Alola Girls Ch. 25 (BBW, WG)

Chapter 25

Oleana sat at the dining room table, tapping her foot anxiously against one of the table’s legs. She checked her phone for an update from Rosa on where Jack would probably be. He needed a bodyguard with him, and for the tenth time in the past hour she scowled at the thought of Nessa.

Suddenly her concentration went to the door to the kitchen which had just swung open and an unfamiliar face appeared. The curvy redhead, scantily clad in sky blue shorts and a top that showed off her breasts and her naked gut, had a very confused look on her face. “Oh, excuse me, I didn’t realize anyone else was in here.”

Oleana squinted at her. Was this an intruder or some random concubine of Jack’s? “My name is Oleana Cosmos,  head of the successor oversight department of Cobal Industries.” She said, hoping to intimidate the random bimbo.

“Oh, nice to meet you. I’m Skyla.” The woman said and extended a hand. Oleana looked at the hand for a moment then made eye contact with the woman.

“And why are you here? Another one of Jack’s concubines?”

Skyla was taken aback. “No... I’m a member of the International Police.” Skyla said, authority rising in her voice. “Jack and his staff are assisting the IP with some things.”

“Oh... May I see a badge then?” Oleana asked, folding her arms.

“Yeah, I’ll go grab it from my room.” Skyla said, turning to leave.

“Your room? You stay here?”

“Yes... As I said, Mr. Cobal is assisting us with a couple things.”

Oleana raised her eyebrows and grunted. “Please get your badge.”

“Why the hell didn’t Hilda inform me of this?” Oleana thought to herself. Perhaps Hilda had held this information back just to mess with things upon her departure. “That fat, stupid, cunt.” She said under her breath.

Skyla re-appeared not long after with a folder, presenting an authentic badge. Oleana had never dealt with the International Police, but them being here was very odd. “So, I was the one who was Hilda’s boss, and due to her incompetence I’ve had to come clean this place up.” Oleana explained to Skyla. “Any arrangements Hilda and Jack made with you, I need to be aware of.”

Skyla shrugged. “Understandable, but I have a feeling Jack thinks differently right now.”

Oleana scowled. “That damn broken window.” She thought to herself. Setting a tone had come with some blowback. She then opened her mouth to speak. “Regardless of the minor speed bump in relations with Mr. Cobal right now, Hilda is no longer in the region or employed, and I’m assuming her duties. Now again, what is Cobal Industries helping the International Police with?”

Skyla smirked. “If Hilda didn’t disclose the purpose of me and my associate staying here, then I’m afraid I’m obligated not to speak on the terms until Mr. Cobal approves.”

Oleana’s neck tensed with anger. “Then you are to leave the premises in a timely manner. Good day, Ms. Skyla.” She finished, grabbing her phone from the dining room table and proceeded to ignore the Skyla.

“My apologies Ms. Oleana, but that is not possible at this time.” Skyla said, and pulled out some papers from the folder her badge was kept in, putting them in front of Oleana.

“And what are these?”

“Contracts.” Skyla replied.

Oleana eyed them and then glared at Skyla. “I have an army of lawyers at my disposal, I’ll have this agreement nullified in an hour. Now I suggest you and whatever associate of yours begin packing.” She finished, getting back to her phone.

“No wonder Jack was so mad at you.” Skyla said lightheartedly. “I suggest you read these contracts though. I’ll be tanning by the pool if you have any questions.” She said with honey in her voice.

When Skyla departed Oleana grabbed the papers and furiously read through them. It turned out, Skyla was correct. Jack and Hilda had made themselves the IP’s bitch for the time being. Perhaps the threat of an expensive lawsuit could get the IP to break the contract, but that would take months. Oleana slammed her fist down and cursed.

Just then, the kitchen door opened and out waddled the ridiculously obese blonde, Lillie. It appeared the little exercise had finished, as she was sweating quite heavily. “Uh... Ms. Oleana...” Lillie began meekly. “Is there anything I can help you with?”

“You could lose about 300 pounds for starters.” Oleana sneered. “And please take a shower, I can smell you from here.”

Lillie’s jaw dropped as her eyes got watery. “M-miss Oleana...” She then started to waddle over to Oleana’s chair.

