KK's Quickies: Pesky Peeping Tom to Dolled-Up Date (3/3)

By the time the girls finished his makeup nearly forty minutes later, Dennis felt dazed. Despite what they’d said about his complexion and bone structure, it still felt like they’d caked every cosmetic in existence onto his face. He couldn’t decide which was worse: the huge, fluttery black false eyelashes clinging to his lids and brushing his cheeks every time he blinked, or his collagen-pricked lips being slathered in waxy, bright pink matte lipstick.

They’d used eyeliner and shadow to further accentuate his eyes, and pencilled his plucked brows darker to match. But it wasn’t the endless assault of brushes, pencils, and powders that had left Dennis so shell-shocked – it was the final result. He could hardly recognize himself! He had never been the manliest-looking specimen, but now, after the girls’ handiwork, he looked one-hundred percent female.

With the addition of makeup, everything about his face, from his pert little nose to his high cheekbones, suddenly screamed “girl!” And not just any girl, either…

“Like I said,” Trish said smugly, bringing him back to reality with a sharp pinch as she clipped large silver hoops to his earlobes. “Sexy.”

Dennis flushed beneath his makeup, but he couldn’t argue. The girl in the mirror, even with her short, masculine haircut, was stunning…the kind of girl who dated handsome jocks, not dweebs like him. Humiliation flooded him at the realization: the only way he could ever get into the panties of a girl that gorgeous was because he was already wearing them!

“You can wear this bracelet, too,” Sally said, slipping the accessory onto his wrist. “But it’s expensive, so don’t you dare lose it.”

Dennis blinked. “Lose it?” he asked, in the breathy soprano the girls had been drilling him on. “Um, where would I lose it?”

The girls looked at each other, and grinned.  As the girls explained their plan, Dennis felt himself starting to hyperventilate with panic. He’d been utterly wrong: they knew about Moe’s involvement, so they weren’t just out to humiliate Dennis, but his partner-in-crime, as well. In order to put Moe at ease, Sally had spent all week sobbing about the photos, and how horrible it was to have absolutely no way of finding out who had done it.

Trish, meanwhile, had been doing something even more devious: talking up the fact that her younger cousin was visiting town, and that she’d gone from flat-as-a-board tomboy to high-maintenance hottie in the space of one summer. The news had immediately piqued Moe’s interest, and Trish had been all too happy to arrange a Friday night date for him and “Jennifer!”

“I can’t do it,” Dennis squeaked, his voice now high-pitched as much from terror as from his own efforts. He shook his head, bouncing the long brunette tresses of his newly applied wig. “It’ll never work! He’ll recognize me straight away!”

“As if,” Trish said, rolling her eyes. “Your own mother wouldn’t recognize you looking like this, and Moe is dumb as a load of rocks, besides.”

“You said I didn’t have to walk anywhere!” Dennis blustered. “I’ll trip up, and give the game away completely!”

“You only have to make it to his car,” Sally said casually. “He’s taking you straight to a drive-in movie. We told him you saw his picture, thought he was super hot, and spent all day deciding what lingerie to wear for him…so it could be a night to remember.”

Dennis’s pretty pink mouth fell open.

“As far as he knows, ‘Jennifer’ is totally boy-crazy, and loves it when a guy takes charge, but still likes to do the shy good-girl act at first,” Trish added. “That way you don’t have to worry about him making a move. Just giggle and smile, and he’ll do the rest.”

“We’ll be all set up to capture the action,” Sally said, holding up an expensive camera that was, Dennis realized bitterly, probably even better than his. “And once we have a few good shots of you two making out, we’ll call you and give you an excuse to leave.”

DING-DONG!

At the sound of the doorbell, Dennis looked up like a deer caught in the headlights. As surreal as it seemed, this was well and truly happening: he had gone from Moe’s accomplice to his hot date for a Friday night, and with everything the girls had told him, not to mention his provocative makeup and outfit, he knew the twelfth-grade jock was going to be very, very pleased to meet “Jennifer” for the first time.

“That must be him,” Sally said, grinning. “Okay, Jennifer. It’s show-time…”

By the time Dennis made it to the stairs, Trish had already let Moe inside, and was chatting casually with him. The jock was clad in his usual tight T-shirt and designer jeans, and Dennis knew, with some bitterness, that it had probably taken Moe all of ten minutes to get ready for this “date”...while he himself had been primped, plucked, and prettified for the better part of two whole hours!

But Dennis’s resentment was replaced by total fear when Moe, drawn to the sound of tinkling jewelry and clicking stiletto heels, turned his head. The jock’s manly jaw dropped open, and a look of sheer lust appeared in his eyes. Flushing furiously, Dennis focused on navigating the staircase, clinging to the banister and shuffling down one awkward step at a time. Moe watched with a bemused grin, clearly torn between disdain for “Jennifer’s” totally impractical shoes, and pleasure at the fact they’d been worn just for him.

“She’s still getting used to six-inch heels, poor thing,” Trish clucked sympathetically, as a blushing Dennis finally arrived at the bottom of the stairs. “But she just loves how they make her butt swish back and forth, right, Jennifer?”

Dennis’s blush deepened even further.

“I don’t mind it either,” Moe chuckled. “You look amazing, Jennifer. Here, this is for you.” He pulled a pink, single-stem rose from behind his back and held it out. “A beautiful flower for a beautiful girl.”

“Oh, how sweet!” Trish exclaimed. “I guess you can be a charmer when you want to be!” She shot Dennis a warning glance. “What do you think, Jennifer?”

Dennis gulped, accepting the rose with one trembling hand. “Th-thank you,” he said, in his breathiest, girliest voice. “Um, it’s so pretty?”

“Not as pretty as you, babe,” Moe said, wrapping his arm casually around Dennis’s dainty waist. “Ready to go?”

Dennis flushed, looking desperately at Trish, hoping against hope that she might bail him out…but she only gave him a cold nod. Sick with anxiety, Dennis turned to his date and flashed him a nervous smile.

“Ready,” he squeaked. “Um, what movie are we seeing?”

The End