Part 5: a new arrangement for a Vassar girl by Mark Danelaw
Part 1: an error in judgement can found here.
It was a few weeks later in Dacre’s office. Mary had finally come to settle up, figuring she owed the man.
Mary’s fingertips hovered over the chair’s leather armrest, not quite touching; as if afraid it might burn her. The office smelled of gun oil and lemon polish. “I, um,” Her tongue darted out to wet her lips, “I wanted to apologize, properly.” The words came out too fast, tripping over each other. “For running, for panicking, for…” Her gaze flicked to the umbrella stand in the corner, the one holding a slender rattan cane amidst the black umbrellas, then darted away just as quickly.
Dacre exhaled through his nose, cigarette smoke curling toward the ceiling, “Apology accepted,” Simple, final, like closing a ledger. He smiled.
She cleared her throat. “I was thinking… about enrolling at Vassar. Pre-law.”
Across the room, Lorraine snorted into her typewriter, “Gonna prosecute bad daddies for spanking their brats?”
Mary’s fingers twitched against the hem of her skirt, a nervous habit Dacre had catalogued weeks ago. The wool blend was new, stiff enough to hold its pleats but soft where it brushed her stocking tops. Vassar colours, she’d dressed for the part.
“Not just spankings,” she murmured, gaze fixed on the umbrella stand’s rattan cane. Her throat worked around the words like they were unfamiliar. “Discipline, structure,” a faint blush crept up her neck, “The kind you…”
Lorraine’s typewriter bell dinged loudly. “Jesus wept,” She didn’t look up from her filing, but the smirk carried, “Princess wants a daddy, not a diploma.”
“Be quiet Carter,” Dacre exhaled smoke through his nose, watching the way Mary’s shoulders tensed. Not the spoiled heiress anymore, just a girl with too much money and not enough sense, standing in an office that smelled of gunpowder and lemon wax
“I guess you don’t have anyone anymore,” he conceded, “Maybe we could work something out, if you are serious.”
Mary’s fingers tightened around the leather strap of her handbag, the scent of new calfskin mingling with the sharper tang of Dacre’s gun oil. She’d practiced this speech in front of her vanity mirror seventeen times, enough to know which syllables made her throat tighten, but now, under his steady gaze, the words dissolved like sugar in tea.
Mary lifted her chin. “I’ll be living alone, off-campus.” Her tongue darted out to moisten lips gone parchment-dry, “There are… certain situations where I…” The umbrella stand caught her eye again, its rattan cane casting a slim shadow across the rug.
Dacre exhaled through his nose, smoke curling toward the ceiling in lazy spirals, “Situations?”
“Late nights, Impulse decisions,” Her patent leather pumps squeaked as she shifted weight. The sound reminded her absurdly of the noise her stockings had made when Dacre peeled them off her trembling thighs that first night in the boxcar. “I need someone to… intercept me.”
Dacre studied Mary over the rim of his whiskey glass, the amber liquid catching the late afternoon light. Her patent leather pumps were polished to a mirror shine, her skirt pressed into perfect pleats, every inch the proper Vassar girl except for the way her fingers kept creeping toward the hem, twisting the fabric like a nervous schoolgirl.
“So,” he said, setting the glass down, “You want me to keep you out of trouble,” His thumb traced the condensation on the glass, “Even when you don’t want to be kept out of it?”
Mary’s throat moved visibly as she swallowed. “Yes.”
Lorraine’s typewriter fell silent.
Dacre leaned forward, bracing his forearms on the desk. The movement made his shoulder holster creak. “Be specific, Mary,” His voice was low, matter-of-fact, “You think you’ll need a good bare-bottom spanking now and then? Some corner time to reconsider your choices?” He was beginning to get as much pleasure out of wringing the humiliation out of the girl as she was being made to admit her submission.
Mary’s blush deepened to the exact shade of the raspberry-coloured welts Dacre had painted across her backside in the boxcar. Her fingers twisted in her skirt fabric, the crisp wool pleats crumpling under her grip like parchment. The umbrella stand’s rattan cane seemed to pulse in her peripheral vision, an accusing presence she couldn’t ignore.
“Yes,” she whispered, and then cleared her throat when her voice cracked. “Spankings, Corner time, when… when warranted… I mean whenever I am told,” Her patent leather pumps squeaked as she shifted weight again, the sound embarrassingly loud in the sudden quiet. Lorraine had stopped typing entirely now, her smirk practically audible from across the room.