“What are you doing, girl?” Oleana asked, to no avail. “Don’t come near me you sweaty cow.” Oleana said, bracing herself in her chair.

The 430 pound Lillie bit her lip and reached out to Oleana, poking Oleana with her sausage like fingers, then Lillie withdrew.

“And what the hell was that for?’ Oleana demanded. “If you weren’t pregnant with one the brat’s brats, you’d be fired.” She folded her arms and Lillie departed without a word.

“Perhaps she did it as some stupid prank or on some dare.” Oleana thought to herself. She then remembered the cameras were still around, and Oleana grimaced. She knew there were cameras in most places, and there could be some in even the bathrooms. “I guess showers are off limits for a while, or at least until I have full control of the property.” She continued to think. Suddenly her stomach rumbled with hunger.

She realized she hadn’t eaten anything since the bag of peanuts on the flight, forgoing the disgusting in flight meal. “I suppose I should eat something...” She pondered aloud, getting out of her seat and walking urgently into the kitchen.

***

Jack took a deep breath as the plane slowed to a halt on the runway. He’d sat at the back of the plane, and kept sunglasses on the whole time. Without any bodyguards he felt quite naked in public. He hadn’t been alone outside of the property for this long since he arrived.

“Welcome to HeaHea City...” The loudspeaker began to drone with the captain’s usual speech upon landing and Jack turned on his phone, unsure of what to expect.

He’d done a bit of texting in the terminal but the girls weren’t responding much. It took a bit, but his phone finally booted up and he saw a missed call from Misty, a voicemail from a number he didn’t recognize, and a call from Skyla. He smiled. “Looks like Oleana hit a snag with her plans for property domination.” He thought to himself, and then began texting the IP agent.

Jack: Just landed in HeaHea. So you finally met Oleana?

Skyla: Yeah. She’s an absolute bitch. And is Hilda really gone?

Jack: Hilda will be back, just gotta deal with the bitch first. Does she know anything about the arrangement?

Skyla: Not a damn thing.

Jack: Good, keep it that way. I’ll be at the Hano Grand Resort in case Anabel and Looker need to contact me. Oleana may try to go through my phone records so we can’t say anything here. Hopefully I’ll be back in a bit to fix things.

Skyla: Good luck dude. Domino and I will miss you and your talents ;)

Jack then went to his voicemail and put the speaker on low. He had no one sitting next to him so he put it up to his ear.

“Hello Mr. Cobal, this is Rosa, one of your new staff members.” It began, her bubbly voice sounding quite innocent. “I heard things got very heated between you and Oleana earlier... I’m sure she said some very hurtful things, she does that a lot...Um... I’d like you to know Nessa and I are nothing like that. I was good friends with Hilda when we were both in Unova, and I know you two are very close and have a special bond, and I’m sure you’re hurting right now. She’s a great gal after all... Anyways, I figure you and Oleana aren’t talking now. But you do need to have a bodyguard with you. Hilda said you were heading to Akala, and staying at the Hano Grand Resort. Please let me know if that’s still the case. We do need to send a bodyguard to you. Please contact me, I’ll do whatever I can to help you, Mr. Cobal.”

Jack grimaced at his phone. “She’s quite nice, but one of Oleana’s puppets.” He thought to himself. The plane had just pulled onto the tarmac and people began to grab their bags from the overhead bins. Every person’s look in his general direction had made him even more paranoid, especially since he didn’t have his Pokemon with him. He did need a bodyguard, even if they were one of Oleana’s puppets.

A little while later, Jack was waiting for his luggage and he decided to give Rosa a text.

Jack: Hey Rosa, it’s Jack. Thanks for the voicemail. I won’t be speaking to Oleana until she apologizes for what she said, I doubt that will happen anytime soon though. Regardless, I do need a bodyguard or two here. Oleana mentioned it would be you and Nessa, and I have to say I have some confidential business I’m doing over here and I will need either Misty, Zinnia, or May with me (it involves the International Police). I’ll be at the Hano Grand Resort soon.

Rosa: Thanks for getting in contact! I understand things with Oleana, but she will need to talk to you about the IP situation ASAP. Your staff will be undergoing some training and will not be available for at least a few days, if not more. Nessa and I will be heading over to HeaHea shortly, and hopefully things can get cleared up when we see you.

