Alola Girls Ch. 32 (BBW, WG)

Chapter 32

After leaving the ranch, Jack stopped by a store and got Rosa more sodas to mix with her rum, as well as he got a tablet computer, making chatting with his ladies a lot easier. Upon getting back to the villa, he scurried to his room and hit up Hilda.

“I’m sorry it’s been so long.” Jack said, grinning widely.

Hilda smiled, letting some emotion slip. “Yeah, but you’re really busy. And you have a lot of women to attend to right now.”

“Yeah...”

The two caught up, Jack telling stories of his adventures on Akala. When he mentioned fucking Kahili, Ivy, and Malva, Hilda started getting hot and bothered.

“Y’know, you could always send me a video. Being pregnant is making me so fucking horny all of the time.” Hilda whined.

“And hungry I see.” Jack said, pointing at the bunch of candy bar wrappers on her bed.

Hilda’s face soured. “Yeah well there’s nothing else for me to do but eat. Any updates on Oleana?”

“Not yet.”

“Hit up Anabel, maybe she can help.” Hilda said.

“Why the hell didn’t I think of that?” Jack muttered to himself.

“Because you don’t have me around to do it for you.” Hilda reminded him.

“I need you here in the near future... I got some leverage on Rosa, she’s become quite the drunk.”
“Rosa? Drinking? Never figured...”

“Kahili tricked her, we’ve been feeding her booze constantly since.” Jack said.

“Can’t wait to see how bubbly little Rosa is when she’s drunk... How about the other chick? They touch Lillie yet?”

“Oh yeah.” Jack said. “Nessa the model is really getting into overeating.”

“Good to hear.” Hilda said. “I ought to check in with my harem sisters, I’ve barely heard from them at all.”

“They’re busy getting physical training, and dealing with that conniving bitch.”

“Yeah... So how was the ranch?”

Jack smacked his head and explained the situation.

“Buy Paniola Ranch? That’s a lot, especially with Oleana breathing down your neck.” Hilda said.
“Yeah... But it’d really help Akala I think. Plus I’d get the best ice cream in the world delivered straight home.” Jack said.

Hilda grimaced. “So that’s what it’s for?”

“Well, partially.” Jack explained. “I have a meeting with the head manager tonight, will learn more.”

Hilda shrugged. “Well I’m not your assistant anymore-”

“You always will be.” Jack said.

Hilda smiled the most genuine smile he’d seen in the past few days from anyone. “Well, if you think there’s a good chance it makes it’s money back, I’d say give it a shot. But don’t drink too much tonight during dinner. You have to put on a good impression for your future subordinate.”

Jack nodded seriously. “Good idea.”

The two paused for a bit, unsure of what to say. Then Hilda lifted up her shirt, revealing her doughy belly. “See how fat your baby is making me? Forget eating for two, it feels like I’m eating for three...”

“Wait you have twins?”

Hilda’s jaw dropped. “What? No... Thank goodness.” She said, giggling. “It’s too early to tell anyways. But I’m eating sooo much right now...” Hilda said, caressing her belly. “Get your dick out big daddy...” Hilda said seductively.

Jack did as told, and began wacking off with his distant baby-mama.

***

Jack got a booth at the Sea House nice and early, drinking water. Nessa accompanied him, as Rosa was getting quite sloppy in the villa and couldn’t be trusted in a serious business meeting.

When the appointed time rolled around, Whitney and and her enormous self waddled in, accompanied by an elephantine looking blonde. She was taller than Professor Ivy and just as hefty, Jack guessed she probably weighed in just north of 520. Her belly stood out most to him, sagging down her front like a waterfall over cliffside. She had long blonde hair, not quite as long as Lusamine’s, but still quite long.

“Cynthia...” He said under his breath, getting quite horny.

“Definitely your type.” Nessa commented quietly. “Look at how every part of her jiggles with every step...”

“Getting turned on over there?” Jack asked.

Nessa nodded. “A bit.”

Both rotund women appeared beside their booth, panting and already sweating from the long walk it surely took for them to get from the parking lot to the beachside restaurant.

“Oh goodness...” Cynthia panted. “So out of shape.”

“Nice to finally meet you, Cynthia.” Jack said, extending a hand. Cynthia put her hand up and bent over as much as she could, continuing to pant as her belly heaved up and down with every breath.

Whitney then put her hand on the booth’s table. “Uh, Mr. Cobal would uh... mind if we got a table? Cynthia and I aren’t going to fit in here.”

Jack smiled, and he took a peak at Nessa who seemed transfixed with something. “Sure. I’ll flag down a waitress...”

“And some extra chairs too.” Cynthia said, starting to catch her breath. “Whitney and I have been enjoying the... ranch discounts.”

