Some Random Smut Collection(R18+)

(Note: There's a part 2 to this, it's chapter 77)

If there was one thing Ash regretted in life, it was that he was ten years old, once upon a time.

His almost tunnel vision obsession with Pokemon when he started his travels had been something that helped blind him to a lot of things in the world around him he should have noticed more. One of them, naturally, had been the issue of romance. For years, Ash traveled the world, often with a bright-eyed and adoring girl in tow who followed him as they both pursued their own hopes and dreams, and he always saw them as friends, not because he lacked interest in them, but because he lacked interest in romance in general. Then there were all the beautiful women he met. Gym leaders and other trainers, even a few criminals or scientists who would have caught the eye of anyone who paid attention to girls and not to Pokemon.

But that was years ago. Ash was no longer a ten year-old boy with a plucky wish to succeed and who needed to find the tools to do it. He was a man now, and he had more to his name than badges and titles like 'quarter finalist' or 'runner up'. Maturity set in both emotionally and as a prospective Pokemon Master, whose bedroom was now a collection of trophies and awards. No longer scraping by only on what money he made fighting random trainers--when he won, that was--he could live comfortably off of the fat prize money he won in major tournaments. His travels lost their aimless nature, no longer simply making his way to the next gym on foot and casually. Moving across the world and to all manner of regions, Ash flew in for big tournaments and took care of his business with purpose and duty.

Which was great. Ash was living the dream in a way that he didn't think he would likely get tired of as he savoured the freedom and success that came from being a bona fide Pokemon Master. But something else had to draw his interest eventually, and he decided it was time to start shifting his focus. He had battling well in hand, and it was time to look for something else he could put his energy and interest into. In that regard, what possible direction could have been better than finally making up for all of his lost time and foolish mistakes?

When Ash received the letter inviting him to compete in the Sinnoh Summer Festival Invitational, he knew the time had come to go all out, and that the first woman he had set his eyes on for the beginnings of his plans to start going for the beautiful women he should have noticed years ago was most definitely Cynthia, still Sinnoh's reigning champion and an absolute beauty. How a young Ash had not noticed the gorgeous blonde's appeal before was beyond him. Not only was Cynthia absolutely stacked, but she had a bit of a nefarious reputation--though no one would ever admit it publicly--of her regularly seducing men and even teenage boys who she deemed talented trainers.

But there was nothing rumoured about it; Ash had even been 'subtly' propositioned a few years earlier when he battled the Sinnoh Elite Four, and back then he was still utterly oblivious to everything she said, the words going right through one ear and out the other at the time. But no longer. Ash wasn't the wiry teenage boy he once was, and it should only have been easier to make up for what he hadn't understood before.

Stepping off of the shuttle bus from the airport, Ash stepped into the grandest hotel in Hearthome City, fresh off the airplane from Kanto and ready to get settled in for his long weekend, which aside from battling was going to be a twofold mix of relaxation when he had the time to, and hopefully fucking Cynthia like an animal when he wasn't. And what a coincidence that as he walked into the hotel lobby, he saw by the check-in desk a familiar silhouette, with long blonde hair reaching down to the legs of a woman whose body was covered by a long black coat, which was loose enough to leave some of her figure a mystery while still showing off the promise of curves just fine.

Ash was a new man now. No longer the same naive teenage boy hyper-focused on Pokemon that he'd been when he first met her, or even a few years ago when he last saw her during his return to successfully challenge the Sinnoh League, he moved with purpose as he walked toward the desk, still traveling with a large camping style backpack, which now thankfully didn't have to hold a sleeping bag as he got used to living out of hotels and not slumming it by camping off the main paths of routes. There was no hesitation in his movement as he eyed the slight bend in Cynthia's posture, knowing exactly how he was going to make his grand entrance and assert himself.

Leaning over the desk and making small talk with the desk clerk she was arranging some room service matters with, Cynthia didn't pay much much to her surroundings. She had a lot on her plate through the long weekend as the celebrity face of the Sinnoh Summer Festival, hosting the tournament, the contest, and generally acting as master of ceremonies. Or mistress, as it were. All she wanted to do was set up what she had to deal with, to get all the pieces in place so that she had it all out of the way, with whatever luxury she could find in the day before it happened to come once it was all set; taking things one at a time now was a good way to keep from stressing herself before everything even started. Paying so little attention to her surroundings, Cynthia didn't think anything of someone coming up beside her.

Until someone squeezed her ass.

For a second, Cynthia froze up, abruptly stopping mid-sentence. The firm dig of fingers into her rear was strong even through her pants and her coat, leaving her to look over her shoulder in dismay and frustration as the fingers released and came down again in a quick swat. Ready to call whoever had done it out, she started, "Excuse m--"

"I have a reservation under Ash Ketchum," Ash said to the adjacent clerk, ignoring Cynthia as he cut her off, handing his trainer ID to them before slowly turning his head and smirking at the champion, whose eyes went wide as her frustrations immediately fell silent.

