Disclaimer: This fanfiction is a derivative work inspired by the animated series The Boondocks. All characters and content from The Boondocks are the intellectual property of their respective owners. This fanfiction is crafted for non-commercial, entertainment purposes only. I acknowledge that I do not own the characters or rights associated with The Boondocks, and this work is produced in the spirit of fan creativity and appreciation. All credit for the original characters and universe of The Boondocks belongs to the rightful copyright holders.
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In the quiet, suburban town of Woodcrest, life for the Freeman brothers was anything but ordinary. The sun was setting, casting shadows over their house, and another evening was happening the same way it always did.
Huey perched on the couch, his eyes fixed on the glow of the TV. Riley, sprawled out in the nearby chair, was completely absorbed in his video game, his thumbs moving with expert speed.
"Riley, you really should consider the consequences of perpetuating the stereotypes that these games propagate," Huey said with a hint of frustration, his words sounding far older than his ten years.
Riley barely tore his eyes from the screen. "Man, quit hatin', Huey! I ain't got time for all that. I'm too busy winning."
They continued their usual back-and-forth, but as the hours passed, Huey couldn't shake the feeling that something was off. Riley, normally quick with a comeback, seemed different tonight. His responses to Huey's jibes were half-assed at best. After a series of terrible losses, he'd paused the game, a troubled expression on his face, like he was wrestling with thoughts he couldn't put to words.
Finally, Huey's concern grew too strong to ignore, and he leaned in closer. "Riley, what's going on with you? You've been acting... different tonight."
Riley's gaze remained glued to the game screen, his knuckles turning white as he gripped the controller. He couldn't bring himself to meet his older brother's eyes, not when the truth weighed him down so heavily.
"Huey, why you always gotta be all up in my shit, man?" Riley replied, sounding irritated. He paused the game suddenly, freezing the chaos on the screen. "I'm just tryna relax here, and you keep buggin' me about stuff that ain't even important."
But Huey wasn't deterred; he leaned in even closer. "Riley, I know you better than anyone. Something's bothering you, and you can't just brush it off like it's nothing."
Riley's facade started to crumble, his frustration spilling over. "Damn, Huey, can't you just leave me alone for once? I ain't gotta spill all my guts to you!"
Inside, Riley's turmoil was a raging storm of emotions he couldn't control. He felt trapped. His anger towards Huey was really a way to mask his frustration with himself. He couldn't take it any longer. His gaming console, once an escape, had now become a source of frustration. He angrily tossed the controller aside, the game forgotten.
The tension in the room lingered as Riley jumped up abruptly from his chair. Huey, undeterred by Riley's attempt to evade the conversation, rose to his feet as well, a determined look in his eyes.
"Huey, I ain't playin' with you right now," Riley snapped, trying to mask the unease in his voice. "Just stay outta shit that ain't your business!"
"Humor me, Riley. You're my little brother, and when you're acting like this, it's my business," Huey insisted, his tone unwavering.
Riley paced across the room, avoiding eye contact. "You actin' like I'm out here doin' somethin' real bad. Ain't nobody got time for your lectures, man."
Huey sighed, a mixture of frustration and concern etched on his face. "I'm not trying to lecture you, Riley. I just want to understand what's going on. You're my family... I care about you."
Riley shot back, "Care about me? You don't know what's really goin' on in my life, Huey. You don't get it."
Huey crossed his arms, maintaining his composure. "Then help me understand. I've seen the fools you hang out with. Ed, Rummy, Lethal Interjection. It's not just about you; it's about the choices you're making."
Riley clenched his fists, defensive. "You judgin' my friends now? You don't know nothin'."
"I know enough to be worried," Huey retorted. "You're my brother, and I can't stand by if you're getting into something dangerous."
Riley's mask of indifference cracked, revealing a flicker of vulnerability. "This ain't about that, Huey," he said, his shaky voice lowering with each word until it was almost a whisper. "You don't know what it's like."
Huey softened his tone, his concern growing. "Then tell me. Help me understand."
