A Sizey Winter Road Trip by PleaseStepOnMeDamnit
Summary: Winter break has arrived, and the city of Chicago is blanketed in thick snow. While some choose to enjoy the winter wonderland, others spend their time dreaming of a warm beachside. At the behest of the excitable Ashley, her boyfriend Jackson and her friend Laura decide to spend their week off of college by taking a road trip down to Florida. However, a mishap with the transportation leaves Jackson experiencing the journey in a whole new way.
Categories: Odor, Breasts, Adventure, Butt, Body Exploration, Young Adult 20-29, Entrapment, Feet, Footwear, Gentle, Insertion, Mouth Play, Legwear Characters: None
Growth: None
Shrink: Minikin (3 in. to 1 in.)
Size Roles: FF/m
Warnings: Following story may contain inappropriate material for certain audiences
Challenges: None
Series: None
Chapters: 4 Completed: No Word count: 6177 Read: 26522 Published: June 09 2022 Updated: August 27 2022
Story Notes:

DISCLAIMER: This is a work of fiction. Names, characters, places and incidents either are products of the author’s imagination or are used fictitiously. Any resemblance to actual events or locales or persons, living or dead, is entirely coincidental.

Any and all recognizable properties mentioned belong to their respective owners, All Rights Reserved.

Copyright. PleaseStepOnMeDamnit, 2022

1. Merge onto I-90 by PleaseStepOnMeDamnit

2. Keep left to stay on I-90E by PleaseStepOnMeDamnit

3. Take Exit 17 to merge onto I-65 by PleaseStepOnMeDamnit

4. Merge left onto I-24E by PleaseStepOnMeDamnit

Merge onto I-90 by PleaseStepOnMeDamnit
Author's Notes:
It's a little short but it's just the first chapter. I hope to make a great story for everyone to enjoy! Minimal sizey stuff in this one admittedly, but it will come.

              *BZZT BZZT BZZT*


              Jackson groaned as his alarm signaled the start of a new day. His eyes burned against the bright sun as streaks of light filtered into his bedroom. As he began to sit up, his phone joined the alarm’s buzzing. Silencing his alarm, he reached for his phone.

              “Where are you?”
              “I just woke up…” he groaned, struggling to identify the caller.

              “Look, Ash and I are gonna get there in 30 minutes, get your shit packed and get ready to go!”

              “Sure thing, Lauren, I’m just getting up.”

              Shooting to his feet, Jackson scurried to his bathroom, freshened up, and ran back to his room to begin packing his bags. Flicking on the radio, he let the morning news fade away into the background as he sorted his belongings. Looking out the window at the snow-covered Chicago skyline, he groaned.

              “At least it’ll be warm in Florida.”

              Thirty minutes later, he sighed as the last bag zipped clothes. Turning his gaze back outside, he involuntarily shivered as snow began to fall from the sky. He sighed as the radio rambled about an incoming blizzard. Despite his inhibitions about Ashley’s sudden trip suggestion, he at least appreciated the opportunity to escape the frigid Chicago winter for a week.

              Throwing his stuff into his suitcase, he lugged his bag to the door. Just as he set it down to take a breath, the doorbell rang. Dropping his stuff, he rushed to open the door, and was greeted with a blast of cold air and his two friends, bundled in boots and coats, standing in front of him.

              “Heya Jack! Mind if we step in for a bit! It’s cooold outside.”

              Jackson stepped aside and allowed the two girls to scrape their shoes off on the mat before stepping inside.

              “Alright, I got my duffel bag, my suitcase, Lauren, Ashley, everything appears to be in order. Make sure there’s enough room for me and my stuff in the back of the car!”

              “Actually… that’s what we came in to discuss. I know your car is in the shop and it turns out that Ashley’s sister is borrowing hers so we’re kinda stuck with mine. We have more than enough room for the bags and everything, however it may or may not be… a coupe. I only have two seats.”
              Jackson stared at the bundled-up tomboy in front of him. “You’re kidding me. Why didn’t you call me earlier? We could’ve made alternate plans, rented a car or something. Hang on, let me see if we can scramble an emergency rental.”

