Chapter 3

Kennedy Vanderholt reclined on her silk-sheeted bed, her glossy brunette waves fanning across the pillow, her teenage body barely contained by a sheer black babydoll dress that clung to her curvaceous hips and full, heaving breasts. For weeks, her nights had burned with Trayvon Jackson’s crude emails, each misogynistic word—”Jailbait slut, I’d wreck that tight pussy with my eleven-inch black cock”—searing her mind as her fingers worked her dripping pussy to shuddering climaxes. She’d trace her swollen clit, imagining Trayvon’s towering, tattooed frame pinning her down, his piercing stare owning her. The thought of his massive, veiny cock, thick as a Red Bull can, consumed her, her obsession spiraling into a desperate need to free him from prison’s grasp.

That morning, Kennedy stood before her full-length mirror, perfecting her weaponized allure. She slipped into a scandalously low-cut pink halter top, her creamy cleavage spilling over the edges, and a white pleated miniskirt so short it barely covered her pert, round ass. Her long, tanned legs shimmered in strappy gold stilettos, each step a calculated sway of her hips. She tossed her hair, her green eyes glinting with manipulative intent, and headed downstairs to her father’s study, ready to wield her spoiled-princess charm.

Richard Vanderholt sat at his mahogany desk, his salt-and-pepper hair catching the morning light, his tailored suit accentuating his broad shoulders. Kennedy sauntered in, her perfume—a sultry mix of jasmine and sin—filling the room. She leaned against the desk, her breasts thrust forward, her skirt riding up to flash a glimpse of lacy pink thong. Richard’s eyes flicked up, a fleeting, guilty hunger crossing his face before he cleared his throat, forcing his gaze to her face.

“Daddy,” Kennedy purred, twirling a lock of hair around her finger, her voice a syrupy blend of innocence and seduction, “I need to tell you something important.” She pouted, her full lips glossy and inviting, knowing the effect it had on him.

Richard set down his pen, his brow furrowing. “What is it, princess?” His tone was indulgent, but wary, his eyes struggling to stay on hers as her cleavage beckoned.

Kennedy perched on the edge of his desk, crossing her legs slowly, the miniskirt hiking higher. “I’ve been writing to this guy ... a pen-pal. He’s in prison, but he’s not like you think.” She batted her lashes, her voice trembling with feigned sincerity. “His name’s Trayvon, and he was totally unjustly convicted. He’s so sweet to me, Daddy, and I just know he deserves a second chance.”

Richard’s face darkened, his jaw tightening as he leaned back in his chair. “A prisoner? Kennedy, are you out of your mind?” His voice rose, laced with shock and anger. “A hardened criminal? Do you have any idea how dangerous that is? You’re sixteen, for God’s sake!”

Kennedy slid off the desk, closing the distance between them, her hips swaying as she stood inches from him. She placed a manicured hand on his shoulder, her touch light but electric, her breasts hovering near his chest. “Daddy, please,” she whispered, her voice a sultry plea, her green eyes locking onto his with practiced vulnerability. “He’s not like that. He’s ... misunderstood. I know you can help him. You’re so powerful, so smart.” She leaned closer, her breath warm against his ear, her perfume enveloping him. “I just need you to hire a new legal team for him. Get him out. For me.”

Richard’s breath hitched, his hands clenching into fists on the desk as he fought the heat rising in him, her proximity stirring a shameful arousal. “Kennedy, this is insane,” he growled, but his voice wavered, his resolve crumbling under her gaze. “A felon? What kind of man is this Trayvon?”

She pouted again, her lips trembling as she pressed herself closer, her thigh brushing his. “He’s innocent, Daddy. I swear. He just needs a chance to prove it.” Her fingers trailed down his arm, her touch lingering, her body a silent promise of devotion. “You’ve always given me everything I wanted. Don’t say no to me now. Please?”

Richard’s eyes darted to her cleavage, then back to her face, his guilt warring with his weakness for her. He exhaled sharply, running a hand through his hair. “This is a mistake, Kennedy,” he muttered, but his tone softened, his resistance buckling under her manipulative wiles. “Fine. I’ll ... I’ll look into it. I’ll hire a legal team. But you stay careful, you hear me?”

