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Chapter 23
by
totallynot
What's next?
The structural integrity test
Vanessa scrambled backward, bubbles clinging to her trembling thighs as she climbed out. The cold air hit her wet skin like needles. Jack followed, dripping onto the tiles, his erection bobbing thick and angry. He seized her wrist before she could grab a towel, dragging her toward the bedroom. Her bare feet slipped on the polished floor.
The penthouse bed loomed absurdly large—a mountain of silk sheets beneath a crystal chandelier. Jack shoved her onto it. Vanessa bounced once, her wet hair plastered across her face. She tasted chlorine and panic. Jack climbed over her, knees sinking into the mattress on either side of her hips. His hands pinned her wrists above her head. The predatory gleam was gone from his eyes; now they held only hunger.
"Please!" Vanessa gasped, arching uselessly beneath him. "Let go of my wrists! I'll do as you say—there's no need to be so rough..." Her voice broke as his thumb dug into the delicate bones of her wrist. She felt terrifyingly small beneath him, despite the immense size of her breasts. The bracelet — that cursed band marking her as public property — bit into her skin where his grip overlapped it.
Jack leaned down until his lips brushed her ear. "Rough?" His chuckle vibrated against her throat. "This is foreplay, shortstack." His free hand slid down her flank, fingers splaying possessively over her hipbone before dipping between her thighs. Vanessa instinctively clamped her legs together, trapping his wrist in a vise of slippery panic.
He didn't **** them apart. Instead, his thumb pressed hard against her clit through the wet tangle of pubic hair. Vanessa gasped, a sharp, involuntary sound ripped from her lungs. Heat flooded her belly—shameful, unwanted heat that contradicted the terror screaming through her veins. Jack’s smile widened as he felt her tremble. "See?" he murmured. "Your body’s smarter than you are." His thumb began slow, grinding circles.
Vanessa bucked, trying to dislodge him, but his weight pinned her hips. "Stop!" she choked out. "Please—just... use my breasts!" The words tumbled out, ****. "They're... they're big enough! You don't need to—"
Jack froze. His thumb ceased its relentless circling. Slowly, he lifted his head, studying her face—the flushed cheeks, the wide, terrified eyes. A slow, calculating smile spread across his lips. "Is that what you want?" he murmured, his voice dangerously soft.
"Yes... that's what I want...", Vanessa panted hastily.
Jack released her wrists abruptly. He rolled onto his back beside her, the mattress groaning under his weight. His erection stood rigid against his abdomen, glistening under the chandelier's cold light. "Prove it," he commanded, gesturing toward his cock with a jerk of his chin. "Show me why I should settle for second best."
Second best? Vanessa almost felt her breasts had just been insulted. Either way, she know she had to perform well if she wanted to salvage the purity of her genitals. She was also surprised that Jack seemed to assume a passive role, wanting her to do the deed herself. The last time on the beach she basically only needed to lie back and endure.
Vanessa scrambled onto her knees, water dripping from her hair onto the silk sheets. Jack watched, propped on his elbows, his expression unreadable. She positioned herself over his hips, her enormous breasts hanging heavy above his erection. Her fingers trembled as she reached down, cupping her own flesh, guiding the soft, wet mounds to encase his shaft.
After Jack's cock had completely vanished into Vanessa's cleavage, she tentatively started to move her mountain of boob flesh up and down, watching her expression closely.
Jack groaned, his hips lifting off the mattress. "Harder," he commanded, his voice tight. "Use your whole body."
Vanessa hugged her breast package tighter until her hands joined with her elbows, squeezing much tighter around Jack's cock. She clenched her abdomen and started moving her entire upper body in unison, as if doing crunches on a slightly more exotic gym device.
Jack cursed under his breath, his knuckles white where he gripped the sheets. "Yes..." he hissed, his hips lifting to meet her downward thrusts. Vanessa felt the friction building—skin against skin, slick with bathwater and sweat. Clopping sounds filled the penthouse suite as pounds of breast flesh slammed against Jack's lower body time after time.
She kept her gaze fixed on his face, searching for any sign he might change his mind. His jaw was clenched, eyes squeezed shut. Good. He seems to be enjoying her "second best" well enough.
Vanessa pushed harder, leaning her weight into each downward motion. Her breasts slammed against his abdomen with wet slaps that echoed in the spacious suite. Jack’s hips snapped upward, driving himself deeper between her mounds. A bead of sweat trickled down his temple.
"Is he close?", Vanessa tried to judge.
Jack's hips bucked violently beneath her. "Faster," he gasped, his voice ragged. Vanessa obeyed, slamming her breasts against his abdomen with rhythmic **** and a quicker pace. The wet slapping sounds grew louder and faster, mingling with Jack's choked groans.
His hands shot up, grabbing fistfuls of her hair. "Don't... stop..." Vanessa kept her eyes locked on his strained expression — the flared nostrils, the sweat-slicked forehead—as she maintained the frantic pace. His cock throbbed violently between her breasts. The frantic rhythm faltered as Jack suddenly arched off the bed, a guttural cry tearing from his throat. Warmth flooded Vanessa's cleavage, thick and sudden, as his release pulsed against her sternum.
Jack collapsed back onto the sheets, chest heaving. Vanessa froze, her own breath ragged, sticky trails of semen sliding down her skin toward her ribs. She didn't move until his grip slackened in her hair. Slowly, she peeled her breasts apart, revealing his softening cock glistening against his abdomen. Bridges of thick cum, much more copious than in the last tittyfuck she experienced, clinged from side to side.
"See?" Jack murmured, his eyes still closed. "Structural integrity... confirmed." A lazy smirk touched his lips. He didn't move as Vanessa slid off the bed, her knees trembling. She grabbed a towel from the floor, wiping her chest with rough, hurried strokes.
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Unfortunate Tales of Vanessa
Sexual Misadventures
Vanessa is just a normal girl who wants a normal life. Too bad her body makes her a target. Watch as Vanessa tries to prove she isn’t defined by her body, and all the terrible situations her body gets her into.
Updated on Mar 2, 2026
by GoodEndingEnthusiast
Created on Apr 23, 2022
by Bigbooblover5
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