Cover of His poor fanny

5 chapters · 16075 words · Read 0 times

Young boy called Charlie gets spanked and wedgied by the various women in his life. Some are his age, some are older, a few are much younger, which embarrasses him. They vary in relationship with him, for example they could his sitter, stepmom, boss, teacher/professor, stepsister, gym/yoga instructor, friends, bullies, neighbours! These spankings vary in location and reason, and Charlie sometimes fights it and other times he submits. In the end he always loses. These punishments can be private or public, routine or unexpected, sexy or humiliating, deserved or unfair. Charlie may even enjoy some of them. There is typically an extra humiliating factor to distinguish each punishment as unique. Occasionally some of the women go to Charlie asking for him to spank them!

Chapter 1: The Babysitter's TikTok Punishment

The city lights glittered beyond the floor-to-ceiling windows, a cold tapestry of blues and whites that did nothing to warm the sleek, minimalist living room. Charlie slouched on the dark leather sofa, the material sighing under him. He watched his stepmother, Helen, strut across the polished hardwood on needle-thin stilettos, her movements as precise and sharp as her eyeliner.

“Yuki, sweetheart, you remember the rules,” Helen said, not even glancing at Charlie.

Yuki Chang stood by the glass coffee table, looking small in an oversized black hoodie that fell to mid-thigh. Her bare legs were smooth and pale. “No snacks after nine, homework before any games, and lights out by eleven,” she recited, a playful smirk touching her lips.

“Good girl.” Helen finally turned her gaze on Charlie. It was a look that made his stomach tighten. “And the most important rule is for this one. He listens to you. Exactly like he listens to me or Jenna or Tanya. If he doesn’t…”

Jenna, perched on the arm of a chair and fixing a hoop earring, chuckled. “Oh, he’ll listen. He always does eventually.”

Tanya, already by the door with her clutch, called over, “Just be firm, Yuki. He’s all bluster.”

Charlie felt a hot wave of embarrassment creep up his neck. “Come on, guys. I’m twenty-two. This is ridiculous. I don’t need a sitter.”

“You need something,” Helen said, her voice dropping into that purr that always meant trouble. She glided toward him. “And since we’ll be out, Yuki is in charge. Let’s make sure she’s fully equipped, shall we?”

Before Charlie could protest further, Helen’s manicured hands were at the waistband of his soft cotton shorts. With a practiced, swift yank, she pulled them down to his knees, exposing his striped boxer-briefs. The air conditioning whispered cool against his skin.

“Helen!” he yelped, trying to squirm back into the couch cushions.

She ignored him, her focus on Yuki. “The key is speed and confidence. He’ll try to negotiate. Don’t let him.” Helen hooked her thumbs into the elastic waistband of his underwear. “For minor infractions—backtalk, complaining—a simple corrective wedgie usually gets the point across.”

She hiked the fabric up sharply. Charlie gasped as the cotton dug deep, the seam pressing uncomfortably tight. A choked sound escaped his lips.

Yuki giggled, a bright, musical sound. “Like that?”

“Just like that,” Helen affirmed. Then she placed her palm firmly on the exposed curve of Charlie’s bottom, now tightly framed by the straining underwear. She brought her hand down once, twice, three times in quick, stinging slaps. The sound was sharp and humiliatingly loud in the quiet room. Each smack sent a jolt through him—a mix of sting, shock, and a traitorous, familiar warmth.

“For more direct defiance,” Helen continued, as if lecturing on horticulture, “a spanking is more effective. Don’t be shy. He can take it.” She smoothed a hand over the skin she’d just reddened, then leaned closer to Yuki. “Go on, give his perky little bum a pinch. Get a feel for it.”

Yuki stepped forward, her eyes sparkling with mischief. She reached out and gave a firm, teasing pinch to Charlie’s left cheek, making him jump. “Cute,” she declared.

“Perfect.” Helen pulled Charlie’s underwear and shorts back up in one brisk motion, leaving him flushed and disheveled. She planted a kiss on his burning cheek. “Be good for Mommy Yuki.”

And then they were gone, the door clicking shut behind them, leaving only the scent of perfume and a profound silence.

Charlie couldn’t look at her. He stared at the distant skyline, his face on fire.

