The Loser's Trophy
Copyright© 2023 by Xanzibar
Chapter 21: Steve Leaves High School On Top
Fiction Sex Story: Chapter 21: Steve Leaves High School On Top - Intense Hardcore Story, DO NOT READ UNLESS you are prepared for some messed up stuff. This story is cruel, mean,and sexy,but the universe it exist in a harsh universe. I basically let my mind go where the story takes it regardless of how dark it is and most likely,(not homicidal but definitely not romantic). A victim of bullying finally gets even with his tormentor only to find that he has already inflicted his greatest defeat before they even squared off. Through the instrument of his mother.
Caution: This Fiction Sex Story contains strong sexual content, including Ma/Fa Fa/Fa Mult Blackmail Coercion Drunk/Drugged Reluctant Lesbian Heterosexual Fiction School Sports Workplace Cuckold Mother BDSM DomSub MaleDom FemaleDom Humiliation Light Bond Rough Sadistic Spanking Gang Bang Group Sex Orgy Interracial Black Male White Male White Female Hispanic Male Anal Sex Cream Pie Double Penetration Exhibitionism Facial Masturbation Oral Sex Squirting Tit-Fucking Voyeurism Body Modification Foot Fetish Leg Fetish Public Sex ENF Prostitution Revenge Transformation
The first thing I noticed on waking was the sickly-sweet tang of latex and chemical sweat, clinging to the air like secondhand perfume and making my lips stick together as I tried to groan. My head still rang from the previous night, Pamela’s monstrous thighs clamped at the hinge of my jaw, her bone-white calves pinning my shoulders, her voice already in my ear even before my vision resolved.
She was straddling my face, of course, the only way she would ever greet me anymore, and now she mashed my nose into her vulva so hard my septum ached. “Get to work, my lil bitchboy. Daddy left a gift for you. It is his turn to get his good graduation day.” The words came out in a parody of sweetness, a kind of venomous snarl that could only come from someone who had spent the better part of a year as my owner, Goddess, Cuckoldress. She never stopped taking her pleasure from smothering freaks like me. Pamela had grown into her role as Steve’s new enforcer the way a vine wraps a dying tree, feeding off the inner rot and then wearing it like a trophy.
I struggled, pointlessly, but she had me by the chin and hair, and she rode my tongue with methodical contempt, as if my humiliation was an overdue household chore. I could feel her breath hot on my scalp, her laughter reverberating through her hips and into my cheekbones. Everything hurt, and every time I tried for a gasp of air she ground harder, until I was blinking away tears and gagging on her. When she finally relented, climbing off and slapping my cheek with a practiced flick of her wrist, I was left sputtering, my tongue raw and my dignity completely stripped.
Pamela leaned over me, letting her breasts swing just out of reach, her lipstick smeared and her eyes wild with delight. “You’re going to make us all so proud today, bitchboy” she said. “The whole city will know what a man you’ve become But first you have a video to watch.”
It was morning and I already had to start with the videos.
Next Vid...
It was my mother and a big mountain of a man. He spoke like he ate nails and looked like he could break her neck with his hands. “The name is Frank. I admit. Calvin mentioned you I thought he was all hype. He does not have as good of an eye for’talent’ as Hector. But Mel says you are one of the best fucks he has had and now I am going to evaluate you. You pass the test then I will find a use for you understand?” My mother, a perfect image of a woman, looked positively miniature beside Frank. She nodded, her eyes cast downward, hands clasped behind her back like a scolded child. “Yes, sir,” she murmured, her voice barely audible. I knew that stance, that tone. It was the same she used with my stepfather, the same she’d used with every man who had power over her.
Frank grunted, circling her like a vulture. “Good. You know your place. I like that.” He stopped in front of her, his massive hands dwarfing her shoulders as he gripped them. “But I wanna hear you say it. What are you?”
Mom’s voice was steadier this time, as if she was reciting a well-rehearsed line. “I’m a fucktoy, sir. Here for your pleasure.”