Dacre tapped his cigarette against the ashtray. “How occasionally is ‘occasionally,’ princess?” His thumb smudged another mark on the glass rim… deliberate this time, judging by the way his eyes flicked toward Lorraine’s desk.
“I… I would need a,” she moistened her lips, “A week, by week arrangement, maybe day by day sometimes… you know if… it would really have to be up to you,”
Mary’s throat worked soundlessly for three heartbeats. The office smelled suddenly overwhelming… stale papers and Dacre’s bay rum aftershave mixing with the metallic tang of her own nervous sweat. “There might be… situations,” she managed, eyes fixed on a water stain marring the desk’s mahogany surface. “Where I’d require more… prolonged and structured discipline.”
Lorraine’s chair creaked as she leaned back. “Jesus H Roosevelt Christ,” she drawled, twirling a pencil between her fingers. “She wants the belt, boss.”
Mary’s patent leather pumps squeaked against the office floorboards and her fingers twisted the strap of her handbag so tightly the leather creaked. “Like I said… monthly would be…” She swallowed hard, the words sticking like honey in her throat, “Insufficient… I would need to know it could get… well more challenging if I didn’t respond satisfactorily.”
Dacre’s cigarette paused halfway to his lips. Behind him, Lorraine’s pencil snapped against the ledger.
Mary’s blush deepened, “Twice a week, perhaps.” The admission came out strangled, her gaze fixed on the umbrella stand’s rattan cane, “More, if… if I’ve been particularly…”
“Brattish?” Lorraine supplied, twirling the broken pencil between her fingers.
Mary’s nod was barely perceptible. The office suddenly felt airless, gun oil and lemon polish and the cloying scent of her own shame thickening the space between them. “It would be… mortifying if anyone knew,” Her voice dropped to a whisper, “But that would be your discretion, of course. There might of course be other things… but not up to me, not if it is going to work.” Mary’s face was beyond puce, more a sunburned raspberry.
Lorraine wanted to mock, but the girl had courage and the wisdom to know what she wanted… needed.
Mary’s fingers twisted the strap of her handbag until the leather groaned. The admission hung between them, raw and exposed like her backside had been in the boxcar. Dacre’s silence stretched, his cigarette smoke curling toward the ceiling in slow spirals that matched the heat coiling low in her belly.
“Other things,” he repeated, tapping ash into the tray. His thumb lingered on the glass rim, smearing another fingerprint just to watch Lorraine’s eye twitch. Mary’s patent leather pumps squeaked as she shifted the sound embarrassingly loud in the sudden quiet.
Lorraine’s pencil scratched across the ledger, deliberately slow, “Like hairbrushes,” she drawled. “Corner time with your skirt pinned up, early bedtime with no supper…” The pencil tip snapped again, “Or maybe…”
“Enough,” Dacre’s voice cut through the office like his belt had cut through the train’s cigar haze. Mary’s throat clicked audibly when he stood, his shadow swallowing her whole as he rounded the desk. The scent of gun oil and bay rum enveloped her, familiar and terrifying in equal measure.
“N-no, she is right, all of that… just as a baseline, but other stuff… scary stuff that could happen if… you know for real, for really real, and… and maybe be other stuff I might not know about or… or…”
His calloused fingers tilted her chin up. Mary’s breath hitched at the contact, her pulse hammering where his thumb brushed her jawline. “You want the embarrassment,” he murmured. “The shame of being turned over my knee like a naughty schoolgirl. Of having your bare bottom on display while you count the strokes… or the minutes….” His grip tightened fractionally. “But you’ll take more than you ask for. Because you don’t know what you need.”
Mary’s breath caught when Dacre’s thumb brushed the underside of her chin, the same way his belt had brushed the underside of her bare bottom in the boxcar. That same electric current shot through her now, tightening her stomach in a way that had nothing to do with fear. “You’re beginning to understand,” she whispered, her voice barely audible over the ticking of the office clock, “Lorraine already does, I think, what she said and… and more… perhaps much more.”
Dacre’s gaze dropped to her trembling fingers still clutching the handbag strap. “There is the belt as Lorraine said,” he mused, flicking his cigarette ash with deliberate nonchalance. “I even have a cane,” His lips quirked at the way her throat moved when he said it. “But you still think that should be the least of it?”
“Maybe Sir,” she squeaked, “Sometimes…”
“This is a big ask for a kid maybe,” Dacre said, he frowned, but he liked the idea, he liked the money that might go with it, but still…
“I am 21 now, old enough to fully consent and still young enough to benefit from… strict guidance,” she countered.
