Chapter 34 (Patreon)

The lights on the boardwalk to the restaurant lit up and illuminated the walkway. A gentle glow from several of the shops added to the serenity and atmosphere. The smell of the salt water, the reflection of the moon off the waves, and the colorful lights from the shops and decorations created an almost blissful experience. They passed couples sitting on benches enjoying the area but saw one woman practically storm off in a huff. It was a lovely little retreat where hearts could come together or fall apart by the looks of things. For Stewart and Victoria, it was beginning to feel more like the prior the longer they were here.

The restaurant they'd selected was a small bistro that catered to newlyweds and couples. The soft glow of the lights outside and the sound of pleasant chatter were inviting as they approached. Stewart had sat himself down on Victoria's palm midway through their little walk. The cool breeze from the restaurant interior washed over him as they walked in. The ambiance was obvious, but Stewart felt his nerves creeping up as they got closer. While he'd made decent impressions and amends with Victoria's family, he had yet to meet Rose. It was clear from how Victoria talked about her that she held a special place in her life. The last thing he wanted was to leave a bad taste in her mouth like he had with Chad.

They found their table towards the back of the humble establishment. A large round table with more chairs than necessary; the host must have figured their party wouldn't consist of three tinies. A lovely burgundy tablecloth was draped over it, and the centerpiece was a green vase filled with a lovely floral arrangement. Pam sat beside Anna, with Chad and Bram sitting on the table in front of them. Stewart looked at the two of them and was surprised at what they were wearing. Pam wore a black dress that was low cut and strapless to expose her toned arms. Her hair was down and lightly feathered to frame her face. Anna wore dark jeans and a red blouse that looked almost uncharacteristic. Her usual scowl was gone, and she looked almost happy as she listened to everyone talking. Her hair was tied back in a ponytail, but it looked natural on her.

Stewart looked over to see the woman he assumed was Rose recounting a story about a date she'd recently been on. He could see a bit of her age in her face, but it was difficult to believe she could be Victoria's grandmother. She wore a pair of black dress pants that were loose and flowy, and she had on a white blouse with short sleeves. Her hair was down, and while he could see some graying roots, it still had a sheen of brown to it. She looked sharp as she laughed with the rest of the table. Her eyes lit up as she spotted Victoria approaching the table.

"There she is!" Rose exclaimed as she got out of her chair and walked around to hug Victoria, "I was starting to wonder if you'd stood the rest of us up. Taking a page from my book by showing up fashionably late, Victoria?"

Victoria smiled and embraced her grandmother while trying to be mindful of Stewart's position, "I told Pam that I was going to be late, Gran. Did she not tell you?"

"I did," Pam said, "Rose has just been excited to see you."

"Almost as excited as I am to meet your new boyfriend," Rose added, pulling away and waiting, "Let's see him, then. Your father tells me that he was a bit of a pain for a while, but he's also said that the little boy has started to become a little man. I hope you've been coaching him without anything physical, Victoria."

"Mom!" Chad exclaimed from the table, choking on the bit of wine Pam had given him, "Please, do not make those insinuations while I'm around!"

"Chad, Victoria is a grown woman," Rose waved him off, "I'm sure she's no stranger to intimacy."

"That doesn't mean that I want to hear about it!" Chad frowned.

"Yeah, I'm not super into hearing about Victoria's sex life either," Anna shrugged.

Stewart was taken aback by how forward Rose was being. That was the last thing he'd expected to hear when he first met this woman. "He's been a gentleman since our first date, gran," Victoria cleared the air, "He's polite, sweet, funny, and charming all on his own."

"I'll be the judge of that," Rose smiled at her, "Come on, let's have a look at the little fellow."

Stewart braced himself for what was about to come. She might grab him, but he was around people that he could trust. Curt as Anna could be, Victoria had assured him that she was vigilant when it came to people his size. "Gran, this is Stewart," Victoria introduced him as she held her hand up.