              Ashley placed her hand on his wrist. “Look, we already checked, everyone is either sold out or too expensive to even be worth it. The coupe will have to do.”

              Gobsmakced, Jackson stared at Ashley. “What? How the hell are we going to be able to all cram into a 2-seater safely? We just can’t… We’ll have to-”

              Ashley’s face formed into a smug smile. “Well… There is a way. You remember my shrinking powers right? Well… on the way here, Lauren and I were talking… and we think we came up with a solution to the problem. What if we shrunk you and just carried you with us in the car? It would solve the issue, you would be able to stretch and move around, we could store you easily. C’mon! I know you like it.”

              Jackson stared blankly. “What?”

              “It’s simple, I shrink you, we find a comfy place for you, we get three people in a 2-seater, we have one less person eating snacks, or well, eating a full-size people portion. It’ll be great.” Ashley’s eyes beamed with pride as she spoke.

              Jackson simply nodded.


              Ashley closed her eyes and focused, holding her hands out towards Jackson. He sighed as the familiar feeling washed over him. Within a few seconds, he found himself eye-level with the tip of her boot. He craned his neck back to look at his girlfriend’s gigantic smug grin. He staggered for a moment as she slid her boot forward, shoving the dirty, wet, black wall in front of his body.

              “Kiss it!”

              Her sadistic glare quickly melted into a goofy grin. “Just messing with ya! You can if you want, I don’t care either way.”
              With a smirk, he planted a kiss on the tip of the boot.


              Ashley gently bent over to pick up her friend. Carefully grasping the miniscule form between her fingers, she lifted him up to her face.

              Meanwhile, Jackson’s world was cast in shadow as her enormous hand descended from above and gently wrapped around his tiny body.

              “There we go, nicely shrunken. You made sure get everything done before we left, right?”

              Jackson nodded, prompting an enthusiastic thumbs-up.

              “Alright, let’s get a move on!”

              Ashley tucked Jackson into a pocket before picking up his luggage. The two girls strolled out the door, locking his apartment behind them. Shielding their faces from the biting cold and wind, they quickly scrambled to the waiting car. Lauren unlocked the trunk, allowing Ashley to toss the suitcases into the back and dive into the passenger seat.

              Closing the door, Ashley briskly rubbed her hands together to warm up. Removing her hat, she flicked on the heater in an attempt to warm up the frigid car. Removing Jackson from her pocket, she inquired.

              “Ready to go?”

              The tiny gave a cheerful thumbs-up.

              “Let’s hit the road then!” Lauren cheered.

              Turning the key, the engine roared to life as Lauren pulled out of the apartment parking lot, officially starting the first leg of their trip.

Keep left to stay on I-90E by PleaseStepOnMeDamnit
Author's Notes:

I'd like to give thanks to Felwinter2187 on Deviantart for providing a second set of eyes to make sure the story came out well. Please go show her tons of love, she's very sweet and an amazing writer.


In other news, this chapter is a lot longer than the first and I feel it's a lot better. I hope you enjoy!

              The defroster roared to life and the fog on the windows faded away as the temperature in the frigid cabin slowly began to rise. Jackson curled up in the pocket, trying to conserve his body heat. As Lauren merged into traffic, she said, “Check on your little boyfriend, make sure he isn’t freezing. I’m pretty sure it’s not safe for tiny people to get so cold. Their bodies can’t regulate their heat well enough to keep up.


              Nodding, Ashley dug into her pocket, searching for her shrunken boyfriend. She hesitated for a moment as a tiny cold hand brushed against her finger, only for her to reach around the two-inch tiny and fish him out into the chilly cabin.


              For a moment, Jackson surveyed where he was. With Ashley’s fingers firmly secured around his waist, he was able to get a good view of the car’s interior. Mercifully, he knew Lauren to be a clean girl, and her car was just as tidy as he had hoped. Cream leather adorned virtually every surface of the vehicle, save for the shiny metal trimming along the dashboard and center console. Lauren pushed a few buttons on the infotainment screen, and slow jazz began to emanate from the car’s speaker.


              “Aww, I wanted to listen to rock!”


