Chapter 45: Dearest Lillie

Jack was finishing up the last knot in his tie when he heard the bedroom door open. "Who is it?"

"Your babysitter," Hilda growled back. She turned the corner into his bathroom adorned in her usual outfit, her breasts threatening to burst out of her top, which had become rather normal. She hopped on the counter, holding a tie in her hand.

"Gonna have to take that tie off," Hilda said.

"Why, what's up?" Jack asked.

"This tie matches Lillie's dress. Serena picked it out," Hilda said, un-furling the tie. It had a deep, dark blue design with purple accents, like an artist trying to portray the night sky.

"She's not wearing white?" Jack asked.

"My lips are sealed, mister," Hilda said with a smile. Jack began un-doing his black and white striped tie and took the tie Hilda held out.

"Anything else going on?" Jack asked.

Hilda eyed him in the mirror. "Not much else really, I'm just bored."

"Is there any special set up or anything-"

"Dawn and Misty are taking care of that," Hilda answered. "Dawn's quite the event planner, y'know."

"I'm not surprised at all. She bossing anyone around yet?"

Hilda giggled. "No, but I can still tell when she silently disagrees with something. I think letting her be helpless in Ursula's hotel room helped calm her ego down a bit."

Jack rolled his eyes. "That and I read some of the articles that came out about her family. They're really getting dragged through the mud."

"Dawn get mentioned in any of them?" Hilda asked.

"Just that she exists, no other specifics," Jack answered.

"Well that's good..." Hilda said. A pause came between the two of them as Jack tightened his tie and inspected the finished product of his double-windsor knot. "Not too shabby there, eh boss?" Hilda said.

Jack nodded but moved silently to the wrack where his jacket rested on a hanger.

"Maybe I should get Zinnia, she's twiddling her thumbs out by the pool..." Hilda mused.

"How long are we waiting?" Jack asked.

"They want to do the ceremony right before sunset, so another hour or so. Serena's got Lillie almost ready, thankfully." Hilda paused for a moment. "So we hired Shauna on as a full-time masseuse to make that happen?"

"Not full-time necessarily.. I wanted to get to know her. I owe Shauna an extravagant dinner date though," Jack explained.

"For the NDAs she'll have to sign we might as well bring her on full-time. She doesn't have to live here if you're not sure," Hilda answered.

"Eh, let's cross that bridge when we get there," Jack said.

Hilda giggled suddenly. "I totally forgot, do you know how to dance?"

Jack shrugged. "Kinda."

"Slow dance I mean, like with a girl."

"Oh... no idea at all then."

"Well that's how we can pass the time," Hilda said, getting up from off the counter and gesturing him to join her.

Jack took a deep breath and relented, walking over slowly. "She really wants to go all out, doesn't she?"

"Yeah, but that's what you get for making a hopeless romantic one of your brides," Hilda replied.

Jack nodded, resigned to his fate of learning how to slow dance. After Hilda put her phone on the bed and had it begin playing a slow dance song, it took two whole minutes to even get the beginning stance correct. Of course it had Hilda's enormous breasts bulging out directly in his gaze.

"Stop staring at my boobs and listen-"

"I can't look at your face and not see them-"

"Turn the sex-drive off for like ten minutes!" Hilda demanded.

"Can you wear something to cover your top for ten minutes?" Jack fired back.

Hilda released her hands from his, stepping away from Jack and pounding the bed with her fists. "This is gonna take a while..."

Hilda's word were quite prophetic. Jack wasn't the most coordinated guy, so mastering some basic steps was a sometimes painful chore for Hilda, whose feet got stepped on quite a bit. After an hour though, Jack finally made it through a song, leading Hilda, and not stepping on her feet at all.

"Finally!" Hilda declared to the ceiling.

"Alright, can I sit down now?" Jack asked.

Hilda scoffed. "You wish. Now comes the actual song you'll be dancing to."

"Fuck."

