Rich White Jailbait for a Black Felon: Kennedy's Thug Obsession
Copyright© 2025 by Depraved_Angel
Chapter 2
Erotica Sex Story: Chapter 2 - Gorgeous, rich, sixteen-year-old Kennedy Vanderholt lives a life of luxury, wealth, and privilege. But what she really craves is a violent black convict by the name of Trayvon Jackson...
Caution: This Erotica Sex Story contains strong sexual content, including Ma/ft Consensual Heterosexual Crime School Rough Group Sex Orgy Interracial Black Male White Female Oral Sex Tit-Fucking
Over the next few weeks, Kennedy plunged deeper into her obsession with violent black criminal thugs, her luxurious bedroom in the Vanderholt mansion becoming a cocoon for her dark desires. Curled on her satin sheets, her silk camisole slipping off one shoulder, she created anonymous accounts on gritty true-crime forums and underworld chatrooms, her laptop glowing with threads about gangbangers and ex-cons. Her glossy brunette hair framed her face as she crafted posts, her green eyes gleaming with illicit thrill. To fuel her fantasies, she took provocative photos, ensuring her face and identifying details were cropped or blurred, then shared them with accounts claiming to be black ex-cons and active gangbangers. The coarse, misogynistic replies flooded her inbox, each one stoking her sixteen-year-old body, her fingers slipping beneath her thong to stroke her slick pussy as she read.
For her first photo, Kennedy posed on her bed, her body angled to showcase her curves. She wore a black lace bra, the cups barely containing her full breasts, her nipples faintly visible through the sheer fabric. A matching thong hugged her hips, the thin straps accentuating her toned thighs. She arched her back, her flat stomach taut, one hand trailing suggestively toward her navel. The image cut off at her neck, her identity hidden. A user, “StreetKing_410,” replied: “Damn, bitch, that body’s built for fuckin’. Bet I’d make that pussy scream with my 10-inch dick. You’d be my slut in a heartbeat.” Kennedy’s breath hitched, her fingers circling her clit, her teenage pussy throbbing at his crude dominance. The objectification—reducing her to a sexual plaything—sent heat flooding through her, her hips bucking as she moaned, her arousal soaking her thong.
Her second photo was bolder, taken in her bathroom’s marble shower. She stood under the spray, water glistening on her skin, wearing only a red string bikini bottom. Her breasts were bare, cropped just above the nipples, the swell of her cleavage glistening. Her wet hair clung to her shoulders, the image ending at her chin. “Gangsta4Life” responded: “Fuck, look at them titties, ready to be slapped and sucked. I’d bend you over and wreck that tight cunt, hoe. You ain’t ready for this thug dick.” Kennedy’s cheeks flushed, her fingers plunging into her pussy, the misogyny igniting her. She pictured his rough hands gripping her, his voice snarling as he “wrecked” her, her teenage body trembling as she rubbed herself, her moans echoing in the opulent room.
The third photo pushed further, Kennedy kneeling on her bedroom floor, her back to a mirror. She wore a sheer white crop top, her nipples hard and visible, and a black microskirt hiked up to reveal her thong-clad ass, her curves reflected in the glass. The image stopped below her eyes, her lips parted in a sultry pout. “ExCon_Dre” wrote: “That ass is beggin’ for a beatin’, slut. I’d smack it raw, then fuck you till you cry. You my kinda jailbait, ready to get owned.” The word “jailbait” sent a jolt through her, her underage status a forbidden thrill. Her fingers worked frantically, her pussy clenching as she imagined Dre’s hands spanking her, his dominance consuming her. She came hard, her body shuddering, her juices coating her thighs, the coarse replies feeding her narcissistic craving for dangerous attention.
Her obsession deepened, finally leading her to a local electronic prison pen-pal program. Nervous excitement churned in her stomach as she browsed the website on her laptop, her silk camisole riding up to bare her midriff. Inmate profiles scrolled by, but one stopped her cold: Trayvon Jackson. His mugshot showed a 6’4” tower of muscle, his dark skin etched with tattoos, his shaved head and piercing stare exuding menace. His rap sheet was a litany of violence: drug trafficking, gang activity, aggravated assault, extortion, pimping. The words “pimping” and “assault” made her pulse race, her teenage pussy tingling as she read. She imagined Trayvon’s massive hands pinning her to a wall, his voice growling “jailbait” as he tore her clothes, his cock filling her brutally. Fantasies of him beating a rival bloody, his fists dripping, then turning that violence on her, fucking her raw as she screamed, flooded her mind. Her thighs pressed together, her arousal soaking her thong, her body trembling with need.