              “You’ll get your chance in a few hours, besides, it’s just before rush hour and everything is just so still. I feel like the jazz pairs well with the snow.”


              Ashley gave an exaggerated pout as Lauren changed lanes towards the highway.


              Jackson shivered between her fingers. Ashley brought him closer to her shiny pink lips, which opened to reveal the cavern of her mouth. Saliva dripped from the massive white teeth and across every surface of the pink maw. Instantly, he was blasted with a wall of warm mint as the aura of her gargantuan mouth washed over him. Jackson stared in awe at the living cave before him. Ashley’s lips began to purse as a gale-force wall of wind and drops of hot saliva washed over his body. His clothes and hair flapped and fluttered as Hurricane Ashley assaulted him with her hot breath. His chill melted away as her breath warmed his tiny body. As the winds subsided, Ashley smiled.


              “Feel better lil’ guy?”


              With a sigh, Jackson replied. “Yeah, feels much better. Like I can actually exist out here with you guys without freezing to death.”


              Ashely pressed the shrunken Jackson against her lips, mashing him against the moist, pillowy surface. “Mwah! Little cutie!”


              Deftly wiping him off with a spare napkin, she set him down on her plush thigh to rest. For a moment, the low rumble of the engine and the melody of Lauren’s jazz music was the only sound in the car as the three sat silent while the car continued to barrel down the highway.


              “Say, what’s for breakfast?”


              Ashley’s icebreaking question was punctuated by an unearthly growl. Jackson covered his ears as her stomach made its desires known.


              “Hang on, let me search for a place.”


              Ashley’s pulled her phone from her pocket, momentarily destabilizing Jackson as she reached for it. Unlocking it, her fingers danced across the screen as she searched for a restaurant. With a cheerful hum, she excitedly showed her find to Lauren. After receiving a nod from her, she turned her phone towards the tiny guy on her leg. Jackson squinted slightly as he stared up at the massive screen above him.


              “How does this place seem? Sound like somewhere you’d like to eat?”


              Staring at the images of the rustic diner on her phone. Jackson returned an enthusiastic thumbs-up.


              Beaming with pride, Ashley cheered, “I always find the best restaurants.”


              Placing the phone in Lauren’s phone holder, Ashley switched to the GPS and leaned back in her seat. While glancing down, she gently stroked the little tiny on her thigh. Her large fingertip effortlessly held him down with gentle force and rubbed along his body, the whorls and spirals of her finger easily obliterating any itch or ache in his back. Overcome by relaxation, Jackson instinctively let out a moan. He immediately caught himself and looked up only to be met with Ashley’s sadistic grin.


              “Was my massage that arousing? Did you like my finger poking you that much? What a horny little tiny.”


              She gently pressed his head into her pillowy thigh with the tip of her finger, smothering him in yoga-pant-clad thigh flesh. She held him there for only a moment, gently teasing him, before returning to massage his back.


              “Well, if you like it so much, guess I should keep going.”


              Ashley’s finger returned to her massage.


              Turning into the exit ramp for the restaurant, Lauren looked over at Ashley’s thigh, before speaking, “Hey, Ash, when we trade off, I’m good to mess with him too, right? Like, you won’t get mad if I play around with him as well.”


              “No problem from me! As long as you don’t hurt him, you’re free to mess with the little cutie as much as you like!” Ashley punctuated her words by jamming her finger into his back, eliciting a series of pops followed by another moan from Jackson.


              “Did… did you just crack his back?”


              Jackson gave a weary thumbs-up. “Yep, it feels amazing. You should do this to more people Ash.”


              The three laughed together as Lauren began to slow down, exiting the highway and turning onto the surface road. Ashley reclaimed her phone as Lauren turned off the road into the diner’s parking lot.


              “Alright, now how are we going to do this. Do we want to leave Jackson small or unshrink him? If he stays small, we’ll have to hide him the entire time in the restaurant, but if we unshrink him, we’ll have to find somewhere private to do it. Thankfully the restaurant is quiet right now but still, we don’t know where the cameras are.”

              Lauren chimed in, “I think in the interest of security, we should keep him small. Plus, it’ll save us money since he can just eat off of one of our plates.” Jackson gave a thumbs-up to her suggestion.


