Author's note: This chapter was written with the assistance of AI.
You peeled back the wrapping paper, your fingers trembling slightly with anticipation. Inside the box lay a plane ticket, its glossy surface catching the light. Your eyes scanned the details—Destination: Hawaii. Your heart skipped a beat.
Jess was leaning against the counter, her arms crossed, watching your reaction with that same mischievous grin. “Surprise,” she said, her voice dripping with satisfaction.
“A vacation?” you managed to say, still processing.
“Not just any vacation,” Jess replied, stepping closer. Her towering frame loomed over you, but there was a softness in her eyes that made it hard to look away. “A tropical getaway. Just you and me. Well, and Nicole,” she added with a sly grin. “I figured it’d be nice to have another regular-sized person there with me, you know?
Her teasing tone was light, but the jab still landed, and you couldn’t help but flush a little. Jess chuckled, clearly enjoying your reaction as she reached down to ruffle your hair—a gesture that only emphasized the size difference between you.
You blinked. “Nicole’s coming?”
Jess laughed, her fingers brushing against your shoulder. “Yeah, she’s meeting us at the airport. Said something about needing a break from school.” She smirked, leaning down slightly to meet your gaze. “Plus, I love seeing how often her ditzy ass squashes you."
You laughed nervously, your mind racing. A vacation sounded amazing. But Jess’s tone had that edge to it—the one that usually preceded some kind of humiliating plan for you.
“So, uh, how are we getting there? I mean... I’m guessing you didn't secretly buy me a ticket as well,” you ventured cautiously.
Jess’s grin widened, and she leaned down, her face inches from yours. “Oh, don’t worry, Ted. I’ve got it all figured out.” She paused, clearly savoring the moment. “You’re gonna be my sneaky little stowaway.”
Your stomach flipped. “Stowaway?”
“Mhm,” Jess hummed, straightening up and crossing her arms again. She glanced down at her feet, then back at you. “You’re gonna ride in my shoe. My sneaker, to be exact.”
Your eyes widened. “Your... shoe?”
“Yep,” Jess said, popping the p sound like it was the most casual thing in the world. “It’s perfect. No one will suspect a thing. You’ll just… hang out in there while we go through security and board the plane. Easy peasy.”
She crouched down again, her eyes sparkling with excitement. “Think about it, Ted. Your tiny, squishy little body, all tucked away inside my shoe, bracing my foot with every step. You’ll be like my own personal living, breathing insole. I’ll get to feel you supporting me, squishing under the weight of my steps, while no one else even knows you’re there. It’s kind of… thrilling, don’t you think?”
Your face flushed at the thought. Jess’s enthusiasm was hard to ignore, even if the idea of being her “insole” made your stomach churn with a mix of embarrassment and something else you couldn’t quite name. She leaned in closer, her voice dropping to a whisper.
“It’s like having my own secret little treasure hidden away,” she added, her breath warm against your ear. “All mine. No one else gets to see you or touch you—just me. And I get to keep you safe and snug, right where I want you.”
You swallowed hard, a shiver running down your spine. Jess’s words were equal parts unsettling and oddly comforting. She made it sound so… intimate. Like being crammed into her shoe wasn’t just a necessity but something she was genuinely looking forward to.
“You’ll take good care of me, right?” you asked, your voice barely above a whisper.
Jess smiled softly, her hand brushing against your cheek. “Of course I will. You’re my tiny treasure, remember? I’m not letting anything happen to you.” Her grin returned, teasing but warm. “Besides, how could I resist having my own personal foot warmer for the flight?”
You chuckled despite yourself, the tension easing slightly. Jess had a way of making even the most ridiculous situations feel… special. Or at least bearable.
“Alright,” you said, taking a deep breath. “Let’s do this.”
Jess’s smile returned, and she booped your nose with her finger. “Good boy. Now, let’s get packed!”
--
The next day, you found yourself standing in front of Jess’s car, Nicole bouncing beside you with an oversized pink suitcase in tow. She was dressed in a crop top and shorts that showed off her long legs and ridiculous curves, her pink hair tied up in a messy bun. She grinned when she saw you, immediately sweeping you up into a hug that left your face buried in her chest.
“Ted! Oh my god, I’m so excited for this trip! Jess told me all about the beach and the coconut drinks and—” she paused, pulling back to look at you with those big blue eyes. “Wait, how are you getting there? Did Jess get you a ticket or something?”
Jess, who was loading her own bag into the trunk, smirked over her shoulder. “Nope. He’s riding in style.”