Jack: I will not be discussing anything with Oleana until she apologizes for her very unprofessional words about my staff and myself. And I know I already said it, but I need one of my three bodyguards here, even if they can only be here for a few hours at a time. This is non-negotiable and would go a long way to making me feel better about all of this.

Rosa: I’m really sorry Jack, but Oleana’s being insistent. I’ll see what I can do on the hourly requests though. Please understand.

Jack cursed under his breath, realizing he could’ve held his location hostage until one of his preferred bodyguards was confirmed to be on Akala. Now he’d be under the watchful eye of Oleana’s puppets. He’d need to enlist the help of a trustworthy trainer when doing the Necrozma business, and realized Leaf could be helpful, so he shot her a text.

He realized he’d been staring at his phone, lost in thought for so long his suitcase was the last thing on the carousel, just circling. Jack grabbed it and headed on over to the car rental counter, while in line he also sent Kahili a text.

Jack: Hey Kahili, landed a bit early. Any chance I could check in early?

Kahili: No, but you all can put your bags in my room and we’ll go from there.

Jack: Some shit happened and I’m here alone for a couple hours.

Kahili: That’s too bad. You can tell me over afternoon dessert.

Half an hour later he was carrying his suitcase to Kahili’s beachfront room, found the room number, and knocked.

“Just a minute!” Kahili called out.

The door opened and Kahili appeared. She’d grown quite a bit since he’d last seen her at the academy dinner. She probably had gained around 50 pounds, and he estimated she had to be around 375 pounds, just a bit skinnier than Misty. Her light blue polo and golf skirt combo  looked absolutely ridiculous on her with all of her blubber pouring out of it.

“Jack, it’s been too long!” Kahili said, enveloping him in her blubber with a hug. Jack had been so stressed recently he hadn’t gotten hard for quite a bit today, a new record for his super-dick and it came alive at the mere look of the wonderfully large former golfer.

“Yeah, thanks for this. Been a crazy day.” Jack said, returning the hug.

“Someone’s thirsty.” Kahili whispered. “Feels like someone needs to fuck their troubles away.”

Jack smiled. “You’re not wrong.”

“You do owe me for that under the table handy.” Kahili said, she then released the hug and turned around, leading her inside with her waddle. He put his suitcase down close to the door and followed Kahili to the bedroom, taking his shirt off as he did. When Kahili reached her bed, she turned and gasped. “You’re really toned, dude.”

Jack smiled. “Yeah, been putting the work in.” He said, undoing the belt on his jeans and dropping them to the floor. Soon his penis was free from its prison and Kahili swooned with delight.

“I knew I felt a monster down there.” Kahili said. “How come you never send me any dick pics?”
“I didn’t think women appreciated them.” Jack said, genuinely surprised.

“Most don’t.” Kahili then took a step toward him and embraced him. They started making out furiously as Jack felt up Kahili’s fleshy body. A hand of his went under her skirt to give her ass a grab, expecting panties, but found out none were there. “I prepared.” She whispered in between kisses.

Jack then pushed her onto the bed and leaned over the massive, 375 pound woman, his dick furiously erect. Jack got her polo off and her bra came off not long after. She didn’t have very big breasts, surprising for a woman her size, but he knew most of her extra weight went to the  pear-shaped woman’s lower half. Speaking of, her skirt came next. He gave her blubber-coated thigs a good squeeze and a shake, then after having his fun, a soft caress “Hey, that tickles a bit.” Kahili complained.

“Oh really?” Jack said, then got on top of her. His hands went to her gut and he began tickling her.

“Damn-eheh, stop it-hahaha!” Kahili cried out as Jack’s fingers played with the enormous former athlete’s blubbery belly. She tried to resist, but Jack had position on her and his muscles thwarted Kahili’s attempts.

“Hahaha... Hey, stop! Ahaha, seriously!” Kahili said. Jack finally relented and looked over her body, a proud grin on his face. Kahili caught her breath from the frantic resistance and then finally spoke. “Okay, this is gonna sound weird...”

Jack realized what may be happening and facepalmed. “Really? That’s your thing?”

Kahili smiled sheepishly. “Dunno why... but yeah.”