              “Alright, it’s settled. Jack, where do you want to ride? I’m more than happy to hide you wherever you desire.”


              Jackson replied, “Could you put me in your bra? It would keep me warm while we go outside.”


              Ashley returned a cheeky smile. “Sure thing, bug.”


              Taking the tiny into her fingers, Ashley pulled her top and bra opened and lowered Jackson in. A wall of warmth slammed him as her body began to vent heat through the opening. The air became humid the closer he got. As she lowered him further, the lights of the outside world began to dim as he descended deep into the cave. To his chagrin, Ashley had forgotten to shower, and her body smelled of old sweat. Then she let go. Instantly, he tumbled down into the depths, bouncing between her soft flesh and the thick clothing that covered it. Each impact left him lightly dusted in her warm sweat as he eventually skidded to a halt in the middle of a large cloth bowl. In the dim light, he could sense the presence of a massive presence before him. The thin window to the outside world high above him provided a view of the massive woman’s friendly wave as the opening began to close.


              With a slight snap, Ashley let go of her clothing, allowing her bra to rest snugly against her breasts. Straightening herself, she opened the door and stepped out into the cold. As she exited, the wind increased, buffeting her with an icy blast of thick snowfall. After briefly looking into the dark, turbulent skies, she and Lauren darted inside.


              Inside Ashley’s bra, Jackson was mercifully spared the cruel blizzard. As she closed her bra, he found himself pressed into a soft wall. Despite the omnipresent smell of sweat, and the quickly dampening surface as Ashley began to sweat in the thick clothing, he quickly found himself comfortable pressed into her boob. However, as she sprinted to the entrance, his girlfriend’s large breasts began to violently jiggle, tossing him around with them as her sweat adhered him to the hot flesh.


              To the delight of the two girls, the restaurant was virtually empty. A single man sat in the corner, hurriedly reaching for his wallet as he perused his bill for breakfast. Lauren sighed in relief as an older woman approached the two.


              “Two in your party?”


              Ashley nodded and the two were led to a small booth by a window in the back corner of the restaurant. Settling into place, the two watched as the waitress set down the menus and walked away. As soon as she disappeared into the kitchen, Ashley reached down into her shirt.


              Buried deep inside the bra, Jackson felt the world shift as his girlfriend dug for him in her bra. Two massive objects wrapped around his tiny body and gently peeled him off her sweaty breast and into the light. The sweat chilled his body as Jackson re-entered the normal world, freshly freed from his girlfriend’s ample chest.


              “Did you like my breasts?” Ashley cheerfully smiled down on her boyfriend.


              “It was tight, but comfortable. I guess I wouldn’t mind being back there.”


              “So you liked my tits, eh? Don’t worry, you’ll get plenty more times to hang out with them.” Ashley punctuated her words with a flash of smugness before opening her menu. “So what do you want?”


              After perusing the menu for a moment, Ashley’s eyes settled on a bacon and sausage omelet. Out of the corner of her eye, Lauren spotted their waitress exiting the kitchen, with two glasses of water in hand. Without a word, she reached over and snatched up Jackson, shoving him between her thighs to hide him.


              In a blur, Jackson went from being on the table to being whisked through the air by fingers from behind. When he came to, he found himself between two dark blue walls. His hand sank into the walls as he tried to climb out of the crevice he was stuck in. The air was thick with heat and a strange smell as he emerged out the top to find himself wedged between Lauren’s thighs beneath the table. Looking around, he saw Ashley’s legs excitedly bouncing under the table as well as the waitress’s frock. As he turned to face his captress, he found himself less than an inch away from her crotch, which radiated heat over his tiny form. Immediately he turned away from the area, blushing madly. Thankfully, he was not trapped between her thighs for long, as the waitress began to walk away, and Lauren reached down to grab him and place him on the table.


              “I’m so sorry about that by the way. I just panicked and shoved you in there.” Lauren looked down on the tiny guy worriedly.


              “It’s ok…” Jackson blushed as he tried to repress the memory of being so close to her crotch.


