Content warnings for this story (click here for guide):
May had been lying in bed with her boyfriend Max, the two of them discussing their respective exes, when she suggested they look up a few old flames on social media.
“Really?” Max squinted. “Is that a good idea?”
“Sure – come on. It’ll be fun to see how they look now. Could be surprising!”
Some of their exes weren’t on social media, but most were. May’s exes were generally musicians, creatives and the odd stay-at-home dad. Max’s were innocuous, attractive women – mostly brunettes or redheads. Many were married now and most were boyish and flat-chested like May.
Then she’d asked about Candy, whose name had come up when Max was listing his former girlfriends.
“Ah, she’s probably not on here.” Max went to shut his laptop lid but May raised an eyebrow mischievously.
“S’matter? What are you embarrassed about?”
“Nothing. She’s just – maybe we should go get some food.”
May ignored his protests. Now she HAD to see this ex. How many Candy Bonets could there be online?
Oh wow. She stifled a snort-giggle. She was online alright.
Candy Bonet was a hairdresser in Max’s home town with bleached blonde hair, huge breasts and a vibrant fake tan. She was wearing high heels in every picture and usually something short and pink by way of an outfit.
“Oh. My God. Max, seriously? Seriously, you dated THIS?”
Max sighed. “I knew you’d be like this.”
“She looks like Budget Barbie. Did you do it for a bet?”
“There’s no need to be mean, May. She’s a really nice girl.”
“Come off it. The conversation can’t have been sparkling.”
Max put down his drink.
“Leave her alone, May. Enough.”
“You embarrassed to have dated a bimbo, Max?” May chuckled, whooping as she noted that Candy was an aspiring model. “It gets better. She’s been Pretty Princess Farborough three times in a row. She did stupid beauty pageants!”
“Mostly for the prize money, yes,” said Max. “How about you stop ripping into a girl you don’t know and we go get some food?”
“Think most of the prize money went on bronzer,” snorted May.
And that was when Max hit his limit.
“This is not a side of you I like,” he said firmly. “You’re being cruel and bitchy to someone you don’t know. Frankly, it’s ugly and I don’t want to hear it from you.”
May was shocked. “I was just – but she’s such a bimbo…” she trailed off.
Max pulled out a chair and took May’s wrist. She resisted for a second but a stern look from him caused her feet to move. Max sat down and stood May next to him while he took down her jeans and panties.
Normally Max’s spankings were light-hearted, but May had a feeling this time would be much harder. As she hesitated, her hands hovering in front of her pussy, Max pulled her decisively over his lap.
His hand landed on her backside with a loud thwack. May gasped in surprise and yelped. Before she could fully process the sting, a second slap hit her.
“OWWWWW!” She looked back over her shoulder in outrage. Her boyfriend’s face was calm and focused as he explained things.
“You’re going to learn (WHACK) that it’s not very nice (WHACK) to pick on someone (WHACK) based on appearance. I’m going to make sure (WHACK) that you never call anyone (WHACK) a bimbo (WHACK) again.”
May was squealing and snotting by this point. As she kicked and wriggled, Max trapped her flailing legs and smacked her in a fast flurry, her poor bottom reddening from his hard palm.
“I’m sorry, Sir!” she tried. Sometimes that got her off the hook. “I’m very sorry!”
Max made a “Hmm” sound and delivered one final blizzard of spanks. He let her up and gave her a hug, and May thought that was the end of it. She rubbed her stinging bottom and scowled at the picture of Candy still on Max’s screen. Stupid ditz, getting her in trouble.
The parcels arrived the day they were meant to go out to a public lecture. They were both interested in archaeology and a guest speaker was coming to talk in the city centre.
“Come in here, May,” said Max, an hour before they were due to set off. “I’ve got something educational for you.”
May entered the bedroom, puzzled. “What is it?”
Her boyfriend gestured toward the bed. “It’s your outfit for tonight.”
May’s eyes widened as she took in the view. There was a pair of frilly white knickers with a pink bow on the bottom, a white ruffled mini-skirt that was barely more than a belt and a baby-pink crop top with “Princess” written in glitter across the bust. On the floor, a pair of pink plastic 5-inch heels lurked.
“You can’t be serious,” she said, looking daggers at Max.
