« Spanking Stories

« Tamsin, Diane and Kate

 

24. Island Games (Part Three)

A driven girlfriend worsens her whipping, determined to win a competition, unaware she already has

 
     
   
«Beginning
     

Doug Diamond reclined in his blue leather swivel chair, twenty floors high, his gaze resting upon the Diamond Cross Air logo emblazoned across his far wall. Below, five tracking screens showed airborne aircraft carrying customers. He loved Sundays in his office. Fewer executives, more coal-face workers.

He'd flown old jets until profits purchased new ones. Customers had showed up because he'd chosen unserved routes with latent demand, setting prices low but fair. Traditional growth had outfoxed his over-priced competitors. They'd dismissed his chances until Diamond Cross Air had eaten their lunch. He owned his airline outright, financing his planes. Private offers valued Diamond Cross Air at four billion. It wasn't for sale.

He'd dialed down risk as his airline grew. Disaster was always a flight away. Superior focus on flawless maintenance, kind service, and efficient operations had earned customer loyalty. He'd stuck his neck out, building his route network, beating major airlines, delivering service where they didn't deign to tread. His leadership team ran a safe airline, but expansion required risk mentality paired with intense safety focus. Maybe one hundred people had the rare combination. He'd cultivated his swashbuckling image. A dash of exuberance tamed with sharp wisdom. He hadn't lost his rebellious streak, targeting it towards new opportunities instead. Like Australia. Major carriers were milking Australia-bound customers. Longer flights presented interesting challenges.

From his window, he spied the city tower containing his daughter. An obedient, beautiful girl, Daisy, had forged her own path. Famous on social media for clever fashion choices, she didn't share his flying spirit. Losing her mom at a young age, he'd given her enduring love and regular spankings. She'd become the lovely young woman he admired. He didn't understand her business, but her substantial earnings commanded respect. They'd had lunch yesterday. She'd described a major designer partnership she was shooting in her clever tv studio. Six sets gave her opportunities to showcase clothes in well-staged environments, indoor shooting lowering her costs.

He stretched his arms, flexing his joints. Behind his spotlit logo lay his safe. Not hidden, but not obvious. His assistant, Anne, knew the combination. It contained no secrets. Except one. Inside lay two iPads. Each held a personal video he'd crafted. He'd filmed one ten years ago, the other several years back. Planned, scripted and filmed in his home study, he'd kept them updated. Teaching himself to edit, he'd improved his personal production standard. It wasn't onerous.

He tapped the letter lying on his blue laminated desk. Heavy black ink showed its source. 'Australian Department of Infrastructure and Transport'. Below, it granted permission for Diamond Cross Air flights. He'd gambled and won. It never got old. He glanced through his glass wall. Beyond, busy desks ran his smooth operations. He'd started his Australian expansion, knowing he'd miss its fruition, but he wasn't out of aces. Every gambler chose what cards to keep. He'd hidden his best ace in plain sight.


On Coral Blue, Diane tore along the spotless white beach in her bright white thong bikini, yelling. Her boundless joy reached the cloudless sky. Tripping, she plunged into the soft white powder, her golden limbs splaying across the sun-drenched sand. Today was her day, Sunday.

Neil landed on her, laughing. "You can't escape," he said. "We're on an island."

"I could swim."

"No chance. You'll take your whipping."

Rolling, she kissed him, delivering deep trust. She released his lips. "Do me proud."

Caressing her cheek, he whispered, "I promise."

Wriggling from under him, she skimmed her cute bikini string, flinging her top just above the waterline before she splashed naked into the sea, diving beneath the cool waters. Following the fish, she held her breath, swimming breast stroke, rising to the surface further along the beach. Glancing around, Neil's clothes pile suggested he'd followed her. Water erupted behind her. His arms clamped around her. She grinned, failing again to escape.

His firm feet planted on the bottom, he held her against his chest. "You're not escaping your whipping."

"I wasn't trying to. It will sting far worse on wet skin."

He squeezed her tighter. He should have known. His girl didn't run from spankings. She ran towards them.

Despite the cool sea, she felt his determined manhood harden against her. "You can't fuck me yet. I need my appetite to withstand my whipping."

Her commitment to punishment made him harder. Pressing himself against her silky butt cheeks, he whispered, "You deserve it, babe."

Her heart thumped. His commitment met her definition of love. Twisting in his arms, she softened her lips onto his. His relentless manhood pressed against her. She separated, giving him space to relax into his responsibility. Wading for the beach, the sea fell away, revealing her route.