Whitney sighed sheepishly. “Yeah, that’s it, nothing to do with the free meals we get at the steakhouse.”

Jack saw Jasmine, the nearly 330 pound waitress waddling over to the group of four and quickly realized the problem.

“So uh... a table would be better?” Jasmine said.

“Yeah.” Cynthia said.

“Great, I’ll just put you all over here...” Jasmine’s voice trailed off

“Too fat for a booth... Why does the thought of me getting that big turn me on so much?” Nessa whispered to Jack.

Jack smiled.” You’re doing an excellent job of trying to seduce me. Sure Oleana still has control over you?”

Nessa grimaced. “Fuck that bitch. Actually don’t, just let me fatten up a bit and fuck me- Oh yeah, we’ll be right over!” Nessa called out mid-sentence to Cynthia and Whitney, waving them over to a table as Jasmine pulled up two extra chairs for the enormous women.

Whitney and Cynthia took up too much space to put them next to each other, so Jack sat next to Whitney and Nessa next to Cynthia. Once they finally got settled in Jasmine looked to them for drink orders.

“Hmm...” Cynthia said, eyeing the menu. “No shakes. I’ll have a beer then...”

Jasmine turned to Whitney, who also ordered a beer. Jasmine then turned to Jack expectantly.

“Water for me, actually.” Jack replied.

Whitney gave him a look. “What, no fun tonight?”

“I don’t usually talk business.” Jack said. “I should probably be sober for this.”

“Well I’m having a daiquiri.” Nessa said.

“Fair enough.” Cynthia said, and with that, Jasmine left to grab the group’s drinks. “I suppose I should decide what I want to eat before we start truly talking business then?”

Jack gave her a slight nod. “Everything I’ve had has been delicious.”

“Not going for the burger...” Whitney said. “I’m spoiled at the steakhouse.” She said, rubbing her belly happily.

“Seafood is definitely the go-to here.” Jack said.

A few minutes later, Cynthia and Whitney had finished listing off their massive orders to Jasmine, and after taking a large swig of beer, Cynthia burped loudly. “It’s time for some business then, shall we?” She asked.

Jack took a swig of water. “Alright, what’s up?”

“Well, the ranch owners are on track to go bankrupt in six months.” Cynthia said.

“That quickly?” Jack said.

“Yeah, turns out the old owners tried a different business venture that... failed miserably. All of the profits from the ranch went to paying for it, and the kids are now stuck holding the bag.” Cynthia explained.

“Sounds like you’re trying to save your job.” Jack said.

“Well of course I am.” Cynthia replied. “I’m quite good at it, our profits were never higher until the previous owner’s death.”

“Okay... With ice cream that good, how did I, a newcomer to Melemele Island not know about the Paniola Ranch?” Jack said.

Cynthia sighed. “The previous owners wanted to keep the Ranch from becoming too touristy, thought it was part of their image. I had to battle quite hard with them to even allow pamphlets at resorts, and we’re only in a third of the resorts on Akala.”

“Sounds like these previous owners were pretty dumb...”

“Their parents were probably first cousins.” Cynthia said.

“And why did you put up things for so long?” Jack asked. “Seems like they wasted you.”

Cynthia took a deep breath and nodded. “I certainly feel that way... When I came to Alola, I was training really hard for the Sinoh League. My Pokemon and I were getting truly tough... My parents figured I could use a break and sent me on a trip to Alola for some relaxation. One of the days I went to the Paniola Ranch and just... Fell in love with the place. I saw ways they could improve, I saw how happy it made the kids of Akala, and I ended my pro training career to work at the ranch... That was a while ago. I feel like I’d be wasting my whole life if I just let the ranch fall apart.”

Jack nodded intently. “What could I do owning it that the current owners can’t?”

Cynthia grinned. “Well, an injection of capital could up production on our ice cream. We could send the ice cream all over Alola.”

“That’s hardly a big revenue driver, I think.” Jack pointed out.

Cynthia nodded. “Right, but it’s amazing advertising.”

“Oh...” Jack said.

“It definitely is the best ice cream, the best home of the best beef in Alola, imagine every resort having Paniola Ranch Ice Cream on its dessert menu. And imagine our ice cream having parlors all across Alola. Demand for Ranch tours would go way up. With higher demand and inflexible supply...” Cynthia said, eyeing him eagerly.

“I see your point.” Jack said. “So how much do you reckon this all costs?”

Cynthia thought deeply for a bit, running the numbers through her head. “So, you could get the ranch for a million, but they wouldn’t accept it outright, probably 1.5 and they’ll screw off finally.” Cynthia thought aloud. “The machinery needed for the ice cream is kind of old, so you actually get the save a buck there if you buy more of the same, but you’d need bigger facilities...” Cynthia continued pondering. “Well, I’d say anywhere between 2.5 to 3 million is probably the expenditure you’d be looking to make.”

