Jack's eyes were closed, standing over his bath tub, his pants around his ankles an he was stroking away. The thoughts of the previous night danced in his head once more, but it just wasn't the same jerking it to the same scenario he just did not too long ago. His enthusiasm waned, his cock still throbbing. "Maybe I should ask Misty for a quick little something," he thought, feeling bad about it.
His mind raced to other women he'd encountered in Alola, Serena, the clothing store worker who'd sucked him off the prior day made him smile. He felt another rush when he remembered Bea the valet girl and soon to be his personal trainer. He imagined what she was hiding underneath her shorts and smiled. His mind then raced to picture the high society girl he was about to meet. Knowing no picture, his mind started to create one and... A face from years ago appeared in his mind. His academy crush who he'd lost contact with not long after graduation, May Birch. She'd long been the girl of his dreams, and he'd been guilty of looking through her social media pictures more than was tasteful before she deleted it a couple years back. but he remembered she had it all, a beautiful face, fun-loving personality, big tits, exquisite curves...
Before he knew it his cock began to spasm and he heard the sound of rope after jizz rope hit the metal basin that was his luxurious bath tub. He caught himself smiling at the thought of remembering May, she seemed like a "girl next door" kind of person to him now, having known him only when he was the broke, mediocre pokemon trainer back in Hoenn. He exhaled, basking in the afterglow of a good fap session. "Oh shit, Hilda," he said aloud, and scrambled to the sink, washing his hands, brushing his teeth, and making sure he looked halfway presentable. His hair seemed a bit off, but the clock in his mind kept ticking. "Yeah I'm gonna need a personal appearance consultant or something," he thought out loud, his mind drifting to Serena once more.
A couple minutes later he was opening the sliding glass door to the deck where his company was waiting, coffee in hand, observing the ocean view. Hilda had reminded him that her name was Dawn Berlitz.
"Apologies about the wait, Ms. Berlitz," Jack said loudly. What had Hilda said? He was supposed to have been in a business meeting? He nodded as his subject turned to him.
From first glance, she seemed a bit younger than him. She wore a daringly short, pink, skirt, Her torso was covered in a black mini-dress. A white hat with a pink Poke Ball design sat atop her head, with long, dark hair flowing from underneath it flawlessly.
"Mr. Cobal," the young woman said with a big smile. "Thank you for welcoming me into your home, unannounced like this."
Jack walked up to her to shake her hand, but she gave him a look with his eyes that made him feel that would be incorrect. He paused awkwardly, feeling the breeze against his face. "Um..." Jack said, shaking his head. "Not sure about the proper greeting for a Sinoh aristocrat."
Dawn's smile darkened. "Well, the Berlitz family is no longer an aristocratic one, those days are behind us," Dawn explained. "But handshakes are just not the way we do things in Sinoh."
"Well my bad," Jack replied, trying to smile to keep the mood up. "I missed the briefing on Sinoh-oan cultural norms," he joked.
Dawn raised her eyebrows and her tone of voice deepened. "A briefing probably wouldn't suffice."
Jack looked to see if Hilda was in sight and could bail him out. She wasn't. "Sorry there wasn't a briefing, it was a bad attempt at a joke."
"Oh," Dawn said, offering nothing else to the conversation.
"How's the coffee?" Jack asked, deciding to take the seat opposite Dawn.
Dawn rolled her eyes. "Not impressive."
Jack couldn't find a more apt comparison for this conversation than having his own teeth pulled. "So you flew in today?"
"Yes, an hour ago," Dawn replied, taking a sip of her "unimpressive" coffee. Somehow she could cringe with her eyes, and she did so as she got some drops of coffee down her throat.
"And your first thought was to come to a stranger's house unannounced?" Jack asked.
"Well, resort check-in isn't for a few more hours," Dawn explained. "And my aunt claimed the view from the deck here was one of the most beautiful in the world, so I figured I'd come by and say hello. My aunt always thought highly of your father."
Jack grimaced. "I don't think very highly of him."
"Well he left you a considerable gift."
"And that makes up for never acknowledging I even existed, never even a phone call or an e-mail?" Jack said, anger rising in his voice as he glared at his uninvited guest.