Stewart stood up on Victoria's hand to wave at Rose for their first meeting. Her eyes locked on him, but it wasn't predatory and hungry as she studied him. She reached out to carefully take him, and Stewart was surprised at just how gentle she was with his little body. It was clear that she had experience handling tinies from Bram and Chad. Rose brought him closer to her face to get a better look at him, and Stewart also got a better glimpse at her. Her makeup was expertly applied, but he could see a few faint lines from her age behind the mask. Still, he wouldn't have guessed she was as old as she was, even from his height.

"Hello there, Stewart," Rose greeted him, bringing her finger close so he could shake it, "So, you're the little darling that's captured my granddaughter's heart."

"Gran," Victoria sighed, blushing, "He's just my boyfriend, that's all."

Stewart exhaled and tried to reign his nerves in as he shook Rose's finger, "I think that might be going a bit far, honestly. She's better than I deserve, ma'am, but it's nice to meet you."

"Suck-up," Anna rolled her eyes from the table.

"Now, now, there's nothing wrong with proper manners, Anna," Rose smirked at her, "He's just being polite, and I can tell he means that by his tone."

"How can you be so sure?" Anna asked, "Guys, lie, no offense to either of you."

"Used to it," Chad shook his head, but he smiled up at Anna, "I've been telling you that not every guy is a liar for weeks now."

"When you get to be my age, you learn a thing or two, Anna," Rose explained, cradling Stewart in her hand, "He's small, but I can see his body language from here. Nothing bad, my little dearie, but you're shifting nervously. He's nervous, but it's not because he's lying about anything. Victoria, what have you told him about me?"

Stewart wasn't quite sure how he felt about being analyzed in such a manner. She wasn't wrong, but this wasn't what he'd been expecting from what he'd heard about Rose. "Just how close you and I are, gran," Victoria said.

Rose smiled down at him, "You're worried that a bad impression might jeopardize your chances with my granddaughter, right?"

She wasn't wrong, but he hoped this wasn't a bad sign. "Uhm, y-yes, ma'am," Stewart admitted, not wanting to lie during his first meeting with Rose, "Victoria has told me that you're like her best friend, and I already got a pretty bad start with her. I'm lucky she was willing to give me a chance, and I don't want to do anything to screw that up."

"Honesty is a sign of growth, and it's a good way to measure a man, no matter the age," Rose chuckled, glancing at Anna, "There's nothing wrong with wanting to make an impact when meeting someone new. Let's have a seat, and you two can tell me about what you've been up to, how you got together, and more. Don't leave anything out; I want all the details."

Rose took a seat, still keeping Stewart in her hand, and Victoria sat beside her. Rose placed Stewart on the table between her and Victoria. Chad and Bram were on the opposite side, near Anna and Pam. The next fifteen minutes were spent looking over the menu, placing orders, and sharing stories about how Stewart and Victoria had gotten together. It wasn't easy hearing how uncomfortable and belligerent he'd been towards Victoria, but he reminded himself that was the past. Stewart knew he'd been as close to unbearable as one could be back then; Amber had made that painfully clear to him. Thankfully, Rose didn't seem to hold it against him. Of course, it helped that both Chad and Victoria were willing to vouch for the changes he'd been trying to embody since he'd shrunk.

Finally, they had come to the conclusion of their shared story, and Victoria finished by telling the rest of the table about their little shopping trip. She showed off the miniature bags she'd carried in, but the conversation slowly shifted to more casual topics. Stewart sat and listened to Rose and Victoria talk and catch up. Part of him had wanted to join Chad and Bram, but he couldn't bring himself to leave Victoria. Despite being left out of the bulk of the conversation, he was content to remain by her side. Listening to the two of them talk was like hearing sisters speaking rather than a grandmother and granddaughter. Rose was surprisingly up to date on most things and trends, and Victoria seemed to lose herself in talking with her grandmother. It was a nice sight to behold for Stewart.