It was fortunate that Ash had said his name, because Cynthia looked in shock at the man standing beside her, who she never would have recognized if he hadn't said anything. The Ash she first met was a spindly, lean kid who couldn't think of anything but Pokemon training. The Ash she met a few years later had matured and grown in so many ways, but he was still coming along at sixteen in ways that hadn't yet finished manifesting-but had manifested enough for her to proposition him in a little bit of her wicked sort of indulgence. But now, as an adult, Ash was something else entirely. His wiry frame had bulked up over his travels and in growing up, broader shouldered and in incredible shape. His black hair was even messier and longer than it once was, but in a more raggedly mature sort of way than just looking like a kid who, without his mom to tell him to, just started skipping his haircuts.

"Ash." Cynthia sounded very matter of fact by way of pure disbelief as she looked at him. It sounded strange to say as she looked at him, sp0otting the smile perking up in the corner of his mouth.

"It's good to see you again," he said, broadening his smile as if meeting an old friend by chance.

"I barely recognized you. You've really grown." Her sentence hung, 'grown' not the conclusion but the prelude to words that drifted off as she decided woman in her thirties calling an eighteen year old any of the things running through her head was a terrible idea. Words that ranged from 'handsome' to 'a hunk' to 'someone I need upstairs and inside of me right now' were all remarkably poor for and she didn't want to embarrass herself any more than she already was. Almost nobody could throw Cynthia off of her game, but then, most of the time she was the one initiating contact and hitting on people too nervous to proposition a champion. Ash was being bolder than most, and the surprise combined with the revelation of how he looked now were enough to leave her at a disadvantage.

A disadvantage Ash wanted to press even further. "Has it really been that long?" he asked, blowing it off as he worked his plan, knowing exactly how long it had been and how jarring the last few years had been. Ash was a late bloomer, but he had most definitely bloomed. "Funny, it doesn't feel like it, and I actually hoped I would run into you because I wanted to talk about something from last the last time we met."

"You did?" Cynthia asked, taking half a second to remember how their last conversation had gone, and as she looked again at Ash, she couldn't help but bite her lip as the realizations hit her hard and fast.

"Yeah," he says, shifting his position so that the clerk doesn't notice his arm moving behind their backs as he goes in for an assertive second grab of her ass. He could feel Cynthia tightening up against his touch as he groped her more openly and aggressively. "You made me an offer last time, and I didn't realize at the what you were asking me. If still stands, I would love to have a second chance at it."

Cynthia's eyes fell again onto Ash, fidgeting nervously as she was fondled and groped so blatantly and openly. She wanted to turn her head over her shoulder and see if anyone was paying any attention to it, but she found herself too taken by Ash's new looks to be able to. "Of course it does," she said, so tragically off of her game that she could hardly live with herself for how poorly this was going, but she knew she had to just accept that she had been taken by surprise. With some time to gather herself, she would be fine again. As the clerks helping both of them turn away to handle the clients' requests, she leans in and says lower, "In twenty minutes, take the lobby elevator up to the penthouse suite."

It almost shouldn't have been that easy. The timing and Cynthia's immediate agreement to what he was after were both signs of the good fortune he hoped awaited him in the tournament. Not that he cared much at all about the tournament, slapping her ass again and smirking. "Wear something slutty, or nothing at all," he said, and that was all the indication Cynthia needed that this was definitely not the Ash Ketchum she remembered. That his travels and maturity had done things to him that turned him into someone very, very different than he once was.

And as much as she loved adorable, bright-eyed trainers for her legally questionable-at-best exploits, she was loving every second of what she saw.

"Here you go, Mister Ketchum," the clerk said, handing Ash his key card. "Please enjoy your stay."

"I'm sure I will," he said, flashing one last smirk over to Cynthia before stepping back and smirking. If anything, twenty minutes was going to be a long time to fill; all he had to do was get quickly settled in and retrieve a little something special from his backpack. A gift, in a sense.

*********************************

Ash had never been up in a penthouse suite before. Accomplished battlers may have been big stars, but that was a lot of money to throw around casually, and Ash preferred a good room in a nice hotel over excessive luxury. It was all sleep either way. But going up to a penthouse on someone else's dime was a different matter entirely, and Ash gladly came back down to the lobby, flagging down the private elevator that went on an express trip up the tall building and right to the penthouse on the topmost floor. He carried with him only a small drawstring bag with him as he buzzed to the top floor.

"Yes?" asked Cynthia over the intercom.

"It's Ash," he said, and within seconds, a little light over the buzzer turned green, inviting him up to the penthouse. He stepped into the elevator, and so began the single longest elevator ride of his life. Not only because there were over fifty floors to race up, but because he was so close now to finally kicking off his plan, which was elegant in its utter simplicity. He had a running mental list of plenty of the gorgeous women he had encountered over the years who in hindsight he felt like an idiot for not going for. Some had made moves on him before, others were simply his kind of woman, but one by one, he was determined to get all of them utterly ensnared and devoted to him in ways that were perhaps almost cruel in the intensity he sought.