The sun dried her skin in seconds, leaving dampness embedded where it would enhance her hurt. She slipped into her stunning thong bikini, enjoying its simple tenderness against her soft skin. Private islands demanded designer bikinis. Designers didn't agree. She'd wasted hours searching for thong bikinis. Those she'd found made unnecessary fuss. The perfect thong bikini had bisected her cheeks at the mall during a layover. Unable to believe her luck, she'd bought it in four different colors, spending far less than paradise deserved.

Marked from her morning whippings, her pristine white thong bikini magnified her punished state. Rising from the beach onto the headland, she stared at the intoxicating white crystals blending into hypnotic aqua. Ben's achievements defied belief. Dropping her gaze to her sandy feet, respect flooded her. He'd caned Kate long before she'd learned her friend shared her passion for punishment. Kate's approval had boosted her certainty in her chosen course. Neil caught up, taking her hand, leading her towards her fate. Pride swallowed her. This morning, he'd twice laid their lashes across her bottom, letting her cries collapse into their clearing, sinking beneath her smoldering sting.

They entered their modest clearing. Among the dense shrubs and tall pines, they'd discovered it yesterday. Stacked beside their palm tree lay three piles. They'd foraged for fresh switches, testing their pain properties on her bare bottom. They'd already stung their distinct brands of wicked agony into her sensitive thighs. Forced to bear it, she'd stolen his toughness, blending it into her bravery. Potent power had flared into frenzied sex, worsening her second whipping.

"Bend over, Diane."

Facing her familiar palm tree, she reached out, bending forward, planting her soft palms on its firm trunk, sweeping her brunette mane onto one side. Ridges marked the trunk below her grip. She focused on them. Kate's display of duty had set sophisticated standards. Yesterday, Tamsin's extra caning had upped the stakes. She regretted giving her friend an unfair advantage. Selecting switches at dawn, Neil had beaten her before breakfast. Before lunch he'd commanded her compliance again, thrashing her thighs before whipping her bare bottom, his unrelenting authority branded for her friends to see. She'd sashayed onto the terrace, sporting a nonchalant expression.

His palm extended its authority across her bare back.

"Lower," he ordered.

Obeying his stern command, her legs straightened, raising her sore butt. She relied on him. His harsh judgements had revolutionized their relationship. Stressed by their finances, she'd asked him to paddle her. Despite rising financial comfort, their strict agreement remained in force.

"Yesterday, Tamsin took your caning for you, Diane. Causing your friend unnecessary pain was despicable behavior."

Guilt plundered her. After agreeing to ignore their phones, she'd checked her messages. Choosing Tamsin's day for her crime, she'd condemned her friend to the cane. A fresh croton switch touched her sensitive skin. Nerves discharged fear beneath its cruel caress. She tensed. Swift sting sliced into her skin. She clenched her teeth, riding its fiery force. She deserved it. Abominable behavior. Harsh blows lined fierce accord down her cheeks. A damning verdict. She bit her lip, forcing herself to respect the switch. Punishing her was its sober duty.

Fresh saplings snapped into her tender thighs. Wicked agony bit deep into her psyche. She welcomed its harshness. Refusing tears, she focused her clear eyes on the sandy ground below. She heard him swap switches. New dogwood flooded her whipped skin in fresh distress. She wallowed in her raging heat, unaware chaos had raged all day in the corporate offices of Diamond Cross Air, her name on everyone's lips. Thick Mimosa scorched her skin. Tough blows struck hard in her delicate crease. Gifting momentary relief, they rose onto her bare bottom. Wholesome, natural agony delivered deep regret. She pictured Tamsin's honorable obedience, touching her toes poolside. "Harder," she begged.

The sweet switch lashed her sore skin. Spared no mercy, she moaned, gritting her teeth against his sincere onslaught. Pain paused. She panted, negotiating with her flaming backside.

He leaned over her. "You've paid for getting Tamsin caned. Your beautiful bottom is bright red. Your thighs too."

'Beautiful' registered. She groaned, "Punish me more."

He checked her bottom. Thorough handiwork had left almost no unwhipped curves. Her thighs sported undeniable overlapping latticework. "Where?"

"Everywhere. I must win."

He sighed. She didn't understand failure. Reaching down, he lifted a mean croton switch from their dwindling pile. He wouldn't fail her.

She pacified her burning skin, urging its continued compliance. The fresh switch settled across her beaten bottom, its light presence indistinguishable from her fiery pain. Air above the island began beating hard. Rhythmic fury besieged them. She lost grip on her tree, rising. Searching upward, her determined stare hunted the helicopter. She caught sight of the blue aircraft circling the island. Yelling at Neil, she said, "An Airbus 135, I think. She's looking to land."