It was Dawn's turn to pause. "I do apologize if I've tread in a sensitive area."
Jack took a deep breath. "Yeah, you did," Jack remembered being nice to this bitch would probably help smooth things out with Hilda a bit, so he got his old "customer service" speak on. "But it's not fair for me to put that baggage on others," Jack sighed. "Can we agree to not talk about that anymore?"
Dawn nodded. "Of course," Dawn's focus turned to the beach, and Jack turned to see what she was looking at, and sure enough, there was Zinnia's Flygon rolling around in the sand having the time of its life.
"Are Flygon native to Melemele Island?" Dawn asked.
"No," Jack smiled. "I just hired a bodyguard today, that's one of her pokemon."
"Looks like it could cause some real damage if you're not careful," Dawn observed.
"Perhaps," Jack said aloud. "Trying to give her the benefit of the doubt for now."
The duo heard the sliding glass deck door open, and out came Zinnia. He nearly gasped when he realized she was just in her underwear. a black bra and black panties, strolling out onto the deck like it was routine. He could tell she just showered as her hair was wet and a little disheveled. He couldn't help but be a bit captivated.
"Hey boss, you know where Hilda went? She's supposed to have some clothes for me," Zinnia asked nonchalantly.
"You check her office?" Jack asked, trying not to let his eyes linger on her svelte, sexy form.
"She has one?" Zinnia asked, still walking towards Jack and Dawn.
"Yeah, take a left to the kitchen hallway and it's the second door on the right," Jack explained.
Zinnia got right up to the two of them and nodded. "Okay, thanks," Zinnia then turned to Dawn. "And you are?"
Dawn cleared her throat, a prude's glance escaping her eyes. "Dawn Berlitz," her eyes immediately returned to her coffee as Zinnia outstretched her hand to shake Dawn's.
Jack smiled uneasily at Zinnia. "It's cool," he said, doing his best to wave her off but not actually wave her off.
Zinnia rolled her eyes and grunted before spinning around and marching back in the house. Jack caught a good peek at her largely exposed booty and felt his member get harder. When the sliding glass door shut, Dawn spoke. "You run a loose ship, Mr. Cobal."
"She's been my employee for less than an hour. We picked her up today from a storage unit, where she's been living for who knows how long," Jack explained, trying to mask the bitterness in his tone. "There's an adjustment period needed for both sides. I'm sure it seems pretty bizarre."
"No it seems very bizarre," Dawn added.
"Yeah... I think I'm probably the furthest thing you can be from a high society guy," Jack explained.
"I assume your mother had quite the child support endowment," Dawn said.
"She blew it all before I was five. She teetered on the edge of bankruptcy until I got the inheritance."
Dawn's jaw dropped. "How unfortunate."
"Stupid, not unfortunate," Jack said, not caring to hide the bitter-ness in his ton this time around. "Probably another subject I don't want to get too deep in, if I'm being honest. I paid her off, a lot more than I had to if you ask my lawyers, and we're no longer on speaking terms."
Dawn nodded. "So you were just another member of the common folk most of your life?"
Jack wanted to gag at the thought of her using "common folk" unironically, but he held it in. "Yeah."
"So what's the plan now? You're here in Alola, you're getting settled."
Jack shrugged. "Probably get involved with some charities, the trainer school seems like a good place for some scholarships," Jack thought out loud. "I was a pokemon trainer, I'd like to keep doing that."
"I meant plans with the company," Dawn said intensely.
Jack grinned. "She's gonna hate me," he thought to himself before he spoke. "Oh I already have a plan. I'm doing something extremely important as we speak."
"Oh?" Dawn said, her eyes getting a little flirtatious for the first time. "I can keep a secret."
Jack leaned in, a shit-eating grin on his face, and whispered. "I'm staying out of the way."
Dawn's mischievous grin faded into a grimace. "I see," she said, taking another sip of her coffee.
Jack cleared his throat. "So what are your plans? For being in Alola, I mean."
Dawn shrugged. "My family was thinking of buying some property out here, so I'm getting a good lay of the land."