And Cynthia would be his first. A prized conquest by any consideration, but also a very bold way to stake his claim. He was no virgin by this point, his fame as a Pokemon Master and his rapidly maturing sensibilities having helped greatly in allowing Ash to have casual bouts to hone his sexual abilities and figure out what he was into, and he brought all of those experiences to the table when it came now to conquering Cynthia. She wasn't going to go down easy, very experienced and one of the oldest women on his list, who despite being in her early thirties had slept around quite a lot. But if he could make her submit to him utterly, then there was no way every other woman he lusted after wouldn't follow suit and shatter for him. It was the promising start to something he knew would be amazing.

When the elevator reached the top with a pleasant ding, Ash was greeted with exactly the kind of sight he'd wanted from his arrival. Cynthia stood in front of the elevator entrance, which fed right into the living room area of the penthouse suite, wearing her coat open and showing off some clothes very different than the ones she had been wearing down in the lobby. Her black pants had been replaced with black black nylon stockings, trimmed with a lacy top that dug into her thighs firmly. A matching set of black lace bra and panties emphasized her full breasts and her hips, leaving just enough to the imagination to get Ash's mind spinning as he stared at her, so happy that he had decided to go for Cynthia first; she looked amazing.

"I should have fucked you years ago," Ash said, stepping out of the elevator, tossing the bag onto a counter and grabbing hold of her. Cynthia was still thinking about Ash in the context of the kind of boy who would never have seized her so aggressive and started to make out with her, so it caught her by surprise when his fingers dug into her hip and her shoulder while going in for a kiss. Not that she minded that he did, of course, his very forward and almost possessive approach to initiating contact leaving her wanting more. Not just of his kiss, but of Ash in general and sensibilities she had never seen before. It was captivating, the way he had grown into someone not only visually enticing to her, but who brought to the table an exciting kind of firmness.

Savoring the warmth of being pulled in tight against a hard, fit body, Cynthia was getting worked up with more efficiency than she could have ever asked for. "There are very few men who would ever talk to me like that, or grab me like this," she said to him, pressing her hands up his shirt and feeling the solid and toned stomach beneath. "But you're not intimidated by me. I'm not used to that."

"Of course not." Ash grabbed Cynthia's ass in turn, reaching inside of her coat to squeeze her through her panties, a much more delightful sensation as only her enticing underwear stood between their bare flesh, and it exposed plenty of her soft, round cheeks for him to fondle directly. "You're beautiful and more experienced than I am. But it's you who should be intimidated?"

Perking an eyebrow in curiosity, Cynthia was nonetheless pulled in deeper by the cocky attitude on display. "And why is that, Ash?" Her hands pressed into his stomach firmer, slowly pulling down and teasing the top line of his jeans, fingers digging into the loops as she pulled him in even tighter against her. "Is there something you have to surprise me with?" With anyone else she would have expected a rather unimpressive penis reveal, but with Ash, she felt like his confidence was backed by something real. There was a certainty he left her with that she needed to see the source of at any cost.

Ash gripped both of her ass cheeks tightly as he pulled her body away from him just a little bit. "Sure I do. Pull it out and I'll show you." He kept up his cockiness and his certainty that what he had would blow Cynthia's mind, and he delivered it with such steady, unwavering flair that she was honestly ready to buy every last second of it, so curious and excited by the prospects suddenly before her.

At that point, if Ash had turned out to be average, Cynthia would have been so phenomenally disappointed with the situation. While she did have some tendencies, she wasn't a complete size queen, but with how much boldness Ash was showing, size was a must if she was going to be enjoying her night now, feeling her pussy get slick with anticipation and her breasts ache. She undid the zipper on his jeans and pushed them down his legs, and the second she caught the size of the tent straining against his boxers, the bulge of a cock so large that even as hard as it was, it was forced to curl against the material that was being pushed to its limits.

Never before in Cynthia's life had an underwear bulge held so much potential to make her dreams come true.

As she pulled his strained boxer shorts down his legs and left him exposed, she nearly stumbled back in surprise, and that seemed to be exactly what Ash had been hoping for given the smile across his lips and the absolute pride with which he stood there. His cock sprang upward, and Cynthia wasn't ashamed to say, "So big," as she marveled at it like a gawking virgin. It was the single largest cock she had ever seen; long, fat, aching as it dripped pre-cum onto the floor of the penthouse suite, and below it dangled an equally massive pair of balls likely about to burst given how full they looked. "How does... Holy shit. You should have fucked me years ago."

"We can make up for lost time," Ash said, smirking as he stepped forward, his cock bobbing about as he took that one single step and reached forward. Now that he knew his cock was stunning on sight alone, he knew that he could push her even further and more boldly, and he was going to take that excuse all the way to its limits as he showed a much more craven approach to asserting himself. He could have guided her toward a bed or tried to gently encourage her down onto her knees in front of him and ask her for some preparation. So many almost gentlemanly ways to get things moving, and he chose to grab a fistful of her hair and drag her over to the couch.