Kennedy squealed, throwing her arms around him, her breasts pressing against his chest as she kissed his cheek, her lips lingering a beat too long. “Oh, Daddy, thank you! You’re the best!” She pulled back, her smile radiant, her eyes glinting with triumph as she sashayed out of the study, her miniskirt swishing, leaving Richard staring after her, his face a mask of conflicted desire and regret.

Kennedy lounged on her silk-sheeted bed, her long, glossy brunette waves spilling over her bare shoulders, her teenage body barely encased in a sheer red camisole that clung to her full, heaving breasts, the lace hem grazing her thong-clad hips. Her laptop glowed, Trayvon’s latest email open, his crude, misogynistic words—”My black dick’s gonna rip you apart when I’m free”—igniting a fire in her core. Richard had delivered, funding a high-powered legal team that unearthed a treasure trove of irregularities in Trayvon’s prosecution: a coerced witness bullied by cops, mishandled evidence conveniently “lost,” a judge with a history of racial bias. Kennedy’s heart pounded as she typed her reply, her manicured nails clicking, her pussy throbbing with each keystroke, slick with anticipation.

“Trayvon, baby,” she wrote, her green eyes sparkling with triumph, “Daddy’s lawyers are tearing your case to shreds! They found so much dirty shit—cops fucked up, and the judge was a total racist. You’re gonna be out soon, and I’m dying to feel that massive cock you showed me.” Her thighs clenched, her pussy pulsing as she imagined his 6’4” tattooed frame towering over her, his piercing stare stripping her bare, his veiny, thick cock claiming her. She bit her glossy lip, her fingers slipping beneath her lacy thong, circling her swollen clit as she pictured his rough hands pinning her wrists, his deep voice growling “slut” in her ear. Her body quaked, a breathy moan escaping as she climaxed, her obsession with his dangerous allure and imminent freedom driving her over the edge.

The next afternoon, Kennedy strutted into the upscale mall with her clique—Madison, Chloe, and Lian—their collective beauty a siren’s call, turning heads and quickening pulses. Kennedy led the pack, her plunging black crop top barely containing her bouncing tits, the hem exposing her toned midriff, paired with denim micro-shorts that hugged her pert, round ass, fishnet stockings accentuating her long, tanned legs in strappy black stilettos. Madison, the blonde bombshell, flaunted a white sports bra that strained against her perky breasts, her ripped denim shorts riding low to bare her athletic thighs, her golden tan shimmering under gold hoop earrings. Chloe, the petite redhead, wore a skintight scarlet dress that molded to her subtle curves, the hem scandalously high, revealing glimpses of her lacy thong with every step, her porcelain skin glowing. Lian, statuesque and enigmatic, shimmered in a metallic gold halter dress with a thigh-high slit, her jet-black hair cascading past her waist, her sky-high heels clicking with cool authority.

At the food court, the girls commandeered a central table, their trays dotted with untouched sushi rolls, mango smoothies, and kale salads, their focus not on food but on the lustful stares they commanded. Kennedy leaned back in her chair, arching her spine to thrust her breasts forward, her crop top straining as she sipped her smoothie, her full lips wrapping around the straw with deliberate slowness, her tongue flicking out to catch a stray drop, locking eyes with a forty-something businessman in a tailored suit, his briefcase forgotten as he stared. She smirked, uncrossing her legs to flash her black lace thong, her fishnets catching the light, making him choke on his coffee.

Madison giggled, tossing her tousled blonde hair, bending over to “pick up” a dropped napkin, her shorts riding up to bare her toned ass, drawing gasps from a trio of college boys at a nearby table, their burgers untouched as they gawked. She winked, crossing her legs to flash her pink thong again, her gold earrings glinting as she blew them a kiss.

Chloe, ever the flirt, twirled a lock of red hair, leaning forward to “adjust” her dress, her cleavage spilling out as she pouted, her hazel eyes targeting a mall security guard in his thirties, his radio crackling as he froze, his gaze glued to her pert tits. She giggled, letting her sandal slip off, her bare foot brushing the floor as she stretched, her dress hiking higher, teasing a glimpse of her thong’s scarlet lace.

