Jack showed his ID and stepped inside. The place looked like a large, indoor shopping mall, except the stores were substituted by bars. He was on the second floor of three by the looks of it. The center of the first floor was a large battlefield for pokemon battles. He was standing on the second level technically, and a crowd of seats were lined the railing to give the best views of the battlefield. He spotted a number of bars scattered throughout the large circle that was the building. The daylight shining through the windows brightened up the place considerably.
Considering it was only 3:30 in the afternoon, the place seemed decently populated. As he took closer looks, most of the bars were closed at this point in time. He spotted the one closest to him that was open and stepped over to it. A ton of TV's were on, with screenings of various pokemon battles. Jack took a seat and eyed the beer taps.
"Good afternoon, what you drinkin'?" a feminine voice said as he turned to see a dark skinned beauty with black hair and streaks of light blue through it. He was already dazzled.
"Good afternoon," Jack said, eyeing the taps, spotting something familiar. "Can I get that Ranchside Lager?"
"Small or tall?" the hot barmaid asked.
"Tall."
The woman nodded and Jack got a look at her body. She had a nice rack, probably C cups, with a tight shirt covering only the upper half of her, leaving her washboard abs for everyone's viewing pleasure. She had tight blue leggings, leaving little to the imagination. She turned around as she poured his beer, and he saw the outline of her thong on her behind. He immediately got excited down below. "Insatiable, goddam," he thought.
"Leavin' it open?" the amazingly hot bartender asked.
"No," he said, handing her his card. He saw her take notice of the exclusive black card, she gave him an extra glance very quickly before going to her register to run the card. The transaction was processed quickly, and she was handing him his receipt with a big smile.
Jack saw the option to leave a tip for the nine dollar beverage, and decided to tip a hundred dollars. He took a sip of his beer, and she came back around for the receipt a minute later. She picked it up and saw the tip, stunning her for a second.
"Sir, I believe you added an extra zero," she said as she turned around.
Jack shook his head. "I'm new in town, first time here, and I'd like to be a regular," he said. "Just trying to make friends."
She eyed him suspiciously, but quickly relented into a smile. "Okay, but no funny stuff."
"Sounds good," Jack said. "But can I get the name of my new friend?"
"Shelly," she said with a smile. "And what cologne do you use? The smell is... intoxicating."
"My little secret," Jack said playfully, getting an eye roll from Shelly.
"Well, keep your secrets," Shelly said just as playfully, then went to the other side of the bar to take the order of another patron.
For the next hour Jack drank a couple beers and watched some of the international pro trainer battles showing on the bar TV's. A guy came and sat next to him for a good while, had a couple beers and a shot, chatted casually, and then left for something called "The Battle Book."
After his second tall glass, Shelly sauntered by. "Need another one?"
"Yeah," Jack replied.
"You should've just started a tab," Shelly said.
Jack nodded. "Never too late to start, right?"
Shelly nodded. 'Better late than never," she then took his glass and put it aside, while grabbing a fresh glass and pouring him another cold beer. His buzzed eyes were mesmerized by her blue leggings. When she came to deliver his beer, he realized he wanted to know something.
"Oh and what's the Battle Book?" Jack asked.
Shelly had his card in hand but stopped. "It's the place you can place bets on trainer battles that take place all over the world," Shelly explained, then pointed across the way to another second story bar with even more TVs. "You can't place bets on the battles that happen here with the book, but they're still fun to watch."
"Battles? Here? Any good ones?" Jack asked.
"There's a local amateur league." Shelly said. "It's usually a lot of fun to watch."
"When is it?"
"Monday through Thursday. They start at 7:00."
Jack remembered it was Wednesday. "Well that works out rather nicely," Jack said, then remembered something. "What time is it? Don't have a phone on me."
Shelly pulled her phone out. "5:05," she replied.
"5:05," Jack said out loud, remembering Misty got off at 4:00. But she might not have gotten the text, or was busy getting ready for a night out. Or she was ditching him. Jack's head drooped. Yes he'd gotten attention from a plethora of ladies today, but the thought of rejection still stung, no matter how illogical it seemed to an outside perspective.
"So here you are," The voice of Misty Waterflower practically sang from behind him.
Jack's heart leapt as he spun around on his bar stool. "Misty!" he cried out in relief.
Misty's yellow tank-top showed off her midriff, and her tight blue short shorts showed off her dazzling figure and legs. She was quite thin except in the hips and breast department. A fertility idol-like combination of features. Misty smiled proudly as Jack remained speechless.
"It's been over five seconds," Shelly chimed in with a laugh.
Jack shook himself out of his stunned state. "Well you look fucking amazing."
Misty smirked. "That's the best compliment you could come up with?" she said, shaking her head with mock-disappointment.
"It was the only thing in my head that wasn't X-rated," Jack said as he turned his barstool around so he could hide his erection as much as possible.