Jack’s hand went to her pussy, which was sopping wet, confirming it. Jack shook his head in disbelief. “Never met a woman with this fetish.”

 Kahili shrugged. ”I’m one of a kind... There’s something about the domination and the whole involuntary laughter part of it... The helplessness...” She rambled.

“Oh you want to be helpless?” Jack asked, then suddenly pinned her down again, this time with his elbows on her arms and began tickling her sides.

“Shit-hahaha!” Kahili cried out as laughter took over. He teased her with his tickling for a good minute and a half until he saw her breathing was getting a little strained, then released her.

“Ugh... I’ve never been so turned on before.” Kahili said, catching her breath again. “It’s so weird talking about it...”

“Then shut up and take this dick.” Jack growled, and angled his achingly erect cock into her pussy.

Kahili yelped at his initial insertion. “Goodness you’re huge.” Kahili said as Jack did his initial, slow pumps. “I used to do a lot of kegels in my day.”

“But now all you do is stuff your fat face, isn’t it?” Jack said, grabbing a tit and squeezing it.

“Y-yeah...’ Kahili stammered as Jack’s pace quickened.

Pretty quickly, Jack realized he was using a lot more force than he usually did than when he usually took a lady to pound town. Perhaps it was just him releasing his anger out. Either way, it didn’t take long until Kahili was crying out with every angry thrust of his.

“Fuuuuuck I... I haven’t been fucked like this... In so loooooong!” Kahili yelled between moans. Jack got an idea and he started caressing Kahili’s gut, then began tickling it, causing a very odd mixture of laughter and sexual moans.

“Jack, aaaah.... uuuuuuhh... cuuuuuhming!” Kahili cried out when she could say a coherent word. Jack felt his cock get doused in her juices while he continued pumping inside her. The thought of her cumming so helplessly got him over the edge, and he knew he was soon as well. A half minute later his cock spasmed with overwhelming pleasure as he shot his seed deep into Kahili. He got out of the orgasmic haze a bit later, smiling ear to ear.

“Welcome to Akala, Mr. Cobal.” Kahili said, red-faced and still in her post-ogasm high.

“Thanks for giving me such a good welcome.”

“I hope you come by often.” Kahili said. “The villa isn’t too far away.”

“Oh I will.” Jack said, taking his spot laying next to her. “Got different bodyguards for now.”

“Oh, any reason?” Kahili asked, genuinely concerned.

Jack took a deep breath. Bunch of bullshit started today...”

“How about lets get dessert then?” Kahili said. “The restaurant is just a few steps away.”

Jack nodded and the two got dressed rather quickly.

The Sea House Restaurant was an open-air restaurant just next to the beach and the little bay the resort was on. Kahili waddled her way to a table, not even needing a hostess. It didn’t take long before a server came for their order.

“Hey Kahili, long time no see.” The server asked. Jack got a a good look at her and was not disappointed. She looked to be a little over 300 pounds, showing off a lot of by just wearing a tube top and a blue cloth hula skirt, showing a good amount of her one of her fleshy thighs. She looked absolutely amazing with her very tanned body and a big red Alolan Cornflower covering one side of her hair.

“Where does the hour go?” Kahili joked. “Time for dessert... I think I’ll have my special, the three slices of cheesecake for starters...” Kahili said, pondering her options. “Can I get a few scoops of ice cream with each, and... a strawberry daiquiri.”

“Yes of course.” Phoebe said, then turned to Jack. “And the friend?”

“I’m Jack.” He said with a big smile. “Hm... I think I’ll go for Rum and Cola.”

“Want some grenadine in it?” Phoebe asked. “Definitely worth it.”

“Sure why not?” Jack said.

Phoebe waddled to the bar, and Jack’s eyes followed her the whole way.

“She’s a looker, ain’t she?” Kahili asked.

“Oh yeah.” Jack said. “She’s been eating here a lot by the looks of it.”

“Yeah, when she gets off she joins me for dinner a lot.” Kahili asked. “Usually have dessert in the room. She’s a good friend.”

“How good of a friend?” Jack asked lasciviously.

Phoebe smiled. “Not that kind of friend. Yeah, you’re really gonna like it around here. Got a few overweight staff here.”

“Can’t wait to meet 'em.” Jack said.

