Chapter 28: Enduring the Game: The Slingshot of Shame

“Okay, then, why don’t you start with taking those things off,” Omari commanded, his tone calm but filled with authority. He leaned back casually, watching her with the kind of confidence that sent chills through Sylvia’s already trembling frame. “It’s almost see-through anyhow,” he added, almost amused by her futile attempt to remain covered.

Sylvia stood frozen, her heart pounding in disbelief. She couldn’t grasp the reality of being ordered to strip so casually by Omari and his friends. The absurdity of the situation—the way they demanded this from her with such nonchalance—was overwhelming. How had she ended up here, in this moment, powerless before them?

Her hands shook as they hovered near the hem of her running shirt. The fabric clung to her body, damp with sweat, almost transparent, offering little protection to her already vulnerable form. Her breath was shallow, ragged, as she tried to muster the courage to defy them, but fear gripped her tightly, freezing her in place. Slowly, she began to pull the shirt over her head. The soft cotton slipped away, revealing her bare chest to the cool air. Her breasts, full and round, were now exposed, her skin flushed pink with embarrassment. Sylvia hugged her arms around her body, but it did little to shield her from the humiliating gaze of the boys.

The final step was harder. With trembling fingers, she hooked her thumbs into the waistband of her white nylon panties, the last shred of dignity she had left. She hesitated, feeling as though time had slowed, each second stretching unbearably. But Omari’s gaze never wavered, unrelenting and expectant. Slowly, painfully, she pulled the panties down her legs and let them fall to the floor, leaving her completely naked.

Standing there, Sylvia crossed her arms over her chest, trying in vain to cover herself. Her hands trembled as they pressed against her breasts, and she squeezed her thighs together, hoping to hide as much as she could. Her long hair clung to her back, slightly damp, her head bowed in shame. She felt utterly exposed, as if the walls of the room were closing in around her, suffocating her under the weight of their stares.

Omari and his friends remained silent for a moment, transfixed. They had expected to see her naked, but the reality of it struck them harder than they had imagined. Sylvia was breathtaking, her skin glowing softly in the dim light, her body far more stunning than any of them could have anticipated. Her large breasts, perfectly shaped, hung naturally, and her modest attempts to shield herself only made her appear more vulnerable, more desirable. There was an air of fragility to her, and it captivated them all, leaving the room filled with a palpable tension that thickened with each passing second.

“Please raise your hands above your head, Mrs. Sylvia,” Omari said, his voice unnervingly polite, just as he often spoke to her in the classroom at the school where she was the instructor. But this wasn’t a classroom. Sylvia stood in her small, dimly lit cabin, her naked body trembling as she cupped her shaven vulva tightly with her right hand, her face flushed crimson with embarrassment. She felt exposed in a way she had never known before, the vulnerability of her situation pressing down on her like a weight she couldn’t lift.

Sylvia hesitated, her mind racing, every nerve in her body screaming at her not to obey. But the fear, the dread of what they might do if she resisted, silenced her defiance. Slowly, painfully, she began to raise her hands. Her fingers shook as she lifted them above her head, her arms now fully exposed, revealing her bare body entirely to their hungry eyes. Her hands, no longer shielding her, left her most intimate parts on full display.

Usually, their eyes would flicker between her full, heavy breasts and her shapely hips, but now their focus was singular. All of their attention, all of their fascination, was fixed on her shaven vulva, freshly exposed under the soft light of the room. Sylvia’s smooth pubic mound gleamed slightly with perspiration, her skin taut and sensitive under their scrutiny. She wanted to disappear, to melt into the floor and escape the intense gaze of the boys who stood too close for comfort.

“Wow, looks like a baby’s butt,” Jumba said, his voice filled with mocking awe as he crouched down, getting a better view. The others laughed, their cruel amusement filling the air, making Sylvia’s cheeks burn hotter.

Kumba squatted down beside Jumba, leaning in closer. “She must have done it just for us, huh?” he sneered, smirking as his eyes roamed over her naked form. “All smooth and ready. Isn’t that right, Mrs. Sylvia?” The taunt in his voice was unmistakable, and the others chuckled again, feeding off the humiliation radiating from her trembling body.