Lorraine’s typewriter clacked once. She was desperate to know how this turned out. Would she get to watch, would Dacre need to delegate?
“Maybe,” he said slowly, rolling the word like a cigar between his teeth, “you need someone who knows how to be even stricter.” His knuckle grazed her cheek, lighter than any belt stroke yet somehow more devastating. Mary’s knees buckled just enough for him to notice.
Mary could only nod. “Maybe,” she whispered.
The silence stretched between them like a taut wire, Dacre’s thumb still tracing Mary’s jawline while Lorraine’s chair squeaked ominously in the background.
Dacre finally spoke; his voice was low and measured. “It could work,” he conceded, exhaling smoke through his nose. “But it’d take some thought, serious commitment.”
Lorraine’s laugh was sharp as a whip crack. “Thought?” She spun her chair to face them, legs crossed at the ankle where her stocking seams gleamed. “Hell boss, she’s practically begging for it.” Her gaze raked over Mary’s trembling form, “You could always test her sincerity right here, right now.”
Lorraine reached into the desk draw and took out the hairbrush. Placing it on the desk she said, “your lap or mine boss. Unless little Miss Vassar’s changed her…”
“I haven’t,” The words burst from Mary’s lips before she could stop them. Her throat worked visibly as she swallowed, but her chin lifted in that same stubborn tilt Dacre remembered from the rail yard. “If… if that’s what it takes to prove I’m serious.”
Dacre looked at the brush and said, “Lorraine knows the drill, if you are in the corner when I get back… and I won’t be long… then I am going to make you regret your little request.” With that he went in search of the bathroom down the hall.
Mary’s fingers froze mid-twist in her skirt pleats. “The… the drill?” she wanted to know, she didn’t want to get it wrong.
Lorraine smirked, “Bottom half off, princess, your skirt, slip, stockings… the whole Vassar ensemble.” She nodded toward the umbrella stand’s shadowed corner. “And you’d better be planted there bare-assed by the time he gets back.”
Mary’s patent leather pumps squeaked against the floorboards as she swayed. “Completely…? I mean so that my… my behind is…?”
“Yes, facing the corner skirt and panties off, bare tushie where he can see it,” Lorraine was in her element. “Like a new-born,” Lorraine purred, plucking the hairbrush from the desk and giving it an experimental swing. The maple back caught the afternoon light with a menacing gleam, “Unless you want to explain why you’re still dressed when he walks through that door.”
Mary’s throat gulped audibly. The office suddenly felt airless. Her fingers fumbled at her waistband, the pearl buttons slipping through her sweaty grip.
Lorraine’s smirk deepened as she leaned against the desk, idly swinging the hairbrush between her fingers. “Clock’s ticking, princess,” she murmured, “Hands on head. Chin up. And don’t even think about covering that pretty backside.”
Mary shook her head in denial or something else as hastily she took her exposed womanhood and turned it to the wall to surrender the delicate target.
The office door clicked open, Dacre’s cigarette smoke preceded him, a blue-grey haze that curled around Mary’s bare shoulders like an accusatory finger. His footsteps paused just behind her. Mary could feel his gaze tracing the dip of her spine, the flare of her hips, the way her stockings gleamed against bare skin above the garters.
Dacre took in the curve of Mary’s bare bottom, pert in profile and offering an even shapelier target full on.
“First lesson,” Dacre murmured, his voice rough from cigarettes and the kind of authority that didn’t need volume. He took the hairbrush from Lorraine. “You don’t get to pick when you’re disciplined, only whether you take it like a brat or a grown woman.”
Behind them, Lorraine’s typewriter bell dinged, a single, mocking punctuation to Mary’s humiliation.
Dacre didn’t rush. He beckoned to the girl with one finger and watched as she crossed her hands in front of her sex. She could have that defiance for now, he decided, it was early days after all. Perhaps to forestall such a suggestion Mary seemed eager to get her front side over his lap quickly. Of course this presented her naked backside to him; her bare bottom now jutting up and curved towards his mercy.
“This,” he said, the hairbrush against Mary’s left stocking-clad thigh, “is the first of three.” He said, “Then twice more within the next fortnight. If you cooperate…” His hand splayed across the small of her back, fingers spanning the dimples above her bare cheeks. “…then we discuss Vassar.”