Unfortunately, he'd neglected to take into consideration just how distracted his girlfriend could be. Stewart was also unaware that it was an apparently inherited trait from her beloved grandmother. The revelation came too late and in the form of a rather animated gesture from Rose. She'd been recounting a story of a date she'd been on recently, and in the process of showing the size of something, she'd accidentally swatted Stewart from his position on the table. Tumbling and rolling were the next two sensations he felt as he hurtled toward the table's edge. His hopes of being seen and saved were dashed as he reached the edge and began falling. He'd never get used to the feeling of being in free fall and he'd come to loathe it from his time at this size.

While it was never pleasant, Stewart had experienced it enough times to learn a thing or two. His life on the line, Stewart did his best to find something to glide towards and grab onto. The closest thing to him was Rose's pants. He grabbed two fistfuls of the material before he met an untimely end as a stain on the floor. He'd saved himself, but he was trapped just below the knee of a woman with no clue that he had gone missing. Worse, he doubted that either Chad or Bram had noticed his departure, given they were quite a ways away from where he'd been resting. This meant that Stewart was on his own and he'd have to find a way to scale Rose's pants to safety. However, he knew from experience that just reaching the chair didn't guarantee his safety. The danger wouldn't dissipate until he'd been found, and there was no telling how long that might take.

Dwelling and sulking wouldn't do him any good, and so Stewart decided to begin his climb. Sad as it was, Stewart had been in similar situations more than once. Perhaps the only upside was that it had given him a stronger resolve and ability to overcome these odds. Just as long as Rose didn't stand or move too much, he'd reach the summit sooner than later. Little by little, Stewart drew closer to level ground. Meanwhile, Rose remained engaged in her story above him. He'd never been more thankful to reach the chair seat as he had this evening as he rolled off Rose's thigh.

Stewart took a moment to catch his breath as he lay on the cushion of the chair between Rose's legs. Certainly not the most ideal spot for a first meeting, but at least he was alive. He'd need to figure out a way to get her attention if he were to be discovered. Climbing up her blouse didn't seem like a smart move, and Stewart's luck was bound to run out sooner rather than later. Tempting as it may have been to explore the titan above him, Stewart didn't like the idea of pushing past more boundaries than he already had. Still, he'd need to figure something out before too much time passed.

As Stewart weighed his options to find a solution, Rose felt the familiar call of nature tugging at her bladder. Entirely oblivious to the missing member of their dinner party, Rose stood up to excuse herself to the restroom as Anna and Victoria began talking. Unfortunately, this spelled trouble for the little man resting between her legs. She scooted forward just a hair, but it was enough to bring Stewart closer to her crotch than he'd been expecting. She stood up, and the simple action nearly knocked him back over the edge again. It was all he could do to grab onto the fabric of her pants yet again and hold on for dear life.

Stewart scrambled as fast as he could to find something akin to safety as Rose stood up. He was trapped on the inner thigh of her pant leg as she excused herself. He didn't have long before she'd be moving, and that would only make his new adventure more tedious and troublesome. He was granted a sliver of additional time when Pam asked a question, but he still didn't have long to figure something out. He climbed as quickly and carefully as he could, hoping desperately to make it somewhere closer to her waist. It wouldn't be the best place, but he'd have more of a chance of hanging on if he could at least make it there. At least, that was his hope in his mind.

Rose's pants were loose in the legs, so it meant he had more to grab. Regrettably, it also meant there was more swaying as she walked. The slight swing of her hips wasn't lost on him, and he realized this woman was open to showing off her figure to anyone willing to take a look. It may have been admirable given her age if it didn't mean that Stewart was in jeopardy of getting flung from his holding place. It seemed that luck was only getting worse, but against all odds, he managed to make it to his destination. His victory was short-lived, though, as Stewart was faced with a different dilemma. The spandex-like waistband left little room for him to grab, and he'd surely fall before long if it wasn't careful and quick.

