Content warnings for this story (click here for guide):
The story so far: After bullying a younger student, Lily, for carrying a china doll to school, tomboy Ash has been given an unusual punishment. Since she hung the girl’s doll on the school flagpole, she has to take its place for a month. And to make matters worse, Lily is her crush Finn’s little sister.
MONDAY
“Aww, look at the pretty princess!”
Ash’s cheeks blazed. She was a picture of prissy pinkness, covered in ruffles, with lacy bloomers and china-doll ringlets. She would have given anything for her jeans and boots right now.
“Fuck off, Pete.”
“Ah-ah-ah!” squeaked Lily, wagging her finger. “That’s not how a nice princess speaks.”
“But he’s -“
“Now Tilly,” said the younger girl, placing her hands on her hips. “I want you to say sorry for using a naughty word.”
“She’s right, ‘Tilly’. It was such a naughty word. It hurt my feelings.” Pete made an ‘Awwww’ face at Ash and mimed crying.
“Get bent,” growled Ash.
“Right!” said Lily, grabbing Ash’s hand firmly and sitting down on the wall outside the science block. “Princess dollies do not say mean things when someone tells them they’re pretty! You’re going over my knee, naughty Tilly!”
“Like fuck I a-” began Ash, indignantly, but her sweet patent Mary Jane shoes had no grip on them and she lost her balance, landing across the 11-yr-old Lily’s lap.
“NO!” she shrieked, scrabbling to get up.
“Shall I help you hold her still?” grinned Pete.
“Yes please,” said Lily. “I’m sure she’s good really, but she needs a little reminder. I brought a little something in case she needed help being a good dolly.”
Pete gripped Ash’s hands and Lily pulled out a wooden spoon.
“Now,” said Lily, “Where’s Tilly’s bottom?”
She pulled up the struggling girl’s frothy frilled petticoats into a huge pink cloud around her waist.
A crowd began to gather and whoop.
“Awww, has Ash been a naughty girl?”
“Love the bloomers, Ash! Who’s your little friend here?”
“Her name is Tilly,” said Lily brightly. “And she’s my dolly to dress up.”
Hoots of laughter rang out as Ash grimaced and tried again to wriggle free. But before she could get so much as a wrist out of Pete’s grip, Lily brought down the spoon.
“OWWW!” cried Ash, eyes wide. How could something so small hurt so much?
“Woo!” called another younger girl – some kid Ash remembered bullying the previous year. “Get her, Lily!”
“OWWWWWWW!” yelled Ash as the spoon came down and down again. She found herself kicking and wiggling, causing her vast skirts to jiggle and fuss.
“Is Tilly sorry for being naughty and saying a swear word?” asked Lily, warmly.
“OWWWWYESSS!” winced Ash, with tears in her eyes.
“Good girl,” said Lily, nodding to Pete to release her. “Now say thank you to the nice man for calling you pretty.”
Ash rolled her eyes to the sky, her bottom on fire beneath the bloomers.
“Thank you.”
“For -” Lily waggled the spoon sternly.
“Ughh, for calling me pretty!”
“Aww,” said Pete. “You’re welcome, princess! That was adorable!”
Ash wanted to die, especially when Lily patted her on the head and praised her with “Good girl, Tilly! Now take my hand and let’s have no more fuss.”
As the small girl led the taller one away, stooping and slipping in her swishy skirts and kiddy shoes, Lily’s older brother Finn watched from a window, chuckling. This was getting enjoyable.
TUESDAY
Once again, Ash’s mum dropped her off at Lily and Finn’s house. Remembering her ordeal yesterday, Ash felt a wave of dread wash over her. She looked pleadingly back at her mother.
“I’m sorry, alright? It was a prank that got out of hand. Anyway, I don’t feel very well.”
“Go on,” said her mother sternly. “You’re not ill in the slightest, and this is the least you can do. Don’t forget, you’re going to be best friends with her for the whole month.”
Ash scowled and knocked at the door. Finn answered and she hung her head in shame.
“Ah, right on time. Lily’s just been talking about her plan for today.” He turned to call upstairs. “Lily! Tilly’s here!”
Lily thundered downstairs, delighted.
“I’m going to make you look so cool today, Tilly! Come up and see what I’ve picked out!”
Ash, clad in her grey band t-shirt and baggy jeans, allowed Lily to grab her paw and haul her up to her room. As they entered, Lily jabbered away happily.
“Yesterday was Princess Day but today I think Tilly’s going to be a fashion doll. Look what you get to wear!”
A mannequin stood by Lily’s bed. It wore a tacky pink sparkly crop-top with “Designer Diva” printed on the front, and a tight white mini-skirt. A pair of tottering plastic see-through heels stood underneath.