Trembling, Kennedy drafted a message to Trayvon, her fingers hovering over the keyboard. She wanted to send a photo, her heart pounding as she debated safety. She opened a folder of edited images, then paused, her impulsivity winning. She chose an unedited photo, her identity fully exposed. In it, she stood in her bedroom, wearing a sheer pink babydoll dress, the hem grazing her thighs, her full breasts straining against the fabric, her nipples faintly visible. Her glossy brunette hair cascaded over her shoulders, her green eyes smoldering, her full lips parted in a provocative pout. The dress hugged her curvaceous hips, her toned legs bare, her sixteen-year-old body radiating underage allure. She looked like a fantasy made flesh, every curve screaming for attention.
She attached the photo to her message: “Hey, saw your profile. Your vibe’s intense. Thought you might like this. – K.” Her finger hovered over “send,” her stomach knotting with fear and excitement. She clicked, the message gone. Panic surged—her face, her real self, now in the hands of a violent felon. She slammed the laptop shut, her chest heaving, her green eyes wide with terror. Had she just fucked up majorly? Her body still buzzed with arousal, Trayvon’s rap sheet burned into her mind, but dread coiled in her gut as she curled up on her bed, waiting nervously for his reply, the Vanderholt mansion’s luxury no shield against the dangerous line she’d crossed.
Kennedy lay awake in her sprawling bed, the Vanderholt mansion’s opulent bedroom cloaked in darkness, the crystal chandelier a dim silhouette above. Her silk camisole clung to her curvaceous frame, the thin straps slipping to bare her shoulders, her thong barely covering her hips. Her glossy brunette hair fanned across the satin pillows, her green eyes wide with restless anticipation. Hours had passed since she’d sent Trayvon Jackson that impulsive, unedited photo, her heart still pounding with a mix of terror and thrill. Unable to sleep, her sixteen-year-old body buzzed with need, her fingers twitching toward her laptop on the bedside table. Giving in, she pulled it onto the bed, the rose-gold case cool against her skin, and opened it, her breath catching as she saw a new message from Trayvon waiting in her inbox.
She squealed, a high-pitched burst of excitement, her pulse racing as she clicked to open it. Trayvon’s words were raw, primal, unfiltered: “Yo, jailbait, you fine as fuck. That body’s built for a nigga like me to wreck. Them titties? I’d suck ‘em till you scream. That tight ass? Bet it’s beggin’ for my eleven-inch cock, thick as a Red Bull can. You my kinda slut, K. Wanna see what a real thug do to you.” His crude, misogynistic language hit her like a drug, her teenage pussy tingling as she read, her cheeks flushing. She pictured his 6’4” muscular frame, his tattooed arms pinning her down, his piercing stare promising brutal dominance. Her fingers slipped beneath her thong, stroking her slick folds, her clit throbbing as she reread “jailbait” and “slut,” her narcissistic craving for his degrading attention igniting her arousal.
Biting her lip, Kennedy typed a reply, keeping it light and flirtatious, her manicured nails clicking. “Hey, Trayvon, wow, you don’t hold back, do you? I’m just a girl who likes a guy with edge. Tell me more about you, big guy. Here’s a little something to keep you interested.” She attached a new photo, taken that night in her bedroom’s full-length mirror. She wore a sheer white crop top, the fabric clinging to her full breasts, her hardened nipples visible through it, and a pink microskirt that barely covered her thong-clad ass. Her toned legs gleamed, her glossy hair cascading over one shoulder, her face fully visible, her green eyes smoldering with a provocative pout. The image screamed jailbait allure, every curve begging for attention.
She hit send, her heart pounding, and barely had time to catch her breath before Trayvon’s reply popped up, his response quick and enthusiastic. “Fuck, girl, you tryna kill me with that body? Them nipples pokin’ through, I’d bite ‘em raw. That skirt’s askin’ for my hand to smack that ass red. I’m a stone-cold nigga, been runnin’ these streets since I was 15. Did five years for beatin’ a snitch bloody, still slingin’ dope and pimpin’ hoes before they locked me up. I’d fuck you so hard you’d forget your name, jailbait. Send more, slut, show me that pussy.” His words dripped with misogyny, his boasts of violence and pimping sending a shiver through her. Her fingers plunged deeper, two digits curling inside her dripping pussy, her thumb grinding her clit as she imagined his fists bloodied from beating a snitch, then turning that power on her, fucking her senseless.