"We're not expecting anybody," Neil said.

She watched the sleek blue helicopter skim the distant house, its darkened glass hiding its occupants. "He's searching for safe sites. It doesn't appear planned." Deafening noise engulfed the island. Already on her toes, her instincts kicked in, declaring an emergency. Ignoring her flaming body, she raced barefoot towards the house. Reaching the lawn edge, she stopped dead. The thundering airbus was flaring just feet above Ben's expansive grass.

Standing clear, she watched the shiny machine settle on its skids. Rotors slowing, its engines subsided. Keeping clear of the quietening aircraft, she and Neil circled the lawn. A man emerged, his unsuitable black suit heading towards their pool, where everyone sat interested in various states of disarray, Tamsin and Kate shifting towels to disguise their whipped thighs.

Addressing everyone, the suit said, "Good afternoon. I'm a lawyer for Diamond Cross Air, seeking Diane."

Ben nodded, assessing the intruder's demeanor, making him wait. Reading urgency, integrity, and serious pressure, he waved towards Diane approaching around the lawn edge.

Seeing Ben's gesture, Diane met the lawyer's shifting gaze, unfazed by her unmistakable whipping. "I'm Diane."

He quoted her home address.

She nodded, swallowing her surprise. "How did you find me?"

"I'm a lawyer for the airline. The company tracked your phone. Your crew app reports your location. Please, may we speak in private?"

Waving towards the house, she led him into the deserted kitchen. White surfaces sparkled. Matching her meagre bikini, they decried his black suit.

He handed her a blue covered iPad. "Diane, I'm instructed to give you this video. You must watch it in private. After which, I'm instructed to follow your orders."

Gravitas overwhelmed the informal kitchen. Lawyers didn't land in helicopters for casual conversations. She headed towards her bedroom, ignoring her exposed state. The ominous iPad weighed down her journey. Closing her door, she perched on her bed, resting the device on her bare legs. Sea breeze teased her half-drawn drapes. Her shaking finger missed the play button. Breathing deep, she tapped the triangle again. Black dissolved. At a sturdy, wooden desk, books stacked behind him, sat Doug Diamond. She'd only met him once.

He leaned on his elbows. "Diane, you're incredible."

Tears welling, she explored his expression. She'd never known his thoughts.

"Landing that jet saved my airline. Offered a free captain's salary, you doubled down, demanding to fly. I loved you right then."

Her tears burst. She paused the video. Fate had called on her. She'd answered. Alone in the empty sky, she'd given everything, trusting her judgement. Doug had gifted her a stunning career chance. She'd seized it. Wiping her tears aside, she tapped the video.

Doug's confidence continued. "Your flight school sent weekly reports. Every page told tales of dedication, determination, and fierce attention. Honesty, accuracy, and healthy adventure peppered your flight reports from Australia. I read every single one. I've never stopped watching you. You're wise, Diane, too wise to not guess what's coming. I've known for months I was dying. I told nobody. My daughter is also learning my news today. You'll cross paths. Trust her. She knows me best. Her pity would have killed me. I'm a gambler, Diane."

She had guessed. His incredible frankness foreshadowed the extraordinary mantle she was about to receive. Incredulity slowed, passing into plain common sense.

"I've met nobody else who balances adventure, risk, and safety. You're a gambler, Diane. A trust structure holds my shares in Diamond Cross Air. You became its sole beneficiary upon my death. You own Diamond Cross Air, Diane. Every red cent. Gamble your way. Every hand you're dealt is a winner. The secret is knowing what cards to keep. I kept you. You're my ace, Diane."

She hit pause. Dignity demanded it. He'd believed in her. More than believed. Years ago, he'd known. He'd entrusted his life's work to her. Gripping the iPad, she shot her gaze beyond the window, cutting across the serene sea. Her heart settled. Beyond the distant horizon lay untold burdens, endless possibilities, and undeniable adventure.

Tapping her video, Doug warned her headless chickens would reign until she corralled them, giving her two key goals to restore instant order. Deluged in responsibility, wealth beyond her wildest dreams took a quiet back seat. Closing the iPad cover, she sat still, his trust plugging the hole in her soul.

After permitting herself a full minute, she stood. Skimming her bikini, she dusted the sand from her feet, grabbing simple black panties and matching bra. Slipping soft black leggings over her whipped body, she found a bright blue blouse intended for smart dinners. Combing her well-ordered closet, she selected low black heels. They'd do. Stepping towards her bedroom door, her heart lightened. Doug's words had set her free. She was a gambler. His ace. She'd once landed a jet, she couldn't fly. An entire fleet shouldn't concern her.