Cynthia shivered and let out a whine of surprise and pain as he tugged her, not too hard but hard enough, over to where he wanted her. This was almost unprecedented for Cynthia, who was used to being dominant with most of her exploits and even with the rest. It's what had made Ash so intriguing from the beginning, his careless and irreverent treatment of her something utterly shocking not only for being from him, but for being given to her at all. Nobody had ever showed the unfettered temerity to do this to her, and it made the tugging sensation on her scalp so much more intimidating.

Ash sat down on the couch, his cock standing upright and as intimidating as any Cynthia had ever seen made all the more worrisome by the way that Ash pulled her face right up in front of it, keeping his grip in her hair as he let her get an up close look at what he was packing, loving the way she stared at him, unable to pull her gaze away from the enthralling sight of it. "You've sucked a lot of cocks before, right?"

"Yes," Cynthia said, nodding with what little slack in the grip in her hair she was given.

"How many?" Ash was in control, and it left him feeling so excited. There was so much more to it than just his hold in her hair; she was staring at his cock, enthralled and so pliable, so vulnerable. That was what he wanted, to know that she was so enamored by the sight of his shaft and by every dominant, aggressive act that thew her so utterly off of her balance that he could do anything to her. Not even giving her time to answer, he cut back in quickly with, "More than you can count, isn't it? Because slutting around wherever you go is exactly what you do. You've sucked so many cocks before, but I don't think you've ever seen one like this. An experienced whore wouldn't be so shocked by it if she had."

There was a disrespect to the way Ash spoke to and about Cynthia. Even when she was with someone who wanted a more intense, maybe even slightly rough fuck out of her, there was always respect for her station and her abilities. She was a world class trainer and people treated her like it, saw the offer of sex as a privilege beyond what they had ever been given before, and they appreciated every second of being given it.

They never called her a whore, never talked themselves or their dicks up by rubbing her experience in her face, and they never managed to have Cynthia quite as completely captivated and ready to go as Ash did. Something about the way he was speaking to her was lighting up parts of her long since neglected by the reverence and submission of boys who were willing to let her have her way with them, because now she was the one who was being subjected to the whims of another.

"Yes," she said, biting her lip as she stared at it. "It's the biggest I've ever seen before, and not only by a little."

Ash smirked as he pulled her face in tighter, and she whined in delight as he did so. "Then why don't you worship it?" he asked, rubbing her face right up against his shaft, the steady, slow roll of his hips guiding the thick cock to grind along her face in the process. He wasn't going to show any patience or mercy to Cynthia as he took at long last what he wanted from her and from this entire situation. Leaning back into the couch and spreading his legs a bit more, he kept his hold steady on her head, ensuring she was held in place as he laid the offer on the table. "If it's the biggest cock that a noted cock addict like you have ever seen, it should deserve it." He'd had enough practice on random girls that he knew now exactly how he was to approach this situation, and he could not have been more ready to go all out with it.

Letting out a shaky breath that made the cock twitch against her face, Cynthia found herself nodding slowly in agreement to Ash's vulgar terms and his desire. She was ready to perform, ready to give him what he craved, her body shuddering with a strange and searing sort of arousal. She had never felt anything like this before, and she was ready to let this strange situation carry her away. Her tongue slipped past her full lips and dragged along his cock as a single bright eye--the one uncovered by hair--stared up at Ash with a needy smolder. "It would be my pleasure," she said with a low rumble in her voice, as if she didn't know how to stop playing the seductress to at least some degree.

The grip in her hair released as Ash left her quite suddenly to her own devices, and it was then when Cynthia truly realized how much she was in over her head, faced now with a massive cock that he was ready to let her get to at her own pace.

It was a lot more than she was ready to handle, but she was determined to do her best as she stared up at Ash, grasping the base of the cock and holding it steady as she dragged her tongue up the cock with a slow and loving lick from very low all the way along its incredible length to the tip.

Licking her way up the cock really made it set in for Cynthia how much she was completely out of her element, shuddering as she stared at Ash in disbelief His cock was more threatening than she had imagined until she could feel the length for herself and realize that at the same pace slipping into her pussy, she would have been fucked like she had never imagined before. And that wasn't even getting into the thickness of the veiny cock, so wide that she was left wondering how she would be getting her mouth around it to suck on it. But all of these challenges, formidable as they were, hit some very primal part of Cynthia deep down. One that had been waiting for this to one day happen to her. A chance to really go all out and enjoy herself in a way so thoroughly indulgent and vulgar that she couldn't have ever imagined she'd be as into it as she truly is. But now, she was ready to learn those uncomfortable truths about herself.

A flurry of licks and kisses followed, peppering the massive shaft with all of the scattered attention Cynthia could provide, all while she tried to kill time and figure out how she was going to possibly pull any of this off. There was so much cock before her, so many things she would have to figure out as she worked at the steady worship of Ash's shaft. Her hand remained steady at his base, giving it a few slow, short strokes while she tried to feel this out. "How is this?" she asked, playing sultry as she stared up at him from behind his cock.

"I expected more from such an accomplished slut like you," Ash said, cutting straight to the point with a wicked smile as he stared down at her, unable to hold his enjoyment about the situation before him. "Come on, stop sucking my cock like a nervous tournament groupie." His hand reached for her head again, pulling tightly on her hair as he threatened, "Or I'll make you."