For a moment, he actually considered opening up to his nosy ass brother. Just a moment. But he was desperate to maintain his facade, shook his head. "Forget this, man. I ain't got time for this shit... I'm outta here."
Huey watched his brother storm out of the room, his brow furrowed in concern. He knew something wasn't right, and he couldn't help but worry about Riley's sudden change in behavior. As the door slammed shut, Huey was left with an uneasy feeling that whatever was going on with his little brother, it was more serious than the foolishness he got up to in the past.
The hours ticked by, and as the sun sank lower, Huey's concern for Riley deepened. It was rare for his younger brother to be absent without a word for so long. Huey paced the living room, his typically calm expression revealing signs of worry.
As the scent of dinner wafted through the house, Granddad Robert Freeman grew increasingly impatient. His voice boomed from the kitchen, "Huey, where's that boy? Tell him to get down here before I have to take my belt off! I've got a hot date, and I can't let that boy ruin it for me!"
Huey let out a sigh, running his hand through his afro, and headed to the dining room where Robert was setting the table. "Granddad, you know Riley's always doing his own thing. You've left us alone for dinner plenty of times. I can handle it. Just go. We'll be fine."
Robert paused, considering Huey's words. After a moment, he grunted, "You got a point there, and if I keep my little chickadee waiting, she might fly the coup. Alright, boy, don't let me down."
Huey nodded as Robert headed upstairs to get ready for his date, singing "gonna get laid, get laid, get lay-aye-aye-aid" as he went. Once his granddad was out of earshot, Huey couldn't help but worry about where Riley could be, especially on a night when his behavior had been so weird.
While back at the Freeman household, Huey was still wrestling with the mystery of Riley's sudden disappearance, in a completely different part of town Riley was living life on the edge with the Lethal Interjection crew. They were getting high and downing hard liquor, despite Riley being way too young for it. But he couldn't risk looking like a bitch in front of his crew, so he went along with it. The night was filled with laughter, loud music, and reckless behavior.
Then, out of the blue, Thugnificent, the leader of the crew, invited a group of ladies to join them. Riley, aware of his age and growing discomfort, felt increasingly ignored and left out. He didn't belong in this world of adult indulgence. He made a quick decision. "I'ma bounce," he told the crew, but they were far too into the ladies to notice the kid leaving.
Feeling more than just a little buzzed, Riley roamed the dimly lit streets, trying to focus enough to stumble his way to the only person he could think of hanging out with at the moment--Gangstalicious. Riley staggered along, his surroundings blurry, as he navigated the barely familiar streets.
Finally, he reached Gangstalicious's crib. The rap star answered his door wearing nothing but a pair of pink silk boxers. Despite the fact that he was high as fuck, Gangstalicious could tell right away that Riley was wasted, and with a lustful leer, he invited the 8-year-old wannabe gangsta in.
"Riley!" Gangstalicious exclaimed, greeting the kid brightly as he entered the plush mansion. "I ain't seen you in a minute, lil' homie. What's good?"
Riley, still buzzing from the drinks he had little more than an hour ago, stumbled through the entry hall and into the rapper's vast living room where Gangstalicious lavishly displayed his wealth with gilded furniture, plush velvet couches, and walls adorned with platinum records. The kid made himself at home, splaying himself out on a couch.
"Yo, thanks, Licious. I had to bounce from Thugnificent crib. They bringin' all those hos up in there crampin' my style."
"Anything for a lil' homie," Gangstalicious said, taking a long drag off a blunt."
"That's what I'm talkin' 'bout. You's a real one, Lish," said Riley, his speech slightly slurring.
"Want a bump, G?" Licious asked, offering the blunt to the young boy.
"Damn, Lish, you's always hookin' a brotha up," said Riley with a wide smile, taking the joint and inhaling deeply from it. "Respect," he said through a cough.
Licious was looking Riley up and down hungrily as the kid lounged back on his couch, still drunk and getting higher by the second. "Listen, lil' homie. Why you ain't wearin' all that sick gear I sent you?"