“You already included ice cream parlors?” Jack asked.

Cynthia shrugged. “Well, one, to start you off.”

“Lets say no parlors yet, but stands on beaches sound like a good idea.” Jack said.

“Oh yeah, I really like that. Low cost and you can really spam it everywhere. Will help get the word out.” Cynthia said. “I’d say that’s about 2.7 million after all’s said and done. Think you can swing that?”

Jack shrugged. “It’s something to think about.”

Cynthia grimaced and took a giant swig of beer, nearly finishing the glass. “Well give a real thought to it. I bet you make it back within three or four years. Which is lightspeed when it’s ice cream you’re selling.”

Jack smirked. “Seems awful fast.”

“Doubling output and selling to restaurants will be a huge boon. Plus the beef side of the business is already perfect.” Cynthia explained.

“What if they don’t buy? Why change their ice cream?”

“Because locally sourced is in, and our product is way better than whatever drivel they’re buying now. Plus most restaurants on Akala have asked about selling Paniola ice cream.”

“If we double production that could hamper quality control.” Jack reminded her.

Cynthia grimaced. “As long as I’m running it, I’m sure we won’t be running into that issue. That’s why I wanted to use the same machinery used...”

The business back-and fourth continued until the appetizers arrived. At that point Jack took over the conversation, mostly talking about his team of Pokemon.

Cynthia pushed aside a massive double order of lobster mac n cheese and sighed with relief. “So good...” She said, rubbing the top of her enormous belly. “I bet my Garchomp and I could take your entire team down, Jack.”

“You have a Garchomp?” Jack asked.

Cynthia smiled. “Like I said, I was a pretty strong pro trainer in my day. Battling is the only way to calm down some of those rough Tauros. My Garchomp is as strong as it’s ever been...” Cynthia then looked down at her elephantine figure and got a little sheepeish. “Even if I’ve softened up a bit.”

“A bit?” Jack teased. “You may be the largest woman I’ve seen in Alola. What are you weighing these days?” Out of the corner of Jack’s eye, he could see Nessa’s head turn and fixate on Cynthia.

Cynthia smiled weakly. “Well, scales and I don’t really see each other anymore...” She said, indicating her enormous gut.

“Doesn’t the old rule ‘a gentleman never asks and a lady never tells’ apply to weight as well?” Whitney chimed in.

Jack chuckled. “Fair enough. But I’ll cut you a deal Cynthia. I’ll buy the Paniola Ranch, but only if you weigh yourself for me in person.”

The the women at the table all collectively stopped their eating. Jack smiled and leaned back. “I take a great fascination in larger women.”

Cynthia looked over at Nessa, working on her second plate and third daiquiri. “Nessa was it?”

Nessa nodded, mouth full of crab cake.

“So your boss has a thing for large women?”

Nessa nodded. “I bet he’s got a throbbing erection right now.”

Jack felt himself tense for a moment as Whitney’s hand appeared on his thigh, finding his erection and giving it a playful squeeze. “Yes he does, boss.” Whitney said, hand retreating.

Cynthia took a deep breath, letting her multiple chins wiggle. “Well, I suppose you’ll have a deal then.” Cynthia said. “For that much money I’m almost surprised you weren’t trying to sleep with me.”

Jack smiled wickedly. “Oh, that’s only if you want to keep your job.”

Cynthia smiled. “That’s more like it...” Cynthia said lasciviously. “What do you say Whitney, a night with Mr. Cobal here and he buys the ranch?”

Whitney blushed. “I was planning on doing that tonight regardless.”

“Can I watch?” Nessa asked shyly.

The two large women smiled at the slender, former model. “If we can find room...”

One hour and nearly ten thousand calories between the three women later, the group of four arrived at the villa.

Cynthia immediately waddled her massive body into the villa and laid out over the sofa. “Ugh I... Need some rest... So bloated.” Cynthia said, lying on her back, her black shirt rode up, exposing her belly button to the world.

Jack had drank quite a few beers and some shots of Scotch once the business talk was settled, so he we was well and truly drunk. His eyes continued to wander to Cynthia’s enormous form, but he was enamored with her enormous thighs, threatening to burst out of her trousers. He’d never seen such a set of thighs. “Cynthia, you’re going to have to take those pants off in a bit. Else I’ll rip ‘em off you.” Jack said.

Cynthia sighed. “If I take them off, I’m not sure they’re getting back on again after that meal.”

Nessa moaned slightly in the corner.

“Hey Nessa- UUUURP!” Cynthia belched loudly. “Come to the ranch with us, you’ll be as big as us very quickly.”