Cynthia still couldn't believe what sort of language and treatment she was receiving, but as it made her ache between her legs even hotter, she did as she was told, licking her way up Ash's cock and forcing her lips open as she leaned forward and tried to take him down. His fat cock was definitely more difficult to get her lips around than she was used to, but she was determined and eager to please, ready to make this work at any cost as she pushed her way down nonetheless. His cock head past her lips as she tried to get a tight seal around the shaft, still staring up at him with the eye not covered by her hair, as if seeking his approval as much as she could, the assurance she was doing a good job. It was something she never sought from her partners, both for the certainty she had them and for the way she mostly concerned herself with her own hungers. But here, she just couldn't help herself.

Ash groaned as he sat there, staring down at Cynthia and relishing in, at long last, being the new man he had always shirked away from. All the other girls he'd fucked before he set his plans into motion were just one-offs, inconsequential girls who liked handsome and strong trainers. Just one-night stands he didn't have any intention of paying any thought to after he was done with them. Not like the girls he'd passed up on, the ones he let get away. He had other things in mind for them, wanted to do things that were so much more than just a casual one-night fling, and with Cynthia down on her knees and working to take his cock deeper past her lips, he was finally there, finally putting into motion everything he'd wanted. Cynthia had been a missed opportunity, but now she was almost hypnotized by a meaty dick that she didn't even try to pretend she didn't want to suck as hard as she could. The new chapter of his life that would involve being a different kind of 'master' started here, and what a beginning it was.

But he needed more, and with his hands slowly creeping up her cheeks, Ash lured Cynthia into a false sense of security with enough affection to keep her docile and expecting hi to be gentle with her. It made it all the more sinister when he instead grabbed her by the hair and slammed her down his cock. She choked in surprise around the dick suddenly slamming down deep, pushing back the back of her mouth and down into her throat, and the thickness of his shaft really started to make its presence painfully known as he claimed her so deep. "I decided I wanted more," he said, grinning as he wrapped his hands up in her hair tightly. "But come on, how could I see such a pretty face and not want to fuck it?"

Cynthia couldn't have articulated an answer even if she had one as Ash began to guide her head rapidly up and down his cock, showing an utter sort of mercilessness in the way he took her so hard and fast. A harsh facefucking was the sort of thing no man had been bold enough to give before to the Sinnoh champion, but the utter carelessness that Ash showed Cynthia continued to dominate and fascinate her as he went all out on his brutal sort of attention. Guided fast and harsh up and down Ash's cock, Cynthia was left gagging as saliva bubbled up around her lips. Primal needs were surging within Cynthia that she had never fathomed before, but as she was so unapologetically turned on now even by the way Ash was so reckless with her, so aggressive. She was having trouble breathing with a big dick down her gullet, but there was nothing but adoration for what she felt in the process.

Relishing in the steady and impatient fucking of Cynthia's face, Ash groaned as he stared down at her. "That's what I was looking for," he said, almost callous as he stared down at her. "Even you're having trouble taking it all. If a slut like you is choking on my cock, then imagine how bad a normal girl has it when I fuck her pretty face. Because I always fuck girls' faces. They need to know their places, right?" He tugged on her hair happily, making her whine and shiver as he continued to guide her brutally along his dick. There was nothing but the purest of delight to be found in subjecting her to something like this, in asserting his dominance so thoroughly, and he wasn't going to be able to last forever, but he didn't have to.

Having his cock drooled all over and choked on by the most beautiful woman in Sinnoh wast he kind of treat Ash saw no shame in losing himself to quickly and efficiently. Not when he had a big surprise waiting for Cynthia. He just relished in a deep, hard fucking of her mouth for the moment, hammering away hard and fast until he was ready to go. His cock twitched in her mouth and her throat the faintest bit of a threat of what he was going to do, before he sharply tugged her head back. Perfect timing left his head gushing into her mouth, splashing her tongue directly with a shot of thick, salty spunk before he drew back all the way.

As Cynthia panted heavily, recovering from the harshness of having her face fucked, Ash came all over her face, painting her features a new shade of white. Dutifully swallowing down the mouthful she was given, Cynthia shuddered, feeling the spunk slip its way down the lining of her throat, slimy and potent as it made its way down to her stomach while more of it landed onto her face. She acted on pure instinct, shivering as Ash's dominance pushed her to react on whims that thankfully continued to prove very correct. "Nobody has ever cum on my face like that before," she said shakily, context given by the way her bottom lip remained firmly between her teeth.

"But you liked it, didn't you?" Ash asked, finally releasing her hair, grabbing his cock and guiding the now very wet and spit-soaked member to drag along her face, almost as if it was no big deal. A completely casual smearing of the cum streaks on her face with his cock. "I can tell. You look like you want me to fuck you so badly right now."

Feeling a swell of shamelessness run through her, Cynthia didn't argue against it. "Yes. You're not like I remember you, Ash, but... Nngh, whatever you're doing, keep doing it, because it's working. You're not treating me like every other guy I've brought up to my room, but I'm loving it."

