Chapter Five — With Pleasure, Boss

Anna's hand shook so badly pulling down Jason's zipper became a hard task. Jason stayed kneeling between her legs, watching her flustered actions with a near-feral look in his eyes.

“The more you make me wait… the more I can't guarantee you'll be able to walk by morning.”

Anna froze, wide eyes meeting Jason's. “I—we can't. Elena—” A breathless gasp escaped her lips, words dying on her lips as Jason pinched her clit.

Pain and pleasure shot to her pussy, and it clenched, needing to be filled. She pushed down his slacks to reveal his boxer briefs underneath, and sucked in a quick breath. His cock strained against the snug fabric, a hard outline she’d only felt moments ago. Heat shot through her as her gaze lingered: she tore her eyes away too late, knowing the smug curl on his lips meant he’d caught her.

He pushed off the couch, dragged the boxer briefs down and his cock sprang free, hitting against his stomach. Anna's mouth went dry and she swallowed as Jason pushed both his slack and boxer briefs off, standing there in all his naked glory.

Anna couldn't take her eyes off his cock. Her pussy pulsed and her heart raced. His length was massive and thick, with veins just as prominent crisscrossing all over it. Without thinking, she reached out but Jason slapped her hand away before she could touch it.

“I want to be inside you. Now.”

Anna swallowed again as Jason climbed back between her legs. “I—I don't think—humph.”

Jason grabbed her thigh and pulled her under him. His voice was gruff. “It'll fit just fine, Honey.” He grabbed his cock, ran the tip along her length. Anna hissed and he tensed, muscles bunching. “You're wet and begging for my cock.”

He ran his dick along her length, coating it with her juices and Anna's legs jerked. He poked at her opening with his tip, teasing, smirking when Anna pushed her hips forward, chasing him.

“What's the magic word, Princess?” He asked, pulling back.

Anna swallowed, biting down on her lower lip. Jason moved his cockhead in a circle around her entrance, and Anna trembled, her pussy aching, clenching agonizingly.

“Please,” she choked out.

He aligned his dick at her entrance, his body taut, veins popping along his neck. “What do you want?”

He moved his hips, smirking at the look of torture on Anna's face despite his control already stretched thin.

“You—fuck me. Please,” Anna begged, and inhaled sharply when his cockhead pushed into her.

“Good girl.”

And then, without warning, he pushed into her with one thrust of his hips. Anna gasped, eyes wide, tears glistening in them as he stretched her out, filling her to the brim, pulsing against her walls. Jason grunted, holding still for a second, stunned at how tight, how fucking good she felt around him.

He circled his hips, pulled out and thrust back into her, and she whimpered, Jason's groan reverberating through her. He moved in and out of her, slowly, forehead furrowed, fingers digging almost painfully into her thigh. Anna's whispered moans filled the room as his dick brushed deliciously against her walls with each slow, calculated thrust.

She reached up to touch him, and he grabbed her hands with one of his, placed it above her. She whined, wanting to run her hands over his taut, rippling muscles.

Jason's pace slowed more. “Don't move, unless I say so.”

Anna nodded quickly, biting on her lip.

“Wrap your legs around me,” Jason grunted, his breath heavy.

Anna obeyed, and they both hissed as Jason's dick hit deeper. Whispered curses spilled from Jason's lips as his pace picked up, and Anna moaned, her legs tightening around him, her walls clenching greedily around Jason's dick.

“Fuck!” Jason cursed. He let go of Anna's hands, and wrapped his hand around her neck instead.

He pulled back slowly, dragging against her clenched walls, then slammed in harder, faster, pounding into her with a rough rhythm that left no space for air between her cries. Anna's nails scrapped against the leather of the couch, looking for something to hold onto. She brought a hand to her lips, bit down on it to stop her whimpery cries.

Jason's pace turned almost feral, each thrust deeper than the last, shattering through her clenched walls, the rhythm building until the couch creaked beneath them. Until Anna's back scraped against the couch as she bounced against him.

Her legs dropped from around him, and she grabbed hold of the hand wrapped around her throat, her nails digging into the arm. Jason's hips snapped forward faster, his dick growing inside her, and Anna thrashed under him, moved her hips forward to meet his thrusts, sobs escaping from her throat.

