Still reeling, she didn't resist as he scooped her up--her lithe frame light in his arms, stilettos dangling, thong skewed--and carried her to the dining room table, a sturdy oak piece steps away. He bent her over it, her breasts flattening against the cool wood, skirt bunched at her waist, thong shoved aside. She gripped the edges, knuckles white, as he entered her hard from behind--his thick cock stretching her, each thrust a jolt that rocked the table. Her waves splayed across the surface, her moans growing desperate as he pounded into her, the rhythm brutal, primal. Just before they climaxed together, he leaned close, growling, "How does it feel to be humiliated?" She whimpered--a soft, broken sound swallowed by the cresting wave--and then they shattered, her pussy clenching around him, his release surging deep as their cries fused, her grip on the table trembling as pleasure overtook her.
He pulled out, stepping back with a harsh, "Get dressed and leave--now." Her legs wobbled as she pushed off the table, dazed and panting, stumbling to gather her blouse and skirt. She barely managed to button the blouse crookedly over her bare breasts and tug the skirt down, thong still askew, before he ushered her to the door with a curt, "Out!" She grabbed her stilettos in one hand, purse in the other, and staggered into the hallway. Outside his front door, she leaned against the wall, catching her breath as she slipped her shoes back on, fumbling to straighten her skirt and smooth her tangled waves. Her fingers shook as she adjusted the misbuttoned blouse, cursing him under her breath, her thighs still slick with their mingled release. Jake stood inside, adrenaline fading into a cold satisfaction--he'd bent her again, but her resilience gnawed at him, a whisper of doubt about how long he could hold this leash. Vanessa, humiliated yet again, felt her fury sharpen into a blade, her mind racing with vengeance as she limped down the corridor, resolve hardening with every uneven step.
The Turn: Third Encounter
At 9 a.m. on Thursday, Jake strode into Vanessa's office at Halstead Financial, closing the door with a soft click that echoed in the tense silence. She looked up from her desk, her green eyes narrowing as he approached, his hazel gaze steady and unyielding. Without a word, he reached into his pocket and placed a small butt plug on her polished desk, its black silicone gleaming under the fluorescent lights. "You're going to wear this," he said, voice low and firm. "Keep it in until I say otherwise." Her jaw dropped, then snapped shut as she shoved it back toward him, snarling, "You're insane if you think I'll do that, you twisted fuck." He leaned in, hands braced on the desk, "You'll do it, Vanessa, or the SEC gets a very detailed email by noon." She glared, fists clenching, "This is beyond sick, Jake--I'll ruin you for this."
"Lean over your desk," he ordered, stepping around to her side. "Pull up your skirt and pull down your panties and hose." Her face flushed with rage, "You're a disgusting pig," but she stood, trembling, and bent over the edge of her desk, her tailored skirt hiked up to reveal sheer pantyhose and white lace panties. She yanked them down together, exposing her ass as she hissed, "I hate you more every second." Jake pulled a small bottle of Astroglide from his pocket, squirting a cold dollop onto his fingers. He spread her cheeks, rubbing the lube around her tight hole as she flinched, "Don't you dare," but he pressed the small plug against her rim, forcing it in slowly. She gasped, then groaned in pain, "Fuck, it hurts, you bastard!" as it stretched her, her knuckles whitening on the desk's edge. He pushed until it settled inside, her breaths ragged, tears pricking her eyes. "You'll get used to it," he said coolly, wiping his hands. "I'll be back to check. Don't even think about taking it out."
At 11 a.m., he returned, locking the door behind him. "Get into position," he said, and she shot him a venomous glare, "You're a sadistic asshole," but bent over the desk again, skirt up, panties and hose down. For the next few hours, she couldn't get any work done as the sensation in her ass was so distracting--every shift in her chair sent a jolt through her, her focus splintering as she cursed him silently. He inspected her, seeing the plug still nestled in her ass, and nodded, "Good girl." He patted her ass gently, the touch igniting a fresh wave of fury as she snapped, "Don't patronize me, you creep." To her shock, he gripped the plug's base and eased it out slowly, her breath hitching as it slipped free. Before she could relax, he produced a medium-sized plug from his pocket, larger and thicker. "No, no way," she protested, but he lubed it up and pressed it against her, forcing it in as she cried out, "You're tearing me apart, you monster!" It sank in, her ass stretching painfully around it, and she slumped forward, panting. "I'll check again later," he said, leaving her seething.