A cruel smile spread across Frank’s face. “That’s right. And today, you’re gonna prove it.”
The camera panned out, revealing a room filled with an array of devices that made my stomach churn. I wanted to look away, to close my eyes, but Pamela’s grip on my chin tightened, her fake nails digging into my skin. “Watch,” she hissed. “Watch what a real man does with a woman like her.”
Frank led my mother to a padded bench, bent her over it. She didn’t resist, didn’t even seem to hesitate. I knew she was putting on a show, doing what she thought she had to. But it didn’t make it any easier to watch. My mother’s lips pursed, a careful, theatrical moue she’d perfected years ago, back when she still thought a little drama could keep men off their worst. She swayed on her heels, the same way she used to in our old kitchen when it was just us and the radio, but here, with Frank looming, the movement was a calculated surrender. The click of her glossy black stilettos echoed in that cold, bare room and made her winter-pale skin seem even more delicate, like she might shatter if he pressed her too hard. I should have looked away, but I couldn’t. The sight of her, the way her body arched, the way her hand drifted along her thigh before she offered it, trembling, to Frank, made something inside me both shrivel and ignite. My cock throbbed, straining helplessly against the plastic bars of my cage, and every desperate twitch only made the ache more excruciating.
Pamela noticed, of course. She always noticed. She slid closer, her legs entwining with mine, her skin so soft and warm it made my own seem raw by comparison. She let her fingertips glide across the ridges of my ribs and the flat of my belly, not for comfort but to prove that she could; that I was hers. Her breath tickled the inside of my ear, her voice syrupy and cruel as she said, “Look at her. Look at what a little slut you get it from.” And when I tried to flinch away she just pressed her body harder into me, grinding her hips against my thigh with slow, deliberate contempt. It felt like being scalded and then frozen and then scalded again.
On the screen, Frank traced the line of my mother’s calf with a single, massive finger, before gripping her ankle and pulling her leg up so she stood almost en pointe. She wobbled, the muscles in her thigh fluttering, but kept her balance, a little miracle of obedience. He spread her legs wide and pushed her forward, making her arch her back and stick out her ass like some kind of twisted ballerina. “You see?” Pamela whispered, a cruel smile in her voice. “She wants it. She needs it.” I didn’t want to believe it, but the camera didn’t lie: my mother’s face had gone slack and blank, her eyes almost glassy. She wasn’t fighting. She was ... waiting.
Pamela’s hands roamed higher, palming my chest, pinching the skin around my nipples. Each touch sent a new spike of heat through my body, ratcheting the pressure in my groin to an unbearable peak. She laughed, not the full-throated cackle she’d use with Steve, but a low, predatory hum, and nipped at my earlobe. “You like this, don’t you? Watching her learn her place. Knowing it’s your place too.” I tried to protest, but all I could muster was a strangled whimper, half fury and half lust.
Frank moved behind my mother, running his hands over her hips and squeezing, testing for some quality only he knew. I saw her exhale, her whole body sagging with anticipation or dread, I could never tell with her. He whispered something in her ear, and she nodded, her hair falling like a curtain over her face. Then he bent her even lower, until her cheek pressed to the cold bench and her ass was high and exposed. The camera zoomed, and the world narrowed to the obscene geometry of her body, every inch mapped by Frank’s greedy palms.
Pamela shifted, sliding one hand down to the bulge of my cage. She tapped the plastic with her nails, the sound sharp and mocking. “Let’s make it a little more interesting,” she said. “Let’s see who breaks first.” Then she grabbed a fistful of my hair and yanked my face toward the screen, so I wouldn’t miss a single second of what happened next.
Frank was unzipping his pants, already hard and thick. My mother didn’t look back, didn’t flinch. She just waited, hands braced against the bench, eyes fixed on some invisible point ahead. The room was silent except for the rasp of fabric and the wet slap of skin, and every one of my nerves was tuned to it, vibrating with horror and arousal and shame.