Sylvia stood rigid, her arms still above her head, her face a mask of shame. The room felt smaller, the walls pressing in on her as she fought to keep her tears at bay. Her breath came in shallow, shaky gasps as the five of them squatted closer, their faces inches from her most private area. The boys crouched low, examining her shaven vulva with vulgar fascination, their eyes roving over the soft, smooth skin, her labia barely visible in the dim light. She could feel their hot breath on her skin, the closeness of their bodies amplifying the horror of the moment.

Omari was the closest, his gaze intense and unrelenting. “Perfect,” he whispered, more to himself than to anyone else, his fingers twitching as if resisting the urge to touch her. The room was filled with a thick tension, the air heavy with Sylvia’s shame and the twisted satisfaction the boys took in her humiliation.

Sylvia’s legs trembled as she stood there, utterly defenseless, her body completely on display for their inspection. Every part of her felt exposed, vulnerable, the heat of their stares making her skin prickle with discomfort. She had never felt so powerless, so small, as she did in that moment. And all she could do was endure, her mind retreating further into itself with each passing second as the nightmare continued to unfold.

“Wow, Snowflake’s pussy is so fat and pink. Is this normal? Is a woman’s pussy supposed to be this fat?” Jumba asked, his eyes wide with curiosity. He had never seen many naked women up close, except in the magazines they passed around and, of course, Sylvia’s during these twisted encounters.

“No, dummy,” Omari scoffed, rolling his eyes. “She played the pussy-whacking game with Matumbo today. I told you that. Her pussy is swollen from that. Before the game, it was plump but not swollen like this, and her skin was white—really white—not this pinkish color. It’s a really pretty pussy when it’s not all swollen.” Omari’s tone was filled with a strange sense of pride, as if he were the authority on Sylvia’s body, having been the only one allowed to watch her “session” at the Aprico Island School earlier that day. He spoke as if it was some kind of privilege, as though what had happened wasn’t an act of cruelty but a game he had been lucky enough to witness.

Sylvia’s heart sank as she listened to them speak about her so casually, so carelessly. How could they call it a game? It had been torture. Matumbo had tied her by her breasts, suspending her painfully while forcing her legs open for everyone to see. He had taken a rubber rod and repeatedly struck her vulva, each blow sending waves of agony through her body. It wasn’t play. It wasn’t fun. But the way they spoke about it, as if she had willingly participated, made it even worse. They acted as if her suffering had been part of some twisted entertainment.

Her thoughts were interrupted by Omari’s voice cutting through the haze of shame. “I just said your pussy was really pretty. What do you say? Don’t be rude.”

Sylvia’s stomach twisted in knots, her mind racing as her humiliation deepened. She knew she had to answer him, knew that any hesitation would only make things worse. Her hands remained obediently raised above her head, her arms trembling as she kept them as straight as possible, just as she had been taught. She had learned that when they told her to raise her hands, they meant high—high enough to stretch her body, to make her feel even more exposed. She clenched her teeth, forcing herself to speak through her quivering lips.

“Th ... thank you,” she stammered, her voice barely audible.

Omari raised an eyebrow, a smug smirk on his face. “Thank you for what?”

Sylvia swallowed hard, her humiliation burning hotter with each passing second. She could feel the boys’ eyes on her, waiting for her response, feeding off her shame. “Th ... thank you for t ... telling me ... my p ... pussy ... is p ... pretty,” she forced out, her voice shaking, each word feeling like it was tearing her apart from the inside.

The boys chuckled softly, their satisfaction palpable. Sylvia’s humiliation was complete, her body trembling as she kept her hands high above her head, her breasts rising and falling with each shallow breath. She could feel her arms beginning to ache, but she didn’t dare lower them. She knew the punishment for disobedience, and she had learned that keeping her hands straight and high, no matter the strain, was the only way to avoid making things worse.

Sylvia stood with her hands raised high above her head, trembling slightly as she fought to keep them still. The boys stood around her, watching intently, their eyes glinting with amusement. She was painfully aware of her nakedness, her body exposed and vulnerable under their gaze. Her large, swollen breasts, having been tightly bound and slapped for hours, ached with every slight movement, the skin still red but no longer as dark as it had been earlier in the afternoon. The marks from their hands were fading, but the deep tenderness remained, a constant reminder of the day’s abuse. Her vulva, naturally plump and firm, was now swollen and pink, throbbing with a dull pain.