Luckily it didn't take long to get down, and he even got a few spins in while keeping in step, a monumental achievement for Jack. As the song wound down, Hilda had a huge smile on her face, and he didn't realize he was beaming too. Jack felt the mood was right, and as the song ended he went in for a kiss, holding his lips to hers for just a few sensual seconds, and when they released the perfect kissing sound.

Hilda shook her head. "Do me a favor and don't do that again," she grumbled.

"Why not?" Jack said with a shit-eating grin.

"Cuz then I'll want to be one of your brides, and we can't have that."

"Again, why not?"

Hilda turned away. "Just can't okay? Besides, tonight's about you and Lillie. Not you and me."

"I'm going to annoy the fuck out of you tomorrow until you give me a straight answer, okay?" Jack warned.

"Fine, just shut up about it right now," Hilda ranted. "I gave you one inch-"

"Don't ever use that phrasing again," Jack teased.

"Ugh!" Hilda groaned hyperbolically. "On that note I'm leaving. Good luck, have fun tonight," Hilda groaned.

Jack had resorted to reading one of the weekly memos the Board sent over, something he hated doing but figured it was a better way to pass time. When a loud barrage of knocks broke the silence, Jack immediately bounced out of his bed-side chair.

The door opened and Bea poked her head out. "We're ready for you, Jack."

Jack smiled. "Great."

As he followed Bea down the hallways, his nerves started to get the better of him. "I'm feeling even more nervous than I did with May's ceremony..." Jack thought to himself.

"Something wrong, Jack?" Bea asked. "I'm surprised you're not hard or at least a little chatty."

"Just a bit nervous."

Bea giggled. "Aw, that's so cute," Bea said mockingly. "How about next time we work out you get a bit nervous so we make it through a session without banging uglies."

"With that bod of yours I can't promise you anything," Jack fired back.

Bea smiled proudly but remained silent as she led him out the door to the deck.

Jack's eyes were met with a pristine sunset. The water had darkened in the twilight, and the shades of pink streaked across the darkening sky. "Couldn't ask for a better backdrop."

"It's gorgeous," said the voice of Dawn Berlitz as she approached him from his right with a box in her hand. "I'm honored to be here, sir."

Jack nodded. "You're welcome."

Jack noticed Hilda following behind Dawn with one of those hand held gas lighters with a long stem. "No time to waste, he's finally out of the room," Hilda ordered Dawn.

"Yes ma'am," Dawn said.

"I told you not to call me that," Hilda fired back.

"Yes, s-sorry..."

The two busy-bodies disappeared as the sliding glass door closed.

"You look really nice, Jack," Bea complimented.

"Thanks..." Jack eyed Bea, she had her usual outfit on and he didn't think giving her a compliment about it back would be taken genuinely. "...I'm lucky to have you here with me."

Bea smiled. "Didn't fall for my little bait," Bea leaned into him and gave him a kiss. "I count myself as one of the luckiest women in the world, being able to live here with you and my fellow brides."

The sliding glass door opened, ending the intimate moment. Zinnia emerged, dressed like she usually was, grey shorts and black top that struggled to contain her blossoming bosom. Zinnia pointed ahead to the edge of the deck. "You gotta go there," Zinnia said casually.

"Oh, right..." Jack released Bea from his hold and shuffled his way on over to the little area they'd set up. The clear barrier at the end of the massive deck had little flowers hanging in the center most part of the barrier. From the center of the decorated area, he had a perfect view of the light vegetation separating the deck and the sand, and he noticed something had been set up on the sand below. "Is that a bed?" Jack asked.

Bea giggled. "Yeah, Serena asked us to get one down there. I guess sex on the beach is something Lillie mentioned she wanted tonight."

Jack shrugged. There was enough distance between his and Ursula's property, and he figured it wouldn't be too much of a problem. Sure, video of him having sex with Lillie was potentially a weapon Ursula could play, but could easily be shot down with a "why were they filming in the first place," or at least so he hoped. It being released to the public would be annoying, sure, but the biggest falloout would probably Lillie's location being revealed-

And then he groaned. The implications of Janine being sent to retrieve Nebby meant Aether knew where Nebby and Lillie were. Lusamine had been playing a very careful game with him. "Maybe Sabrina knew Nebby's location, but not the ambush?" Jack thought to himself. "She said so herself, she doesn't get everything..."