And then, with a grunt, Frank entered her. No preamble, no mercy. My mother gasped, the sound sharp and almost animal, but she didn’t cry out. She took it, just like she’d taken everything else in her life. Her fingers dug into the padding, knuckles white, but she held her ground, even as he pounded into her with the force of a wrecking ball. On the other side of the screen, Pamela ground herself against me, biting my neck and whispering filth in my ear, until I felt like my whole body might tear in two.
I whimpered as I watched my mother offer her leg to Frank to feel and felt Pamela’s soft legs at the same time.
My mother pursed her lips and swayed as seductively as one possibly can. The clicking of her glossy black heels made her pale skin pop made my dick strain against my cock cage. To make matter’s worse Pamela started teasing me with her body sliding her smooth skin against my body to make the arousal ten times worse. I whimpered as I watched my mother offer her leg to Frank to feel and felt Pamela’s soft legs at the same time. Her hands were everywhere, her touch a relentless torture, designed to keep me on the precipice but never allowing me to fall. I could feel her damp heat, the slickness of her sweat, the way her body moved like a serpent, all muscle and malice. Her teeth sank into my shoulder, hard enough to leave a mark, and her laugh was a hot puff of air against my neck. “You’re shaking,” she cooed. “Is it too much for you, baby? Watching mommy take it like a good little whore?”
On the screen, Frank’s pace quickened, his massive body a blur of brutal motion. My mother’s knuckles were white, her breath coming in ragged gasps, but she pushed back against him, meeting each thrust with a determination that was both horrifying and mesmerizing. Pamela’s hand slid down, cupping me through the cage, her fingers tracing the outline of my imprisoned cock. “Look at him use her,” she whispered. “Look at how much she loves it.”
I couldn’t tear my eyes away. The room, the screen, Pamela’s touch, it all blended into a nightmare of sensation. Frank’s grunts filled the air, each one a brutal punctuation to his relentless rhythm. My mother’s face was a mask of concentration, her eyes closed, her lips moving in silent, desperate prayers.
Pamela’s mouth was in my ear again, her voice a venomous purr. “He’s close, isn’t he? Look at his face. Look at how he’s using her. Like she’s nothing. Like she’s just a hole for his pleasure.” Her hand tightened around my cage, the pressure almost unbearable. “Is that what you want? To be used like that? To be nothing?”
I couldn’t answer, couldn’t think. The world had narrowed to the cruel dance on the screen and the equally cruel touch of the woman pinning me down. Frank’s movements became more erratic, his grunts more guttural. My mother’s body was slick with sweat, her hips moving in a desperate, involuntary rhythm.
And then, with a final, brutal thrust, Frank stilled, his body shaking with release. My mother collapsed onto the bench, her breath coming in heaving sobs. Pamela’s grip on my cage tightened to the point of pain, her laugh a cruel, triumphant sound. “There you go, baby,” she whispered. “That’s how a real man does it. That’s how you’ll never be.” I did not know it was possible, but she became more meek before him. Even calling him in a soft sex kitten voice, “Daddy”.
As Frank pulled away, my mother remained still, her body a ragged, exhausted mess. The camera zoomed in on her face, capturing the moment her eyes fluttered open, stark and empty. It was over, but the echo of it lingered, a haunting reminder of the power dynamics at play.
Pamela finally released me, her touch lingering like a threat.
A brief pause of black screen then another scene from the same night played.
Next Clip...
The scene came back I do not know what happened by my mother followed behind Frank like a cub. She was naked her thighs were caked in his cum, her hair disheveled with more cum in there.
“If I tell you to walk naked in public you do that, got it whore?” Frank said grabbing my mother and giving her quick slap, not hard but enough to make his point. My mother nodded, her eyes downcast, submissive. “Yes, Daddy,” she murmured, her voice barely audible. Frank’s lips curled into a satisfied smirk, and he turned to face the camera, his massive frame blocking my mother from view. “See that? That’s a well-trained slut,” he said, his voice a low rumble. “Now, let’s see what else she can do.”