              Ashley smirked down on him. “What, too close for comfort to her crotch? You know, you’re only one question away from spending time in my panties. Say the word and I’ll do it. Up to you!”


              “I’ll think about it. In the meantime, can I get some of that water?”

              Ashley picked up a spoon before sinking it into her water cup. It emerged with a small puddle inside, which she held up to Jackson. He eagerly drank up as much of the ice-cold water has he could, leaving little more than a slight dent in the water level of the spoon. Ashley then held the spoon up to her own mouth before effortlessly sucking up its content.


              “That spoon looked like it was enough to fill a bathtub for you, but it was just a spoonful for us.” The two girls laughed heartily at Lauren’s observation.


              After several minutes of waiting and idle chatter, Jackson ducked for cover as the waitress returned with two plates and cups of coffee. He stumbled as the plates impacted the table, only for Ashley to brush him out of view once more. The two thanked the waitress as she left.


              Jackson emerged from behind the table sign to come face to face with a giant plate. Climbing up, he stood before an omelet the size of a small house, with Ashley’s massive knife and fork deftly carving out a chunk. He watched in stunned silence as the massive piece of food ascended towards Ashley’s enormous mouth. Her teeth made short work of anything unfortunate enough to be caught on the fork, and anything in the omelet was instantly obliterated into mush by the shiny white pillar. A chill ran down his spine as he watched her unconscious show of power, a simple activity to her but a potential danger to him. As he walked along the rim of the plate, he tripped on a piece of hashbrown and fell down on top of the omelet. As he rushed to scramble off of the steaming surface, a metal spike suddenly hooked his pant leg and pushed it into the egg. Looking up, he saw a fork pinning him down, and a knife carving out the piece he was on. In desperation, he screamed for help, but Ashley had stopped paying attention, instead chatting to Lauren about an upcoming movie. The world rushed upwards as the fork elevated the piece towards her enormous mouth.


              Once again, Jackson found himself staring into the cavern of his godlike girlfriend, her teeth once again glistening in anticipation for the next morsal. Her first bite sliced though the omlete slice like a guillotine, and quickly mulched it into a slurry. As she swallowed the chewed food, she opened her mouth for another bite. His screams fell on deaf ears as the morsel passed between her lips. As her mouth closed behind her, the fork removed itself from the bite, granting Jackson his freedom. His minor victory was quickly overtaken as she began to chew. Instantly, her mouth became the site of a raging storm, as food chunks flew every which way as she chewed. Her hot mouth filled with saliva, drenching him in chewed food and Ashley spit. Out of desperation, he made his way under her enormous tongue, just in time as she swallowed, sucking everything above him down her throat. Frustrated, angry and scared, he staggered to his feet in the muggy, sweltering omelet scented cavern and kicked her gumline as hard as possible. Ashley winced for a moment before her mouth reopened, flooding light into the cave. She reached in and grabbed a hold of the offending object before pausing.


              When Jackson re-emerged into the light of day, soaked in saliva and chewed up piece of food, Ashley was on the brink of tears. Panicking, she bolted to her feet and rushed to the tiny bathroom, locking the door behind her. She turned on the water and began scrubbing the battered tiny with tears streaming down her face and a torrent of babbled apologies pouring from her mouth. When the torrent subsided, Jackson looked up at his girlfriend’s pained face, her cheeks turned a glistening scarlet, soaked with her frantic tears.


              “Please…” she stuttered out, just barely maintaining her fragile composure, “Don’t hate me, please, I’m so sorry I didn’t see you, I didn’t notice anything, I could’ve killed y-”


              “Ashely stop!” Jackson shouted, mustering as much project as his tiny body could produce. “Calm down, I’m still alive, you didn’t kill me. It’s ok, you can calm down now.”


              The massive girl looked back at her sopping wet boyfriend on the counter. With a sniffle, she dried her tears and composed herself.


              “Wash your face off Ash, it’ll be alright. I’m fine, no injuries, I’m just a little shook, that’s all.”


              He moved to the side as she leaned over the sink and splashed cold water over her face, soaking him in another blast of water. Once she had suitably scrubbed away her tears, she straightened herself, and held Jackson under the dryer. The hot gale that blasted from the vent quickly dried off his soaking clothes, even down to his underwear and socks. Concealing Jackson in her fist, she took a deep breath, driving out the last of her worry, and returned to her concerned friend.