With every step Rose took, Stewart came closer to taking a nasty spill. Two options lay before him from where he stood. One was trying to climb Rose's blouse, and the other was a small opening near her waistband. The latter was incredibly invasive, but the prior meant pushing his little body past its limits. He wasn't sure if he could make another climb, and the higher he went, the more dangerous things became. It went against all his decisions up to this point, but he made his choice as he weighed his possibilities. Shameful as it felt, Stewart caved to the potentially safer, albeit more perverse, option. He just hoped that it wouldn't end terribly for him.

While he knew it wasn't the gentlemanly thing to do, he didn't see another way to save himself. He just hoped that he could avoid anything to make his predicament any worse than it already was. He hoped he could catch himself on Rose's panties before falling too deep into the abyss. Stewart tried to push himself down and nestle himself in the band, but Rose turned a corner and caused a shift in his trajectory. The sudden turn of events caused him to miss his mark entirely, and Stewart suddenly found himself falling and sliding against the more intimate sides of Rose's hips. He needed to do something quick lest he wind up falling through.

It was dark, but Stewart rolled the dice and threw himself to the side. Whichever way he went, he'd be faced with different perils. Either he'd be closer to Rose's titanic ass, or he'd come face to face with her mature flower. Whichever way, he'd be getting closer to Rose than he could have ever hoped. His luck continued in its spiral as he found his body smacking against two large, meaty spheres. Of course, it was the ass. It was always the ass with him. Time and again, Stewart found himself getting acquainted with the backsides of the women in his life. Bernie, Amber, Victoria, why would Rose be any different?

Rose's cheeks were firmer than any he'd dealt with before. Stewart was used to cheeks having a bit more give and spring, and while Rose's were still soft, he could feel the definition with every step she took. Each step caused his body to shift and twist as her butt worked as she walked. Slowly, dreadfully, Stewart was being dragged closer to the canyon that was Rose's crack. It was agonizing knowing what was coming and where he was going, but it was made worse by the fact that there was nothing he could do to stop it. Fighting and struggling would only exhaust his energy, and Stewart knew he'd need to save it for his final destination. Stewart could only sit back and ride the waves inevitably as they unfolded.

The ride was over before he knew it, and Stewart knew he was close to Rose's backside's entrance by the scent flooding his senses. The smell of sweat and the shamefully familiar earthy odor of ass was something that Stewart had learned all too well. The jostling and bouncing from Rose's steps were still present, but Stewart found himself sitting on the underside of the backside of her panties. Her steps threatened to push him into the abyssal canyon before him, and Stewart was facing down the darkness in front of him. Too close, and Stewart could find himself getting pulled into the depths of that foul canyon. Caution was key to his survival here, but momentum was working against him.

How far was the damn bathroom from the table? Stewart asked himself this question repeatedly as Rose's steps began pulling him closer to her crack. Planting his feet did nothing to stop the pull, so he tried to push against the walls of flesh, quickly closing in. While Rose hadn't worked up any sort of tremendous sweat, there was a slight sheen from how long she'd been sitting at the table. This meant that Stewart didn't have a way to catch himself. He was drawing closer to getting a first-hand look at the inside of Rose's crack. This wasn't what he wanted and wasn't how he envisioned this evening. Devoured by the hungry ass of his date's grandmother, it was something out of one of the many stories he'd read online.

The powerful odor grew stronger as Stewart was on the verge of getting sucked into the depths of Rose's ass. He needed to get out of this before things escalated further. Stewart's face was pressed into the fleshy expanse as he tried to stop himself. Rose's panties were beginning to ride upwards, and that meant his attempts to save himself were once again thwarted by fate. Pushing with his arms and his legs as best he could, Stewart tried to slow his entry. Things took another undesirable turn as Rose's cheeks clenched a bit because of a sudden stop. The force was enough to break his concentration and leave him disoriented. His attempts at saving himself were shattered, and he was left seeing stars as he was sandwiched between her cheeks. It was clear just how much time she put into her physique from the strength these two spheres carried.

