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KK's Quickies: Pesky Peeping Tom to Dolled-Up Date (Full PDF + Bonus Epilogue)
🕑 Added 2023-10-09 14:22:06 +0000 UTCNearly a year later, as Dennis stared dejectedly into the mirror, he couldn’t help but think back to that fateful evening at the drive-in theater. The dolled-up freshman had been totally terrified, especially as Moe’s hands began to roam, but something unexpected threw a wrench into the girls’ diabolical plan: despite having been told that “Jennifer” was hot to trot, Moe, upon sensing Denny’s nervousness, backed off entirely.
“We can just watch the movie, then get an ice cream sundae and get to know each other better,” the high-school senior had said. “What’s the rush, right?”
As they did just that, with Moe acting a perfect gentleman, Dennis’s dread only increased: he was sure that at any moment Trish and Sally would text him a reminder of their plan, and he would be forced to start flirting and simpering to ensure Moe made his move. But the evening wore on, and no text arrived, and eventually Moe dropped him off back at Trish’s house with a single peck on the cheek, claiming a girl like him was worth the wait!
Dennis had staggered inside on his six-inch heels, feet and calves aching, shaken from the experience of going out in public as another guy’s sexy date with not a single bystander seeing through his disguise. But his ordeal was to get even worse, because Sally and Trish were waiting for him with a gleam in their eyes.
“I’ve never seen Moe like that,” Sally said, hefting the camera she’d been using to spy on their date. “He was looking at you like an adoring little puppy! Whatever you did to him, he fell for you…hard.”
“Moe wasn’t always such a jerk,” Trish added thoughtfully. “Maybe all he needs is the right girl to bring him around.”
Dennis had gaped in disbelief as the girls outlined their new plan: in order to keep Moe on the hook, and off the prowl, he would be expected to keep playing the role of “Jennifer” – sending the twelfth-grade jock gushy texts and cute selfies whenever possible. The girls assured him he could still be Dennis at school, and that they wouldn’t expose him as the peeping tom, but in exchange, he was about to become Moe’s long-distance girlfriend!
Living a double life had been intensely stressful. Since the girls insisted he get used to doing his own hair and makeup in order to send Moe flirty selfies, his room quickly filled up with feminine accoutrements, and his photography was forgotten in favor of learning to blend his eye shadow and accessorize his outfits!
It wasn’t long before things came to a head, and his mom discovered all the girly stuff stashed in his closet. He’d come agonizingly close to telling her the truth about the whole thing, including his own fault in it, but instead he’d blurted out the only excuse he could think of: that he was secretly trans, but not yet ready to come out of the closet.
Rather than shock or disappointment, his mom had been utterly delighted. She’d always wanted a daughter, and assured him that she would help him through his “transition” however she could. Before long, Dennis only got to be himself at school, while “Jennifer” was around for practically every other waking hour!
There was only one light at the end of the tunnel: the fact that Moe was graduating at the end of the year, and heading off to Spring State on a football scholarship. That meant he would be out of the girls’ hair, and Dennis would finally be allowed to drop the act…or so he thought. But Sally and Trish had grown attached to having their very own personal dress-up doll, and decided that even after Moe moved away, “Jennifer” would be here to stay.
Though he’d begged and pleaded, his complaints had fallen on deaf ears – the girls were determined to make “Jenny” a hottie worthy of rounding out their popular girl trio. That summer, with his mother’s eager blessing, Dennis been put on female hormones to help round out his hips and butt, and made to follow a strict diet to shrink his already-tiny waist to truly doll-like proportions. Finally, in order to finish the job the estrogen had started, he’d been carted off to an expensive plastic surgeon upstate, where he’d been forced to act thrilled at the prospect of getting his very own C-cups!
Now, as he forlornly adjusted his cleavage in the mirror, he realized he had a nicer rack than Sally or Trish ever did. But his hourglass curves weren’t the only thing different from a year ago: wigs were now a thing of the past, since his own hair had been grown out, given extensions, and bleached to a shade more befitting a girly-girl like “Jennifer.” The cascade of blonde hair reached the small of his back, and required constant brushing to maintain.