Nessa giggled nervously.

Whitney then appeared next to Jack, guiding him to sit on the couch. She then took off her top and unclasped her straining bra, freeing her enormous milkers. “Much better...” Whitney cooed as she undid Jack’s pants, freeing his cock.

Whitney tongued his shaft a little bit then paused. “So you want that model over there to get nice and fat like us?” Whitney asked dirtily.

“Fuck yeah.” Jack said.

“You bring her over to the ranch and we’ll set her up in a private room. Then we’ll tie her up and force thousands of calories down her throat.” Whitney said, then giving his whole shaft a delightful lick.

“Ooooooh...” Nessa cooed as Jack noticed she had a hand down her pants.

“And we’ll keep doing it, as she grows and grows... Then one day she’ll come over, and we’ll feed her so much she won’t be able to move...” Whitney continued.

Nessa’s moans got louder with every phrase.

“And then...” Whitney kept on. “...We’ll just keep her at the ranch. The only pig on the farm. We’ll just keep stuffing her until she’s the fattest woman in Alola...”

“Iiiiing AAAAAAH!!!!!” Nessa belted out as her body convulsed with an orgasm.

Whitney smiled proudly and began sucking him off in earnest. After all of the build up, it didn’t take long for Jack orgasm as well. When Jack came back out of the pleasant haze, he saw Whitney spitting his cum out of her mouth.

“Oh goodness... Kahili was right. Shouldn’t have... tried to swallow.” Whitney said.

Jack then eyed her, feeling his erection rising just as strong as earlier.

“Oh you’re fucking kidding.” Whitney said, eyes nearly in terror as his member reformed to full mast. Whitney took a deep breath and shook her head before getting off the ground and onto the couch with him. He climbed on top of the near 450 pound beauty and began riding her. It didn’t take more than ten minutes before she was shrieking in orgasm.

Jack dislodged from her, still erect and having not cum, eyeing Cynthia. “Your turn.” Jack said.

Cynthia sighed. “So... full... Help me out of this will you?”

Jack obliged, hopping off the couch and pulling the well over 500 pound woman from the couch, and guiding her to the bedroom.

“You know, I’ve got a scale in my bathroom.” Jack said.

Cynthia looked at him in pure horror. “Oh please no.” Cynthia said. “I haven’t weighed myself in a few months.”

“She’s probably too heavy for it.” Whitney said.

Cynthia nodded. “I’m probably past 500, most scales don’t go past 400, right?”

Jack smiled. “And how would you know?”

Cynthia smiled sheepishly. “Well... Can we do a rain check?”

“Nessa!” Jack called out down the hallway. A few moments later she appeared with just a shirt on.

“Find out how high the scale in my bathroom goes.” Jack commanded.

Nessa darted in and a minute later came out with a grin. “Online it say it goes up to 550, actually.”

Cynthia’s jaw dropped. “Well fuck.” She then waddled into the bathroom, her enormous body jiggling and rippling with every motion.

She approached the scale, which Nessa had put in the center of the master bathroom, but Jack stopped her.

“Strip down.” He ordered.

“So this is how our ‘owner- manager’ relationship starts?” Cynthia asked humorously.

“Well, we could do anal...”

Cynthia shook her head vigorously. “I’ll take the embarrassment before you put that monster cock of yours up my ass.” Cynthia said, taking her black jacket and pants off. He finally got a great look at her ham-like thighs, they were all he’d dreamed about and more.

“Well, last time I weighed myself I was 462 pounds...” Cynthia said nervously.

“And how much do you think you weigh now?” Jack asked. He saw Nessa waiting anxiously, biting her lip with delight.

“Well... I hate to say it but I think I’m a bit over 500...” Cynthia said, looking down at her body.

“Specifically?” Jack asked.

“505 maybe?” Cynthia said, last shreds of hope in her voice.

Jack smiled. She was definitely over 500, but 505 wasn’t very close, he suspected.

 Cynthia hopped on, having a hard time fitting her portly self onto the scale due to her excessive leg fat. She looked up to the ceiling, knowing she wouldn’t be able to see the numbers on her scale due to her enormous belly overhang.

Nessa crawled down to get a look.

“What’s it say?” Jack asked.

 “Taking a while to stabilize...” Nessa said, and after a few moments she put her hand up. “524!” She announced.

Cynthia gasped, while Whitney covered her mouth, probably hiding some laughter.

“Better not laugh Whitney, I bet you’ll be this big in just a few months.” Jack teased. That stopped Whitney.

“Well Mr. Cobal, you got me.” Cynthia said. “You better fuck me so hard I forget this happened.”

Jack smiled confidently. “You’re with the right guy then, big mama.”