Lian, cool and untouchable, sipped her smoothie with glacial precision, her manicured nail tracing the glass rim, her almond eyes locking onto a silver-haired executive in a pinstripe suit, his Rolex glinting as he shifted in his seat, his wedding ring no match for her sultry stare. She uncrossed her legs, the slit of her dress parting to reveal her sleek thigh, her movements deliberate, leaving him visibly flushed.

“Girls,” Kennedy purred, tossing her hair, her voice a sultry mix of smugness and tease, “Daddy’s lawyers are wrecking Trayvon’s case. They’ve got the cops by the balls—shady witnesses, lost evidence, the works. My thug’s gonna be out soon.” Her pussy tingled as she recalled his latest email: Gonna fuck you till you can’t walk, jailbait. She licked her lips, her breasts heaving, savoring the heat pooling between her thighs.

Madison’s blue eyes widened, her sushi roll hovering mid-air. “Kennedy, spill! What’s in those emails? Is he as nasty as you wanted?”

Chloe leaned in, her dress slipping higher, her voice a conspiratorial whisper. “Come on, girl, don’t hold out! How hot is this guy making you?”

Lian’s lips curved, her cool gaze piercing. “You’re practically glowing, Kennedy. What’s this thug saying to make you so obsessed?”

Kennedy smirked, relishing their hunger for details, her green eyes glinting as she played coy. “Oh, you know, just ... stuff,” she teased, twirling a strand of hair, her crop top riding up to flash her underboob. “He’s real intense, talks about ... dominating me. Makes me wet just reading it.” She paused, her thighs pressing together, her pussy throbbing at the memory of his words: I’d suck them titties till you scream. Their gasps fueled her, but she held back, batting her lashes. “It’s private, girls. Let’s just say he’s all man.”

Madison pouted, tossing her hair. “Ugh, Kennedy, you’re killing us! Give us something!”

Chloe giggled, nudging her. “Yeah, don’t be a tease! Is he, like, super freaky?”

Lian arched a brow, her voice smooth. “You’re hiding something big, aren’t you?”

Kennedy grinned, her body buzzing with their attention, her breasts heaving as she leaned forward, her voice dropping to a sultry hush. “Okay, fine, you nosy bitches,” she purred, drawing out the moment. “His emails are pure filth. He talks about his eleven-inch black cock, thick as a fucking Red Bull can, how he’s gonna pin me down, fuck me raw till I’m screaming his name. I’m soaking just thinking about it.” She licked her lips, her pussy pulsing, their wide-eyed stares egging her on. “But that’s not all. I ... I visited him in prison.”

Madison’s jaw dropped, her smoothie straw clattering to the table. “What?! You went to a fucking prison?”

Chloe squealed, clapping her hands, her dress hiking higher. “No way, Kennedy! You’re insane! What happened?”

Lian’s eyes narrowed, a flicker of awe crossing her face. “You’re serious? What did you do there?”

Kennedy savored their shock, her voice slow and deliberate, dripping with sensual detail. “I snuck in while my parents were away, wore this tight pink crop top, white miniskirt, no bra—my tits were practically spilling out. The guards tried to warn me about Trayvon, said he was dangerous, but I didn’t care. I walked into that visitor room, and there he was—huge, tall, all muscle, tattoos everywhere, his eyes eating me alive.”

She paused, her fingers grazing her neck, her pussy throbbing as she relived it. “We talked through the glass, those shitty handsets, and he was so fucking crude, calling me ‘jailbait,’ telling me to show him my tits. I was so turned on, I couldn’t help it—I lifted my top, let my breasts bounce free, pinched my nipples till they were hard, moaning his name while he watched.”

Madison gasped, her hands flying to her mouth. “Kennedy, you didn’t!”

Chloe’s eyes were saucers, her voice a squeak. “You flashed him? In a prison? That’s so hot!”

Lian leaned forward, her cool facade cracking. “And he just ... watched?”