Yuki plopped onto the couch beside him, tucking her legs underneath her. The oversized hoodie rode up, giving him a fleeting glimpse of frilly white panties hugging her plump backside before she settled. “So,” she said, popping a piece of gum. “You wanna order pizza?”

They did. They ate it straight from the box, watching dumb videos on her phone. Charlie slowly unclenched, the awkwardness ebbing away in the face of pepperoni and shared laughter. Yuki was easy to be around, funny in a dry, observant way. She didn’t act like a tyrant. For a couple of hours, it almost felt normal.

But it hung there, unsaid, in the space between them. Every time he shifted on the couch, a faint reminder throbbed. Finally, during a lull, he set his soda down a little too hard.

“What’s up with you?” Yuki asked, her head tilting.

“Nothing.”

“Charlie.”

He ran a hand through his messy dirty-blond hair. “It’s just… weird, okay? Having my pants pulled down in front of you. Being told I have to… obey you. You’re nineteen.”

She nodded slowly, chewing her gum. “Yeah. I get that.”

“You do?”

“Sure. It’s super weird and kinda messed up.” She shrugged. “But it’s also the deal, right? Helen pays me to sit you. Those are my instructions.”

He groaned, leaning back. “It’s humiliating.”

“It’s supposed to be,” she said simply, not unkindly. She was quiet for a moment, studying him—his embarrassed frown, the defensive hunch of his shoulders. A slow, new idea dawned in her eyes. “You know what might make it less weird?”

“What?”

“Practice.”

Charlie blinked. “Practice what?”

“The whole… thing.” She swung her legs to the floor and stood up, facing him. Her hoodie dwarfed her, but her gaze was suddenly, intensely focused. “It’s weird because it’s a big production. Helen does it to make a point. But if it was just… routine. No big audience. Just you not listening, and me correcting you. It’d just be a thing we do. Less pressure.”

A strange, hollow feeling opened in Charlie’s gut. He knew where this was going. A part of him screamed to say no, to walk to his room and lock the door. Another part, the secret part that had thrummed with guilty warmth under Helen’s hand, uncoiled with a quiet, eager dread. “You mean… right now?”

“Why not? Consider it training. So next time, it’s not this huge embarrassing event. It’s just Tuesday.” She held out her hand. “Come on. You mouthed off about the pizza crusts. That’s backtalk. You know the rule.”

He stared at her outstretched hand. The city lights blurred beyond her. His heart hammered against his ribs. It was the dumbest, most insane idea he’d ever heard.

Slowly, feeling like he was moving through deep water, he put his hand in hers.

Her fingers closed, cool and firm. She didn’t yank, but her pull was inexorable. She sat back on the couch and guided him across her lap. The leather was cool against his chest. The world tilted, the room upending so all he could see was the floor and the distant, indifferent glow of the single floor lamp. Her hoodie was soft against his cheek.

He felt her hand slide down his back, a ghost of a touch, before it came to rest on the seat of his jeans. “See?” Yuki’s voice was calm, almost gentle above him. “No big deal. Just practice.”

Her hand rose, and the world held its breath.

Her hand rose, and the world held its breath.

It fell not with a wrathful crack, but a crisp, measured smack. The sound was louder than he’d expected, a flat, clarifying report in the quiet room. The sting was immediate, a sharp, focused heat blooming through the denim. It wasn’t the brutal punishment Helen could deliver; it was a statement, pure and simple.

Smack.

Another, on the same spot, layering the sensation.

Charlie’s whole body jerked with the second one. A choked gasp escaped him, his fingers curling against the leather couch. His face burned, a blush spreading from his cheeks down his neck, hotter than the spanks.

“See?” Yuki said. Her voice was conversational, almost detached. “Not so cosmic. Just a consequence.” She landed a third spank, then a fourth, alternating cheeks in a slow, rhythmic pattern. Smack. Smack.

“You’re… really doing it,” Charlie mumbled into the couch cushion, his voice thick.

“Well, yeah. You agreed to practice.” Smack. “Gotta commit to the bit.” Her hand came down again, a little softer this time, more of a pat. “How’s the humiliation level? On a scale from one to ‘I want to melt into the floor’.”