Outside her bedroom, the company lawyer waited. He handed her a single page. She scanned it, nodding. Minutes of the emergency board meeting earlier this afternoon. Folding it into the iPad cover, she walked towards the pool.

Pool discussions had failed to resolve events, except their gravity. Tamsin, seated opposite the nearest bedroom passage, saw her friend first. Shoulders set back, her cherished flight partner exuded confidence she hadn't realized she'd missed. She shushed the others.

Kate recognized Diane's extraordinary stature. Monstrous responsibility had captured her truest friend.

Jake saw his old boss emerge, conveying absolute authority. Humble, intelligent, and sharp, he'd first seen her impressive demeanor in their outback hangar.

Ben marveled at Diane. Before Kate, she'd given him endless girl advice. Now, he employed exceptional female leaders. Her gorgeous beauty radiated unrestrained command.

Neil watched his obedient girlfriend march outside. Under those leggings, her sexy skin bore his tough whipping. They all knew. Nobody else would guess. Her welted bottom and legs proved her colossal need to succeed. Her recent uneasiness had gone, replaced by remarkable calm. Calm, he recognized. He'd seen it one afternoon long ago as global headlines screamed 'Barista lands jet'.

Diane stopped on the sun-warmed stone patio, facing her friends. The lawyer, suit coat draped over his arm, took position three feet behind. Her whipped backside burned. Her legs melted in self-respect. Silence spread. Deep inside her, words rumbled, emerging into coherent speech. "Neil, I love you. Ben, thank you for sharing your wonderful paradise. I apologize, but I must leave."

Pausing, she passed her gaze over her closest friends. Tamsin, her trusted co-pilot. Jake, her friend's stunning outback success. Kate, their natural role model. Ben, favorite of girls everywhere. Neil, her boyfriend. Bending before him stood as her greatest achievement. It had called for incredible guts until she'd landed her stricken jet in a straight line. Next to that, asking him to paddle her had proved simple.

Adopting a solemn tone, she said, "It's my sad duty to tell you Doug Diamond died earlier today. He loved his airline, preparing for its future." Gesturing towards the lawyer, she said, "This gentleman brought me a profound, personal video from Doug." Her voice cracked. Collecting herself, she didn't succumb. "I've received Doug's shares in his airline. Four hours ago, in my absence, the board appointed me CEO of Diamond Cross Air."

Great gasps filled the shocked space.

Unable to suppress a modest smile, she stepped forward, waving towards the helicopter, circling her raised finger. The helicopter's blades began turning. Twin turbo whine filled paradise. Amid the emerging cacophony, she moved towards her future. Smiling at her friends, she paused on the richest. Grinning at Ben, she raised her voice. "Sorry, mate. I can't sit around your pool. I've got an airline to run."

Kate shouted, "Hang on, babe." Standing, she glanced around. "Who won?"

Tamsin stood in support.

Diane shifted her gaze towards Tamsin. Her friend radiated happiness. Kate's question hung over them. Long ago, she'd insisted Ben produce his supposed new girlfriend. Kate had brought genuine friendship. Flying beside Tamsin had bred unbeatable trust, proven way beyond words. Yet she needed words. Her heart provided. Wrapping Kate and Tamsin in her arms, she said, "You're my best friends. I won when I met you."

Tears cascaded. Between floods, Kate whispered, "Go."

Grinning through her downpour, Tamsin added, "Boss."

Diane stepped away, wiping her tears. Carrying fresh strength, she turned. Stepping beneath the rotor wash, she climbed aboard the helicopter, beside the lawyer.

She sensed Doug would have appreciated this moment's epic location. He'd dreamed up her training course. She'd lived it. Light on its skids, the Airbus lifted from the lawn. Waving to her truest friends, utter beauty unfolded beneath her. The aircraft dipped, gaining speed. Raising her gaze to the horizon, she drew its endless future into her heart. She belonged in charge. Scrolling her phone, she selected Diamond Cross Air HQ. Her call passed with alacrity to her new assistant.

"Good afternoon, Miss," her assistant said. "I'm Anne."

"Anne, nice to meet you. Please set up an all-hands meeting tomorrow at 8am." She'd watched several. Headquarters staff lined the atrium walls, filling the vast lobby. Video screens carried the show into their airport crew lounges. Active flight crews replayed the video in the crew app later. Doug had advised everyone needed to see her, her simple presence conveying massive confidence.

"Consider it done, Miss."

"And cut the miss. I'm Diane." She heard Anne's breathing relax.

Her assistant said, "He loved you, Diane."

She smiled. "I know, now. I loved him too. I'm on my way."