He stepped aside, revealing my mother once again. She was on her knees now, her hands clasped behind her back, her breasts heaving with each breath. Frank walked over to a table in the corner, his heavy footsteps echoing through the room. He returned with a leash, a collar, and a set of high heels even more taller than the ones my mother had been wearing.
“Put these on,” he commanded, dropping the items at her feet. My mother hesitated for a moment, her eyes flicking to the camera, but she quickly complied. She slipped into the heels, her legs wobbling slightly as she stood up, her body already exhausted from the previous ordeal. Frank handed her the collar, and she fastened it around her neck, her fingers trembling. Once it was secure, he clipped the leash to the metal ring at the front, giving it a sharp tug.
“Come on, bitch. Time to show the world what you’re made of,” he growled. My mother followed him, her steps uncertain, her body swaying precariously on the heels. The camera followed them as they made their way to the door, Frank leading my mother like a dog on a leash.
Pamela, beside me, let out a low laugh, her eyes gleaming with malice. “Look at her go,” she purred. “Such a natural. Just like you, isn’t it, baby?” She turned to me, her fingers tracing the line of my jaw, her nails digging into my skin. “You’re going to be just as obedient, aren’t you? Just as eager to please?”
I couldn’t respond, my throat constricted with a mix of horror and arousal. Pamela’s grip tightened, her voice a harsh whisper. “Aren’t you?” she demanded.
I nodded, the movement jerky and involuntary. Pamela’s smile widened, her eyes shining with triumph. “Good boy,” she cooed. “Now, let’s see what else is in store for your little mommy whore.”
The screen flickered, the scene shifting to a bustling street. Frank led my mother through the crowd, her naked body on full display, her head held low. People turned to stare, their eyes wide with shock and disgust. Some pulled out their phones, snapping pictures, their harsh laughter and mocking permeated the background. They felt like daggers. My mother kept her eyes on the ground, her steps never faltering, her obedience unwavering. They were in the redlight district my mother right next to the other hookers. The hookers all scurried over to Frank to give him his money. Frank towered over the other pimps, his massive form drawing both respect and fear. The hookers, a blur of cheap perfume and even cheaper clothing, huddled around him, their hands outstretched with crumpled bills. My mother stood silently among them, her naked body and expensive heels a stark contrast to the worn-down surroundings. The other women eyed her with a mix of pity and envy, their gazes flicking between her and Frank, understanding the power dynamic all too well.
Frank counted the money, his thick fingers handling the bills with practiced ease. He looked down at my mother, a cruel smile playing on his lips. “Good girl,” he rumbled, tucking the money into his pocket. “You’ve earned your keep today.” He turned to the other pimps, his voice a low growl. “She’s fresh meat. Make sure your girls know their place.”
The other pimps nodded, their eyes lingering on my mother’s body, a silent promise of more degradation to come. Pamela, watching beside me, let out a satisfied sigh, her body pressed against mine, her breath hot on my neck. “See that, baby? That’s where you come from,” she whispered, her voice a sultry purr. “That’s where you’ll end up if you don’t behave.”
On the screen, Frank gave the leash a sharp tug, pulling my mother away from the crowd. She stumbled, her heels catching on the uneven pavement, but she quickly righted herself, her eyes never leaving the ground. They walked down the grimy street, the neon lights of the sex shops and strip clubs casting a garish glow on my mother’s pale skin. She was so short that she had to take little running steps to keep up with step with each one of his.
Frank led her to a dirty alleyway; the walls were covered in graffiti and grime. He stopped abruptly, turning to face her, his eyes cold and calculating. “You’re going to work here,” he said, his voice leaving no room for argument. “You’re going to suck and fuck whoever comes down this alley. You’re going to make me proud, aren’t you, bitch?”
