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KK's Quickies: Rebellious Skater Boy to Reluctant Girly-Girl (Full Story)
🕑 Added 2023-08-18 15:00:05 +0000 UTCVince banged through the front door with his skateboard, his afternoon plans foiled once again. “Stupid mall cops always kicking me out,” he muttered angrily.
“Could you keep it down, Vince?” his older sister called from upstairs. “We’re studying!”
“Shut up, bitch!” he retorted. “Quit trying to tell me what to do, just because mom’s not home doesn’t mean…”
He trailed off as his sister came down the stairs with her extremely attractive friend Brittany in tow, wearing the shortest shorts Vince had ever seen in his life.
“Uh, hi, Brittany,” he stammered.
“Hey, Vince,” Brittany said, smiling slyly. “We were just talking about you! In fact, we were having an argument, and I had a little bet in mind to settle it…”
“Yeah?” Vince gulped. “Uh, what is it?”
Vince wasn’t sure he liked the sound of this bet, but he wasn’t going to miss a chance to strip down in front of Brittany and show off his abs. “Like what you see?” he asked leeringly, standing in only his jockey shorts in his sister’s room.
“I certainly do,” Brittany giggled. “I’m definitely going to win this bet. You are way too manly to pass for a girl, Vince.”
“Got that right,” Vince said. “Hey sis, hurry up and grab me some clothes! I’m freezing!”
“Coming!” his sister called from the wardrobe.Vince had to admit he felt a bit less manly now that he was wearing a pair of his sister’s panties and a matching bra.
“Nice and smooth,” Brittany remarked, running a hand flirtatiously along Vince’s chest. “Do you wax?”
“Uh, yeah,” Vince lied, not wanting to admit he hadn’t grown any body hair yet. “Got to look good on the beach, you know? Sis, why am I wearing this stupid thing? I don’t have boobs!”
“Not yet,” his sister smiled evilly. “Now, Brittany, do you want to do his nails or his makeup?”
“These fake nails come off, right?” Vince whined, shifting uncomfortably as the cold gel inserts in his bra made his nipples harden. “And all this gunk on my face?”
“It’s not gunk, it’s high-end cosmetics,” his sister said primly. “And yes, to both. But not until I win the bet!”
“Give me a mirror,” Vince said testily. “I want to see how stupid I look.”
“And spoil the surprise?” Brittany tut-tutted. “No way, handsome!”
Vince did his best to strike a manly pose despite the fact he was wearing a ruffled miniskirt and off-the-shoulder crop top. His reflection in the mirror was startlingly feminine, but he wasn’t about to let on. “So Brittany wins the bet, right?” he demanded eagerly. “Nobody would ever think I was a real girl. I mean, look at me!”
“Not so fast, little brother,” his sister smirked. “Time for the piece de resistance… Brittany brought a wig from drama class!”
Vince grumbled as he Brittany and his sister fussed with the wig for at least twenty minutes before finally letting him get up and walk over to the mirror. When he did, his jaw dropped! With the dark tresses spilling over his shoulders, thick eyeliner, lip gloss, trendy top, flirty miniskirt and ballerina flats, he not only looked like a girl, but a total hottie like the ones he loved checking out at the mall.
“Holy shit,” he whimpered. “I’m… I… You made me a…”
“Babe?” his sister suggested as she was smirking. “Hold still, you need some clip-ons.”
Vince was too shocked to resist as she added hoops to his ears and handed him a pink purse.
“Time for the last part of the bet!” Brittany chirped. “To see if you make a believable girl or not! Since me and your sister already know the truth, we need some outside opinions. And I think the shopping mall is a great place to get them, since there’s always boys hanging around ogling at cute girls who are shopping.”
“I have a feeling the mall cops will let you back in this time, little sis,” Vince’s sister smiled. “Come on, it’s time for “Vanessa” to make her debut…”
One full year later, Vince stared dejectedly into the mirror as he thought back to that fateful day at the mall. After coercing him into going to the mall dressed up as her little sister “Vanessa”, Vince’s sister had made it her mission in life to convince their mother that Vince truly wanted to be a girl, first by hiding her things in his laundry, then by planting a fake diary on his laptop for their mother to “accidentally” find, and finally by creating a new Facebook page for “Vanessa” loaded with pictures from their excursion to the mall.