Kennedy’s grin widened, her body trembling with the memory, her voice a sultry drawl. “Oh, he did more than watch. He pulled out his cock—huge, veiny, fucking massive—and started jerking it, his eyes never leaving my tits. I kept playing with myself, rubbing my nipples, my pussy soaking through my skirt, and he came so hard, splattered the glass with his cum, growling my name. The guards flipped out, dragged him away, but I was shaking, cumming right there in the booth.” She tossed her hair, her crop top straining, her pussy pulsing as their jaws hung open. “That’s how bad I want him, girls. And I’m getting him out.”

Madison shook her head, awe in her voice. “You’re a fucking legend, Kennedy. That’s the wildest thing I’ve ever heard.”

Chloe bounced in her seat, her dress slipping higher. “I can’t believe you did that! You’re, like, fearless!”

Lian’s lips twitched, her envy barely masked. “That’s ... next level, Kennedy. He’s got you hooked.”

Kennedy smirked, her green eyes glinting with triumph, her body buzzing with their worship. “Wait till he’s free, girls. Trayvon’s gonna own me, and I’m gonna love every second.” She arched her back, her tits straining against her top, drawing fresh stares from the businessman and college boys, her reign as Queen Bee unchallenged, her obsession with Trayvon’s dangerous allure burning brighter than ever.

Kennedy sprawled across her king-sized bed, her glossy brunette waves fanning over silk pillows, her teenage body draped in a sheer pink babydoll dress that clung to her full, heaving breasts, the hem riding up to bare her lacy black thong. Her laptop pinged with an email from Trayvon’s legal team, announcing his release date moved up to just one month away—thirty days until her 6’4” tattooed thug would be free. Her heart raced, her pussy throbbing as she pictured his massive, veiny cock claiming her for real. “Fuck, yes,” she whispered, her green eyes gleaming with ecstasy, her fingers grazing her slick clit through her thong, a shuddering moan escaping as she imagined his piercing stare owning her.

Her mind raced with plans to make his release unforgettable. Trayvon deserved a gift, something to blow his mind, and Kennedy knew exactly what: a pair of obscenely large, pornstar-style fake tits, the kind that would make his jaw drop and his cock hard the second he saw her. She smirked, picturing herself strutting in front of the prison gates, her new, impossibly round breasts bouncing in a skimpy top, Trayvon’s crude growls—”jailbait slut, them titties mine”—ringing in her ears. Her pussy pulsed at the thought, her fingers dipping deeper, her body trembling as she climaxed, her obsession with his dangerous allure driving her to make it happen.

The next morning, Kennedy stood before her full-length mirror, perfecting her weaponized allure. She slipped into a scandalously low-cut white halter top, the fabric so tight it molded to her curvaceous hips and perky tits, her creamy cleavage spilling over the neckline, her nipples faintly visible through the sheer material. A black leather miniskirt hugged her pert, round ass, barely covering her thighs, paired with strappy silver stilettos that made her long, tanned legs shimmer. She tossed her hair, her glossy lips parted in a practiced pout, her green eyes glinting with manipulative intent. She sauntered downstairs to her father’s study, her hips swaying, her perfume—a sultry vanilla—trailing behind her, ready to wield her spoiled-princess charm.

Richard Vanderholt sat at his mahogany desk, his salt-and-pepper hair catching the sunlight, his tailored navy suit accentuating his broad shoulders as he reviewed contracts. Kennedy eased the door open, her stilettos clicking on the hardwood, her breasts bouncing with each step. She leaned against the desk, her cleavage thrust forward, the halter top straining as she crossed her arms, pushing her tits higher. Richard’s eyes flicked up, a fleeting, guilty hunger crossing his face before he cleared his throat, forcing his gaze to his papers.

“Daddy,” Kennedy purred, her voice a syrupy mix of innocence and seduction, twirling a lock of hair around her finger, “I need to talk to you about something super important.” She pouted, her full lips glossy and inviting, knowing the effect it had on him, her body a jailbait temptation.

Richard set down his pen, his brow furrowing, his tone cautious but indulgent. “What now, princess? You’ve already got me funding a felon’s legal team.” His eyes struggled to stay on her face, darting to her cleavage before snapping back, a flush creeping up his neck.