Gangstalicious had started a clothing line that, amongst other things, included skirts, and tops that resembled sports bras, but for guys.
"Shit, my granddad be trippin', Lish. That was some fly ass gear and Young Reezy was workin' it too, not gon' lie. But then granddad trashed it all," Riley told him, the joint now down to a nub and the kid breathing it in like a pro. "That's why I ain't been over in a minute. Thought you was gon' be pissed."
"Nah, you know me, Riley. We homies. You been keepin' my secret, so I got you. Come on," Licious said, already leaving the room.
Riley dragged himself off the couch and followed the gangsta like an obedient puppy.
In one of Licious' massive bedrooms, the gangsta leaned back on his elbows on a king size bed as he watched Riley's shadow pouring out of the huge walk-in closet.
"Damn, Licious!" Riley exclaimed, his shadow moving to and fro. "It's like a whole store in here!"
"Well you know, lil' homie. I gotta keep this mug stocked and shit. Never know when--"
"Check me out!" Riley exclaimed, coming out of the closet and interrupting Gangstalicious. "Young Reezy be stylin'!"
Riley was wearing a white sports bra that Gangstalicious markets as a wife beater, and a beige skirt, a new model different from the previous skirt-shorts combo that Licious originally designed.
"Lookin' good, lil' homie," Licious said, licking his lips. "You likin' the new model?"
"Yeah, Lish! It's dope!" Riley said, spinning around to show off his new gear. "I wasn't sure at first. You know, looks like a skirt and shit, but then I was like, Licious the man. He know what he doin', and this shit tight so I'm like 'fuck it'."
"Yeah, no you right, lil' man. I'm just out here tryin' change up the game, you know? Niggas gotta get wit the new shit if they wanna live gangsta like ya boy."
Gangstalicious had gotten up and was checking Riley out hard. The little boy was oblivious to the lustful leer that his idol was giving him as he excitedly checked himself out in the full length mirror.
The mixture of weed and alcohol flooding his system had him giddy, he couldn't help smiling from ear to ear as he looked himself over in the mirror.
Gangstalicious had stripped down to his birthday suit, standing proudly behind the small boy, smiling at how incredible he looked in that sports bra that showed off his smooth midriff and that little skirt showing off his slender legs and tight, little bubble butt. Gangstalicious knew the kids would look good in this new design, but Riley was something special.
For his part, Riley's head was swimming with so much intoxication and so many thoughts that he barely paid attention to the man standing just a foot behind him. He saw Gangstalicious' naked body in all its glory as he continued to gaze at himself in the mirror.
Normally, Riley would give one of his trademark "nigga that's gay" remarks, something he used as much to hide from himself as he did to be a smart ass. But there now with his inhibitions down, he didn't feel the need to put up the same front he displayed to his brother, Huey, earlier that day. He wanted to be there with Gangstalicious. He, Riley, was one of the only people who knew the rapper was gay, so knew, even in his intoxicated state, that Licious' house was one of the only places he could be himself, the "himself" that, in a sober state, even Riley would deny existed, despite the couple of previous encounters he'd had in the rapper's home.
As if reading Riley's mind, Licious stepped forward and draped an arm over the kid's shoulders.
"And look at you too, lil' homie. You look good. Real good," Gangstalicious said softly, lowering his voice so that the effect would last. "Real good, like a real nigga."
Riley nodded along, drinking in the sound of the man's voice, feeling his breath in his ear, feeling the rough stubble rubbing against his cheek. And then he felt something else. A tongue on his earlobe.
Riley turned his head slightly and looked at the big man, the child's eyes seeing everything but yet still focusing on nothing at all.
The grin he gave told Gangstalicious everything he needed to know: the kid liked what he was doing. Licious grinned widely, knowing that this would be the moment to fully induct the kid to his hidden world.