Take Exit 17 to merge onto I-65 by PleaseStepOnMeDamnit
Author's Notes:

Another short one, but it ended nicely where it did.

             Lauren looked at her friend with a worried expression. Surprised at her friend’s sudden panic, she almost went to the bathroom to check, when she returned with puffy, scarlet eyes.


              “Ash… are you ok?”

              Ashley sat quietly before Jackson spoke up. “She accidently almost ate me. It’s ok though, I’m alive.”


              Ashley mumbled quietly before speaking, “No… Look, to make up for it, I’ll let you do whatever you want to me. I can’t just get away without giving you something in apology. Whatever you want, time in my panties, in my bra again, say the word and I’ll place you there for as long as you want.


              Jackson pondered for a moment as the girls continued to munch on their breakfast. Taking a shard of bacon into his hand, he replied.


              “Well, I guess… maybe some time in your shoe might be fun.”


              Ashley looked down nervously. “A-are you sure? My feet get quite smelly and dirty, plus, I walk quite hard on my feet. I could crush you and not even know it!”


              “You won’t be walking on me for much, I just want to cuddle your feet. You like shoving your feet in my face enough, so I think we’ll both have fun.


              “Fine, you can sit in my boot for a while. After we get in the car.”


              The three continued to eat their breakfast. Ashley placed bits of her food on a napkin for Jackson to eat. Eventually, the tension broke, and the group resumed their normal cheerful chatter. Jackson finished what he could before hiding as the waitress presented the bill to the girls. Ashley handed over her card with a smile. As the waitress walked away, card in hand, Jackson peeked out from behind the display.


              “Is it time for me to be placed?”


              “I guess so, let’s make this quick before she gets back. Wedge yourself between my toes so I don’t crush you by mistake.”

              Her words sent a slight chill down his spine as she removed her boot. Gently taking Jackson in her hand, she lowered him towards the dark cave. As she lowered him in, a wall of heat and humidity slammed him. Looking back, he saw her bus-sized foot eagerly wiggling its toes. Nearing the bottom of her boot, her fingers suddenly released, sending him plummeting into the cavern. He landed on her sweat-soaked insole with a damp splat. As he came to, he suddenly became more aware of the powerful stench of her foot. Every surface reeked of old sweat, and Jackson coughed slightly in the musty, stale air. Suddenly, a voice from above boomed down.

              “Hey, start running, I’m going to put my foot in.”


              The cave rustled and shuddered as a massive, dark mass entered through the top shaft. The light went from minimal to nearly dark as her foot slid in. Instinctively, Jackson began to run, rushing to the toe of her boot with the foot hot on her tail. Turning around, he pressed himself against the front wall as a toe larger than him settled less than an inch from his tiny body.

              “Now climb between my toes!”


              Scrambling in the darkness, Jackson reached around the massive toes until he nestled himself into a crevice. The sweat smell reached its peak between her toes, and the skin around him was cold and damp. Her toes gently gripped onto him as she stood, shifting her weight. Outside, the two girls gathered their things and returned to the car. Inside the boot, Jackson was violently tossed around with each step, leaving him clinging to her toe to avoid falling beneath her feet. As she walked towards the exit, a loud crunch echoed through the cavern as an object that was caught in Ashley’s path crushed beneath her boot. Another chill greeted Jackson as he realized that Ashley was completely unaware and didn’t even pause at the crunch underfoot.


              The two quickly returned to Lauren’s car, jostling Jackson around even more. As the two dived in, Jackson lost his grip and bounced of the ceiling of her shoe. Above, Ashley slid into her seat and buckled in, granting the weary Jackson a bit of respite. From there, it was smooth sailing. Inside the shoe, Jackson was already getting used being inside. The stench that left him reeling now suddenly became highly pleasant, and Ashley’s warm foot was more than willing to supply more. Her foot was like a furnace, emitting a powerful heat, which the thick winter boot radiated inside the space. Wiping sweat from his brow, he nestled between her toes as his phone buzzed.