“Yes Sir,” Mary’s blush was as fire on her face, she tried to keep her breath even but her heart rate was already elevated.
“The first three… encounters… if you do come back for more, that is, are on the house. After that I will charge standard day rates seven days a week for as long as our arrangement lasts,” he told her. That was a reliable chunk of change for him and he wouldn’t feel he was taking advantage.
“I’ll pay you double, to ensure your flexibility and discretion,” Mary said at once, despite her submitted posture, she sounded almost like a grown up.
“Fair enough,” Dacre agreed, “But real work always comes first.”
“Yes Sir,” Mary said.
Lorraine grinned; she just scored a pay rise.
Mary’s pulse hammered where Dacre’s thumb brushed the base of her spine. The implication hung between them, no negotiations, no safe words, just his judgment and her obedience stretching across four years of lecture halls and dormitory beds.
“Mr Dacre, it has to end when you say so, only when you say so,” Mary said her voice hesitant and thick in her throat, “And not just this spanking…”
“You don’t know what that might…” Dacre frowned, he was up for chains, leather, rubber and all the dark that came with it… professionally and otherwise, but this kid had no idea…
“Please Mr Dacre, as hard and as long as you say… no matter if I beg… no matter what you do…” Mary insisted, “I trust you.”
Mary gasped as Dacre’s arm hooked around her waist, yanking her forward with the same effortless motion he’d used to disarm Dutch’s men. The abrupt descent over his knee sent her silk blouse riding up, exposing the vulnerable swell of her backside to the office’s stagnant air. The first smack landed before she could brace, a sharp, and the second so quickly after that Mary could scarce tell them apart. Dacre spanked hard and fast and then slow and harder until she began to wail, a continuous keening warbling note that was worse pain than she had ever felt.
“My bottom hurts, my bottom hurts,” she yelled.
“That is the idea sister,” Lorraine grinned, adjusting how she sat so that her thighs had better access to each other.
The brush’s oval left a ghostly imprint on Mary’s skin, pale at first, then deepening to raspberry pink as Dacre worked systematically from crest to thigh. She had hoped and expected to bear the spanking with dignity; determined to prove her Vassar composure, but in a minute flat she was a bawling kid and in eternal bottom hell.
Lorraine’s chair creaked as she leaned forward, her breath audible and a hand straying to massage her squirming thighs.
The brush confirmed a searing impact that made Mary’s vision blur. She’d expected pain, even wanted it in some shameful corner of her mind, but this relentless escalation tore through her defences like tissue paper.
She tried not to beg, that seemed like a betrayal, but she always knew she would. “No more, no more Mrs Dacre,” she was shrill. Her bottom burned, ached and stung all at once, “No more, please Mr Dacre… the deal is off…”
Even in purgatory, deep down Mary thanked God that the man was uncompromising and ignored her. She was now free to indulge in the relief and strangely satisfying pleasure of futile begging.
The brush continued, igniting a burn that radiated outward in concentric rings. Her fingers scrambled against the office floorboards, her feet kicked like a well spanked movie heroine, only there was no comic relief, no relief at all.
“You… you said three,” she gasped, twisting to glimpse Dacre’s impassive face over her shoulder. It was a pathetic deliberate misunderstanding, but in that moment she needed a moment of false hop.
His thumb pressed into the hottest welt, the pressure just shy of cruel. “I said three sessions,” The brush cracked down again, this time catching the crease where thigh met buttock. Mary’s shriek bounced off the wood-panelled walls, “Not three strokes.”
She knew that of course, but she was desperate now. The pain crested in waves now, each new impact layering over the last until Mary’s entire world narrowed to the searing heat across her backside.
The brush lifted again, Mary could hear the faint whistle of air before the maple connected with a wet-sounding smack that sent her stockings twisting around her knees. Her breath came in ragged gulps now, her blouse sticking to her sweat-slicked back as Dacre’s grip kept her pinned over his knee like a misbehaving child.
She’d lost count somewhere after the first million billion, the numbers dissolving into whimpers that sounded suspiciously like more pleading. Not for mercy… but for something darker, more insistent. The pain had crystallized into a sharp, bright clarity that cut through every wannabe Vassar-bred pretence.
“That’s it, princess,” Lorraine murmured, her voice thick with something that wasn’t mockery anymore, “Let it out.”