Licking his lips, Licious began working his way down the young boy's face, planting kisses everywhere he could. His arms encircled the smaller body, pulling the youngster close, wrapping his arms around his waist, embracing him.
At this point Riley was completely lost in his world, a world where Gangstalicious, the world famous rapper who could have anyone he wanted, was kissing him, stroking him, taking control of his thoughts, making his dreams come true. And though he didn't want to admit it to anyone, including himself, Riley wanted this. The child couldn't think of a moment he'd been happier in his entire life.
After kissing the boy's neck and rubbing his torso, Licious found his target. His hand gently slid up the boy's slender legs, under the man skirt he was wearing, and cupped Riley's boy cock through the thin fabric of his underwear. The kid was already rock hard and Gangstalicious gasped, momentarily shocked at how big the kid was.
Licious had a lot of experience with cock. The young boy had to be 6 inches, and thick. Licious smiled widely at the pleasant, unlikely surprise, grasping the erection firmly, squeezing it lightly, enjoying the pleasant tingle he got every time he touched the child.
"I'm can't wait to make you cum, lil' man. You ready for it?" Licious whispered in the boy's ear, continuing to stroke the hardness between his fingers.
He heard Riley moan, a long drawn out moan that sent shivers down his spine.
Gangstalicious leaned down and was whispering sweet nothings into the boy's ear as he continued to manipulate the unnaturally large boy cock. His other hand slipped into the back of Riley's underwear, searching for his prize.
His fingers ran across the boy hole. Warm. Wet. Smelling like cherry. The rapper took his hand out momentarily to sniff his fingers, to lick them, to take in the scent and flavor of the young boy who idolized him. Then he shoved his hand back in, finding Riley's hot hole once more.
Riley groaned again, not because he wanted the big guy to stop but because he wanted him to keep going.
"Let me taste it," Gangstalicious said quietly, sucking on the boy's ear lobe and letting his hot tongue slide along it. "Tell me what I'm about to do is good, aight?"
Licking his lips, Riley tried to speak, only coming out with unintelligible mumbles and groans. He nodded his head slowly, trance-like, and Licious wasted time in removing every piece of clothing from the boy before placing him face down on the king size bed.
Gangstalicious took a moment to drink in the image of the young boy splayed out on his bed. It was the first time seeing him fully naked. His little ass was firm, round, and tight. His boy cock was definitely 6 inches long, possibly 6.5 inches, and had a nice thickness to it with a beautiful flared mushroom head.
Licious leaned down toward Riley's bubble butt, taking a cheek in each hand and, massaging them roughly, spread them wide. He was ready to feast. He'd waited too long already. He wanted to feel that fat ass in his mouth, pushing against his tongue. He wanted to suck the juice right out of the kid's little hole. And the fact that Riley wanted it, lying there, moaning lewdly, just made it better.
The man started licking the boy's crack, running his tongue up and down the crease, tickling the puckered hole with his tongue. He flicked it, teased it, nipped it with his teeth. The boy jumped slightly, letting out another moan.
Licious used his tongue to get tight boy hole good and wet, then used his thumbs to spread the kid's opening wider. Licking harder, tonguing more forcefully, trying to shove his tongue into the boy's waiting asshole, knowing the kid wanted it.
As he continued to feast on the boy's hole, dripping wet with the rapper's spit, Gangstalicious began to work a finger into the boy. He felt Riley tense up, knowing what was about to happen, and he pushed the tip inside anyway, breaking through the resistance, giving the boy some time to adjust.
When Gangstalicious felt Riley start relaxing, he pushed in another finger, stretching out the boy's asshole, preparing it for penetration. When he felt Riley relax even more, he inserted a third finger, wiggling them in and out of the hole while making his way deeper. Riley let out an audible gasp when the extra digits were stuffed inside him, almost crying out, pleading with the man.
Gangstalicious thought it was hilarious, how such a small thing could turn an 8-year-old black kid into a total slut. This was gonna be a fucking pleasure ride, alright. But first, he wanted to have a little fun, so he pulled his hand away and put his fingers deep in Riley's mouth, watching as the kid sucked them clean.