“I am serious,” he said. “You’re going to find out what’s it’s like to be judged on your appearance. You’ll make such a cute ditzy little bimbo. I’ve even got you a fluffy pink pen to write down your notes at the lecture. Not that anyone will believe you understand a word. Aww, but you’re trying your best.”
“I can’t go out in this,” protested May. “I’ll look like an idiot.”
“That’s part of the lesson,” said Max. “You’ll know you’re smart and capable, but what will others think when they see you tottering in?”
He pulled out the chair once again. “Do I need to spank you into your supercute outfit?”
May was frozen to the spot. “I…can’t…”
Max sighed and pulled her over his lap once again. This time he brought out a hairbrush, which landed cruelly on the previous day’s spanking. May bucked and wailed, whining every time the brush hit her bottom.
“Lesson learned?” Max said at last, and May nodded frantically. “Are you going to play dress-up like a good girl?”
She hesitated again, but caught sight of the brush and nodded dolefully. Max smiled and picked up the fluffy white panties and May blushed from head to tomboy toes as she stepped into them and pulled them up. The pretty pink bow presented her bottom adorably.
Next came the skirt, which was swishy and incredibly short. She felt certain that every movement flashed those sissy knickers to the world.
Before she could pull on the t-shirt, Max brought over a large padded bra.
May snorted. “That’s way too big for me. Nice guess, Max.”
“The cups are,” he said, smiling wickedly as he fastened the hooks and eyes. “But I think you’ll find the band is just right.”
Once the band was fastened around May’s chest, and the straps pulled up onto her shoulders, she felt her boyfriend’s hand reach around into each cup and stuff a huge fake breast inside to fill it.
“Nooo!” she whined, but as she stomped in frustration, she saw the fake boobs bob ludicrously. Max pulled the Princess t-shirt on over her head, and it stretched tightly over her jiggly new tits.
“Such a girly girl,” chuckled Max, and May scowled.
Next came a blonde wig, which was swept into high bunches, curling down to her shoulders and bouncing as she moved. She was handed pink sparkly lip gloss and blusher, and ordered to put on enough that it showed, which she did, furious at the indignity.
Finally Max strapped her into her plastic shoes, and locked them onto her unhappy feet.
“Perfect. Ah, nearly forgot something. Back in a moment, sweetie,” Max said, heading downstairs to the kitchen. He never called her ‘sweetie’, thought May. Ugh – just get this over with.
While he was gone, she tried to stand up and nearly fell right back down. She attempted a few steps but wobbled and tottered like a baby deer, her tits jiggling and her panties flashing. It was impossible to walk in these stupid things – she looked like …like a…she could hardly bear to admit it.
After a couple of minutes, Max returned with something in his hand, and instructed her to take down her panties and touch her toes.
“Now, if you don’t want another hairbrush spanking, stay still,” he said, and May felt something moist being pushed into her bottom. A plug? Her knickers were pulled back up and skirt fluffed out over the top.
For a second nothing happened, but then an unbelievable burning sensation began.
“What the hell?” She gasped, looking accusingly at Max.
“Ginger,” he grinned. “To put a little cheerleader pep in your step. You’re going to be such a perky little doll at the big talk!”
May stood up, swaying in her ridiculous heels, fresh waves of fire running through her bottom. Max grabbed his car keys and took her hand, then led her to the mirror.
May’s mouth fell open at the figure she saw there. She was a blonde, big-titted, tottering bimbo, a silly little princess being led around by her boyfriend. She was the kind of girl she would mock mercilessly – an airhead whose biggest concern was her lipstick staying fresh.
“Here’s your pencil,” said Max, handing her a sparkly object with a fluffy plume. “And if you need help spelling any long words, I’m sure I can say them very slowly.”
May glared at him.
“You’ve made your point. Can I please take this crap off before going out in public?”
Max grinned and shook his head.
“Not a chance. You’re going to be my silly trophy girlfriend. I’m looking forward to introducing you to all those scholars and telling them how grumpy you were at having to go to a boring lecture. I’ll roll my eyes and tell them I promised you a shopping trip for pretty dresses if you sat through all the smart-people stuff. Then I’ll pat you on the head, hand you your little handbag and they’ll watch you wobble off on your heels. And you know what they’ll call you when you’ve gone?”
May blushed and winced. She did indeed.