In his daze, Stewart lost another few inches in the battle against Rose's ass. He was driven further in, and the walls of her butt surrounded him. Thankfully, she didn't seem to have had gas or anything too foul to muddle and assault his senses, but the scent of an ass was still powerful. Sweat and earthy tones pervaded his prison, and Stewart resisted the urge to gag. Doing so would only further his progression into this expedition, bringing him closer to her brown eye. A thought occurred to him that rattled him to his core. As small as he was, there was the chance that her asshole could envelop and devour him, not unlike her crack already was. Of all the ways to go, this had to be one of the worst he'd ever imagined. Sucked in and eaten by the asshole of an unaware woman, it was equally degrading and terrifying to consider. Alas, it was sadly a terrible real possibility for him.

His panic levels were reaching new highs at this thought. While maybe not the worst way to exit the world, it was certainly up there. Struggling and squirming, Stewart tried to wrestle his way out of the chokehold that Rose's monumental ass had on him. This couldn't be how he met his end; it couldn't! He'd only just started to make progress with Victoria and her family, and he couldn't see himself giving that up so easily. It wasn't fair, but his struggles only earned him deeper entry into the confines of the canyon, threatening to swallow him whole. No matter what he did, it seemed fate intended to make this ass his tomb. His body was getting exhausted, and soon, he'd have nothing left to give.

As Stewart became more and more sure of his imminent demise, his luck seemed to finally take a positive turn. He'd given up on slowing his entrance by pushing against the fleshy walls and resorted to gripping tightly at Rose's panties. It wasn't much, but the satin material was all he had. Light flooded his tomb, and a wave of vertigo crashed over him as Rose pulled her bottoms down. As a result, he was pulled free from her backside and left staring up at her as she sat on the toilet. It was probably not the best view of a woman he'd only met, but it was a relief to know her ass wouldn't eat him. The fluorescent lights were blinding, but they were a welcomed sight compared to the smelly darkness he'd been enduring.

Now, Stewart was faced with another choice. He could stay where he was and hope to be seen or try his luck on the bathroom floors. The latter was fraught with perils and dangers, but he'd be safe from an unwitting end. However, staying put meant he'd potentially be driven face-first back into the abyss sooner than later. Neither option seemed to be ideal, but they were the only choices he had. A decision had to be made, and he knew he didn't have much time.

Rose had felt something irritating her backside as she walked to the bathroom. It had been difficult to stop and flirt because of it, and she had every intention of investigating the source now that she was in private. It was like an itch that she couldn't scratch, and no proper lady would have dared do so in public. The feeling went away once she sat down to relieve herself, so she assumed that maybe it was something in her panties causing the problem. She glanced down as she wiped herself and spotted something moving in her panties near the backside. That was odd. Had a bug gotten in her underwear?

Stewart had decided to try his luck at getting back to Victoria on foot. The thought of being swallowed by an asshole was far from the top of his list of wants, and the risk was too great. He'd been moving towards the edge as best he could when he was suddenly grabbed. He panicked a bit at first but managed to calm himself as he realized he'd been discovered. That was a small relief, but now he'd have to explain himself. Hopefully, this wouldn't demolish any goodwill he'd earned with Rose thus far.

"Well, what do we have here?" Rose asked as she brought Stewart up to her face, "Seems I've got a little stowaway in the form of Victoria's boyfriend. Care to explain just what you're doing in my panties, young man?"

Stewart hated the fact that he couldn't read her tone almost as much as the situation he'd found himself in. All he could do was tell the truth and hope that she believed him. So, Stewart quickly explained everything that had transpired. It had only been a short while, but it had felt like an eternity to him. He told Rose about how he'd been knocked off the table, his climb to save himself, and his unfortunate excursion into her pants. He was careful to emphasize the fact that he'd merely been trying to save himself from meeting an untimely end. All the while, Rose sat and listened without saying a word.