              “How are you holding up?” Ashley’s text read.


              “It’s alright, quite hot in here though and I don’t have any water, so I’m a bit worried about that, but it’s ok. Smells lovely in here.”


              A soft giggle resonated from outside the boot. “Water? Look around, there’s plenty of water!” A soft toe wiggle accentuated her playful comment, rubbing a bit of sweat across his body. With a sigh, Jackson stooped over and licked one of her toes, filling his mouth with the salty liquid. Satisfied with his hydration, Jackson leaned back between the soft toes. Lazily, he typed out a text to Ashley.


              “Can’t really see anything in here, to be honest. It’s pitch black in here without my light.”


              “Just think of it as one of those sensory deprivation chamber things, just with my feet.”


              “Don’t think those smell like sweat, and aren’t they supposed to be super quiet?”


              The toes Jackson was nestled between suddenly clamped down, squeezing him tightly.

              “Quit texting me, focus on enjoying my feet instead.”


              Jackson put his phone to sleep with a soft click and closed his eyes, savoring the dark, murky cavern as much as he could. With not much else to do, he found himself drifting off to sleep.

Merge left onto I-24E by PleaseStepOnMeDamnit
Author's Notes:

Sorry for the delay! I got a little busy in my personal life, but here it is!

               A cold draft washed over Jackson’s body as he awoke in the boot. Looking around, he noticed that her warm foot had been removed from the shoe, and the inside was cold and wet. Light streaked into the cave as he surveyed the illuminated worn cavern around him. Suddenly, the enclosure began to rise and tilt. The insole became his ceiling as he dropped and began to roll down the toe box until he plummeted through the opening. He landed with a gasp on a soft, warm surface. Looking up, he was greeted with Ashley’s beaming face.


              “Damn, you slept a long time! We’re already in Indiana, you slept through Gary, but you didn’t miss much. We’re out in the countryside about to stop for gas and a bathroom break. Also, you’ll be chilling with Lauren for the next leg of the trip, probably until we get to the hotel.”


              Jackson returned a thumbs-up as Ashley shoved him into her jacket pocket.


              “By the way, you smell like feet”


              Ashley shoved her shoe back on and stepped out into the cold. She dashed into the convenience store and towards the bathroom. Outside, the bathroom, Lauren leaned against a wall. She flashed a slight wave as Ashley walked towards her. Reaching into her pocket, she pulled out Jackson and placed him into her palm.


              “Can’t have this little guy watching me use the bathroom.”


              Ashley left the two as she went into the bathroom, leaving Jackson staring up at the gigantic girl above him. Lauren stuffed him into her breast pocket as she roamed the aisles of the store, past displays of a wide variety of candies, jerkies, and snack foods.


              “See anything you want?” Lauren mumbled to her passenger as she idly scanned the back label of a box of candy.


              “Some chocolate would be nice”


              “Alright bug, but whatever you don’t eat, I get, ok?”


              “Of course!”


              Lauren gently stroked Jackson’s head as she grabbed a bar. “Let’s get checked out.”


              As Lauren meandered to the checkout counter, Ashley suddenly ran up and hugged her from the side, smashing Jackson between two soft meteors. His shouts for attention were instantly muffled as Ashley’s breasts slammed into Lauren’s. As the two embraced, a faint wiggle caused Ashley to step back.


              “Damn, little guy just got probably the best squish of his life. There’s more where that came from if you’re interested.”


              Jackson’s enthusiastic thumbs-up elicited chuckles from the girls. “Alright, let’s pay and get back on the road.


              As Ashley went to the counter to pay, Lauren returned to the car.


              “Alright, I need to get something out of my bag in the back, just climb wherever you want to sit.” She muttered to the tiny as she set him on the seat, before walking away. Jackson looked up at the center console, separated from him by a canyon and a high cliff. With nowhere else to go, Jackson sat on the seat while waiting for someone to return. A few moments later, the telltale thud of the trunk closing signaled Lauren’s return. The door swung open, blasting Jackson with cold air. As he moved his arms away from his face, he immediately noticed that Lauren was not watching out for him. His shouts for her attention were ignored, and the seat was soon cast in the massive shadow of Lauren’s ass. In desperation, he began to run, but his size meant he couldn’t escape before her ass slammed like a jean-clad meteor into the seat. Jackson was instantly slammed and pressed into the seat as Lauren adjusted herself. Moments later, Ashley returned, carrying a small bag.