Jack's stomach got queasy at the thought of them being neighbors. "Well I can assure you I won't be selling any time soon."
Dawn nodded. "Once I saw the view I knew there was no chance. And I think we're looking a bit bigger in scope."
"So a full on castle?' Jack asked jokingly.
Dawn shrugged. "Probably just another luxury neighborhood development, castles aren't in vogue right now. Maybe in a decade or so the castle will materialize."
"Oh, cool," Jack said while laughing internally. She didn't think he'd been joking with the castle question.
Jack's focus turned to the sliding door once more, as Lillie came out in her all-white outfit carrying a tray with two water glasses. Lillie's tits wobbled with each step. Dawn gave Lillie a once-over and rolled her eyes, going for another sip of coffee. "Pardon me for interrupting," Lillie squeaked. "But was anyone interested in some water?"
Jack smiled but shook his head. Dawn didn't even acknowledge Lillie as Lillie got to the table.
"Thanks for offering," Jack said.
Lillie nodded, then gave Dawn another look, seeing if the seated woman had changed her mind. Lillie then turned with the tray, but she lost her balance and fell. Her torso hit the edge of the table, with her head bumping into Dawn's shoulder. The glasses of water hit the deck and shattered.
"ExCUSE you!" Dawn said, looking like she'd just been violated. Jack realized this meant Lillie had touched Dawn, and he looked curiously at Dawn's face to see any sudden change.
"I'm so sorry," Lillie squealed, tears forming in her eyes.
"Yes, you should be," Dawn said, a daze coming over her. She made eye contact with Jack, and it looked like Dawn's mind had gone blank for a moment. She shook herself out of the momentary lapse in brain function. "That's probably my signal to leave."
Jack smiled sheepishly as Lillie desperately picked up shards of broken glass behind Dawn. "Yeah, sorry about that. Staff needs some more training," Jack said, doing his best to smooth the faux-pau over.
Dawn shook her head as she got out of her seat. "It needs a LOT more training I assure you," Dawn took one last look at the sea and then turned back to Jack. "Thank you for your company Mr. Cobal, the view was delightful," she then turned to leave, and strutted to the sliding door.
As the door shut loudly, Lillie let out a sob. "I'm so sorry Jack."
Jack got on the ground to help with clean up, and he did steal a glance at Lillie's breasts as gravity worked its wonders on their enormous, dangling forms. "Don't worry about it Lille, it was a shit conversation anyways."
"You don't have to help, I'm supposed to," Lillie said, tears streaming down her face.
"It's your first day, and I thought Hilda would give you some proper training before sending you out here," Jack paused as he was unsure why Hilda had sent Lillie out in the first place.
Lillie shook her head. "Hilda didn't tell me to, I just figured I could be like a waitress to you and your company," Lillie explained. Lillie had a handful of broken glass, and she suddenly yelped, having pricked herself.
"Let's go inside and get you a bandage," Jack said.
Lillie looked up at him, a genuine smile on her tear-covered face. "Thanks Jack."
"Don't mention it," Jack said, getting off his hands and knees with some glass in one hand. "Just leave the glass on the table, I'll get it later," Lillie did as ordered, and followed him inside.
Fifteen minutes later, the glass had been cleaned up and Jack was sitting in Hilda's office, de-briefing her on the conversation. "Fucking Lillie," Hilda said, as Jack wrapped up the story.
"It's her first day, she's had no training," Jack said a little defensively.
"Yeah, now I'm gonna get yelled at by Oleana because she ruined your meeting," Hilda ranted, then spun her swivel chair back to her computer screen. "It would've been so much easier if I had just ordered you delivery two days ago."
Jack hadn't thought of how his life in Alola would be different minus Lillie. Lillie and Nebby would've been picked up in the wilderness by who knows what kind of person. Hilda wouldn't have had to deal with the international police's Aether investigation. They wouldn't have needed to go to the trainer academy to visit Kukui, where he stupidly revealed who he was. That had set him off on the desperate attempt to enjoy the Melemele nightlife, where he'd thrown Hilda under the bus by not informing her what he'd done. Plus Lillie wouldn't have bungled the meeting with Dawn Berlitz, although personally, he preferred never having to talk to the stuck-up bitch ever again in his life. He also came to a sad realization. "Now that I think about it, Lillie has made your job a lot harder. That's not fair to you."