"So, that's what happened," he finished, "I was going to try to make my way out of here and back to the table before you found me. Honestly, I was just trying to save myself, I swear."

Rose was quiet for a moment before smiling at him, "I believe you, Stewart."

"Y-you do?" Stewart asked, quickly adding, "That's great, but my sister would be skeptical."

"Like I told Anna, I've learned a thing or two at my age about reading people," Rose replied, setting him down on the toilet paper dispenser as she stood up to pull her bottoms back on, "My son and grandson have also been this size for some time now, and they tend to get themselves into trouble more often than not. You're lucky that I felt you, dear, and you're lucky it was me and not Anna."

Stewart's face paled at the idea of being caught by the fiery teen in such a predicament. "You're not gonna tell her, are you?" he asked, genuinely afraid of what she might say.

"I'll have to tell them something, but we don't need to share all the details," Rose assured him, grabbing him carefully and exiting the stall, "Some things are better left unsaid, but what a way to meet someone for the first time. Tell me, did you enjoy the ride, little man?"

The relief he felt from her assurance was replaced by a sudden discomfort at her last question. There was a playfulness to her tone, but there was also a hint of curiosity that wasn't lost on him. "Truthfully, not particularly," he answered, "It was scary, to put it lightly."

"Hmm, I suppose that makes sense," Rose shrugged as she walked over to the sink, "I had a date with a little man who begged me to let him sleep in my ass a month ago. He was a strange little fellow, but he was sweet enough. We didn't see each other again afterward, but I've been curious if more men are interested in things like this. It seems that some guys have been enjoying their new lives more than others."

The thought that someone could actually enjoy what he'd just gone through was strange to him, but he'd read enough to know that the world was becoming more and more unusual by the day. "It's not for me," he finally said as Rose finished washing her hands, "I just want to live and maybe one day get back to living a normal life that doesn't involve threats of getting crushed and smothered."

"Let's hope that one day that can happen," she said, "Come on, let's get you cleaned up before we rejoin everyone."

"Yes, ma'am, thank you," Stewart smiled at her as he undressed.

Rose was delicate and gentle as she washed him under the sink. She made sure that the water was warm before giving him a small shower. His clothes were stained with sweat, but that would be a story for another time. He was confident that she'd have a story in mind to cover his nudity, and Victoria had a change of clothes for him. They left the bathroom and made their way back to the table. The scene they walked into was one of confusion as Victoria, Anna, and Pam were searching for Stewart. The food had arrived, but nobody had touched it. Apparently, Victoria had noticed the absence of her boyfriend while they were away.

Stewart felt a swell of joy as Victoria took him from Rose and held him close. She gave him another kiss and smiled as she lovingly rubbed his back. Rose explained the situation as best she could, taking responsibility for his dangerous adventure. Rather than tell them where he'd wound up, she lied and mentioned that he'd wound up in her flats. It seemed to be a plausible scenario that both Chad and Bram had been in before. It explained the absence of his clothes, and nobody seemed to question the story's validity. It meant his integrity was safe, and Victoria was blissfully unaware of where he'd been.

Stewart was given a change of clothes and stayed close to Victoria throughout dinner. They ate and talked about his unfortunate outing which slowly faded to the back of his mind. It had been an eventful day, and it was only their first one here. There was no telling what sort of hijinks awaited them at the wedding and the parties around the corner, but it was already shaping up to be a rather eventful weekend for all of them. Stewart was just glad that he'd managed to survive his ordeal and that he'd kept his standing with Rose and the rest of the family intact. Things had nearly ended poorly for him, but he'd come out relatively unscathed for the most part. Now, he just had to see what awaited the next few days. He recalls something about... a bachelor party?