Misty then took the stool beside him and gave him a pat on the back. "Sorry I took so long, took a while to explain why I was leaving the restaurant."
"How so?"
"They didn't believe I was going to work for... a guy like you, let's say," she informed him as she noticed Shelly was listening intently.
"Don't tell me this guy's some pimp or something," Shelly said, amused.
Jack rolled his eyes. "Definitely not. I'm too much of a simp for that life."
Misty and Shelly both laughed, but Jack noticed Misty's body inch closer to his, and Misty's hand found it's way to his crotch, which was responding in it's now usual way: being achingly hard.
"Yeah you are," Misty said with a knowing grin.
"So can I get anything started for you?" Shelly asked.
"What kind of tequilas do you have?" Misty asked.
Shelly grabbed a small menu booklet. "Pages five to eight. It's easier to ask what we don't have, honestly," she said, then went to help a couple customers who had come up to the bar.
"How drunk are you?" Misty asked.
"I have a very good buzz," Jack said. "Maybe a little drunk."
"Down to do a tequila shot with me?" Misty asked.
"I'm not a huge fan of tequila," Jack said.
Misty shook her head. "Then you haven't had a good enough tequila then," she then pointed to a tequila on the menu, and all Jack noticed was the $25 per shot price tag. He hadn't had an alcohol so fine, even during his time in Castelia. Mostly because his handlers had kept most alcohol out of his reach. "Want some?" she asked.
Jack put his hands up in defeat. "You're the expert."
When Shelly came back around, Misty ordered two shots of tequila, and an Alolan Blue for herself.
"Hope my new boss hasn't been too annoying to you," Misty told Shelly.
Shelly giggled. "I thought he was a bit creepy at first with that $100 tip," she admitted. "But he's alright."
Misty looked at him, skeptical look on her face. "He's definitely not a creep. Just a little clueless."
"I'll take your word for it," Shelly said as she finished pouring the two tequila shots. She slid them in front of Jack and Misty, and she looked at the two expectantly.
"Sorry... I need a chaser," Misty said.
Jack and Misty avidly watched Shelly mix Misty's drink, and when Shelly had it all wrapped up, she presented it to Misty with a ponderous look. "You're familiar."
Misty smiled uneasily. "Yeah, you might recognize me."
"You've battled here a few times, haven't you?" Shelly asked.
Misty nodded. "Guilty."
"You'd have the Goldeen costume?" Shelly said excitedly.
Misty nodded. "Yeah."
"I like the mermaid costume more though," Shelly said.
Misty shrugged. "So did I."
"Haven't seen you around here much recently," Shelly said.
Misty nodded. "Started working more, bills piling up."
"Shame. Well as a fellow water type trainer I was always a big fan. Any chance we see you on the battlefield again?"
Misty eyed Jack coyly. "Well, if my new boss is okay with it."
Jack realized both woman's eyes were on him. "Of course I'd be okay with it."
"Well, welcome back to the Club League then!" Shelly cheered.
Jack and Misty took their tequila shots in their hands and cheersed, then took a big gulp as the spicy liquid went down their throats. Jack closed his eyes as the shot went down, and did his best not to cough, which he was successful at. His eyes opened to Misty sipping her Alolan Blue quickly.
"Wow, that was really good," Jack said, compared to other liquors he'd shot before.
Misty nodded, then put her little backpack on the bar and took her phone out. Jack figured he ought to mind his business and then took a sip of his beer.
Misty turned her attention back to him as he noticed she'd already slurped down half of her Alolan Blue. "So boss, what's a typical day for you?"
Jack shrugged. "Haven't had a typical day so far, so I'm not sure."
"What do you expect to be a typical day?" Misty asked.
"Well, I want to get in better shape, so I got the number of a girl who's a personal trainer-"
"She hot?" Misty asked.
"Well of course," Jack said. "She's got some fucking muscles too."
Misty closed her eyes for a moment and nodded. "Cool. So you want to start working out, what else?"
"Well, I want to get better at training my pokemon."
"You any good?" Misty asked.
Jack shook his head. "I was really small time in Hoenn, got a few badges and joined a guild before the trust fund kicked in."
"So you want to be a legit pokemon trainer."
"I figure I'll want to do some hiking around the island, maybe catch some cool pokemon," he said, thinking hard on what he was really planning to do in Alola. "There'll be charity events I get invited to every so often."
"So what would you say your goals are?" Misty asked.
"Besides being happy and healthy?" Jack said. "Probably being a respectable pokemon trainer, and I want Alola to be better off than when I got here."
Misty nodded. "I like it," Misty then took a hardy sip of her drink, getting it down to the dregs. She then leaned over and whispered in her ear. "But you forgot the part where you fuck the crap out of me and the rest of your girlfriends every day."