My mother nodded, her voice a soft, resigned murmur. “Yes, Daddy.”
Pamela’s nails dug into my skin, her voice a harsh whisper. “Watch and learn, baby. This is your future. “Frank towered over the other pimps, his massive form drawing both respect and fear.
Pamela, watching beside me, let out a satisfied sigh, her body pressed against mine, her breath hot on my neck. “See that, baby? That’s where you come from,” she whispered, her voice a sultry purr. “That’s where you’ll end up if you don’t behave.”
The scene jumped ahead to what must have been hours later because it was starting to get light outside. My exhausted mother was in a different set of heels metallic ones a miniskirt and sheer mesh top. She was made to crawl to Frank with the money from her John’s in her mouth.
Frank took it and slapped my mother’s ass. She meekly pouted and said, “Thanks Daddy”
“That’s a good whore” Frank said with a smile on his face.
The video ended with Pamela mounting my face and squirting hard over me. Making me thank my Goddess afterwards for the gift of her juices.
Graduation Ceremony Deacon High School
I was not allowed to sit in the crowd. Instead, I stared at the laptop screen, my fingers gripping the edge of the desk until my knuckles whitened. On screen, Mrs. Simmons, the woman who had handed me detention slips and lectured about college applications, clicked across the locker room tiles in stilettos. The boys’ faces flushed red as they formed a line outside, sneaking glances at each other, half-smirking, half-uncertain. The captain went in first. My stomach clenched as she sank to her knees, her outfit. I turned away but Pamela yanked my chin back toward the screen. “Graduation party prep,” she whispered, her breath hot against my ear. The invitation cards for tonight’s event lay scattered across the bench behind them.
“Bitch get in here and make sure he gets the virtual experience. Dawn padded in from the back office. She was entirely naked save for a slave collar she crawled in between my legs and soon my member was being suctioned into her mouth. Her mother was on screen doing the same for the well hung member of their football team enticing her to come to the afterparty at Hectors.
Next Vid.
Steve practically strutted across the threshold of the classroom, his letterman jacket slipping from his broad shoulders with the same easy arrogance he’d worn all four years, but now the room was empty except for my mother and a single streaming camera. She greeted him with a squeal of delight so piercing that for a moment I thought she’d stepped on a tack. But then she was on him, arms thrown around his neck, laughing, gushing, burying her face in the side of his throat, inhaling him like she’d discovered a new drug. “Oh, you perfect man, you champion, you god, you absolute stud!” she cooed, her voice syrupy, trembling at a pitch that was half-innocent cartoon, half-pornographic moan.
He stood there, arms folded, grinning down at her as she ran her hands over his chest, her fingers trailing over the stitched “S” on his varsity sweater. “You ripped it out there, didn’t you?” she said, her voice vibrating with a helium-high giggle. “I watched every second. You’re going to be a star, baby. My MVP. My Daddy.” She kissed the base of his jaw, then dropped to her knees, immediately attending to the bulge in his jeans with both hands, gazing up with eyes wide and glittering with awe, longing, and the frantic adoration of a teenager at her first pop concert.
“Tell me you want me,” she purred, and Steve obliged, yanking her up to straddle him against the teacher’s desk. My mother wrapped her legs around his hips with athletic desperation and started grinding, her skirt riding up, her heels clattering against the particleboard. She babbled between gasps, her high voice melting into wet reverence. “You’re everything I ever needed, Daddy. I’m the luckiest slut in the world. Please, please, ruin me. Make me your little toy. Make me forget who I was before you.” She said it like a prayer, and he responded by biting her lip, spanking her ass, and laughing.
She moaned so loudly I thought the glass would rattle. “Yes, yes, I love it!” She dug her nails into his back, writhing, putting on a show for the camera, shamelessly crooning, “No one makes me feel the way you do, Daddy. No one ever could! I belong to you, forever, just say you want me, just say you love me, please,”