Omari stepped forward, a smirk playing on his lips. “As promised, I will give you the magic healing oil,” he said, his voice light but mocking. “You do need it desperately, we all can see.”

Sylvia’s breath caught in her throat as he spoke. She knew he was right. The oil could soothe her pain, heal her bruises, make her skin smooth again. It was real magic, something she had come to rely on in her torment. But the price was humiliation. She braced herself, mentally preparing for what was to come. She knew they would rub the oil on her themselves, their hands exploring her body in ways that would make her squirm with shame. But this time, she told herself, she would fight it.

“I’m going to focus,” she thought, squeezing her eyes shut for a moment. “I’ll think of something else. I won’t let myself get aroused.” But deep down, she knew better. She always told herself this, always tried to resist. Yet each time, her body betrayed her, the embarrassment of being so easily aroused overwhelming her. She hated it — hated the way she would lose control, how her body would heat up, how she would fight against the rising sensation only to end up with a humiliating squirting orgasm, helpless to stop it. But she couldn’t help trying, desperate to preserve whatever shred of dignity she had left.

Omari’s grin widened as if he could read her thoughts. “But,” he added, his tone shifting, “we’ll play one game before I give you the oil.”

Sylvia’s heart sank. She knew what “game” meant. It meant more pain, more humiliation. A game for them, but a torment for her. She looked at him, her voice trembling as she begged softly, “Please ... I’m already so sore...”

Omari raised his hand as if to reassure her, though his eyes gleamed with mischief. “Yes, I know. So, we won’t play with your titties or pussy, okay? What do you say?” His voice was smooth, taunting, as if he were doing her a favor.

Sylvia, grateful but still terrified, stammered, “Th ... thank you...”

Omari chuckled softly, nodding. “Yup, in fact, the game we’ll play is good for you. A training of sorts.” He circled around her slowly, watching her body tense at his words.

Her brow furrowed in confusion. “W ... what?”

Omari stopped behind her, his voice lowering as he explained, “How to squeeze your asshole is the game.” He paused, letting his words sink in. “You know, as much as you like sticking things up your ass, and as often as you do that, your asshole might, sooner or later, get loose. I mean, I’m sure it’s tight now, you’re young, but it’s gonna become like an old woman’s asshole soon if you don’t do this type of squeezing exercise.”

Sylvia’s face flushed red with humiliation as she realized what he was saying. The shame of it burned in her chest, but she couldn’t argue. It was true, and the boys knew it too. Though the magic oil made her body tight and whole again within minutes, she felt a creeping worry. What if she did get loose over time? She hadn’t thought about it before, but now Omari’s words echoed in her mind, filling her with doubt.

But the thought of doing the rectum squeezing exercise in front of these boys, with them watching her every move, made her stomach churn. Her anus, still tight after just a week of torment, didn’t need this training — not now, not in front of them. She glanced at Omari, her mind racing, but she knew she had no choice. The shame would only deepen, and the magic oil would only come after the game.

Kumba stepped forward, a smirk on his face as he crouched down and set two small wooden boxes that he brought with him and placed them on the floor. Each one was about 10 centimeters in length and height, just wide enough to place a foot on, but not so large that Sylvia could stand on them comfortably. The boxes were positioned slightly wider than shoulder-width apart.

“Stand on these,” Kumba ordered, his voice firm but casual, as if this were just another routine task.

Sylvia hesitated, the weight of their eyes on her body making her stomach twist. Slowly, she lifted one foot and placed it on the first box, her toes hanging over the edge. The wood was smooth but small, forcing her to balance carefully, her heels and toes extending beyond the edges. She placed her second foot on the other box, her legs apart. The position wasn’t terribly difficult, but it was unstable enough to keep her constantly shifting, her feet aching as she worked to maintain her balance. Her heart raced, the humiliation of standing like this in front of the boys swelling in her chest.

Omari’s voice cut through the silence, calm yet commanding. “Now,” he said, stepping closer, “bend over slightly. About 45 degrees, yes ... yes ... like that. Now, reach back and spread your buttocks.”

