Babysitter in Training (2/6)

Tyler groaned as his mom stood in front of him, arms crossed with that no-nonsense look she always got when he tried to squirm out of something. “You’re going,” she said firmly. “Chloe’s parents specifically requested you. They said you were a hit last time, and Chloe was so excited when she heard you’d be babysitting again.”

“Mom, please!” Tyler whined. “It’s—uh—it’s just so much work! Can’t they find someone else?”

His mom arched an eyebrow. “Unless you’ve suddenly found a job in the last hour, I don’t see why you’re complaining. At least babysitting earns you some money.”

Tyler groaned. He knew there was no point in arguing when his mom had that tone. Thirty minutes later, he was trudging up Chloe’s front steps, muttering to himself about how this couldn’t possibly get worse—except it did.

When Chloe’s parents opened the door, he immediately noticed Chloe wasn’t alone. Her friend Sophia was lounging on the couch, a mischievous grin already plastered on her face. “Oh, Tyler! Perfect timing,” Chloe’s mom said cheerily. “Sophia’s staying over tonight, so I hope you don’t mind keeping an eye on both of them.”

Tyler forced a smile. “No problem,” he mumbled, his stomach twisting into knots.

The moment the front door shut behind Chloe’s parents, Tyler turned to the girls nervously. “Okay, well, you two have fun, and I’ll just be… uh… nearby if you need me.”

Chloe and Sophia exchanged sly glances as Chloe stepped forward, her grin widening. “Oh, don’t worry,” she said sweetly. “We’ll have plenty of fun—starting with dressing you up again! Chloe showed me how cute you looked last time,” she added, making Tyler’s stomach sink. “I can’t wait to see how we can top that!”

Tyler raised his hands nervously, trying to keep things calm. “Uh, thanks, but… not this time, okay? Let’s just—uh—find something else to do.”

Chloe arched an eyebrow, her grin turning mischievous. “Oh, that’s fine. We can always have some fun posting this photo to my socials instead.” She held up her phone, showing the picture of Tyler from his last babysitting gig. Tilting her head as if in thought, she added, “Hmm, how does, ‘Doesn’t Tyler look so cute in this dress and heels?’ sound?”

Tyler’s face turned bright red. “Fine! Fine! Just—just don’t post anything!”

The girls wasted no time. They dragged Tyler upstairs to Chloe’s room, which was decked out in pastel pinks and whites, with plush animals lining every surface. Chloe rummaged through her wardrobe before pulling out a pink gingham dress with puffed sleeves, delicate lace trim, and a fitted bodice. “Here, try this on,” she said, holding it out to him with a knowing grin.

A few minutes later, Tyler stood awkwardly in the dress as the girls fussed over him, adjusting the skirt so it flared out perfectly. Chloe picked up a matching white lace choker and clasped it around his neck while Sophia busied herself braiding his hair into two neat pigtails, tying each one with a ribbon.

Sophia worked on his makeup, dusting Tyler’s cheeks with soft pink blush, adding a subtle shimmer to his nose and brow, and carefully applying eyeliner and mascara to frame his eyes. She finished with a rosy lip tint. At the same time, Chloe painted his nails with pale pink polish, blowing lightly on his toes between coats to help them dry faster, leaving Tyler squirming in embarrassment. “There,” she said, admiring her work. “Perfect! Now for shoes!”

From under the bed, Chloe pulled out a pair of white slingback heels with a sleek, glossy finish. She knelt down in front of Tyler, sliding the heels onto his feet with exaggerated care and fastening the straps securely around his ankles. The open-toe design showed off his freshly polished toes, making his cheeks burn as he caught sight of how dainty his feet looked.

“Wow,” Sophia said, sounding genuinely impressed. “You’re so natural in them,” she added, snapping a photo before Tyler could react.

Once Tyler was fully dressed, the girls weren’t content to simply admire their handiwork. They immediately began testing how well he could play the part, starting with a clumsy curtsy. Tyler stumbled awkwardly, his cheeks burning as the girls burst into laughter. It only encouraged them further as they found a plush bunny for him to hold, instructing him to pose sweetly while they snapped photo after photo.

The teasing didn’t stop there. They had him practice delicate walks across the room, careful twirls to show off the flared skirt, and even bashful waves that made him cringe inside. The relentless attention and endless instructions left Tyler mortified, but the girls seemed to be having the time of their lives.

By the time Chloe’s parents returned, Tyler was back in his normal clothes. The girls had undone most of their work, but when he asked about the polish on his toes, Chloe had just smiled. “But it suits you so well! I mean, no one will even know unless you want them to,” she teased, leaving him red-faced as he slipped his shoes back on.

“So, how was everything?” Chloe’s mom asked cheerfully.

Chloe beamed, clasping her hands together dramatically. “Oh my gosh, Tyler’s like the best babysitter ever! We had sooo much fun!” Sophia chimed in with an enthusiastic nod. “He’s seriously amazing!”

Her parents exchanged approving smiles before handing Tyler a generous tip. As he shuffled toward the door, Chloe called out behind him, her voice dripping with playful innocence. “I can’t wait for you to babysit me again, Tyler!”

Tyler’s shoulders slumped as he stepped outside, already dreading the next time. Deep down, he knew there’d be no escaping it.