While he’d barely been able to hobble to Moe’s car in his six-inch heels, now he handled stilettos like a pro, mincing gracefully around his redecorated bedroom as he packed his purse for the evening. Life had had one final surprise in store for the hapless freshman, soon to be sexy sophomore: when Dennis’s “coming out” made the rounds on social media, Moe, off on vacation overseas, had finally put two and two together…but instead of being furious at being tricked, he’d called Dennis up and humbly asked for a date when he came home on the last day of summer.
So now, nearly a year after their first date, Dennis was once again primping and preening to look hot for Moe…only this time, he was doing it all on his own. His knowledge of makeup had increased exponentially under Trish and Sally’s tutelage, meaning his eyeliner was on point and his sparkly layered pink eyeshadow was perfect. He’d even added a little beauty mark to off-set his pouty, poppy lips.
As he stared miserably at his gorgeous reflection, he realized he was now the kind of girl he once would have killed to date…or photograph in her underwear. Trish and Sally had already been talking his ear off about all the cute guys they could set him up with when school started in the fall, which meant that Moe’s invitation, against all odds, was a life-line.
If “Jennifer” was going steady, albeit by long distance, with Spring State’s quarterback, it meant that the other horny guys would back off, and the girls wouldn’t pressure him into dating anybody at school. But in order to keep Moe’s affections for the entire year, Dennis was going to have to make this evening one to remember…
Blushing furiously, Dennis slipped the condoms inside his little clutch purse and snapped it shut just as the doorbell rang. It was show-time again, and this time, he couldn’t afford to keep a PG rating! Nervously biting his collagen-plumped lip, Dennis made a few final adjustments, tossing his long blonde hair, freeing his dangling hoop earrings, and fluffing up his out-thrust cleavage. Then, pasting a pretty smile onto his face, he swished his way to the front door.
Moe was waiting on the front step, looking manlier than ever thanks to the small beard he’d started growing out, and his lustful expression as he drank in the sight of his date, lingering on Dennis’s silicone-stuffed boobs, made the feminized freshman flush.
“Hi-hi, Moe,” he squeaked. “Sorry I took so long getting ready, I couldn’t find my earrings…”
“No worries, gorgeous,” Moe said suavely, pulling a pink rose from behind his back. “Like I said, you’re worth the wait.”
It was the same color of rose he’d brought on their first so-called-date, clearly meant as a reminder of that evening, and Dennis accepted it with a nervous smile. As he waved goodbye to his mom and gracefully descended the front steps, heels clicking on the cement, he felt Moe’s hand wrap possessively around his waist.
“So, you still taking photos?” the jock asked casually.
Dennis swallowed, thinking of his camera lying forgotten in the back of his closet. “Um, mostly selfies,” he admitted, embarrassed beyond belief to sound like such an airhead. “I just, like, don’t have time anymore.”
“Makes sense,” Moe said. “A girl who looks as good as you deserves to be on the other end of the camera.” He paused thoughtfully. “But I guess it’s a good thing you were into that artsy-fartsy shit, or we might have never met, you know? You ever think about that?”
Dennis flashed back to that fateful afternoon, ambling along in comfortable sneakers, jeans, and a T-shirt, eager to get a glimpse of Sally in her underwear, and compared it to the present: stuffed into a flirty pink dress that showed off his boobs and legs, off on a date with the Spring State quarterback!
“All the time,” he murmured sadly to himself, then, remembering his goal for the evening, flashed Moe his prettiest smile and batted his eyelashes flirtatiously. “I guess I’m a pretty lucky girl, huh?”
Moe grinned, sliding his hand downward to caress Dennis’s butt. “I have a feeling both of us are getting lucky tonight,” he said. “Let’s go, beautiful.”
The End
Comments
liv
If you ever decide to expand on one of these shorts this one would be perfect
Taigan
I hope she remembered to pack lube along with the condoms.