Ash smirked as he kept Cynthia in a world of constant surprises, hosting her quickly and without warning up from her knees and pulling her to straddle his lap. "That's because I'm not looking at you as a champion," he confessed, pushing her coat off of her shoulders, and Cynthia gladly let it fall to her feet, rubbing her sleek, stockings-clad legs against his outer thighs. "I'm treating you like someone I want to fuck."

"Mm, so you're always this respectful and polite to women you want to fuck?" she teased, licking her lips as she settled down happily into his lap, hardly minding the way he spoke to her at all but loving the chance to tease him for it.

"When they're lucky enough to get it." Ash reached around Cynthia's back as he stared into her gorgeous cleavage, the black bra in his face and pushing her tits up perkily enough that he wanted to see them bare. He undid the bra clasp with ease and slipped it off of her arms, and it was only after she had already exposed her tits that Cynthia realized what she had just done.

Cynthia never fully understood why she was like it, but for reasons beyond her control, she lactated when aroused. Her pussy worked as it was supposed to, getting slicker and needier as her arousal built, but when she got really, truly horny, her breasts produced milk. It was a point of embarrassment for her and a great reason to wear black, but as Ash exposed her plump, round breasts before his hungry eyes he couldn't help but notice the little drips of white around her perky nipples, and before she even knew if Ash was going to figure out what was going on with her, she was already lit up with shame.

"Is that milk?" Ash asked, leaning forward and licking at her nipple curiously. It was exactly what he thought it was, and that was left him curious. Curious enough that even as Cynthia whined and shifted her gaze away in worry, Ash pressed onward, wrapping his lips around one of her nipples and sucking on her tit, at which point a little spray of milk into his mouth made him pull back in shock. "What the fuck?"

"I... It's a--I don't know why it happens. But when I get horny, I start to lactate. Nobody has been able to explain it to me, but it's what happens. My breasts immediately get so painfully full of milk and it just comes out." The feeling of his gaze upon her left her squirming, vulnerable and submissive in ways she hadn't been expecting to feel, but now it was digging in deeper, and even more worrying than the fact that she was having this secret bared was that the penetration into her dignity had her squirming. "You don't think it's weird, do you?"

"I think it's very weird," Ash said, grabbing both tits and squeezing them tightly. Her overly sensitive breasts, ready to leak with the slightest of provocation, didn't even have to be properly milked when she was properly desperate, and even a nice squeeze had milk dripping out, splashing against Ash's palms as he snickered, fondling her and soaking in her embarrassment. "Like you're a slutty cow." Burying his face back into her chest, he sucked on her nipple again, and this time he drew noisy cries from Cynthia as he did so. "And you get off on it, don't you? You get off on having your tits leak milk, just like you're getting off on having someone finally make you his bitch."

The word 'bitch' in particular sent a shudder up Cynthia's spine as she was further dominated and talked down to by Ash, who continued to knead her tits and leave her feeling as embarrassed as she was felt up and laid into by Ash. But at the same time, the words spilled so easily from her mouth that she couldn't even fight it all, conceding to everything with a ragged, "Yes, I do. My breasts are so sensitive, and you're touching them just right, and--oh! Arceus, yes, please don't stop!" Her head rolled back as Ash sucked more aggressively on her tit, not caring in the least bit about how vulgar and raw this looked, the utterly shameless nature of her submission driving her deeper and needier down.

Ash continued to suck on the gorgeous breast as his other hand reached down her body, grabbing at her ass again. A few healthy squeezes left her squirming about in his lap, brushing up against his cock as he focused with an unrelenting eagerness at her breasts. He was exploiting her weakness, and how could he not? Strange as it was, he found it hot, as much an angle to push and humiliate her over as it was something for him to enjoy, and the way she was rubbing up on his dick in her needy build was all the better. She was so desperate and vulnerable, ready for him in ways that he would always be able to brag about. He had brought Cynthia herself down low with need.

Her panties had to go, and as Ash pulled them down, Cynthia not only didn't fight against it, she was happy to wiggle her gorgeous hips and ease them off of her body slipping down her long, sleek, still stocking-covered legs as she slipped up briefly from his lap to let them go down. As she tried to climb back in, hands grabbed at her hips, and she knew what was coming as Ash brought her in close, pulled her very slick pussy up to the head of his cock and rubbed her slit back and forth a few times so he could feel just how wet and hot her aching twat truly was. "Beg me for it," he said sternly, cold and domineering in his approach to getting what he wanted out of the bounty hunter with pointed, heavily charged words.

Nobody had ever made Cynthia beg, but she found herself all too easily letting go of all her decency and composure to whine, "Please let me have your cock. I can't stop thinking about it, it has my tits to the point of bursting, and I need to get fucked so badly. Nobody has ever treated me like this before, and I'm loving every second of it. So fine, Ash, if you want to make me your bitch, then fuck me hard enough that I'll know I never need another cock again, and that you can own me. Break me down into your slutty property."