Ugh, thought Ash. I’m going to look like a demented bimbo. Can anyone even walk in those heels? I mean, it’s a bit less full-on than that horrific frillfest yesterday but it’s still cringey as hell.
“I don’t know if I can walk in those heels…” she began.
“Is Tilly being good for you, Lily?”
Finn popped his head round the door. Ash blushed.
“Well,” he fixed her with a sly smile. “Are you being good for my sister? We can always ask your Mum to carry out her spanking threat, otherwise. You did look very cute yesterday.”
Ash reddened further, embarrassed by her crush’s attention.
“I think she’s shy,” Finn said to Lily. “I think you should dress her up like the most popular girl in school, like in your Barbie videos!”
“That’s my plan!” sang Lily. “Come over here, Tilly. We’ve got to get you dressed and then do allll your makeup!”
“Hmm,” said Finn. “I think the mannequin might have more curves than Tilly. Is the outfit going to fit?”
Ash crossed her arms over her perky little breasts, scarlet at Finn’s description.
Lily looked back and forth between Ash and the dummy, then nodded sagely.
“I got an idea!”
***
Clip-clop, clip-clop, clip-clop!
Lily dragged her doll along at quite a pace, keen not to be late.
Wolf-whistles and hysterical laughter followed her all the way down the corridor, as her fellow students photographed the pair on their phones, made kissy sounds, and hooted.
Ash bristled with humiliation, but she couldn’t shout at them, not after yesterday. Lily had definitely packed her stinging spoon. Besides, it was could do to stay upright. The plastic heels were so high she towered over Lily and found herself hunched over, clattering noisily along as the intrepid girl pulled her to class.
Earlier, at the house, Finn had been right. The outfit laid out for her was designed for someone with a juicy bottom and big tits, neither of which the tomboy possessed. Somehow Lily had found a big padded bra, into which she had stuffed two huge gel pads. She had done the same for a pair of padded knickers, and the results jiggled ridiculously.
“Perfect!” she’d said, and tugged Ash’s crop top down to strain over her new boobs. “Now she really does look like my fashion doll! OK, now the skirt!”
With some effort, she heaved the stretchy mini up over the bubble-butt knickers.
“10 minutes, Lil!” called Finn from downstairs.
“Makeup! Makeup!” bustled Lily, and set to work smearing powder and paint over Ash’s face. She grabbed a big blonde Malibu wig from a dummy head nearby and plopped it onto Ash’s head, then scuttled downstairs to ask Finn something.
Ash stood up and walked toward the mirror. As she caught sight of herself, her mouth dropped open.
A ditzy airhead stared back at her, with orange foundation, sugar-pink lipstick, huge lashes and masses of fake blonde hair in a perky side ponytail. Her new boobs and butt were comically bimboish, squished against the tight crop top and spray-on mini. Even just standing here, she wobbled a little on the stripper heels.
Finn came in behind her.
“I told Lily to get in the car while I brought ‘Tilly’ downstairs. I saw the size of those heels…”
He was gobsmacked by Ash’s new look. “Hehe…Wow…”
Ash was furious, mortified and…something else. She hated being seen like this, but something about the way Finn mocked her made her go hot and cold all over.
“Underwear…” she began, shakily, feeling the breeze between her legs.
“Oh yes,” said Finn, ruffling her ponytail. “Lily must have forgotten. Here!”
He tossed her a truly hideous satin thong with a pearl string.
“Perfect for Sixth-Form Barbie!” he grinned, as Ash looked at the garment, crestfallen. She looked fondly back at her cotton underwear, crumpled on the bed, then attempted to step into the thong.
Not used to the heels, she stumbled and Finn caught her. One of her fake boobs tumbled out and she cringed as she righted herself, leaning on his firm forearm.
“I think dizzy Tilly needs some help dressing, doesn’t she?” whispered Finn, and Ash felt a rush of blood to her head.
“A bit wobbly on her tiptoes, isn’t she? Put a hand on my shoulder.” Finn crouched beside Ash and held open the thong for her to step into. He tugged it gently up, hoisting her mini-skirt briefly and catching just the tiniest glimpse of her pussy before smothering it in snug satin. Ash found herself flushing as his hands brushed her thighs, moving across her bottom as he adjusted the string of pearls before smoothing down her tight skirt once more.
“Oh – we’d better not forget this, had we?” he said wickedly, picking up her fallen padding. “Can’t go out looking lopsided, can you?”
Before Ash could snatch the gel pad from him, he briskly lifted her top and slipped his hand inside the empty bra cup, pushing the soft padding snugly into place against her hard nippled. Ash closed her eyes, dizzied by his firmness, and heard him laugh softly.
“Right!” said Finn, clapping his hands together. “I think this fashion doll is ready to go. Let’s get my sister and Tilly to school!”
Head whirling, Ash came back to reality, as she minced toward the car.