"Jack, you okay?" Bea asked.

"Shit, yeah, just got lost in thought."

"I've never seen you so hung up about a girl, I'm starting to get a little jealous here..." Bea's toothy grin gave away the joke.

"However will I remedy that?" Jack asked rhetorically.

Jack noticed the sliding glass door open once more, and May, Misty, and Zinnia appeared, excitement very apparent in their respective demeanors.

"Okay, looks like we're starting," Bea said, her joking attitude having disappeared. "Stand here, and look to the sunset. When you hear music you can turn around," Bea ordered as she moved him herself to the position.

Jack turned around as ordered, a giddy smile taking over his whole body, besides the butterflies in his chest. He heard Bea's footsteps as she dashed up the deck, presumably to wherever the other brides were supposed to meet. A good minute passed before he heard the outdoor speaker system begin to play soft ukulele music. He turned around slowly, hoping to give his movement some dramatic effect.

The sight that met his eyes froze him. Lillie and Nebby had appeared just outside of the sliding glass door, Serena beside her. The first thing that caught his eye was Lillie's dress wasn't white. It was the deep, purple and blue color that matched his tie, and seemed to match Nebby's own cosmic colors. Her hair had been carefully styled with two braids hanging down in the front, and the rest of her hair down in a perfect arrangement behind her. The dress miraculously covered her hulking mammaries, something he didn't actually have an issue with.

Jack and Lillie's gazes met for a few, intimate moments, until Serena whispered something to Lillie. Lillie then began the slow descent down the deck to him with Nebby following close behind her. He noticed she didn't have heels, but walking with dress appeared to be quite difficult. Jack didn't mind though, as he got to bask in Lillie's elegant beauty as opposed to the power of her eye-catching chest. Jack then noticed the other brides following behind Lillie, careful not to draw too much attention.

Lillie was absolutely glowing, her big, green eyes already damp with tears of joy and a sincere smile on her fair face. Jack offered his hand to her as she approached, and she stepped to him, accepting it, and raising her other hand expectantly. Jack offered his other hand, and the two of them stared at each other, glowing. Nebby chimed excitedly as it floated beside the couple, looking up at them curiously.

"Lillie..." Jack began, assuming he should say something. "...Your beauty, it's blowing me away."

A tear fell down her cheek. "Thank you Jack," Lillie squealed lowly.

Jack then noticed the other brides had encircled the pair, all of them holding hands too, and Serena then opened her mouth to speak. "Jack Cobal, it is our pleasure as your brides to present to you the next to join our sisterhood, Lillie."

Lillie turned her to attention to the girls happily, Jack imagined she was trying to thank each and every one of them with her eyes.

"It has been just a short time since our last induction ceremony..." Serena began. Jack remembered fondly the last ceremony for May had taken place in the lounge. It had been much less formal, and May had chosen the lounge for its proximity to the bedroom. "...but we are all delighted to welcome Lillie, whose devotion to Jack knows no bounds."

Lillie gushed and mouthed "thank you" to Serena, who just smiled proudly. Serena then turned to May.

"To do the formal induction, the newest member of our sisterhood, May, will do the honors," Serena said.

May stepped forward and moved in close to Jack and Lillie. Jack chuckled as he saw more happy tears pour down Lillie's cheeks. Lillie nodded.

"So am I," Jack replied.

May pulled out a little note pad and began to read. "Lillie, do you wish to become a bride of Jack Cobal?"

Lillie nodded some more. "I do."

"Second, do you agree to share him with your sister-brides, and any other woman Jack desires?"

"I do," Lillie repeated.

"Third, as long as you are Jack's bride, do you promise to support, help, and be available for Jack and your fellow brides?"

"I do," Lillie gushed.

Jack smiled as he felt the focus shift to him.