Everything that Cynthia said was music to Ash's ears, a confirmation of what he had been after. This was victory, and he was all too happy to slam her down onto his cock, pulling her into his lap and sheathing the entirety of his massive cock into her. The incredible tightness of her hot, wet, desperate cock was an amazing thing for Ash to feel, to leave him squirming happily as he felt her stretch out around his cock. He stuffed her quickly and unceremoniously full and forced her body to take his cock and get used to it. "Pretty tight for a slut."

"So big," Cynthia whined, head leaning forward as her hands grabbed Ash and held desperately tight onto him. She wasn't ready for it, but she couldn't pull back now, bottom lip trembling as she pressed up tight against him. Never before had she felt so penetrated, but even as her body felt a certain swell of intensity that maybe should have left her wanting to go slow, she knew that Ash wasn't going to want to go slow at all. So she took some initiative, starting to grind her way up and down atop his cock, determined and ready to deliver as she played his game. "No cock has ever filled me up like this before."

"And no other cock is going to feel good again anymore, is it?" Ash asked, grabbing hold of Cynthia's dripping breasts again, pinching her nipples and making them leak with more of her warm milk. His hips started to move, steadily guiding Cynthia to ride his lap hard and fast. Her slick, greedy twat felt amazing around his cock but he needed more. "Now that you've had something this big, no other cock is going to make these fat tits start dripping milk."

Cynthia shook her head, whining as she rode Ash's cock. The feeling of utter fullness proved more addictive and enthralling than she imagined it would be, and once she started moving she found herself utterly unable to stop, bouncing hard and fast up and down the throbbing dick inside of her. She had come too far to have concerns now, even as he continued to tease her over her lactation, as he spoke in crude terms about her and her body. She had stopped making any shame or show of how much she was guiltily loving his dominant streak. A big cock and a treatment unlike any she'd been shown before were doing things to Cynthia on a level she could never have imagined until she was right there and taking every harsh second of it.

One hand went to Cynthia's hip as Ash started to gear up for an even harsher, more intense fucking, one that had him thrusting upward as hard as he could into her needy hole. With her breasts bouncing in his face as he feasted on one of her perky, lactating nipples, he felt like a king. With Cynthia moaning louder and steadier amid all of the hard, fast fucking, Ash knew he had her right where he wanted her, pressing further with his advantage, slamming up into her and fondling her ass with his other hand, doing everything he could to make his claim to her body even more apparent, and she certainly wasn't playing the idiot about things.

"Fuck me like you own me," she moaned. "Make me cum harder than I ever have before, and I'll be yours." She felt so good, writhing in need and carnal indulgence against him, but the more she got the more she needed, greedier even as he milked her breasts and went further and deeper into the rough use of her body. It was hard to be content with what she got, no matter how amazing what she was already receiving was; she just knew that Ash had more, that he could really impress her even more than he already was.

But she had no idea just how much, as Ash caught her by surprise with a harsh push to the side, shoving her down onto her back atop the couch as he climbed forward and started to fuck her raw from above. He took the reins utterly, no longer leaving anything up to Cynthia as he grabbed one of her legs and pulled it up over his shoulder, coming into her from an angle of penetration that immediately left her howling in surprise, throwing her head back as he straddled her other leg and hammered her pussy deep and hard. There was no hesitation or patience in what he did to her as he showed her an all out sort of aggression unlike anything yet.

"You're already mine," Ash groaned, hammering her pussy relentlessly as he slammed into her. "You were mine the second I decided you would be. This is just making it official." Brimming with cockiness and aggression that knew no end, he staked his claim to her, all of his energy and his focus behind fucking Cynthia as hard as he could. The deal was sealed in his mind; her eager submission and her rapturous response to his cock were all the signs he needed that she was his, and he used her still bubbling desires against her, turning them on their head and showing that she never stood a chance against him. He went all out in fucking her raw and had no intention of slowing down as he made sure that she caught up with reality, to shatter any thought she could have had that there was a way to go back from this.

As Cynthia heard his harsh, possessive words and felt the utter ravishing of her pussy, she was in paradise, gasping and bucking needily against Ash as he gave her the kind of raw treatment she had craved and been left wanting for too long. She hadn't known just how bad she needed something like this, but once she had it, she responded to it intensely, loving the way that Ash seized control and the bombardment of intense, twisting pleasure worked magic through her aching body. Her hands went for her breasts, grabbing and squeezing her nipples, pinching them as milk continued to drop from them. "You do, Ash. You own me, I swear it. You own me and these slutty, milk dripping tits."

"Damn right I do," was Ash's sole, cocky reply, for once being brisk and steady as he focused on the final stretch of hammering her pussy hard and fast. He showed her no mercy, focusing on the thorough use of her body as his balls slapped against her thigh from the force of his savage thrusts down into her greedy hole. Even after a nice hard fucking and Cynthia loosening up and getting 'used to' his cock, she was still amazingly tight, which left Ash very hopeful for their future as he fucked the gorgeous blonde as hard as he could, all while her breasts heaved. He was so reckless, so driven, and the conquering of such an experienced body, of a woman about twice his age, was the sweetest of pleasures.

