« Spanking Stories

« Clare, Jessica and Anya


1. Caught

Spanking Story


A personal assistant comes during her strict office caning

Part 2»

Incongruous in his open-plan designer appointed penthouse, Mark's morning coffee mug rested on the dark oak dining table, FMI staring at him, blatant royal blue letters on his white china mug. He doubted many employees remembered the full company name. He'd been CEO of Fisher Malate Investments since he was twenty-five, earning tens of millions in salary, bonuses and stock options. Reinvested by FMI, his massive investment portfolio attracted the wrong women.

FMI's high-tech trading platform was white-labeled by smart brokerage firms. Its blend of lightening trades and streaming news delivered simplicity. Their own trading house drove innovation in their tech products, helping sales of their technology compete for prominence on their profit line.

Twisting his mug, he observed the letters repeated. FMI drove him, his penthouse dominated the city skyline, and he'd accumulated a supply of frequent girlfriends who entertained him. But the benchmark for girls was Clare. Beyond beautiful, his personal assistant exuded confident guts. He trusted her to execute any task, navigate or destroy obstacles, and deliver.

Five nights ago, he'd worked late. Visible through his glass office wall, she'd appeared consumed by her laptop. He'd enjoyed her flawless shoulders, elegant neckline and flowing brunette tresses, including her entire body in his nighttime fantasies. For the past year, she'd been a frequent star.

She wasn't just sexy; she broadcast inner strength and supreme confidence missing in most girls. Their professional relationship prevented his dream, however possible it felt. Slipping on his suit jacket, he polished off his coffee.

Clare finished reading the draft magazine feature about her powerful CEO. Emailing her approval to their media department, she placed her printed copy on her neat, modern desk. His firm, chiseled jaw and thoughtful expression lay staring back at her.

Having held feelings for him since he'd hired her, she'd given up on her errant thoughts. They were isolating her. Mark was off-limits. She was only his assistant.

Placing his approved list of speaking engagements on top, she covered his distracting photo. Old Clare would have slipped it underneath. She glanced through the glass wall beside her. Preoccupied by his laptop, he didn't look up. Clear of urgent tasks, she returned to her intractable problem.

FMI's computer surveillance system had once leveled false accusations against a senior lady in accounting by classifying several innocuous websites as porn. To avoid further awkward incidents, Mark had suggested she scrutinize the misuse report before passing genuine incidents to HR.

Flicking the latest report back onto her laptop screen, nothing had changed. Staying late five nights ago, in case Mark needed her, she'd begun her evening's entertainment. Impatient to re-join her heroine in her romantic online story, its adult status hadn't occurred to her. She thought of adult content as photos and videos.

Hovering her cursor on the red cross again, she considered deleting her embarrassing entries. But the surveillance system might record her treachery. Her guilt would destroy her. Fear of discovery would haunt her, and Mark would lose trust in her. A fatal situation.

She'd reported employees to HR with ease, their transgressions recorded for posterity. Reading the report yesterday, she'd already delayed her fate by twenty-four hours. Her name, highlighted in red, had sent her reeling. She hadn't slept. The head of HR would reprimand her. But worse, they would record her webpages in her employment file. Everyone would discover she enjoyed reading about girls getting punished.

It wasn't just idle curiosity. She'd always held herself to account. Tough taps from her riding crop on her thin panties had stung and marked an event worthy of unpleasant private punishment. More dramatic than painful, the crop had marked her bottom and boosted her self-respect.

Formal punishment had begun during her first job. Personal assistant to the founder, she'd screwed up. Desperate for intense pain to eviscerate her profound guilt, she'd visited Miss Roberts. The strict disciplinarian had scolded her, delivered six severe strokes of the rattan cane to her thin panties, and sent her home sore. Her genuine punishment had burned for hours. After her initial agony had worn off, she'd become horny as hell.

Pumped full of self-respect, she'd apologized to her boss, accepting his criticism with grace. Miss Roberts caned, strapped, or paddled her often. She booked appointments and her guilt didn't fester. She walked tall, her bottom sore, knowing she'd received proper punishment.

Her conscience wouldn't allow her to delete her red highlighted entries. Miss Roberts could punish her, but was powerless to delete the evidence of her offenses. Caught later, her treacherous deceit would allow no forgiveness. She must throw herself on Mark's mercy. Although embarrassing, it might contain the fallout.

Getting him coffee, she asked, "Can we talk?"

"Of course," he said, waving her in and smiling. A year ago, she'd called before he'd posted a job ad, her grapevine placing her ahead of the pack, and talked herself into a job. At the top of her game, she nailed deals and navigated his relationships with dexterity. He watched her place her laptop on his desk and settle into a black leather chair. Her short, black, stretchy dress was one of his favorites.