"And Jack Cobal, do you wish for Lillie to be one of your brides?"

Jack nodded. "Yeah."

"Do you promise to satisfy and please her, as well as every member of your brides to the best of your ability?"

"Yes."

"Do you agree to support, provide for, and protect Lillie and the numerous offspring potentially produced by her?"

"I do," Jack said, not realizing how much emotion he was putting behind it.

"You may kiss your bride!" May declared.

Lillie's lips met his in a frenzied passion, and Jack picked her up, the two making out fiercely. He could tell Lillie had been practicing, or at least had been given advice by the brides. It took a bit for Jack to hear the collective cheers of Nebby and the women around him.

When the two broke apart, both beamed happily. "I love you," Jack whispered.

Lillie pushed her face into his shoulder. "I love you too, Jack," Lillie gushed.

The two held each other, feeling the warmth of each other's bodies, nothing in the world outside of them mattered. He wasn't sure how long this lasted, but when he finally came back to reality, he noticed the brides had dissipated, buzzing around with tasks they had to do. Jack noticed the table and two chair setup was still empty, and he saw Serena waiving him over. "First dance," Serena said, hushed.

Jack picked up Lillie again, truly noticing the strength in his arms as his new bride didn't feel too heavy. He walked them over to where Serena indicated, who dashed out of the way. He heard the soft ukulele music fade and the song he and Hilda had practiced slow-dancing to earlier. He set Lillie down and took position. Lillie's teared-up eyes held nothing bliss behind them, and Jack felt warm and fuzzy inside, being the reason for that. So the two danced. He caught glimpses of Dawn and Hilda watching, and he thought he saw a view of Selene as well.

When the song ended, the group applauded and cheered as loud as they could. Jack moved in for a kiss, winning her lips once more.

"Jack... I'm so happy..." Lillie sobbed.

Jack nuzzled his head next to hers, standing cheek-to-cheek. "This is only the beginning..."

Serena waved frantically to get his attention, and pointed to the table overlooking the bay with the chairs side by side. Jack got the cue and led Lillie over there slowly.

Moments later, Mallow and Dawn arrived with decadent food. As the sun disappeared from view, the two dined by candlelight. Each bride came and congratulated them individually. When the entrees were served and Jack and Lillie began eating, Hilda surprised Jack by coming by.

"That was beautiful, you two," she said, no hint of her usual snark or sass.

"Thanks Hilda," Jack said.

Lillie smiled. "Hilda, I owe you so much, if you hadn't let me stay that night-"

Hilda shook her head. "No, it's fine. I'm so glad I did. Besides, I know you two would have ended up like this eventually."

Lillie gasped as she realized something. "I can't wait for your ceremony."

Hilda's smiled died. "Let's just focus on you two tonight, deal?"

Lillie nodded enthusiastically. "Of course."

Hilda winked at Jack before turning away.

Jack and Lillie continued chatting, Lillie listing off what she and Serena had to do for the preparations. The sun had truly set by the time crab-stuffed dumpling entrees were finished, and Dawn brought out a creme brulee in a heart-shaped dish with a candle on it.

"What's this?" Lillie asked, indicating the dessert dish.

"Creme brulee," Jack replied. He'd had it once in Castelia. "It's a fancy dessert from Kalos. Very sweet."

Lillie nodded, looking at him expectantly. "Did you want to blow the candle out?" Lillie asked.

Jack gave her confused look. "I think it should be done together."

"Oh, right..." Lillie giggled. He could tell the faintest blush in her cheeks thanks to the candlelight. Jack counted down with his fingers and the two blew on he candle simultaneously. Lillie took a spoon and dipped it uncertainly into the dish, then put the spoon in front of Jack.

"Oh, this thing..." Jack thought to himself. He never quite understood the appeal of feeding one's significant other, but he obliged his new bride and opened his mouth. He engulfed the spoon in his mouth sensually, fixating his gaze on Lillie, who got almost a little uncomfortable as she watched.