Cynthia felt like a blushing teenager getting fucked for the first time, as Ash's massive cock hammered deep into her and the absolute bliss of surrender hit her so hard. There was a savage edge to how he fucked her, a thrill that didn't tire or wear down even as they kept at it, as he writhed hotly beneath Ash, feeling his cock hit her so deep and so hard every time. Delightfully stretched around his shaft and damn near bottomed out each time by the massive dick, she was having the time of her life, and didn't even feel as much shame as she should have for the way her breasts trickled with their warm white milk. She would come to sink back down into embarrassment in time, but for the moment, the initial high was more than enough to keep her going.

But not for as long as she hoped. Her body had been too primed for this, too readied for release, and she couldn't fight for too long against the mad delights surging through her body with an almost intoxicating effect. Getting fucked into a state of disastrous, sloppy need was Cynthia's new favorite thing she never knew she needed, writhing happily on her back as she took him in hard and fast, right up until that final moment when she lost control at long, screaming, "I'm yours!' as her spine arched and a powerful orgasm surged through her with electrifying delight. Everything burned hot within her, an incredible rush of pure need made all the better by the trembling, throbbing desire within her to just get fucked. "So cum in me now and mark me, Ash!'

It was a wish come true when Ash slammed balls deep into Cynthia's pussy and did just that. With her hole spasming around his cock he couldn't resist it any longer, feeding her greedy pussy shot after shot of burning hot cum pumped deep into her, his cock head so deep that the cum was pumped almost directly into her womb, flooding her with more than she could handle and delighting in the way she bucked and writhed hotly in the process. He was more than happy to give her what she wanted and to mark her, at least in the way she deemed 'marking', as he had other plans still for her once the thrill of blowing a load inside of the Sinnoh champion died down a little bit.

Ash pulled up from Cynthia before long, watching as cum dripped from her sloppy, well fucked hole. His dick was still rock hard as he pulled back and admired his handiwork, Cynthia a panting mess on the couch, hair out of her face and both eyes staring in frazzled elation at him. She was a mess, shivering and whining as satisfaction simmered within her. "I had to talk things up to keep you moving, but that was a lot better than random tournament groupies."

Cynthia stared at a little strand of cum still connecting the head of Ash's cock to her pussy, which quickly began to leak with his white spunk as it mingled with her own juices. "And I haven't been this satisfied after one round in a very log time," she purred, biting her lip as she reached down to break that little strand and lick her fingers clean. "Although, you'd better not be done with me yet. I'm going to--hey, where are you going?"

Slipping off of the couch, Ash walked over to the bag he'd tossed onto a nearby counter. "Don't worry, I'm not done fucking you by a long shot," he said, grabbing the bag and carrying it back over to Cynthia. "But if you really want me to, there's something you have to do first." He opened the bag and pulled something from it. Something he offered toward Cynthia with a smile. The blonde gasped as she beheld the sight before her. It was a mostly simple black collar, save for the front, which had a Pokeball symbol at the front of it. "I can't put you in a ball, so I need some other way to mark that I'm your master," he explained.

The gall that Ash showed in such a gesture left her almost boiling. She couldn't believe what she held in her hands now, the ballsy declaration of pure, actual ownership he was pushing on her now, that he had clearly been planning some or all of this the whole time in his twisted little mind. He really did see her as his property in some bizarre way, and he was basically asking her to commit to even more of the way he spoke to her and the sexual light he saw her in. She didn't even need to think about his offer as her mind snapped to her immediate answer.

She put the collar on.

"So, do I have to call you master now?" she asked, slipping it easily on for someone who had never worn a collar before, using her fingers to shift the position of it around her neck.

"I was expecting you to have a harder time with it," Ash admitted, not that he minded at all as he watched her slip the collar onto her neck. "You can call me master if you want. Especially during sex."

Cynthia shrugged it all off. "I didn't need to think about it very much, or hear your terms. I think I know exactly what they are, so let's see if I can get this right. I'm your slut from now on, I live to worship your cock, and no other man is allowed to fuck me from now on, right? I can live with that, one round of sex has me a lot happier than I thought I would be all weekend. So, you want a girl to call you master. I can do that. Judging by the shit-eating grin you're wearing, I also think you want more than one girl to call you master. I'm less happy about that, but I think we can come to a good compromise on one condition."

Ash was all ears for whatever Cynthia wanted as, outside of their sexual games, she became someone slightly more assured and certain of what she wanted. "And what is that?"

"I put in a leave of absence after this tournament is over. Arceus knows I need a vacation anyway. And I follow you around and keep getting that cock in me every time I need it." She slipped off of the couch, cum leaking from her twat as she sank down to her knees in front of Ash, grabbing his sticky cock and lifting it up slowly.

"But I don't think you'll mind those terms very much."

"Kiss on it?" he asked, smiling as he left hanging where he wanted her to lay that agreement-sealing kiss. Which was good, because he discovered that Cynthia was exactly his kind of slut when she decided to lay her lips onto his balls, and once the deal was sealed, to start working one into her mouth.

Things were about to get real good for Ash Ketchum.