At 2:30 p.m., he was back, and she tensed as he locked the door. "Over the desk," he commanded, and she complied with a bitter, "I'll make you pay for this, you sick fuck," pulling her skirt up and her undergarments down. The medium plug remained in place, and he rubbed her ass cheeks slowly, patting them as he murmured, "You're doing well--obeying me suits you." She bristled, "Fuck you," but stayed still as he slid it out, her relief short-lived. He replaced it with an even larger plug, its girth daunting as he lubed it and pushed it in. She struggled hard, her body resisting, "It's too big, damn you--I can't!" she sobbed, her expanded hole burning as it forced its way in, finally settling with a sharp whimper from her. "Keep it in," he said, stepping back. "I'll see you before the end of the day."
Before 5 p.m., he returned, and Vanessa's anxiety spiked, her eyes wide with dread as she anticipated an even bigger plug. "Position," he said, and she bent over, trembling, "Please, no more, you asshole," her skirt and undergarments dropping again. He grazed the end of the large plug with his fingertips, inspecting her ass, and she held her breath. "You've been a good girl," he said softly, calming her fears, "taking your punishment so well." She spat, "I despise you," but relief flickered through her rage. "Be at my place at 8 p.m.," he added, "and keep it in." She straightened, yanking her clothes back into place, her anger simmering as she stormed out, plotting defiance she couldn't yet enact.
That night, she arrived at his apartment, wearing a provocative outfit he'd suggested for her--a shimmering silver blouse with a low-plunging neckline clinging to her braless 34B breasts, nipples faintly visible, paired with a leather miniskirt barely covering her thighs, black stockings, and stilettos, the large plug still in her ass amplifying her discomfort. She stepped inside, eyes wet with tears, and he locked the door, guiding her to the dining room table he'd used the night before. "Bend over the table," he said, and she hesitated, then leaned forward, lifting her miniskirt as he lowered her stockings and panties ever so slowly, taking in the beauty before him--her smooth, pale skin, the curve of her hips, the plug nestled tightly in her ass. He gently rubbed her ass cheeks, his fingers brushing the plug's base, moving it slightly in and out, drawing a sharp gasp from her as her body tensed, a reluctant shudder rippling through her. "You're vile," she sobbed, but her hips twitched faintly in response.
He pulled the plug out slowly, her breath catching as it slipped free, then entered her ass with his thick cock--stretching her further, thrusting deep and steady as she gripped the table's edge. He slapped both of her ass cheeks hard, the sharp cracks echoing as red handprints bloomed on her skin, her gasp turning to a moan. She rocked back to meet him, heat building as he pounded her ass with increasing force, the table creaking under the onslaught. He reached around, his fingers finding her clit, rubbing fast, slick circles as she gasped, her pussy dripping despite her protests. Her waves splayed across the wood, her stockings slipping down her thighs, and she got into it--her hips grinding against him, her moans deepening, a hungry edge to them as he fucked her harder, his cock filling her ass completely, the tight heat driving him wild. He varied his thrusts--long and slow, then short and brutal--her ass clenching around him with each plunge, her breath hitching as pleasure overtook her resistance. "I'm sorry, Jake--I was horrible to you!" she cried out, her voice breaking as they neared their climaxes, her apology spilling just as violent waves of pleasure crashed through her--her ass pulsing around him, her pussy spasming under his fingers, her scream sharp and unrestrained. He followed, groaning low as he flooded her with thick spurts, his thrusts slowing as they rode out the aftershocks, her body trembling beneath him.