He grabbed her legs, placed it on his shoulders, and held them together with an arm by her knees, his other hand holding her in place by her waist. A sharp cry escaped from Anna's hips as his thrusts got rougher, harder, faster, hitting places she never knew existed. Her back arched off the couch, her cries getting louder, her nails digging into the couch as her high rolled in.

Skin-on-skin slap, wet sounds, all mingled with her cries, with Jason's grunts, the air thick with arousal.

“Fuck—you feel so fucking good,” Jason growled.

Anna's walls stretched to let him in with each thrust, and then, squeezed deliciously on his dick as he pulled out as if unwilling to let it go, driving him crazy in the process. Anna felt like his dick was hitting all the way to her stomach with each thrust forward, branding her, sending a jolt of both pain and pleasure to her core.

Jason’s thrusts turned relentless, pounding into her until Anna’s cries broke into breathless sobs. Her nails clawed at the couch, her body trembling under the sheer force of him.

Jason shifted her hips higher, tilting her pelvis so every push drove him straight into that hidden spot inside her. Anna’s back arched off the couch, her cries turning breathless, her nails digging into the leather.

“Jason—oh god—” she cried, her head snapping back as her walls clenched hard around his cock.

Jason grunted, snapping his hips faster, rougher. He slowed, deliberately, rolling his hips in a tight, circular motion, his cock dragging against her walls, then spearing forward sharply. Each rock made her shudder, each thrust wrung a broken moan from her lips.

Anna thrashed, eyes rolled back in their sockets, her back lifting high off the couch as a tremor rocked through her whole being. The lift only made Jason hit her spot harder, faster, and her vision went blank, stars dotting behind her eyes as an orgasm so strong hit her.

Anna shattered around him, her whole body shaking under him. Her scream broke against his lips when he suddenly let go of her leg, and leaned forward, caught her mouth in a kiss, swallowing the desperate sound of her orgasm. He kept thrusting forward aggressively, hand on the armrest, even as her pussy convulsed around him, and a roar tore from his throat.

He slammed deep inside her one last time, holding her there, spilling himself as she collapsed against the couch, chest heaving, body still trembling from the aftershocks. Jason stayed inside her for a beat, his breath ragged against her neck, their sweat-slicked bodies rubbing together, then pulled out slowly, watching her body spasm around the loss.

Anna's lashes fluttered, her throat working as she gasped for air. She was still trembling when Jason straightened, smirk tugging at his lips. He grabbed her still peaked nipples between his index finger and thumb, and squeezed, hard. Anna gave a muffled cry, arching.

His hands roamed her body — rubbing, squeezing, pinching, teasing — and Anna's eyes widened in shock as her body responded, his fingers leaving a trail of fire as they moved.

“I—I don't think I can go another round.” She released a breathy sigh.

“Told you, Princess,” he rasped, sweeping her up and slinging her over his shoulder like she weighed nothing. Anna let out a weak yelp, her fist pressing against his back in protest, but she was too spent to fight. Jason strode toward the bedroom. “One night you won’t forget.”

******

It was sometime after three when Jason slipped out of bed. Anna lay tangled in the sheets, utterly spent, her breathing soft, her body limp with exhaustion. Jason lit a cigarette, took a deep drag, and cracked his neck as he reached for his phone. He tapped on his chat with his personal assistant.

Jason: Prepare the jet to leave in two hours.

It took a few minutes before ellipses appeared under his text.

Ethan: Copy that. The plan?

Jason: Went smoothly. You'll get a bonus for being on standby, Ethan.

Ethan: With pleasure, boss.

He dropped the phone onto the table, smoke curling around him as his gaze slid back to the bed. Anna stirred faintly, rolling onto her side, her hair spilling across the pillow. The duvet slid down slightly, revealing a rosy peak. Jason’s expression hardened. His next drag was slow, deliberate.

He stepped closer, looming over her sleeping form, his voice low, almost tender—almost.

“Enjoy your dreams, Princess. When you wake up, everything changes.”