Kennedy slid onto the edge of his desk, her miniskirt riding up to flash a glimpse of her lacy thong, her long legs crossing slowly, the motion deliberate. “First, thank you so much for getting Trayvon out,” she cooed, her voice dripping with gratitude, her manicured hand grazing his arm, her touch light but electric. “The lawyers moved his release up to next month—can you believe it? You’re, like, my hero, Daddy.” She batted her lashes, her green eyes locking onto his, her breasts heaving as she leaned closer, her perfume enveloping him.

Richard shifted in his chair, his jaw tightening, his voice gruff. “I’m glad it’s working out, Kennedy, but you need to be careful with this man. He’s dangerous.” His eyes betrayed him, lingering on her cleavage, his hands clenching the desk as he fought the heat rising in him.

Kennedy pouted, her lips trembling, her voice a sultry plea. “I know, Daddy, and I’m so grateful. But ... I’ve been feeling really bad about myself lately.” She uncrossed her legs, letting her skirt hike higher, her thong’s lace peeking out as she shifted, her breasts jiggling. “I don’t feel confident, like, at all. I think ... I think I need breast implants to feel good about myself. It’s about self-esteem, you know?” She tilted her head, her hair cascading over one shoulder, her eyes wide with feigned vulnerability.

Richard’s face darkened, his voice rising with disbelief. “Breast implants? Kennedy, you’re sixteen! You’re perfect the way you are—what’s this nonsense about self-esteem?” He leaned back, running a hand through his hair, his eyes darting to her tits, then away, his guilt warring with his frustration. “This is absurd. I’m not funding some cosmetic surgery for a teenager!”

Kennedy slid off the desk, closing the distance between them, her hips swaying as she stood inches from him, her breasts hovering near his chest, her halter dress barely containing them. “Daddy, please,” she whispered, her voice a seductive purr, her hand resting on his shoulder, her fingers trailing down his arm, lingering. “It’s not about vanity—it’s about feeling secure in my body. Don’t you want me to be happy?” She leaned closer, her breath warm against his ear, her perfume intoxicating, her thigh brushing his knee, a silent promise of devotion.

Richard’s breath hitched, his hands gripping the desk, his resolve crumbling under her proximity, her underage body a relentless temptation. “Kennedy, this is crazy,” he growled, but his voice wavered, his eyes locked on her cleavage, his arousal shaming him. “You don’t need this. You’re beautiful—too beautiful, if anything.”

She pouted again, her lips quivering, her body pressing closer, her breasts grazing his chest as she tilted her hips, her skirt riding higher. “But I don’t feel beautiful, Daddy,” she whined, her voice trembling with practiced fragility. “I need this, just like I needed you to help Trayvon. You always make everything better.” Her fingers slid to his tie, adjusting it slowly, her touch lingering, her green eyes pleading, her body a weapon she wielded with precision.

Richard exhaled sharply, his face a mask of conflicted desire, his hands twitching as he fought the urge to touch her. “This is a mistake, Kennedy,” he muttered, his tone softening, his resistance buckling under her manipulative wiles. “You’re relentless, you know that?” He shook his head, his voice resigned. “Fine. I’ll take you to a plastic surgeon—for a consultation, that’s it. Just ... give me some peace and quiet, all right?”

Kennedy squealed, throwing her arms around him, her breasts pressing firmly against his chest, her lips brushing his cheek, lingering a beat too long, her perfume enveloping him. “Oh, Daddy, you’re the best! I love you so much!” She pulled back, her smile radiant, her eyes glinting with triumph as she sashayed out of the study, her miniskirt swishing, her hips swaying, leaving Richard staring after her, his face flushed with guilt and regret, his hands trembling on the desk.

Kennedy sauntered into the sleek, marble-floored office of Dr. Michael Stein, a renowned plastic surgeon, her glossy brunette waves cascading over her bare shoulders, her teenage body poured into a scandalously tight red tube dress that hugged her curvaceous hips and full, bouncing breasts, the hem barely covering her pert, round ass. Her strappy gold stilettos clicked with each sway of her hips, her long, tanned legs shimmering, her perfume—a sexy jasmine—filling the air. She’d come to secure her gift for Trayvon, whose release was now just weeks away: turning her body into a vision to make his eleven-inch black cock throb the moment he saw her. Her pussy pulsed at the thought, her green eyes glinting with determination as she prepared to wield her jailbait charm.