Jack grabbed his spoon and got a sliver, then putting it in front of Lillie's mouth. She covered the spoon with her mouth and moaned suddenly. "So good..."

Jack smiled as he withdrew the spoon from her mouth. Lillie then grabbed her own spoon and dipped it for another spoonful, this time putting right into her own mouth. "I suppose that's all of that," Jack thought, taking his spoon and going for a couple scoops of the sweet cream dessert himself. He left the rest of it for Lillie, who seemed positively enamored with the dish.

Once there was nothing but small streaks of cream in the dish, Lillie sighed contentedly. "This has been so perfect," Lillie said. "Thank you Jack."

Jack shook his head. "Your fellow brides put a lot of work into this to make it as special as possible. You should thank them most of all."

Lillie nodded. "Yeah... I never had sisters before, is this what it feels like?"

Jack shrugged. "I wouldn't know, you'd have to ask them."

Lillie nodded. "I wonder who we add next..."

Jack smiled. "You mentioned Hilda, I don't think she wants it though. There are a couple of other girls who I think would be interested."

"Really? Like who? Mallow?"

Jack shook his head. "No clue about her." Mallow was quite beautiful, and had gotten even more so with her subsequent "enhancement" from Lillie, but Mallow seemed like the last bastion of him not fucking every resident of the property. "Although with Janine and Anabel here, I suppose that'll change," he thought to himself.

"So who else?" Lillie asked.

"There's that Roxie girl, the bartender from Kukui's party. And one of Ursula's bodyguards is trying to seduce me, although I doubt we allow her to join."

Lillie nodded.

"Why the interest?" Jack asked.

"Because the girls went so far to make my night special, I want to do just as much for the next one," Lillie explained.

"It's only fair..." Jack said in agreement.

Lillie smiled and shook her legs excitedly. "So Jack, now that dessert is done..."

Jack smiled. "Finally," he thought to himself. "You ready?"

Another happy tear dropped from her eye. "Yes..." Lillie cooed.

"The bed down there?" Jack pointed to the beach. Lillie nodded. "If that's alright..."

"Of course," Jack responded, hoping Ursula didn't do anything dumb on Lillie's special night. Jack got up and took Lillie's hand, helping her up since movement seemed a little constrained in her dress. Lillie spun into him once up.

Jack noticed Serena had stealthily appeared and started pantomiming lifting something up. "This could get annoying," Jack thought, but he swept Lillie into his arms. Jack then slowly made his way to the wooden steps leading to his private beach. With Lillie blocking his line of sight, he couldn't actually see where the steps were. He took it slowly down the dimly lit staircase, hoping he wouldn't fall down it like he fell down the airstair on his first day in Alola.

Upon reaching sand, Jack silently rejoiced. His pace quickened as he continued carrying Lillie to the bed. The wind had been non-existent, thankfully. It was dark enough to where Ursula's surveillance equipment was probably useless. "I can get that out of my mind then," he thought to himself, re-focusing on Lillie.

He laid her on the bed delicately. He stepped back and began getting un-dressed, the warm Alolan night kept him from any shivering.

"I don't know if I can get un-dressed with help..." Lillie said worriedly. "But I can lift my dress up..."

Jack shrugged, getting his arms out of the sleeves of his shirt, revealing his increasingly toned body to his companion. "Whatever works for you, my dear."

Jack then un-did his belt and dropped his slacks and underwear in one motion, then crawled onto the bed.

"I've wanted this for so long..." Lillie squeaked.

"So have I," Jack whispered back.

Jack then got on top of Lillie and began furiously kissing her. Lillie's body flailed underneath him, he figured it was her excitement getting the better of her. One of his hands found its way to her covered breast, and he felt her bra, but he massaged it carefully.

Lillie moaned with surprise and delight at the motion, and Jack's other hand slid closer and closer to Lillie's inner legs. Jack felt his erection springing to action, he hadn't gotten release since Zinnia attacked him after his workout. Once Jack reached Lillie's sweetness through her dress. He could tell she didn't have any panties on, and he began to caress around. Lillie began to shiver with desire, her legs flailed desperately.