Gangstalicious licked his lips, looking down at the now sobbing boy, tears streaming down his cheeks in a confusing mixture of shame and desire. Fuck yeah, this is going to be good, the rapper thought.
Gangstalicious kissed Riley's mouth softly, tenderly, and slid one hand behind the boy's neck, pulling him close to kiss him deeply. Their tongues met in the middle, swiping each other as they searched for their partner's insides. They made out passionately, while the rapper began fondling Riley's tight ballsack and fat boy cock. Riley shudder, whimpering with desire.
Gangstalicious sucked Riley's tongue greedily as he expertly worked the kid's boyhood. As the kissing intensified, he reached under Riley's legs, lifting them onto his shoulders, letting Riley straddle his face as he swallowed the boycock in one motion.
With a large moan, Riley pressed his rod deep inside Gangstalicious' mouth, holding onto the gangsta's head as he sat on the man's shoulders, thrusting it in and out with the inexperienced quickness that only a preteen could have.
Gangstalicious closed his eyes and moved his hands to cup Riley's round ass, spreading the boy's cheeks and teasing his boy hole with thick fingers as he expertly used his full lips, talented tongue, and experienced throat muscles to give mind-blowing pleasure to the boy's throbbing dick.
Riley shuddered violently and moaned loudly again as he came hard, his oversized preteen cock spasming rapidly in Gangstalicious' mouth. As Riley was still caught in the intensity of his boygasm, Licious quickly put him face down on the bed once more and mounted him, aiming an achingly hard 10 inch member at the boy's glistening hole.
He rocked back and forth slowly, the head of his dick painstakingly prying its way into the impossibly small hole. Even with Gangstalicious' earlier tongue and finger work, Riley was tight... so unbelievably tight. Grabbing the boy's hips, Licious pushed more forcefully and the angry-looking flared head popped into the boy. The intrusion woke the boy from his euphoric trance and caused him to scream out in ear-piercing pain at the same time Gangstalicious moaned loudly.
The feeling of the slick, young hole stretched around his swollen prick turned the gangsta into an animal. Not giving Riley the time he had planned on for the kid to get used to his size, Licious started thrusting his big meat with reckless abandon into the tight ass
Riley cried out loudly as he was brutally fucked by the 20-something rapper. The young boy attempted to buck his hips forcefully, trying to buck Gangstalicious off, but he was much smaller and it only served to use up the little energy he had left.
His small body quivered and shook uncontrollably as Gangstalicious kept pounding his butt like there was no tomorrow. Gangstalicious ignored the screaming and moaning that the poor child was making and continued drilling the tiny hole.
Every second, Riley was being hurt more than the last, and he didn't think he could take any more, but Licious wasn't going to stop until he got his rocks off. If that meant taking advantage of a naive 8-year-old, then so be it.
Fucking Riley was like taking heroin; powerful and wonderful. Every muscle in his body was tense and the screams of pain mixed with the loud, harsh grunts of lust became music to his ears. His pulsing cock moved faster and faster inside the hot ass, massaging the boy's insides with every movement.
Suddenly, Riley's screams turned to moans, his whole body starting to stiffen up as he went through his second orgasm of the night. He clenched the bed sheets as Gangstalicious gave the boy's hole another hard thrust, causing his asshole to bulge outward slightly and draw more of Gangstalicious' cock inside of him.
The gangsta slammed his cock inside Riley once more, burying himself completely in the boy's ass. He moaned loudly and tightened his grip on Riley's hips as he pumped his cum inside of him, sending 8 thick jets of hot semen deep into the barely conscious 8-year-old's bowels. When the final, large wave of cum filled the boy, Gangstalicious pulled out, allowing his shaft to pulse for several seconds before collapsing beside the boy. He smiled at the tiny creature, wiping the sweat from the young boy's face. "Oh yeah, you're definitely gonna remember this," he said as he leaned over and kissed Riley softly on the cheek.