Babysitter in Training (5/6)

Tyler sat on the edge of his bed, staring at the pastel package Chloe had sent him earlier that morning. The box itself looked innocent enough—pink wrapping paper and a bow. But his phone buzzed, pulling his attention to the real problem.

“See you tomorrow for a playdate, Tiffany! Don’t forget to come dressed up! 💄👗” the text from Chloe read, cheerful and mocking all at once.

His stomach twisted as he fired back. “No way. Not happening.”

A moment later, her response appeared: “Oh, come on, it'll be so fun! Besides… I bet Caroline would LOVE to hear about how the cute, girly Tiffany is actually Tyler, her awkward old high school classmate. Should I tell her?”

Tyler groaned out loud, his thumbs hesitating over the screen. She wasn’t bluffing—he knew that much. If Caroline found out, the humiliation would be unbearable. He had no choice. “Fine,” he replied, feeling utterly defeated.

Almost immediately, Chloe texted back: “Great! Be here at 3! Oh, and 13-year-olds don’t drive. Better ask Mommy to drop you off! Have fun explaining that! 😘”

Tyler’s jaw dropped as he read the message, his heart sinking. He couldn’t believe it—she actually expected him to ask his mom for a ride. But what choice did he have? Caroline couldn’t find out. She’d tell everyone.

That evening, Tyler awkwardly approached his mom in the kitchen. His words came out rushed and jumbled, but eventually, he managed to stammer, “So, uh, remember how I was babysitting for Chloe and her friends? Well, um, they won a bet last time, and… uh… they kind of asked me to dress up for them. As a joke!”

His mom turned from the sink, drying her hands with a dishrag. “Dress up?” she repeated, raising an eyebrow.

Tyler nodded quickly, his face burning. “Y-yeah, just like, you know… nothing weird. They’re kids, Mom. It’s just for fun, and I thought it’d make babysitting easier for me since they’d stop giving me a hard time.”

She looked at him for a long moment, clearly trying to figure out if she’d heard him correctly. “Well… it’s a bit unusual, but I guess at least you’re taking this babysitting job seriously. Sure, I can drop you off.”

The next morning, Tyler spent hours on YouTube, furiously watching tutorial after tutorial. Every step felt agonizing—foundation, contour, blush, eyeliner, lipstick—and he lost count of how many times he had to start over.

When he finally finished applying his makeup, he glanced at himself in the mirror. His lips were glossy and pink, his cheeks lightly blushed, and his eyeliner—after three painstaking tries—gave him an innocent, doe-eyed look. His wig was pulled back into a high ponytail with a dainty pink bow perched neatly on top, completing the look.

With his face done, Tyler turned his attention to the outfit Chloe had provided. The satin pink dress shimmered softly as he pulled it off the hanger, the ruffled hem barely grazing mid-thigh. It clung snugly to his waist, flaring out into bouncy ruffles that swished mockingly with every movement. The matching white lace thigh-high stockings slid up his legs, making his cheeks burn even more. Finally, he slipped into the floral platform heels, wobbling as he adjusted to their towering height.

He stood in front of the mirror, taking it all in. The dress, the stockings, the makeup, the bow in his hair—it was all so perfectly… feminine.

“This is so embarrassing,” he said under his breath, his reflection staring back at him with wide, innocent eyes that didn’t feel like his own.

Tyler awkwardly tottered into the kitchen, his heels clicking softly against the floor. His mom nearly spat out her tea when she looked up and saw him, her eyes widening in shock.

“Tyler… wow. That’s, uh, quite the outfit,” she said, her voice faltering slightly.

Blushing, Tyler adjusted the hem of the dress nervously. “The girls picked it out,” he mumbled. “I just looked up some random makeup tutorial. It’s no big deal.”

His mom blinked, then cleared her throat awkwardly. “Well… um, you did a good job. I’m sure they’ll appreciate the effort.”

The car pulled up to Chloe’s house, and Tyler’s heart sank as he stared at the front door, dreading what was waiting for him.

“Do you need me to walk you to the door, sweetie?” his mom teased, a playful grin spreading across her face.

Tyler’s cheeks flushed bright red. “No! I-I’ve got it, thanks.”

She giggled softly. “Alright, alright. I’m sure the girls will be so excited. Have fun!”

Tyler groaned as he fumbled with the door handle, stepping out quickly before she could say anything else.

Teetering on his heels, Tyler approached the front door, each step clicking loudly against the pavement. His stomach twisted with nerves as the rustle of his dress swishing around his legs made his cheeks burn even hotter.

“I can’t believe I’m doing this,” he muttered under his breath. Taking a deep breath, he raised his hand and knocked twice, his heart pounding as he waited for the door to open.