              “Yo, where did Jackson go?”


              “I set him down on the seat to get comfortable somewhere in the car. Look around the center console.”


              After a momentary glance around the car, Ashley stared at Lauren.


              “You put him on the seat right? Get up.”


              After a momentary pause, Lauren immediately understood and raised her butt off of the seat. Ashley’s hand zipped into the gap and snatched Jackson off of the seat.


              “Lauren, you have to be more careful with him, you could’ve killed him!”


              “I’m… sorry.”


              Ashley grabbed her hand and gently placed Jackson in her palm. “Please take good care of him.”


              Climbing in herself, she started the car and pulled out of the gas station. Jackson sat silently on her palm, staring into the middle distance.


              “Jackson, look, I’m sorry. I did not realize that you couldn’t get off the seat, and it was a really bad idea for me to place you.”


              “Oh no, I forgive you, it was actually quite nice. I wouldn’t mind going through that again, though maybe with less clothing in the way. I just have nothing to say at the moment.”

              Lauren sighed in relief, “Hey do you want your chocolate now?” After receiving a small nod, she dug into the bag and fished out the chocolate bar. Tearing into it, she began breaking it into pieces before placing a small chunk on a napkin in front of Jackson. Staring at her fingers, she groaned slightly as she stared at the melted streak of chocolate on her fingers. With a slight smirk, she placed the digit next to Jackson.


              “Look, some more chocolate for ya!”


              Without a word, Jackson began to lick at the melted glob on Laruen’s warm finger, cleaning up the slightly salty chocolate.


              Ashley glared at the scene out of the corner of her eye. “Oh, so now you’re licking other girls’ fingers?” She exclaimed with an exaggerated pout, “Keep it up and I’ll make you lick chocolate from my toes.”


              “You act like that’s a bad thing. I’d lick your toes even without chocolate, and you know it.”

              Ashley and Lauren burst into giggles. “You’re on bug, you have some work to do when we get to the hotel tonight.”


              Jackson returned to his chunk of chocolate as the car retuned to silenced, with only road noise filling the void.


              The next few hours came and went as farmland and forest soon gave way to the suburbs of northern Indianapolis. Lunch came in the form of pastries at a local restaurant before the group returned to the road.


              “Say, where are we actually staying for the night?”


              “Knoxville.” Ashley commented. “Even got a hotel picked out, it’s a nice one so y’all will be happy.”


              “Sounds cool!”


              “They got a pool?”


              “Of course, we can play in it if you want. Of course, you’ll remain small, but surely you’d love to swim in the ocean surrounded by giant, beautiful islands.”


              Jackson smiled warmly.


              “I bet you like that, don’t you? Don’t worry, in just a few hours, you’ll get to swim the sea of giants.”


              Jackson began to blush, prompting a chuckle from Lauren.


              “Tell ya what, I’m gonna give you just a small taste of tonight right now!”

              Lauren snatched up Jackson and began unzipping her jacket. Without ceremony, she shoved him between her breasts and gently massaged the large round orbs, squeezing the tiny between the mounds. As the impromptu massage came to a halt, Jackson crawled up, popping his head out of her cleavage.


              “Just gonna leave you there for a bit, hopefully it’s a bit more comfy than the center console.”


              The drive continued through the afternoon. Indiana gave way to Kentucky, which in a few hours, gave way to Tennessee. As the sun began to set in the sky, Ashley merged onto an exit ramp. A few minutes later, the group pulled into the hotel parking lot.


              “Alright, Lauren, hide him, I’ll go check in and get a cart. Get everything ready to load up.”


              With this, Ashley walked towards the entrance while Lauren seductively pushed Jackson further down between her breasts, hiding him from view. Stepping out, she opened the trunk and began pulling out bags. Moments later, Ashley returned, pulling a cart. The two tossed their bags onto the cart and walked into the hotel for the night.

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