“Solid seven,” he grunted, but the tension in his shoulders had begun to ease. The pain was fading into a deep, steady throb, a physical anchor in the weirdness of the situation.

Yuki chuckled, her free hand resting lightly on his lower back. “We’ll work on that. The goal is to get you to a comfortable three. Just a thing that happens, like taking out the trash.” She delivered a final, almost playful volley of light, quick smacks that made him squirm more from surprise than pain. Then she stopped, her palm simply resting on the now-warm seat of his jeans.

They stayed like that for a long moment. The city hummed. Charlie focused on his breathing, on the weight of her hand. The initial, scorching embarrassment was cooling into something else—a strange, vulnerable intimacy.

“Okay,” Yuki said softly. “Practice session over.” She gave his bottom a gentle squeeze and nudged him up.

He slid off her lap, avoiding her eyes as he straightened his clothes. The denim felt abrasive against his sensitized skin. He risked a glance. She was just watching him, that same little smirk playing on her lips, but her eyes were softer.

“So,” he said, brushing imaginary lint off his shirt. “Pizza was mediocre. We got any better contraband?”

“Helen said no snacks after nine,” Yuki singsonged.

“Helen’s not here,” Charlie countered, a tentative grin breaking through. “And I’m the one with the recently disciplined ass. I think I deserve a treat.”

She laughed. “Fine. But you’re getting it.”

He returned from the kitchen with a bottle of Helen’s good pinot noir and two glasses. “She’ll notice,” Yuki said, but took the proffered glass.

“She’ll assume I drank it alone in a fit of rebellious despair. Which is way more on-brand for me.”

The wine was velvety and rich. They drank, and the last of the formal stiffness dissolved. They talked about nothing—stupid movies, awful people from high school, the weird architecture of the building across the street. The wine warmed Charlie from the inside, softening the residual sting from the outside. Yuki kicked her feet up on the coffee table, her hoodie riding up. He tried not to stare at the strip of skin above her frilly panties.

By the time the bottle was half empty, a lazy, comfortable silence had settled. Yuki swirled her glass, watching the legs slide down. Then she sighed, a contented, bored sound.

“I’m bored,” she declared.

“We can watch something.”

“No. I wanna make something.” She fished her phone from her hoodie pocket, her movements slightly looser from the wine. “I need a new Tik Tok. Film me.”

Before he could answer, she was on her feet, placing her phone in his hands. She scrolled through her music, bit her lip in concentration, and then a bass-heavy, syrupy song filled the room. “This one. Just get my ass. That’s the whole bit.”

She positioned herself in the open space before the windows, the city a dazzling backdrop. She hit play on a draft, watched the choreography once, a simple, hip-heavy grind, then nodded to him. “Okay. Go.”

Charlie pressed record. Yuki transformed. The casual girl from the couch vanished, replaced by a creature of pure, confident motion. She swayed, dropped into a deep squat, and popped her hips in time with the beat. Her oversized hoodie fluttered with each movement. She turned, bending over, and shook her backside directly at the camera.

The thin, frilly fabric of her white panties strained, becoming nearly translucent under the focused light from the floor lamp. With each rhythmic shake and clench, Charlie saw everything—the full, plush curves of her cheeks, and between them, the distinct, intimate outline of her pussy lips, pressing against the delicate lace.

His mouth went dry. The phone felt suddenly heavy in his hand. He was supposed to be framing the shot, but he was frozen, watching.

She finished the sequence, held the final pose for a beat, then spun, flushed and grinning. “Did you get it?” She bounced over, plucking the phone from his slack grip. She watched the playback, nodding. “Yeah, that’s good. The lighting is kind of perfect.” She glanced at him, her eyes mischievous. “You’re a good camera man. Want to be in the next one?”

“In it?” he croaked.

“Yeah. A duo. It’s a trend—like, a domme and her subby boy-toy. I do the powerful dance, you do the, you know, worshipful, follow-along stuff. It’s funny. It’ll get likes.” She was already searching for another sound, her fingers flying over the screen.

The wine-fueled warmth in Charlie’s stomach curdled into cold dread. “No. Yuki, come on. No way.”

“Why not? It’s just a stupid dance.”

“It’s not just a dance. It’s… I’m not doing some submissive routine on the internet where people I know can see it.”