Nicole tilted her head, confused. “Style?”
Jess knelt down and slipped off one of her sneakers, holding it up like it was the most normal thing in the world. “Right here.”
Nicole’s eyes widened, and she clasped her hands together with a delighted gasp. “Oh my god, Ted! You’re going to be Jess’s insole? That’s so sweet of you! I bet you’ll be the comfiest insole ever—like, seriously, she’s gonna have the most supportive, squishy footrest on the entire plane!”
You sighed, feeling your cheeks flush. “Yeah, sure, I guess.”
Jess smirked, clearly amused by Nicole’s enthusiasm. “Oh, absolutely. Ted’s the best little helper anyone could ask for.”
You groaned internally, knowing there was no way to explain to Nicole that this wasn’t exactly your idea of a thoughtful gesture. She just kept grinning at you, completely oblivious.
“Honestly, Ted,” Nicole continued, setting you back down gently, “if I ever need an insole, I’m totally borrowing you. You’re just too perfect for it!” She giggled, patting your head like you were some kind of adorable pet.
Jess isn’t going to let me live this down anytime soon, you thought, resigning yourself to your fate as the world’s most accidental—and apparently world-class—insole.
Jess ruffled your hair affectionately before slipping the shoe back on. “Don’t worry, squirt. You’ll be fine. Now, let’s get moving—we’ve got a flight to catch.”
The drive to the airport was filled with Nicole’s endless chatter about how excited she was for the trip and Jess’s occasional teasing remarks about your upcoming “ride.” The idea of being trapped in Jess’s shoe for hours wasn’t exactly appealing, but you reminded yourself that it was for a good cause—a tropical vacation with your girlfriend.
When they arrived at the airport, Jess parked the car and turned to you with a grin. “Alright, shrimpy. Time to get cozy.”
She leaned down and scooped you up effortlessly, holding you in one hand while she removed her sneaker with the other. The sight of her bare foot—long and tan, with perfectly painted toenails—was oddly mesmerizing. Before you could overthink it, Jess lowered you into the shoe.
The inside of Jess’s sneaker was a dizzying assault on your senses. The warmth was suffocating, and the smell—a potent mix of stale sweat, leather, and the faintest trace of her perfume—was almost unbearable. You wrinkled your nose, trying to hold your breath, but the cloying scent seemed to seep into every fiber of your being.
“Uh, Jess,” you stammered, your voice muffled by the confined space. “It’s… really strong in here. Maybe there’s another way—“
Before you could finish, Jess’s massive big toe pressed into your face, cutting off your protest with unrelenting force. Her toe, nearly the size of your entire head, smothered your mouth, tasting of salt and musky skin. You couldn’t even gasp—her weight was too much, pinning you down against the sole like you were nothing more than a squishy insole.
“Shh, Ted,” Jess cooed from above, her voice laced with amusement. “Don’t be such a baby. You’ll get used to it in no time."
You struggled for a moment, trying to push against her toe, but it was useless. Jess barely even seemed to notice your feeble efforts as she adjusted your position further, flattening you beneath her foot until you were nestled snugly into the crevice of her sneaker. The pressure was intense, her toe still dominating your face while the rest of her foot pressed down on your body, molding you into the perfect shape for her comfort.
“There we go,” Jess said, her voice brimming with satisfaction.
You couldn’t answer—not that she expected one. Jess gave a little wiggle of her toes, as if testing your resilience, and you felt the heat of her skin radiate through every inch of your flattened form. The smell was overwhelming, and the taste of her toe lingered in your mouth, but there was no escaping it now.
Jess slipped her foot fully into the shoe, and you were plunged into complete darkness. The walls of the sneaker closed in around you, the warmth and scent intensifying with every passing second. You could feel Jess’s weight shift slightly as she stood up, her foot pressing down on you with each step.
“Don’t worry, Ted,” Jess said softly, her voice vibrating through the shoe. “I’ll take good care of you. Just hang in there, okay?”
You wanted to argue, to plead for release, but all you could do was lie there, trapped beneath her foot, wondering just how long this tropical getaway was going to feel like a punishment.
“Alright,” Jess said, her voice muffled from inside the shoe but still audible. “Let’s do this.”
As she walked through the airport with Nicole beside her, you couldn’t help but think about how ridiculous this situation was. Here you were—a 20-inch-tall man—trapped inside your girlfriend’s sneaker while she casually strolled through security like nothing was out of the ordinary.
You just hoped you could survive the next few hours without losing your mind.
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