Jack nearly coughed in shock and got tense. He for sure had forgotten to mention it. "Yeah... definitely," he stammered.
Misty's hot breath pulsed against his ear. "I've been thinking about that massive cock of yours since I last saw you... I'm gonna need it inside me real soon."
Jack nodded nervously. He noticed Shelly was observing the two from a distance. He made eye contact with her. "Can I get another couple shots?"
Shelly smiled, "I can do that," Shelly said as she walked over to the duo, giving them a knowing glance. "You think you're gonna close out for the time being?"
"Yeah," Jack said.
Shelly poured the shots quickly as Misty remained silent, her hands all over him. The two took their shots and he finished his drink, and Shelly came with the bill. Jack tipped another $100 and got out of his seat gingerly, hoping his massive erection wouldn't be obvious for the world to see.
"So where to?" Jack asked. "Your place?"
Misty shook her head. "Too far. Let's just find a bathroom."
"Kay," Jack said, seeing a set of bathrooms with people milling in and out of them. That wouldn't do. He then turned around and saw Shelly observing them some more. He walked over quickly, the shots starting to hit him made him a bit unbalanced.
"Any recommendations on a... private place?" Jack asked the bartender.
Shelly smiled knowingly. "Take the elevator," she pointed directly behind Jack. "Third floor, turn left, second set of bathrooms." Shelly said, then waved playfully. "Have fun."
Jack gave her a wink and turned back around. Misty still had her claws dug into him as they entered the elevator. He pressed the 3rd floor button, and right as the door started to close, an eye-catching young woman scampered into the elevator. She had a studded black jacket over a pink-mini dress. Her hair was partially shaven on one side, but the part that was most eye catching was her enormous rack. It wasn't as big as Lillie's, but it was quite impressive.
"Sorry," she said softly. "Just trying to get a pre-work drink."
Misty stirred and looked over at the attractive newcomer. She looked up at Jack, and nodded her head in the direction of the girl and licked her lips. Jack smiled back.
"Wish I worked at a place I could have a drink before work," Jack said.
The newcomer eyed him, and he noticed she made a glance at his crotch, probably seeing enough to know he was packing.. "It's one of the perks. I'd tell you to come by but you two look occupied."
Misty then smiled. "The day is young," Misty said, eyeing the girl.
The elevator arrived at the third floor and opened it's doors.
"I work at the strip club down the street," she said quietly.
Misty's jaw dropped. "Well I know where we're going later."
The girl smiled. "You're too kind."
"My guy here is a big spender. What's your name?"
The girl shifted her eyes a bit uneasily. "Just call me Marnie."
"Marnie," Jack said out loud, committing it to memory.
"Save some dances for us, Marnie," Misty said, then led Jack out of the elevator in the direction Shelly had spoken of. Before he knew it, they were in a lone, handicapped bathroom making out. He never thought of himself as a good kisser, but Misty's enthusiasm forced him to keep up, breathing seemed optional.
She started to dry hump him and moan, and it didn't take long before his hands were pulling down her shorts. She didn't have any panties on, and his right hand began to rub up against her already moist pussy. The moaning became even more intense, and Misty pulled up her tank top, revealing her bra, then undid it, letting it fall to the bathroom floor.
His left hand went to work on her right nipple as he started kissing her neck.
"Fuuuuck, you tease," she said, gyrating. "C'mon," Misty moaned desperately.
Jack squeezed Misty's breast, causing a slight cry of pain before his right hand left her pussy and went for his belt. He freed his achingly erect member from its confines and Misty put her pussy up against his shaft, smearing his cock with her juices.
"I've never taken... this big before," Misty warned.
"This will be the last time you ever say that to me," Jack said. He then gave her breast a tight squeeze, causing a louder cry.
Then he maneuvered his shaft in, and Misty gasped. Misty felt absolutely amazing inside, her pussy was extremely slick thanks to her natural lubricants. Misty then straddled him, her back against the wall and eyes full of desperate desire.
"I'm not sure you can take all of it," Jack teased.
Misty squirmed. "Give me time, you'll loosen me up," Misty moaned.
Jack started thrusting slowly, methodically. It took more strength than he realized to keep the slender woman in position, and required much more balance on his end than he anticipated, but after half a minute of thrusting, he found a groove.
"Oh fuck!" Misty cried out. Her pussy had somehow got even sleeker, and he realized he was pushing noticeably deeper inside her than before. "You're... stretching me."
"There's still more to go," he grunted as he thrusted.
"Fuuuck, give it to me," she moaned, and so he did.
A bit later, he wasn't sure how much time had passed, but he felt like his endurance had improved. "Or maybe that's from all the use today," he thought as he thrusted.
Misty let her head tip back, resting on the wall. Her eyes closed and she gritted her teeth like she was in some sort of pain. "Fuck you're so close."
Jack then pulled back and wound up, then plunged himself as deep as he could. This caused her to get louder.