“So don’t show your face. I’ll make you wear a mask or something. But you have to do the movements.” Her tone was light, but it had an edge now. A challenge.

“I said no.” He crossed his arms, leaning back into the couch. “Film yourself shaking your ass all you want. I’m not your prop.”

Yuki stopped scrolling. She looked at him, the playful glint in her eyes hardening into something sharper. She slowly set her phone down on the glass table. The click was definitive.

“Here’s the thing, Charlie,” she said, her voice dropping into a low, melodic register that was neither friendly nor angry. It was calm. Absolute. “We had our practice. That was for theory. But you just directly refused an instruction. That’s not theory anymore. That’s real disobedience.”

She took a step toward the couch. He instinctively shrank back.

“Helen told me what to do with disobedience. And we’re way past a little practice spanking.” A smile, cool and knowing, touched her lips. “You had your wine. You had your fun. Now, I think it’s the perfect time for some real degrading punishment. Don’t you?”

The words hung in the air, cold and precise. All the wine-warm comfort drained from the room, leaving only the sterile glare of the city lights and Yuki’s unwavering gaze.

“You’re not serious,” Charlie said, but the quiver in his voice betrayed him.

“As a heart attack.” Yuki didn’t blink. “Stand up.”

“Yuki, come on. It was a joke.”

“I’m not joking. Stand. Up.” The mommy-voice was gone, replaced by something flat and immovable. It was the voice of someone holding all the cards and knowing exactly how to play them.

His limbs felt like lead, but he pushed himself off the couch, the denim of his jeans whispering against the leather. His heart was a frantic bird trapped in his ribs.

“Good boy.” She picked up her phone again, tapped the screen, and pointed the camera at him. A red recording light glowed like a malevolent eye. “Now, the punishment for direct defiance is full humiliation. That’s the rule. So, let’s get you undressed.”

“No.” The word was a weak puff of air. He took a step back, hitting the edge of the glass coffee table. “You can’t.”

“I can. Helen gave me full authority. And you agreed to the dynamic when you didn’t lock yourself in your room.” She took a step forward, the phone steady in her hand. “Take off your shirt. Or I’ll do it for you, and it’ll be worse.”

His hands trembled as they went to the hem of his t-shirt. The fabric felt suddenly thin, worthless. He pulled it over his head, the motion awkward, and let it drop to the floor. The air-conditioning raised goosebumps on his arms and chest.

“Jeans next.”

“Yuki, please.” His face was molten. “Don’t film this.”

“Too late.” She zoomed in on his fingers fumbling with the button of his jeans. “This is going on my private story. All my friends back home will see what happens to bratty boys who break the rules.” She giggled, a sharp, delightful sound. “They’re gonna love your embarrassed little face.”

The button popped. The zipper grated down. He pushed the jeans and his boxer-briefs over his hips in one mortifying shove, kicking them off his ankles. He stood there, completely exposed, covering himself with his hands, staring at the floor. The cold air was a shock against his naked skin. Every instinct screamed to run, to hide, but her voice and that unblinking red light pinned him in place.

“Hands at your sides,” she commanded, her voice dipping back into that purring, melodic tone. She was enjoying this. Really enjoying it.

He forced his hands down, clenching them into fists at his thighs. The camera lens felt like it was scraping over every inch of him.

“Aw, look at you,” she cooed, circling him slowly. The phone captured his profile, his back, the red marks from her earlier spanking still faintly visible on his bare bottom. “All blushy and hard. You are a subby little boy, aren’t you?” She stopped in front of him, the phone angling down. “Even your body betrays you. That’s the funniest part.”

He couldn’t speak. Shame and a sharp, unwelcome thrill twisted together in his gut. His own arousal felt like the ultimate betrayal.

“So,” Yuki said, lowering the phone slightly. “Here’s the new deal. You can do the TikTok dance with me. The submissive one. And if you do a good job, I’ll delete this footage of you standing here like a naked, ashamed statue.”

He swallowed, a flicker of desperate hope cutting through the haze. “Okay. Okay, fine. I’ll do the stupid dance.”

“Naked?” she prompted, a wicked eyebrow raised.

“Yes! God, yes, whatever. Just delete it after.”