"I've been foolish," she said. She reached forward, highlighted the report on her screen, and spun her laptop towards him. Steeped in shame, she watched as he checked the webpages she'd visited. Her hands clasped in her lap, she gazed at her laptop lid.

"Did you consider not reporting yourself?"


"You've shown integrity. Had I discovered later, I wouldn't have forgiven your deceit." Glancing over her webpages, he'd understood her embarrassment. "Are they all similar?"


The phrase 'Bend over' drew his attention. A swift glance confirmed the heroine was getting a severe caning she deserved.

"Have you reported yourself to HR?" He hoped she hadn't.

"Not yet. I'm sorry. I'm ashamed. It was stupid. I was hoping you would forgive me."

"Do you deserve to escape justice?"

"No." She recalled the employees she'd consigned to this fate. "I deserve no leniency."

"Good. You shouldn't expect it. But a negative note on your employment record won't reflect well on either of us. I won't let you off. In your senior position, I should hold you to a higher standard. You won't repeat this madness, will you?"

"No, never."

"You deserve some of your own medicine."

Her heart flipped, falling through her stomach. "Do you mean?" she left her question hanging.

"Yes, Clare. You need caning." His eyes snapped to her exquisite legs.

Her short, black, body-con dress had slid up her slim legs. She always left the soft jersey material where it lay. Someone should appreciate her legs and he was handsome, single and powerful. His glance took some sting from his words.

"By you?" she asked.

"Unless you wish to share your transgression with others?"

She'd admired his biceps more than once. Imagining the pain they could inflict sent a shiver through her. The idea of bending for him dampened her black string panties. Paying for her mistake in shame, pain, and embarrassment beat the public alternative.

He watched her trademark confidence return to her face. "I'll expect absolute obedience, Clare. It will be a serious punishment. You deserve it."

She swept her long brunette hair aside and said, "Thank you. I accept."

"I'll cane you hard. Your bottom will be uncomfortable for several days."

Placing her shaking hands on the chair arms, she said, "I'm sorry. You're being very kind."

Deleting her errant entries, he spun her laptop back to her.

Straightening her dress sleeves, she asked, "When will you punish me?"

"I'll bring a cane tomorrow and punish you when everyone's left. You'll bend over my desk and present your bottom in your underwear." He intended to maximize her shame and deliver discipline worthy of her senior position.

Her sex clenched as she rose. "How many strokes will I get?"

"I'll decide tomorrow," he said. "Expect it to be substantial. Remember, you're a world class personal assistant and I need you."

She smiled and left his office, grateful for the professional compliment.

In front of her bedroom mirror, she stripped to her black string panties and smoothed her hands over her bare bottom cheeks. Tomorrow night they'd carry red cane marks advertising her shameful disobedience, not from Miss Roberts, but from Mark, her boss. Clear evidence of her serious disobedience, and visual proof she hadn't escaped punishment.

Hot shame drenched her and rammed her hand into her string. Pressing one hand against the wall mirror, she circled her clit fast as she watched herself masturbate. Her boss was going to give her a formal caning. She imagined him standing over her. His strict command hardened her desperate clit. Visions of herself in total surrender to him blasted furious pleasure into her panties. Her legs gave way, and she shuddered to the floor.

Relieved of her immediate stress, she shifted to her bed to get comfortable and focused on the delicious formality. She imagined standing before him, stripped to her underwear. He was forthright about her failings, delivering a harsh scolding. She took his strict dressing down on the chin, grazing her glistening nipples, picturing a proud, but humble, personal assistant ordered to bend over his massive modern desk.

She'd failed him and wanted his harsh censure. An official caning in his office thrust delicious disgrace and intense pleasure through her obedient core.

In the morning she faced her bedroom mirror in her fresh underwear. The mirror reflected an obedient and humble girl, ready to accept her painful punishment.

Forty floors above the city lights, she entered his office. Everyone had left, and she'd locked the main office door. He stood next to the window, flexing his golden rattan cane between his hands. Her breathing sped up. This morning, she'd noticed his gym bag in the corner, guessing its contents.

"You understand the computer use agreement you signed, don't you?" he asked.

His stern tone rammed a rod of solid obedience the length of her spine. "Yes, sir."

Her instinctive, humble form of address cascaded humility through her core.

"Are you paid to read adult stories?"

"No. I'm sorry." She hadn't considered her work ethic.