“But don’t get your hopes up, I’m the biggest here.” Kahili warned him.

“Right, right.” Jack said. “So, about all that BS with the staff...”  He explained a bit of the situation, paraphrasing most of it, and ending with the huge fight with Oleana.

“That’s awful.” Kahili said. “So you’re going to have a couple skinny bitches looking after you?”
“Yeah.” Jack said. “There’s some business stuff I’m doing here on Akala, kinda confidential. I don’t want them to know what it is, but I need someone to help escort me to and fro.” Jack explained.

“Well I can. I’ve got some pretty strong Pokemon on me.” Kahili said. “But it’s gotta be outside of my mealtimes...” Kahili said.

“And when are those?”

“Most of the day.” Kahili said sheepishly, rubbing her gut with pride. “Where do you think this all came from?”

“Yeah, you’re right.” Jack answered.

“I know a couple trainers who can keep their mouths shut, if you’re looking.” Kahili said.

“I’ll definitely let you know." Jack said. Then his lust got the best of him and asked something he had a suspicion on. “So, you ever get any visits from Aether Foundation?”

“Not a lot but sometimes.” Kahili said. “Lusamine is known to make an appearance here when she’s on Akala.”

“That explains the staff, then.” Jack thought to himself.

The conversation flowed pretty easily, the rum, cola, and grenadine was a perfectly sweet mix, and Kahili inhaled a couple Daiquiris before her decadent desserts arrived. Even Phoebe was licking her lips as she brought them out.

“I’m about to get on my lunch, mind if I join you two?” Phoebe asked as she laid the platter of cheesecake slices in front of Kahili.

“Of course.” Kahili said, winking at Jack.

The conversation became much more one-sided as Kahili began to devour her dessert, and then Phoebe joined them, bringing a double bacon cheeseburger and a shake. He was mesmerized by her as she sat down, putting her belly overhang on full display.

“Okay, I gotta ask you something that’s been bothering me since you first came up here, Phoebe.” Jack began.

“Oh?” She replied.

“How does the cornflower stay?”

Phoebe laughed and smiled. “Alolan secret, dude.” She paused and eyed him up again. “How you know Kahili?”

Jack shrugged. “We kept running into each other at these fancy dinner parties, and I finally got my ass over here.”

Phoebe nodded knowingly. “Yeah, how do you like it so far?”

“Well I had quite a welcome...” Jack winked at Kahili. “But I haven’t gotten to my accommodations yet.”

“Where’s he staying?” Phoebe asked, turning to Kahili.

Kahili gulped down the last of her second slice of cheesecake. “The villa.”

Phoebe’s jaw dropped. “Oh so you’re not kidding on the fancy dinner parties. Kahili tries to downplay it, saying she just goes there for the food.”

“Which is *mmph* right.” Kahili chimed in before consuming a large scoop of ice cream.

“Ooooh you better give me some good tips. How long you here?” Phoebe said playfully.

“No clue yet.” Jack said.

“You booked the villa for three weeks. We don’t do that normally, even for the offseason.” Kahili said.

Jack shrugged. “Well I’m not sure how long this business crap will take, so I figured I’d reserve it as long as I could.”

“Braggart.” Kahili said, beginning her third slice of cheesecake.

“Well it’s working.” Phoebe said, winking at him. He wiggled his eyebrows playfully.

Kahili rolled her eyes.

Jack and Kahili continued hanging out for a while, waiting on his room to be ready, drinking copious amounts of alcohol as they did. Phoebe had to go back to work, but promised to join them if they were still around when she got off.

“Oh crap, it’s that time already?” Kahili exclaimed, looking at her phone, seeing it was 3:30. “You’re check-in is probably ready.”

“Great.” Jack replied. “I’m gonna go get the key then.” It didn’t take very long at the front desk, and within a few minutes he was walking to the edge of the resort, seeing the spacious house he’d be staying in for the duration. “No wonder Phoebe was impressed.” He muttered as he opened up the door and peaked inside. It had lots of windows facing the sea, so it was very bright. The main living room had a number of couches and a dining room table. He dashed inside and checked out the master bedroom ,seeing a huge bed, arm chairs, and a huge TV in the room.

“Man, I should’ve come here a lot sooner.” He said to no one in particular.