Her grin widened. “But see, after this display, a normal dance seems too easy. The punishment has to fit the crime of defiance. So you’ll do the dance… but you’ll be in uniform. A proper little-boy uniform.”

From the pocket of her enormous hoodie, she produced a large, folded white item. She shook it out with a crisp snap. It was a disposable adult diaper, stark white and padded. From her other pocket, she pulled a single, bright blue pacifier.

Charlie’s breath hitched. “No. No way. That wasn’t the deal.”

“The deal changed when you made me pull out the big guns.” She tossed the diaper onto the couch beside him. “Put it on.”

“I only get a diaper when I’ve… when I’ve made a mess,” he stammered, repeating a rule from some deeply buried, humiliating past scenario.

Yuki’s eyes lit up with pure, unholy delight. “Oh, Charlie. That is such a good point.”

She dropped her phone onto the couch cushion, the recording light still glowing. Then she sank to her knees in front of him. Her hoodie pooled around her on the polished floor. She looked up at him, her expression one of mischievous concentration.

Before he could process what was happening, her cool fingers wrapped around his already-hard cock. He jolted, a strangled sound escaping his throat.

“Yuki… what are you…”

“Making a mess,” she said simply, her tone practical. She began to stroke him, her movements slow and knowing. Her other hand cupped his balls, gently rolling them. “Since you only get diapered when you’re messy, we need to make a mess. It’s only logical.”

His protests died in his throat, smothered by a wave of sensation so intense it short-circuited his brain. He was trapped between the utter degradation of the situation and the shocking, undeniable pleasure of her hand on him. He squeezed his eyes shut, his head falling back.

“Look at me,” she whispered.

He forced his eyes open, looking down at her. She was watching his face, studying every twitch and gasp. She stuck her tongue out, pink and waiting, just below the head of his cock.

“Come on,” she urged, her strokes becoming faster, more insistent. “Make a mess for Mommy Yuki. Do it.”

He couldn’t fight it. The coil in his abdomen tightened, snapped. With a choked gasp, he came. He came over her outstretched tongue and her fingers.

She held his gaze, her tongue flat and waiting, collecting it. A smug, victorious sparkle danced in her eyes. Then, with deliberate slowness, she pulled her tongue back into her mouth and let the pearly fluid drip from her lips onto his thighs and stomach.

“There,” she said, her voice a little thick. She grinned, a drop clinging to her chin. “Now you’re definitely messy.”

The reality of it crashed over him—the wet warmth on his skin, the taste in her mouth, the recording phone capturing it all. He felt dizzy, hollowed out, utterly conquered.

She didn’t reach for a towel. Instead, she leaned forward and began to clean his lower half with her tongue. The soft, wet strokes over his sensitive skin were a fresh, shocking intimacy. She licked his thighs, his stomach, even the spent length of his cock, with a clinical thoroughness that was more humiliating than any act of passion. When she was done, she stood up, wiped her mouth with the back of her hand, and walked casually to the hall closet.

She returned with a familiar yellow bottle of talcum powder. “Bend over the couch,” she instructed, her tone all business now.

Mechanically, he obeyed, leaning over the back of the leather sofa, presenting his reddened bottom to the room. He heard the shake of the bottle, then felt the cool, powdery spray dust over his skin. Her hands smoothed it over him, patting and spreading with a brisk, efficient touch. The scent of baby powder filled the air, cloying and infantilizing.

Then came the rustle of the diaper. She guided his legs into it, lifted it between his thighs, and fastened the tapes snugly at his hips. The padding was thick, crinkling with every slight movement. It felt absurd, restrictive, a blatant brand of his submission.

Finally, she popped the blue plastic pacifier between his lips. The silicone nipple filled his mouth, silencing any potential protest.

She picked up her phone, bringing the screen close to his face. The video now showed his own wide, dazed eyes, the pacifier, the white bulk of the diaper visible over his shoulder. “There’s my good boy,” she whispered into the microphone, her voice sweet and sticky. “All clean and comfy. Now, are you ready to dance for me?”

He could only nod, the pacifier bobbing in agreement. The deal was sealed. The dance was no longer a silly alternative to punishment. It was the final, performed proof of it.

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