"Jack... I need you..." Lillie begged.

Jack gave her one last kiss. "So do I."

Jack lifted Lillie's dress up and slowly lowered himself inside of Lillie. She was extraordinarily tight, as he knew she was a virgin at this point. He could barely fit half of his shaft inside of her, but what could fit felt divine as she was sopping wet.

"Finally..." Lillie gushed.

Jack began to to pump his manhood inside of her, slowly as he could hear a bit of pain in Lillie's moans. He felt himself go a bit too deep and Lillie's moans stopped abruptly. Jack froze, praying he hadn't hurt her. "Lillie, are you-"

"Mhmm," Lillie said, her mouth still closed. "It's okay Jack, Misty told me it would hurt a little the first time."

Jack smiled, unsure if she could see it. "Well, I want our first time to be as painless as it can be."

Lillie kissed him. "I know, I love you Jack..."

And so the delicate love-making continued. Jack was very careful as his pumps gradually turned into thrusts. He could feel himself getting deeper and deeper inside her, very slowly, but he managed to avoid another painful situation, or at least he figured since Lillie didn't yelp or freeze up. He caught himself by surprise when he felt his loins begin to boil up for an eruption.

"Lillie, I think I'm gonna cum soon..."

"Yes," Lillie moaned with delight. "Please..."

Jack's thrusts got a little faster so he didn't try to go as deep. It didn't take long. "Lillie, I'm-"Jack groaned with pleasure as he felt his seed firing into Lillie's pussy. His dick spasmed fiercely, he realized it had been almost twelve hours since he'd gotten release, a feat he hadn't accomplished since getting to Alola.

It took a full minute for his loins to simmer down, and he withdrew himself from Lillie. He wished there was more light so he could gaze into her eyes, so he settled for a kiss. "Lillie, I want to look into your eyes..." Jack whispered lowly.

"Well Jack, we did it here and... that's probably most of the bleeding I was going to do..."

The reason why the bed being set up in the dark now became clear to him. "You want to come to my bed?" Jack asked.

"More than anything..." Lillie cooed.

Jack left his clothes on the bed and led Lillie back up the stairs. He noticed the table had been cleared as if him and Lillie had never been there. Serena waited at the sliding glass door with a smile. "Round two for you too?" Serena asked.

Lillie nodded enthusiastically. "Yes, but can you help me with-"

"The dress," Serena finished with a laugh. "That's why I'm here."

Jack noticed a bit of a red stain on Lillie's dress, and tried to ignore it as he figured Lillie would feel a bit embarrassed about it. Serena got behind Lillie and began loosening the threads, until finally she could lift it off of Lillie.

Jack got to see Lillie's naked lower body for the first time. He noticed the bit of red around her legs. Lillie immediately moved to cover herself, but Jack just got behind her and emrbaced her. "It's perfect Lillie, it's all a part of you," he said, trying to comfort her.

Lillie relaxed in his arms. "Thank you Jack..."

Serena put the dress aside and came to un-clasp Lillie's bra. Once finished, Lillie's bra fell to the ground and Jack whirled Lillie around to get look at her huge, naked, tits for the first time. They were everything he'd imagined and more.

Lillie blushed, her nevers still bothering a bit, apparently.

"I finally get to look on all of you..." Jack said, moving in for another kiss.

Lillie giggled with glee. "Yes, finally..."

Serena caught Jack's eye as she did the lifting motion one more time out of sight of Lillie. Jack did as asked, sweeping the naked Lillie off her feet. Serena had already opened the sliding glass door. Jack noticed the trail of rose petals that led to his room. "You spoil me," Jack thought to himself, grateful to his brides.

He followed the rose petals to his room, which had dozens of candles littered around it, and rose petals on the bed. He placed Lillie on the bed and got on top of her, his erection raging once more. This time, Lillie grabbed him and tried to pull him onto her, legs spread for him.

Jack smiled in anticipation. "This is going to be a great night," he thought to himself.