside of her. "Oh Arceus, I'm going to be perpetually horny." She moaned, feeling spikes of pleasure as she wiggled her hips.

                "Don't worry, I'll take good care of you." Sasha purred, continuing to rub at her pussy.

                "When are you going to fuck me already?" She complained, grinding back against his touch.

                "When are you going to ask?" He laughed, causing her to give him a death glare. He fixed the tail so that it was pointed more towards the back of her body, and she rose on shaky legs. checking herself out in the mirror she was rather impressed by how well she pulled the outfit off. Sure her sandy blonde hair made it a bit odd, but maybe she could dye it red?

                With the tails positioned properly nobody could tell where they were attached to her without getting a close look up her skirt. Grinning mischievously she walked towards the bed, swishing her hips and feeling the tails wag behind her, biting back a loud moan as the plug shifted within her. Reaching the bed she climbed on to it, once more getting on her hands and knees and shaking her tails back at Sasha.

                "Pretty pretty please with sugar on top?" She asked, giving him her best puppy, or fox in this case, eyes. Sasha shook his head and rose to his feet, fishing out his already hard erection as he approached. Liz shivered in anticipation as he grabbed her new tails in a firm grip, pulling them roughly out of the way and applying delicious pressure to the plug. With another hand resting on her hips he plunged into her, filling her to the very brim.

                If having one thick object lodged inside her was wonderful, two at once was the most amazing feeling she'd ever felt. Never in her life had she felt so full, and she knew that every moment after this she'd likely feel empty by comparison. His manhood stretched her to almost painful levels, rubbing up against all the most sensitive bits within her and bumping against her cervix every time he bottomed out.

                Her hips rocked back against him furiously, driving her further and further into a delirious haze of pleasure, until she pressed back against him and shook with a very noisy orgasm. The feeling of her insides rhythmically clenching against both his dick and the plug prolonged the feeling of ecstasy, until she was calm enough to allow him to continue.

                And continue he did, on and on passed even her second orgasm of the night. When she wasn't fucking herself on him he held a maddening slow and steady rhythm, much like everything else in life, and seemed to have limitless stamina. When she had finally exhausted herself, and lay her head down on the bed, he kept her ass up in the air and continued on, pushing himself in and out at a rather leisurely pace.

                She swore she could have passed out from exhaustion and woken in the morning to him still going, but eventually she caught her second wind and began thrusting her hips back against him, working quickly to her third orgasm of the night. When she had finally reached her peak she pushed back against him again, and felt her muscles clenching at his cock. To her surprise the feeling was also accompanied by a deep groan on his part as he emptied a massive load of searing hot cum into her. The feeling of it filling her made her cum even harder, and when he withdrew she clenched instinctively to keep the feeling inside.

                The two collapsed into the bed, and neither bothered with covers, instead content to just lay spooning against each other, basking in the afterglow. "Are you going to do that more often?" She asked, signing contentedly.

                "Only if you're a good girl." He replied lightheartedly, giving her a small squeeze against himself.
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A Friendly Wager	By : Almister Category: Pokemon > General Views: 13438 -:- Recommendations : 2 -:- Currently Reading : 0
Disclaimer: I don't own Pokemon, I make no money from this story.

A Friendly Wager