Sylvia’s mind froze. Her breath came in sharp, panicked gasps. She had known they would push her, but this ... this was beyond what she had braced herself for. The words echoed in her head like a cruel joke, and she felt the tears prickling at the corners of her eyes.

“Please ... please, I can’t. Please, don’t make me do this,” she begged, her voice breaking as she looked at Omari with wide, tear-filled eyes.

Omari gave a mocking sigh, his grin widening. “Come on, Sylvia. You did that in front of all your students at your school this morning. All 16 of them, and Principal Tuwme, and me, of course. So why do you think my buddies here aren’t up to your ass-cheek-spreading standard?”

Sylvia’s shame was unbearable. The memory of that morning hit her like a wave of nausea. She had been forced to perform this degrading act in the school yard, in front of everyone, her students watching her. She had been ordered to obey Matumbo, and the humiliation of spreading her buttocks while her students looked on had been one of the worst moments of her life. But even then, they were far enough away that it felt less intimate, less horrifying than what she was facing now.

Here, the boys—Omari, Kumba, Jumba, Akil, and Nia—stood just inches behind her, their eyes locked on her exposed body, waiting, eager. They were close, so close she could feel their presence like a physical weight pressing down on her. How could she possibly spread her buttocks and expose her anus to them, so intimately, so shamefully?

Sylvia began to sob softly, the tears spilling down her cheeks as she shook her head, her voice trembling. “Please ... I can’t. I can’t do this...”

But the boys only chuckled, their laughter light and cruel, feeding off her misery. Omari stepped forward again, his eyes narrowing. “Would you rather gat pussy-whacked? We’ll give you pussy-whacking if that’s what you prefer, but I recommend against it. I don’t think you’re ready for pussy-whacking with your pussy already so swollen.”

Her legs trembled, and her mind spun in a whirl of fear, shame, and helplessness. The weight of the pressure crushed her, her body aching from the torment, her heart heavy with dread.

With Omari’s thinly veiled threat of “pussy whacking” hanging in the air, Sylvia’s trembling hands slowly moved behind her, hesitant and shaky. Her mind screamed in protest, but her body obeyed, driven by fear. She reached back, feeling her palms press against the soft, vulnerable flesh of her buttocks. The humiliation was suffocating, choking her in a way that made it difficult to breathe. Her heart pounded in her chest as her fingers curled into her skin, pulling her cheeks apart. The sensation of the cool air against her exposed, private areas made her want to disappear, to sink into the ground and escape the eyes devouring every inch of her shame.

The boys squatted down behind her, positioning themselves to get a better look. Their faces were only inches away, their eyes fixated on her spread anus, their expressions a mix of amusement and fascination. Sylvia’s cheeks burned with the intensity of her humiliation. She couldn’t stop the tears that welled up and slipped silently down her flushed face, her body shaking as she fought to stay upright on the tiny wooden boxes beneath her feet.

“More, snowflake,” Omari’s voice cut through her internal panic, calm but commanding. “Spread them as wide as you can. We want to see that pretty white asshole spread.”

Her whole body flinched at his words. Pretty white asshole. The vulgarity of it made her feel as though she was being stripped down to something less than human. With a deep, shaky breath, Sylvia forced her hands to pull wider, feeling her muscles stretch painfully as her buttocks parted further. Her sphincter tightened, resisting the unnatural strain, but she kept pulling until she felt the stretch at its limit, her flesh exposed in the most degrading way possible.

Her shame was overwhelming, pressing down on her like a crushing weight. She couldn’t believe this was happening, couldn’t comprehend how she had ended up in such a position, spreading herself open like an object in front of these five boys. Her breath hitched, and her sobs grew louder as she stood there, completely powerless, her body trembling with the effort to maintain the position.

Omari’s voice broke the silence again. “I promise this isn’t going to be as painful as, say, anal caning. I don’t think you’ve had that yet, right?” He paused, smirking as Sylvia shivered at the mention. “Oh, that, I’ve heard, is much worse than pussy whacking. But we’re not doing that. That’s a punishment. Here we’re just playing, right? You okay with that?”

Sylvia’s throat was tight, her voice barely a whisper as she replied, “Y ... yes...” She knew she had no choice. Saying anything else would invite something worse. The thought of anal caning made her blood run cold, her body stiffening in fear. She didn’t dare imagine the pain of that. If spreading herself for this humiliating “game” was the lesser painful option, she had no choice but to endure it.