Unable to convince his mother that it was all a lie, Vince was forced to see a therapist, who diagnosed him as a transsexual teen in classic denial, and was immediately put on hormone therapy to avoid building any masculine muscle, budding instead into a gorgeous girl with a bombshell figure… Which he was now expected to put on display in his new bikini!
“Hurry up, sis!” his sister called gleefully. “Time to hit the beach! Brittany will be meeting us there, so she’ll get to see you in your cute new swimsuit. I bet you’ll have the boys all over you again, and this time I want you to give at least three of them your phone number, understand? It’s high time “Vanessa” started dating!”
“Vanessa, quit primping and let’s go already!” Vince’s sister ordered, marching into his room where he was still preening anxiously in front of the mirror.
She’d managed to bully him into an ultra-tarty outfit: a short, tight miniskirt with thigh-high stockings to show off his long, slender legs while leaving a teasing strip of milky thigh exposed, four-inch stiletto pumps encasing his dainty feet, and a tiny halter top designed to expose as much midriff as possible while still squeezing his firm, round breasts into an enticing cleavage. With his dramatic eyeliner, loads of mascara, and glistening lip gloss, not to mention the large hoops dangling from his ears and diamond stud glinting in his belly-button, he looked every inch a gorgeous, sexed-up, slutty little party girl looking for a wild night at the club!
“Can’t I wear something else?” he begged, running a hand through the new gleaming blonde highlights in his dark hair. “This skirt is so short and my boobs are practically falling out of this top!”
“You look hot, little sister,” she smirked in reply. “You have an awesome body, and you have to get used to showing it off. How else are you going to land a hunky boyfriend?”
“But I d-don’t want a boyfriend!” Vince stammered.
“Whatever, it’s time to go!” his sister said, handing him his purse. “I told someone we would be there at eleven, but you took so long getting ready…”
Every head turned as Vince and his sister clicked their way into the club on their stiletto heels, and Vince realized blushingly that with his slutty top and tiny skirt, his sister had made sure he would be getting the lion’s share of the male attention tonight. He let her lead the way up to the bar, concentrating on maneuvering in his designer shoes, which forced him to take small mincing steps and accidentally lend a very sexy and feminine sway to his hips. He hated the way his breasts quivered slightly with each stride!
To his surprise, a tall, well-muscled young man gave his sister a friendly hug at the bar before turning to give Vince a lustful up-and-down ogling. “This is my little sister Vanessa I told you about,” Vince’s sister beamed. “She’s the reason we’re late… Primping in front of the mirror all the time, you know her type.”
“I’d say the primping was worth it,” the young man grinned, taking Vince’s hand and brushing his cheek with a small kiss. “I’m Sean. You look gorgeous tonight, Vanessa.”
“Th-thanks!” Vince squeaked, totally terrified as Sean slid an arm casually around his tiny waist.
“Sean is a semi-pro skateboarder,” Vince’s sister announced proudly. “You know, back when Vanessa here was in her tomboy phase, she actually tried skateboarding a little herself. Of course, she’s way too much of a girly-girl now to get her anywhere near one of those things! She’d be scared of breaking a nail, or scratching those sexy legs of hers.” She tugged Vince away for a second and leaned in close. “He’s a real hunk, don’t you think? I told him you’re shy, but love athletic guys and loosen up after a few drinks. Don’t worry, there are condoms in your purse.” She smiled at Sean as he once again put his arm confidently around Vince’s delicate waist. “I’ll leave you two to get to know each other better!”
Vince was trembling in his high heels as his sister disappeared into the club. Sean pulled the feminized boy onto the dance floor, running one hand over his pert backside and then slyly feeling up his chest. “So you used to like skateboarding, huh?” he said, chuckling. “I bet you still remember how to grind…”
Vince smiled nervously, long lashes fluttering, as Sean encircled his waist from behind. God, he really missed the days when his biggest problem was getting kicked out of the mall...
Comments
zebulon
That's a very good idea!
Nicegent42
Suggestion. If you do the other character we voted on ad a short story too, when you make it a pdf, join it to this one. Draw maybe two extra images, 1 combined cover and one image at the end with the two new "girls" next to one another. Then put it up for sale on lulu.com