"My fucking cervix!" she cried out. Jack knew female anatomy and he wasn't actually hitting her cervix, but the idea of being so deep was incredibly hot all the same. "You're so deep..."
Jack then got back to thrusting in his rhythm, which he realized he'd picked up the pace of.
"Fuck I'm gonna cum, you're gonna make me-" Misty's words got lost in her moans, and she let out a belting scream for a moment, then her moans turned into a euphoric hum as her body quivered with pleasure. "Yeeeeeeees!" she said with a feverish look on her face.
He slowed his thrusting down as he felt her body respond less and less.
"Did you?" Misty asked, words being a bit hard at the moment.
Jack shook his head but smiled. "No need."
Misty shook her head. "It's my first day, you need to cum, inside me."
"You okay for round two?" Jack asked, concern entering his voice.
Misty smiled. It was a different smile than the one she had mid-orgasm, or the lascivious one from the bar. It was a grateful smile, pure and simple. "I got myself a keeper," Misty said. "And my pussy isn't gonna let go," Misty said, tightening her legs together, a symbolic way of imprisoning his cock inside of her.
"Challenge accepted," Jack said as he thrust his cock inside her. Misty howled in pain for a moment, but he began pumping rhythmically as before. Jack noticed one of her breasts was getting awfully close to his face, so he stretched his neck a bit and took her nipple in his mouth, licking, caressing, and kicking it as much as he could while still keeping the position and his thrusting on point.
His brain couldn't think on much else, but he heard Misty's moans of pleasure echo in the background. His eyes were closed, so he just felt her warmth, her wetness. His whole world was her in that moment, and all the poetry and things about love he'd read and never understood began to become a bit more clear.
He then felt a force push against his ribs, and he opened his eyes and noticed it was Misty's hand.
"Fuck you, you're... gonna make me cum... again..." Misty said angrily.
"Your pussy's gonna let go then," Jack said.
"Fuuuuck, I need your cum," Misty whaled.
"You need to... up your... dirty talk..." Jack said.
Misty groaned in frustration. "Can't... dick so... deep..."
"You lose," Jack said.
"I... lose-" Misty moaned in defeat, her pitch soaring high as another orgasm wracked her body. Jack kept pumping into her, and he felt the feeling he'd been trying to keep down. He knew there was no way to stop it, and it was coming very quickly.
"Gah, M-misty..." Jack said, his defenses crumbling.
"CUM!" Misty demanded, her heard shaking as a seizure of pleasure overcame her. "Cum inside me, boss!" Misty cried out.
That did the trick, as he felt all pressure die in his member. His jaw stood agape as he shot rope after hot, sticky rope deep into Misty's guts.
The haze of pleasure overcame him, as it had before. His legs felt like they were on fire, and once he'd squirted his last squirt, he pulled out and re-balanced himself. Misty's legs fell to the floor.
"Fuuuuuck," Misty groaned, her arms going to the wall to help her balance. "I'm so sore."
"Same," Jack said, catching his breath. "Legs are... on fire..."
"Sorry... Felt too good."
"Don't apologize," Jack said as he sat on the bathroom floor. It didn't feel wet so he figured it was at least fine to sit for a couple minutes while he gave his legs a break.
Misty started to clean herself up, and they both noticed white loads of cum dripping out of her. "That's what I call a creampie."
Jack nodded in agreement.
"I've never had that happen before," Misty then said.
"A creampie?" Jack asked.
"Wha-no!" Misty said. "A guy not only made me cum before he did, but made me cum twice before he did."
"Well you did blow me earlier today." Jack said.
"I guess," Misty said. "Still. I think I'm gonna like working for you if this is the perk."
"I'm gonna love having you work for me if this is our routine."
"Can't be too routine," Misty said, then put her hands in front of her stomach, mocking a big belly. "I'll have a dozen kids."
"At least." Jack said, half-joking.
Misty's eyes popped in terror at the thought. "Leave all them for Lillie."
"You don't want kids?" Jack said now feeling pangs of regret for not using protection.
"No, a couple kids are fine," Misty said. "I get the real conservative, family-oriented vibe from Lillie though." Misty explained. "She'll give you twenty if you're not careful,"
Jack grinned. "I'll cross that bridge when I get there."
Misty then started to get up, but had a worried look on her face. "Fuck," she said plainly as she got up unsteadily.
"What's wrong?"
Misty smiled sheepishly. "I'm not gonna walk right for the rest of the day."
Jack smiled with pride. "Mission accomplished."
Misty then gasped.
"Now what?" Jack asked, perplexed.
Misty's jaw remained agape. "You're seriously getting hard again?"
Jack sighed. "Just half-chub... The more you talk about Lillie and I having 20 kids though..."
"Aha... I'll be sure not to bring it up," Misty then eyed him wickedly. "Unless I need a good pounding."