Omari pulled something from his pocket, and Sylvia’s heart sank as she saw what it was. A slingshot, small but menacing in its simplicity. The Y-frame glinted in the light as Omari held it up, displaying it casually to the others, who chuckled in anticipation.

“Let me explain the rules of this game,” Omari said, still grinning. “We’re gonna take turns. Each of us will give you a small shot on your asshole with this.” He paused for effect, letting the words sink in. “Five shots from each of us. So, that’s 25 total. If you fall off the wooden boxes, we start from zero again. That’s the game. When we finish all 25, you win. See? That’s almost not fair. Basically, this game ends with you winning. Isn’t that right, boys?”

The absurdity of it all struck Sylvia like a physical blow. Her mind reeled, unable to comprehend how they could frame this torment as something she could “win.” She stood there, her body shaking, her legs trembling on the small wooden boxes as the full weight of what was about to happen sank in. Her hands still spread her cheeks, exposing her vulnerable anus to the boys, and now she was expected to hold that position while they shot at her with a slingshot. The thought made her stomach churn, her fear spiking as she imagined the sting of each shot hitting her most sensitive area.

It’s going to hurt, she thought, the realization dawning on her in full. She could almost feel the sting of the slingshot already, the sharp bite of the rubber band releasing and striking her tender, exposed skin. The boys’ laughter and jeers filled the air as they prepared for the game, and Sylvia’s sobs grew louder, her body shaking with fear and shame. Tears streamed down her face as she stood there, helpless, awaiting the inevitable.

She could only hope, as Omari had said, that it wouldn’t be as painful as she feared. But the thought of the slingshot hitting her anus, spread wide by her own hands, was almost too much to bear.

Omari crouched low behind Sylvia, his eyes gleaming with anticipation. He held the slingshot inches from her exposed buttocks, the Y-shaped frame perfectly aligned with her stretched anus, positioned like the bullseye of a cruel target. The leather pouch, usually meant to hold a stone, was empty. This time, it was the leather itself that would strike her tender, vulnerable skin. He grabbed the leather strip, pulling it back slowly, the tension in the air thick as Sylvia’s breath came in shallow, panicked gasps. She could feel the eyes of the other boys on her, waiting, watching.

Omari stretched the band back as far as it would go, and with a swift motion, he released it.

Swiissshhhh—thwack!

The sound of leather smacking bare skin echoed in the room, sharp and stinging. Sylvia’s scream tore through the air, an agonized, high-pitched wail that seemed to vibrate through her entire body. “Auuuuuuueeeeeeee!” The pain hit her like a shockwave, unexpected and searing, shooting through her spread anus and radiating into her lower body. It was unbearable, worse than she had imagined, and it took everything in her not to topple off the small boxes beneath her feet.

Her hands instinctively flew from her buttocks, clamping them together in an attempt to protect herself from the pain, her body reacting uncontrollably. She swung her hips forward, back, then up and down, her legs bending awkwardly as she tried to ease the burning sting in her anus. Her knees bent and straightened in jerky, desperate motions, making her body bob up and down like a puppet on invisible strings. She was almost doing knee bends, her thighs trembling as she bounced up and down on the boxes, squeezing her buttocks tightly as if trying to force the pain away.

The boys erupted in laughter, their amusement rolling through the room like a wave. Omari’s laughter was the loudest, echoed by Kumba, Jumba, Akil, and Nia, all of them doubled over in fits of hilarity. The sight of Sylvia—this naked white woman, once so composed and proper—now reduced to a spectacle, squeezing her buttocks together and bouncing in place, her face contorted in pain, was too much for them to handle.

“Hahahaha! Look at her go! Uuuuuaaauuu, auuuu!” one of the boys mocked, imitating her cries as Sylvia continued to bounce, the absurdity of the motion making her humiliation complete.

She could hear their laughter, feel their eyes on her, and the shame of it all only intensified her agony. Tears streamed down her face as she whimpered, her body moving uncontrollably in its attempt to find some relief. Each jerk of her hips, each bend of her knees, only seemed to make the boys laugh harder. Sylvia’s face flushed bright red, her sobs lost in the cruel cacophony of their mockery.