Kennedy moaned softly, her teenage body trembling, but she kept her reply playful, teasing. “Oh, you’re bad, Trayvon! Love a guy who takes charge. I’m just chilling in my big fancy house, dreaming of someone real. What’s it like being such a badass? Here’s another pic to keep you up.” She attached a photo of herself lounging on her bed, her silk camisole hiked up to bare her flat stomach, her thong peeking above low-slung satin pajama shorts. Her legs were spread slightly, her hand resting near her inner thigh, her glossy hair fanned out, her green eyes sparkling with flirtatious heat. The image was pure provocation, her sixteen-year-old curves a siren’s call.
Trayvon’s reply came fast, his tone blunt and crass. “Goddamn, jailbait, you teasin’ with that pussy peek. I’d rip them shorts off and fuck you raw, make that rich-girl cunt mine. I’m a king in here, runnin’ the yard, breakin’ niggas who step outta line. Used to pimp bitches like you, had ‘em beggin’ for my dick. I’d choke you while I pound you, slut, make you scream my name. Show me more, hoe, I know you wet for this thug.” His vivid description of choking and pounding her sent her over the edge, her pussy clenching around her fingers, her juices soaking her thong. She pictured his massive hands around her throat, his eleven-inch cock filling her, his gang king swagger dominating her completely. Her moans grew louder, her hips bucking as she rubbed herself, her teenage sexuality spiraling.
Trying to keep it light, she wrote back, her fingers trembling. “Trayvon, you’re too much! Sounds like you rule everything. I’m just a naughty girl who likes a strong man. What else you got for me? One more pic, just for you.” She attached a final photo, taken kneeling on her bed, her silk camisole pulled down to bare one breast, the nipple hard and pink, her thong tugged low to reveal the top of her shaved pussy. Her glossy hair fell over her face, partially obscuring it, but her identity was clear, her green eyes peeking through with raw desire. The image was brazen, her underage body a blatant offering.
Trayvon’s response was immediate, his words a guttural snarl. “Fuck, slut, you showin’ that tit and pussy like a real hoe. I’d wreck you, jailbait, fuck that tight cunt till you break, then make you suck my dick clean. I’m a beast, been shankin’ fools in here, runnin’ contraband, still pimpin’ from my cell. You mine now, bitch, I’d own every inch of you. Keep ‘em comin’, I ain’t done.” Kennedy’s body shuddered, her fingers working frantically, her clit pulsing as she imagined his shank-scarred hands claiming her, his beastly dominance breaking her. She came hard, her pussy gushing, her moans echoing in the luxurious room, her teenage body convulsing with pleasure. Her laptop glowed, Trayvon’s words searing into her, her arousal insatiable as she lay panting, the dangerous thrill of his misogyny consuming her.
Over the next several days, Kennedy glided through the marble halls of her ritzy private school, her glossy brunette hair swaying, her sexy skirts hiked scandalously short to reveal her toned thighs, her white blouse unbuttoned just enough to tease the swell of her full breasts. Her green eyes sparkled with secrets, her lips curved in a knowing smirk as she strutted alongside her gorgeous friends—Madison, Chloe, and Lian—each a vision of wealth and allure. Madison’s blonde hair bounced in a high ponytail, her skirts rolled up to show off her tanned legs, her blouses tied to bare her midriff. Chloe’s red hair cascaded over her shoulders, her outfits clinging to her petite curves, her pouty lips glossy. Lian’s jet-black hair was sleek, her tailored blazers accentuating her statuesque frame, her skirt slit subtly higher than regulation. The quartet drew stares from students and teachers alike, their beauty a weapon they wielded with arrogant ease.
At lunch one afternoon, they claimed their usual table in the cafeteria, a sunlit space with floor-to-ceiling windows overlooking manicured lawns. Kennedy leaned forward, her cleavage straining against her blouse, her voice low and conspiratorial. “Girls, Trayvon’s driving me fucking wild. His messages? So raw, so nasty. Last night, he told me he’d choke me while he fucked me with his eleven-inch cock. I came so hard I soaked my sheets.”
Madison’s blue eyes widened, her fork pausing mid-air. “Oh my God, Kennedy, you’re insane! An actual convict? That’s, like, so hot. What’s he say exactly?” Her crop-top blouse rode up as she leaned in, her voice thick with curiosity.