Babysitter in Training (3/6)

Tyler shifted nervously as Chloe’s mom handed him a glass of lemonade. “Thanks so much for coming over again, Tyler. The girls were thrilled when they heard you were babysitting today!”

“Uh, no problem,” he muttered, shooting a wary glance at Chloe and Sophia. They sat on the couch, whispering and exchanging mischievous grins. He didn’t need a sixth sense to figure out what they were planning.

As soon as the door clicked shut behind Chloe’s parents, the girls sprang into action. “Alright, let’s get started!” Chloe said with a grin.

Tyler didn’t resist. What was the point? He followed them upstairs silently, his stomach sinking when he saw what was waiting for him on the bed: a pastel pink lace dress with dramatic bell sleeves, corset lacing, matching platform heels, and a sleek blonde wig.

“Sit down,” Sophia ordered, pushing him gently into a chair as Chloe started gathering everything they’d need. They worked like a tag team, slipping the lacey dress over his head and tying the corset back just tight enough to cinch his waist but not so tight he couldn’t breathe. Tyler fidgeted as the soft fabric of the bell sleeves brushed against his arms, and the light petticoats swished around his legs.

Next came the calf-high socks. Sophia carefully slipped them onto his legs, making sure the frilly tops sat just right. Then Chloe knelt down to buckle the pastel pink straps of the platform heels around his ankles, completing the delicate ensemble with a flourish.

“Perfect!” Chloe said brightly before spinning him around to sit at her vanity. Tyler groaned inwardly as Sophia secured the blonde wig onto his head, pinning it in place before brushing it into a sleek style. Chloe was already digging into her makeup kit, dusting his cheeks with a rosy blush and carefully applying shimmery eyeshadow to his lids. A quick flick of eyeliner and a coat of mascara followed, and finally, Chloe leaned in to finish with a glossy pink lip gloss.

“Okay, sit down for just a sec,” Chloe said, motioning toward the floor. Tyler reluctantly lowered himself onto the carpet, his petticoats fanning out around him as Chloe leaned in to attach a pink lace bow to the wig. She adjusted it carefully, tilting her head as she made sure it looked just right, while Sophia busied herself fiddling with the dress and the bows to make sure everything was perfectly in place.

Ding-dong!

The sudden sound of the doorbell made Tyler tense, his eyes widening. “Who’s here?” he asked nervously, glancing between the two girls.

Sophia got to her feet quickly, her face lighting up. “Oh, it’s my sister!” she said excitedly, heading for the door.

Tyler remained frozen in place, dread pooling in his stomach as he listened to the muffled sound of voices at the door. A moment later, Sophia reappeared, followed closely by a tall, confident brunette. “Hey, girls!” Caroline said brightly, stepping into the room.

Tyler’s stomach dropped. Caroline?! No, no, no… it couldn’t be. He stared at her, horrified, as memories from high school came flooding back. Caroline was in his graduating class.

Her eyes immediately landed on him, and she froze for a moment, her gaze sweeping over his carefully assembled look. Then, her face lit up with delight, her hands clasping together as she let out an audible squeal. “Oh my gosh, look at you! You’re so adorable!” Caroline gushed, practically bouncing on her heels as she stepped closer. “That dress, those little bows, the heels—you’re like a little doll!”

Tyler stiffened as Caroline crouched slightly to meet his eye level, her wide smile only growing. “What’s your name, sweetie?” she asked, her voice dripping with warmth.

Tyler opened his mouth, but no sound came out. His brain scrambled for a response, but Chloe beat him to it. “Her name’s Tiffany,” she said brightly, stepping in smoothly. “She’s a classmate of ours, but she’s a little shy.”

Caroline gasped again, her hands still clasped. “Tiffany, huh? Oh, that’s the cutest name! You’re absolutely precious,” she cooed, leaning in even closer. “You must have spent so much time getting ready. Look at how polished and perfect everything is—it’s just the sweetest thing I’ve ever seen!”

Tyler’s face burned as he squirmed under her attention. “Th-thank you,” he eepped in his highest, most delicate voice, desperately trying to sound as girly as possible. The effort only made his cheeks flush brighter as Caroline’s grin widened.

Caroline clapped her hands together, her excitement returning. “Of course! It’ll be so much fun. You girls are going to have the best time! Now hurry up, let’s get going!”

Chloe and Sophia grabbed Tyler’s hands, helping him to his feet. “Come on, Tiffany,” Sophia teased with a wink, practically dragging him along as he stumbled after them, barely keeping up in his heels.

Caroline led the way out to her car, and Tyler awkwardly climbed into the back seat, his dress puffing up as he sat down, staring out the window with his stomach churning. He wasn’t sure what was worse: pretending to be a giggly, girly girl or having Caroline figure out who the girly girl really was.