And yet, she couldn’t stop. The pain was too intense, too sharp, and every movement felt like a futile attempt to escape it. The sting from the leather still burned, a deep ache that wouldn’t fade, and her body, in all its shame, responded helplessly.

Omari was on the verge of telling Sylvia to stop her frantic movements and get back into position, but the sight of her awkward, erratic motion was too amusing. He crossed his arms, leaning back slightly as he watched her hips jerk forward and back, her knees bending and straightening in a ridiculous, desperate rhythm. Her buttocks clenched tight, as if that would somehow shield her from the pain, and her toes gripped the edges of the wooden boxes as she bounced up and down, her legs struggling to maintain balance. The more she tried to steady herself, the more absurd her movements became—small, sharp bends of her knees, her buttocks flexing and releasing, her hands fluttering uselessly at her sides.

Omari chuckled to himself, letting her continue. It was just too funny. He watched as her desperate gyrations slowly lost their intensity, the motions growing smaller. Her breath came in ragged gasps, and her cries turned to soft whimpers as the stinging pain in her anus dulled into a throbbing ache. Finally, her movements slowed to a stop, and she stood trembling, her body glistening with a thin sheen of sweat, her face wet with tears.

“That was one,” Omari said with a smirk, his voice cutting through the room. He turned to the group. “Akil, you want to take the second shot? Remember, we all get five shots max. But if you want more, make her fall off the blocks. That’s the game, right?”

Akil grinned and stood up, stepping forward with the slingshot in hand. His eyes gleamed with anticipation as he moved behind Sylvia, positioning himself just like Omari had done. The tension in the room thickened as the boys watched Akil prepare for his turn, all of them snickering under their breath. Sylvia, still panting softly from the first hit, felt her body stiffen with dread. She knew what was coming, but her legs trembled so much she feared she might lose her balance before Akil even released the slingshot.

Akil squatted down, getting close to her again, his face just inches from her exposed buttocks. He lined up the Y-shaped frame with her stretched anus, aiming carefully like he was preparing for a perfect shot. He pulled back the leather strap, stretching it far behind him as Sylvia whimpered, her breath catching in her throat. He grinned, enjoying her fear.

With a sudden flick of his wrist, he let go.

Swiiiishhhh—thwip!

The leather smacked against her tender, exposed skin with a sharp snap, the sound cutting through the air like a whip.

“Auuuuuuhhhhhh!” Sylvia’s scream was immediate and piercing, the pain shooting through her body with such intensity it felt like fire spreading from her anus. Her hands flew back to her buttocks again, instinctively trying to protect herself from the assault. Her legs buckled slightly, causing her to wobble on the boxes, her toes curling desperately to keep her balance.

The boys erupted into laughter, even louder than before. They watched as she jerked and flailed, her knees buckling and straightening in an uncontrollable dance of pain. Her hands squeezed her buttocks together, trying to block the pain, but her trembling legs made her look like she was about to collapse.

“Look at her go!” one of them shouted through fits of laughter. “She’s gonna fall!”

Akil stood back, grinning, his eyes sparkling with amusement as Sylvia bounced up and down, doing her absurd little knee-bends again, her hands clamping her buttocks shut. She swayed dangerously on the boxes, her body twisting and writhing in pain as she desperately tried to stay upright.

The men laughed even harder as she teetered on the edge of falling, but somehow, despite the burning pain and the overwhelming humiliation, Sylvia managed to stay on the boxes, her sobs filling the room as she continued her frantic, jerking motion.

“Almost had her!” Akil said, chuckling as he watched her struggle to regain her balance. The other boys slapped him on the back, still roaring with laughter as Sylvia’s pitiful, broken sobs echoed around them.

Sylvia’s voice trembled as she begged, her words spilling out in desperate, breathless gasps. “Please ... please, Omari ... please ... it hurts too much. Really, please...” She was on the verge of breaking, her body shaking from the pain and fear. A part of her wanted to protest, to challenge him, to say, You said this wasn’t painful. You called it a small sting. Have you ever felt it yourself? But wisdom—or perhaps fear—kept her silent. Instead, she just begged, her tear-streaked face a picture of raw helplessness.