Babysitter in Training (1/6)

This caption was originally released on DeviantArt, but I’m excited to share it here on Patreon as I’ve been working on follow-up parts to expand the story! I’m posting it here for your convenience, so you can easily catch up before diving into the rest of the story. Enjoy!

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Tyler never expected to spend his Friday night babysitting. But his parents were done with his excuses, and when the neighbors asked for a sitter, they didn’t hesitate to “volunteer” their 22-year-old, unemployed son. The ultimatum was clear: behave, or he was out on the street. Begrudgingly, he showed up, figuring he could survive a few hours lounging on the couch.

At first, it seemed easy. Chloe, the 13-year-old he was watching, barely acknowledged him, scrolling through her own phone and humming along to a playlist. Tyler thought he had it made—until Chloe got bored.

“Hey,” she said, setting her phone down. “Do you wanna play something? Maybe cards or a board game?”

Tyler barely glanced up. “Nope,” he replied, eyes glued to his screen. “Go play with your dolls or something.”

Chloe arched an eyebrow, her lips twitching in disbelief. “Seriously?” she shot back. “First of all, I don’t even have dolls. Second, what’s the point of you being here if you’re just going to ignore me?”

Tyler rolled his eyes. “You’re old enough to entertain yourself. I’m just here to make sure you don’t burn the house down.”

Chloe crossed her arms, leaning against the back of the couch. “Huh. You know, I suddenly don’t feel very safe with someone this inattentive. Maybe I should call my parents and let them know you’re too busy staring at your phone to do your job.”

Tyler’s stomach dropped. If her parents came home early and complained, his parents would definitely kick him out. Panicked, he put his phone down and sat up. “No, wait! I’ll play anything you want, okay? Just—don’t call them!”

Chloe’s lips curved into a sly smile, her eyes sparkling as she noticed the nervous edge in his voice. “Anything?”

After what felt like an eternity of waxing, Chloe gleefully dragged him into her room. “Okay, let’s find something cute for you to wear.” Before he could protest, she tossed a pastel pink dress into his lap. It was outrageously girly, with a flared chiffon skirt and delicate ruffled straps. Before he could even open his mouth to object, she dangled a pair of sheer white tights in front of him. “These will look so cute with the dress,” she said with a grin.

Reluctantly, Tyler pulled the tights up his freshly waxed legs, grimacing as they clung snugly to his skin. The dress came next, and as he slipped it on, the soft fabric and flowing skirt made him feel even more ridiculous.

“Hold still!” Chloe ordered as she grabbed a brush and began working on his hair. She tugged and twisted until it was smooth and glossy, then carefully styled it into loose, soft waves. Satisfied, she tied an enormous lace bow into his hair, right at the crown of his head, making it impossible to ignore how utterly girly he looked.

“Now, makeup time!” she chirped, pulling out a pink cosmetic case. Tyler groaned, but Chloe ignored him. She worked quickly, dusting a soft pink blush onto his cheeks and adding a hint of shimmering highlighter. Next came the eyeliner, which she expertly winged out on both sides, giving his eyes a dramatic, feminine flair. She finished with a coat of mascara and a swipe of glossy pink lipstick that shimmered under the light. When she stepped back, she clapped her hands together in delight.

“Oh my gosh, you’re adorable! But wait—something’s missing.” Chloe rummaged under her bed and pulled out a pair of pastel pink Mary Jane heels with chunky little bows on the toes. Ignoring Tyler’s protests, she handed them over with a smug look. Left with no choice, Tyler slipped his feet into the heels, struggling to fasten the straps as Chloe giggled. “They fit perfectly!” she said, clapping her hands. “We’re the same size!” As he wobbled to his feet, the added height from the chunky heels made him feel even more ridiculous.

“You’re perfect!” Chloe announced, grabbing his hand and leading him out of the room. Tyler stumbled after her, the heels making every step unsteady as she paraded him through the house. She made him practice strutting back and forth, exaggerating his steps as she stifled her laughter at his awkward, unbalanced movements. When he muttered a complaint or hesitated, Chloe held up her phone with a knowing smirk. “Keep going! Or should I send a picture to your parents and let them see how fabulous you look tonight?”

Just before her parents came home, Chloe finally let him change and scrubbed off the makeup. Tyler was still reeling from the humiliation when her parents stepped inside.

“So, how was everything?” her mom asked.

Chloe grinned. “Tyler was amazing! Honestly, he’s the best babysitter ever. I want him to come over every time you guys go out!”

Her parents exchanged impressed glances before handing Tyler a generous tip. Too stunned to argue, he shuffled out the door, Chloe waving cheerfully behind him.