Hilda shook her head slowly. "Life ain't fair, boss," Hilda took another exhale. "Another blunder like this and I can kiss my position good-bye."
"I won't let 'em," he said, trying and failing to sound like he had authority.
Hilda turned her to show her smirk. "Gonna have to do better than that," Hilda said. "But I appreciate the sentiment."
"I promise I'm gonna make things easier for you. We're all adjusting to new things."
Hilda rolled her eyes. "Don't hate me if I don't believe you," Hilda teased. "If you want to make things easier on me, can you go check up on Misty? Haven't heard from her since she moved her stuff in. I was gonna, but..."
"Sure thing," Jack said, getting up and heading for the door.
"Oh, and can you close the door?" Hilda asked.
Jack gently shut on his way out and made his way to the east wing where the staff rooms were. He found the door with a print of a painting depicting a scene of the sea, dotted with water pokemon swimming at all levels of the sea. He took a moment to admire it before knocking on the door.
"Come in," Misty said.
He opened the door and saw Misty had gotten to decorating her new room rather quickly. Her boxes were open and mostly empty, with picture frames leaning against the wall below open spaces. "Oh, hey there," Misty said as she got up from bending over.
"Hey," Jack said, admiring what had been done in so little time. "Looks good in here."
Misty shook her head. "Still got a long way to go," she then turned to the neutral grey comforter on the bed with matching grey pillows. "This bed spread will be the first on the list of things I need to change."
"Not watery enough for you?" Jack teased.
Misty shrugged. "Well I do have my theme."
Jack went over and embraced her, giving her a kiss. "Finally have some alone time."
Misty smiled. "I'm still sore from last night."
Jack immediately let go. "Oh, sorry... that wasn't why I came here but," Jack realized he wasn't doing himself any favors fumbling around with his words.
Misty shook her head with a grin. "It's a good kind of sore," she wiggled her eyebrows provocatively. Jack felt his member stiffen even more.
"Damn I do want you though," Jack said.
"Want? Is that all?" Misty teased.
"Fucking need," Jack growled as he embraced her again, intensely kissing each other, tongues intermingling. Misty's hands clawed in to his back as she squeezed him closer to her, which he returned in kind. Misty's hands then found their way to his pants, and she undid his belt, button, and zipper quickly. His pants fell to the floor unceremoniously, his cock creating a tent in his boxers.
Jack broke off their make out session. "Just wondering, should I be using protection?"
Misty rolled her eyes. "No need, I've got an insert."
"Okay, probably should've asked that question earlier," Jack said, drinking in Misty's beauty.
Misty did a little jig for him, then pointed to the bed. Jack sat down like an impatient child waiting for a snack. Once he was fully seated and ogling her, she pulled her shirt off. Her shorts came next, and then the bra fell off. She swayed her body back and forth, making her breasts wobble with each movement.
Jack took the time to get his own clothes off as she strip-teased for him. And once her panties had gotten around her ankles, Misty climbed on his lap, shoving her boobs in his face, which he began to tongue ferociously.
"Oh yeah," Misty sighed. "I think I'm gonna like this new job," and before he knew it, his back was on the bed and Misty was on top of him.
***
Back in Hilda's office, her eyes were fixated on her computer screen, and one of her hands was on the mousepad, while her other was in her shorts, rubbing up against her nether regions. On the screen was an HD view of Misty's room. Hidden cameras were sprinkled throughout every room as a security precaution, or that was the excuse at least. Hilda smiled as she realized Jack being a crazy pervert was probably genetic. "And speaking of crazy perverts," Hilda moaned as Misty had begun riding him.
"Fuck fuck fuck, I needed this," Hilda justified to herself as her other hand leaving the mousepad and massaging her left breast, only so much since her bra was in the way. "Ugh, bras," she moaned as she pushed her finger deeper in her pussy.
"I'm gonna like this job so much," Hilda grunted as pleasure began to really cement itself in her mind. "Fuck the shit out of her, Jack..."