The brush landed diagonally across both cheeks, igniting fresh fire where the skin was already tender. Mary’s sob caught in her throat, half pain, half something else entirely. She hated this. Hated the way her body arched into each stroke despite herself, hated the wet heat pooling between her thighs that had nothing to do with tears. She hated that she needed this more than anything in the world and loved that she hated it with a stone cold certainty..
“Please, oh please, I’m sorry” she bawled, she needed to beg, especially as Vassar girls didn’t beg. But the pain had carved through her resolve like a hot knife, leaving her raw and exposed in ways she didn’t understand.
The brush landed again and again… hard and fast, slow and harder. Mary’s bottom was every colour red with the beginnings of small white welts.
Lorraine’s pencil snapped mid-stroke. She didn’t bother pretending to work now, her legs crossed tight at the ankle where her stocking seams gleamed, her gaze locked on the way Mary’s backside darkened under Dacre’s precision. The sight sent liquid heat pooling between her own thighs. She shifted subtly in her chair, the wood creaking beneath her as she imagined Dacre’s hands, those same hands currently holding Mary in place turning their attention to her next. The thought made her catch her breath.
Mary’s whimper when the brush landed for the umpteenth time sounded suspiciously like gratitude. Her back arched, pressing her punished flesh harder against Dacre’s knee, an unspoken plea for more. Lorraine saw it. Dacre was too focussed on the job at hand and perhaps a little on something rising in his pants. The brush answered with another stroke landing where Mary’s thigh met her fire red bottom, drawing a ragged cry from her throat that ended in a choked sob.
Lorraine’s knuckles whitened around the pencil as Dacre landed more spanks the sound crisp as gunshots in the still office. Mary’s thighs trembled where they draped over his knee, her silk stockings stretched taut over twitching muscles. Lorraine’s own legs shifted unconsciously, her garters digging into overheated flesh as she watched Mary’s backside deepen to a shade that matched the inkwell on Dacre’s desk.
Dacre was panting himself as he stopped. Mary squirmed and bucked her behind up and down, humping his thighs.
Lorraine’s own thighs pressed together involuntarily, the seam of her stockings digging into overheated flesh. She’d been in Mary’s position more times than she could count, but watching it from this angle, seeing the way Dacre’s fingers spanned Mary’s waist, the way Mary’s punished flesh darkened under his relentless precision, sent liquid heat pooling low in her belly.
“You can get up,” Dacre said.
Mary was sobbing hard, tears in freefall, a gratifying release. She didn’t hear at first. Then with encouragement from his touch she obeyed, her movements slow and unsteady as she pushed herself upright. Her blouse was fabric rucked up around her waist. Dacre’s gaze raked over her, the way the angry red welts dominated her bare bottom, the angry red giving way to purple.
“Back to the corner,” he said, nodding toward the umbrella stand. Pulling herself together Mary’s breathing was still rapid, as if she had run a race, but she didn’t protest. Her legs trembled as she shuffled forward, her punished flesh pulsing with each step.
Lorraine watched with dark amusement as Mary positioned herself, forehead pressed to the wall, hands clasped behind her back, her punished bottom on full display.
“You can stay there for at least an hour,” he said, he realised only then that he was hard where it counted, “And I don’t give a damn if anyone come in.”
“Yes Sir,” Mary agreed, but she was till panting hard. Her bottom was so on fire that it was hard to believe the spanking had stopped.
Her forehead pressed against the cool wallpaper, her punished flesh throbbing. The pain was electric, a bright, clarifying burn that stripped away every pretence until only raw truth remained. She’d had expected humiliation, expected to feel small and broken. Instead, an odd serenity settled over her like a well-worn sweater.
The corner smelled of arousal. She inhaled deeply, her red hot bottom pulsing with each breath. Behind her, Lorraine’s typewriter clattered in sharp bursts, the sound somehow soothing in its routine cruelty. She should’ve felt exposed. Should’ve burned with shame at the way her blouse clung to her sweat-slicked back, rucked up around her waist to leave her crimson-welted backside on display. Instead, she felt… clean.
All the lies had been spanked out of her, leaving only this quiet certainty: Dacre’s discipline wasn’t cruelty. It was a blade honed sharp enough to cut through all the uptown nonsense. Her fingers flexed against the small of her back where he’d ordered them clasped. The position ached, her shoulders protesting the strain, but the discomfort grounded her. Each twinge reminded her she was exactly where she belonged. She had lost her family, even betrayed by her sister, but she no longer felt alone. Her future was bright, bright red maybe, but hopeful all the same.
The final part can be found here: Part 6; The Final Redemption
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