"You're smarter than this, Clare. But you broke the rules and deserve punishment. I'm permitting you to avoid public embarrassment. But you're a senior employee. You must receive a severe caning. Twelve hard strokes on your panties."

She met his eye, pleased he hadn't gone easy on her. "Thank you."

Despite her vivid imagination, bending before him, stripped to her panties, would demand all her courage. Ashamed of her inappropriate behavior, she would humble herself as he demanded.

He held her gaze. He'd considered six strokes, but she held a powerful position. Simple mistakes were unacceptable.

Pointing towards his desk, he ordered, "Raise your dress."

His graveled voice vibrated in her sensitive sex, dampening her panties. She'd planned to wear a formal suit to her punishment, but she couldn't raise the pencil skirt. Instead, she'd worn her long-sleeved black jersey body-con dress again. Lifting the stretch-cotton to her waist, she caught his eye. Ripping it over her head, she faced him in only her white lace underwear. She'd failed him. She needed absolute humility to win back his respect.

Her white lace bra and matching pretty panties were extra humiliation she'd assigned herself. The skimpy lace panties exposed her bare bottom. She owed it to herself and him to suffer maximum embarrassment and pain. Facing his desk, her hands by her sides, her sex heated at her humiliation.

His respect for her soared. "Bend over."

Her hardened nipples grazed the inlaid leather through her lace as she complied. Her delicate panties rose, exposing her bottom as she clutched the far side of his desk.

He stepped into position and the cane tapped her bare behind. "I hope you learn your lesson, Clare."

The cane fired into her smooth cheeks. A line of white heat lanced her bottom. She inhaled and eased her breath through her teeth. He'd hurt her. Another hard, punishing stroke drove respect into her soul. Searing her bare flesh, each agonizing stroke reached its peak intensity before another arrived.

"It's hurting. Isn't it?" he said.

"Yes, sir."

The fierce heat in her pain packed bottom screamed native respect. Her gross stupidity deserved his hardest strokes and acute suffering.

"Do you deserve more?"

"Yes, sir. Thank you" Her answer escaped her lips as her sex flung molten pleasure at her pain. His tough tone tested her self-control. Her knuckles went white, gripping the desk. Desperate to cram her hand into her panties, red alarm lights burst in her brain.

The cane fired fresh fury into her virgin skin, forcing her forward over his desk. Her nipples scored the leather through her lace as her sex pressed against its limit.

"Four more strokes," he said.

His tough tone wrapped around her sex, squeezing intense pleasure through her. Her bottom burned, but she still craved his cruel strokes.

She hissed as excruciating heat scorched into each remaining gap on her bare cheeks. Had he informed HR, they'd have learned she loved this. News of her disgrace would have spread at rumor pace. By lunchtime, her international co-workers would have known she enjoyed getting thrashed. Instead, he was punishing her. Gratitude flooded her mind as flames roared through her sex, licking the thinnest edge of her control.

"Last one," he announced.

A complex mingling of shame, honor, and pain besieged her. Her sex teetered on a precipice. The cane struck her sensitive skin. A fresh weal erupted across both cheeks. Pain surged and slammed against her sex. She came hard and cried out as her legs shuddered, her punished body convulsing with pleasure. His exquisite delivery of proper agony had blown a fuse in her brain, shattering her control. Embarrassed, she stared at his desktop.

Dropping the cane, he stroked her exposed shoulder. "Come here."

With shaking arms, she lifted herself off his desk and buried her face in his chest. His powerful arms encircled her, sheltering her mortal embarrassment.

"It's okay," he whispered. "It's a privilege."

"I'm sorry," she said into his chest.

"Don't be," he demanded. "I was very hard on you."

She nestled into his muscular chest, hiding her face, but couldn't shirk her duty. She gathered every ounce of her courage and stepped back, meeting his eyes. "Thank you for caning me. It hurts, and I deserved it."

"It's dealt with," he declared.

She smiled, proud to have thanked him and preserved a small piece of her dignity.

"Get dressed," he ordered.

Glad to have a focus, she slid her soft black dress over her underwear. The fabric caressed the raised weals, decorating her exposed bottom. She spun to face him, his well-dressed assistant, again. "Have you caned someone before?"

"It's why I understood you."

Her bottom testified to his experience. "Would you let me cook you dinner as thanks?"

His gaze examined her and contemplated her overture.

She doubled down on her gamble. "Receiving a formal caning from you has left a powerful impression. I'm not ready for this evening to end." Patience was her strong suit. She counted. If she got to ten, she'd offer them cover to escape unscathed.

She reached eight.

"I'd love dinner," he said. "I don't want the evening to end either."