Chapter 20: Graduations Part I

My Graduation

The next week after that harrowing ordeal at my neighbors. I was greeted by Steve and Pamela. “So Bitchboy, I am going to be taking your whore mother today. She is already in the car. I need you to make sure my clothes are washed. I also need the carpets steamed, and the entire house deep cleaned you are staying home today. But I am going to update a folder on your cloud drive. You will pick up your trophy every time one comes in and do your bitchboy duties as you watch what is happening to your mother.”

Steve slammed the door shut as he guided my mother, who was in a daze, to his car. Pamela gave me a smug grin before she too left, leaving me alone in the house with a list of humiliating chores to complete. I glanced at the ominous folder on my cloud drive, dreading what I would find inside.

The aroma of burnt toast wafted through the house, and I knew that I had better tend to it before it set off the smoke alarm again. As I closed the front door, my thoughts drifted back to my helpless mother and the dismaying tasks that lay ahead. Pamela’s words echoed in my mind: “You will pick up your trophy every time one comes in.” The gravity of my position as a subservient bitchboy weighed heavily on me, and I began to question how I had ever ended up in this situation.

Two Hours Later...

I was still moving furniture around preparing to steam the carpets when my phone buzzed to let me know my cloud drive had just been updated. I sighed as I stopped what I was doing, took off the little clothing I had on and picked up my MVP trophy.

Next Video...

In the utilitarian confines of the men’s locker room, complete with cold metal benches and a floor littered with discarded athletic tape, my mother teetered on the slippery tiles. Her appearance was transformed, or rather, deformed, into that of a willing fucktoy. She wore a garish, barely-there mini dress that strained to cover her thighs and left nothing to the imagination. Her feet were ensconced in glossy black heels so high she had to clutch the grimy lockers for balance, each step a precarious shift like she might topple into shame at any moment. Steve loomed over her with a predatory grin, an unscrupulous confidence emanating from him like a stench. He hadn’t even bothered to close the door behind them; the scene was a public spectacle. A nervous, acne-ravaged student lingered in the threshold, shifting from one foot to the other, anxiety written across his face. “Don’t be shy, kid,” laughed Steve, extending a hand to collect a crumpled wad of cash. The student handed over the money with trembling fingers, his eyes darting between Steve and my mother as though he feared they might both vanish if he blinked.

Steve pocketed the cash with a sneer. “Here she is, all dressed up for you,” he taunted, clearly savoring the degradation. His voice was loud, booming, echoing off the tile and reverberating through the locker room with cruel clarity. “You paid top dollar, so get to it, bitch! Give the kid his money’s worth.” He barked the order like a drill sergeant, and my mother sagged at the words, her shoulders slumping. She looked at the student with an expression torn between numb compliance and desperate helplessness, a glance so defeated it might as well have been chains.

As the door swung shut, leaving the three of them alone in their sordid tableau, my mind reeled with the vivid, unwelcome image of my mother doing everything the young man had ever fantasized. I could see her on her knees, see the acts about to take place...

The acrid scent of charred bread permeated the house, demanding my attention lest it trigger the smoke detector once more. As I secured the front entrance, my thoughts drifted to my vulnerable mother and the daunting challenges ahead. Steve’s command haunted me: “Retrieve your trophy with each arrival.” The weight of my subservient role pressed upon me, prompting introspection on my current predicament.

Two hours passed...

Amidst rearranging furniture for carpet cleaning, my device alerted me to a cloud drive update. Sighing, I halted my task, shed what little clothing I wore, and grasped my MVP trophy. I thought I was watching a repeat until I saw a different young buck from off the streets.

In the same stark men’s locker room, with its frigid metal benches and floor strewn with discarded athletic tape, my mother teetered precariously. She stood transformed into a reluctant trophy, donning a gaudy, revealing mini dress that barely covered her thighs. Teetering on impossibly high black heels, she clung to the grimy lockers for stability. Steve towered over her, exuding a malevolent confidence. The door gaped open, exposing the scene. A nervous, acne-scarred student hovered at the threshold, fidgeting anxiously.

“Come on in, kid,” Steve goaded, palm outstretched for the proffered cash. The student relinquished the money with shaking hands, his gaze darting between Steve and my mother.

Pocketing the money, Steve sneered. “She’s all dolled up for you,”just like I promised” he taunted, reveling in the humiliation. His voice boomed through the room. “You paid premium, so get to it! Give the man his money’s worth.” He barked the order, causing my mother to wilt, her expression a blend of resigned compliance and mute desperation.

“Yes Daddy, Of course Daddy” she said in a honeypot purring voice like she was acting out a character in a movie.

As the door closed it was replaced with another video.

Next Vid clip...

“Don’t worry Ms. Powers, I will not tell anybody. I know I just a meager janitor but I dreamed of this for such a long time” He sneered out in a nasally voice. The man wore the most hideous wired frames he ever saw.

The so-called “meager janitor” was named Gary, and he had lusted after my mother since the day she’d started working at the school. He’d always been just a silent admirer, a voyeur in the shadows of her life. Now he was presented with an opportunity he never thought possible: to possess her, even if only for a fleeting moment. His heart pounded in his chest, each beat matching the pounding of his arousal. “I’m going to make you pay for every time you ignored me, Ms. Powers,” he hissed, his nasally voice taking on a perverse edge.

Gary’s hands trembled as he fumbled with his pants, as if undressing in front of a goddess was an honor too great for him to comprehend. My mother, on the other hand, steeled herself for what she knew was about to happen. Her eyes flickered to the door, searching for an escape that wasn’t there. Steve’s words echoed in her head: “Give the man his money’s worth.” As if on autopilot, she leaned in pulled a slow kiss before going down on her knees and placing his dick in her mouth.

As my mother serviced the janitor, I couldn’t help but feel an overwhelming sense of both disgust and arousal. I despised myself for even considering such perverse thoughts about my own mother, but the situation was so twisted and depraved that it threatened to consume me. My cock hardened against my leg as I watched her submit to Gary’s every command. He grabbed fistfuls of her hair, grunting in pleasure as she moaned in humiliation.

In the background, Steve sat on a nearby bench, legs crossed, and smirking as he watched her debase herself. “That’s right, you filthy whore,” he sneered. “Be a good little cock-hungry bitch for your son to see.” His words only ignited a fire within me, one I didn’t know whether to extinguish or fan.

As the janitor neared climax, he roughly shoved his member down my mother’s throat, her eyes watering from the force of it all. He groaned loudly, his seed shooting down her throat as she gagged on his bitterness.

“Good remember it is more than that if you want to go the extra mile. Remember send a message to this website, and I promise to always deliver” Steve said. The janitor was more than ecstatic to get a top-notch blowjob from his boss.

My mother clicked out of the locker room her heels teetering very tall. She looked like someone in the red-light district and less like someone who was vice-Inspector of a high school.

My cock hurt within its cock cage. Fuck I never thought I would miss being able to cum to my mother’s debauchery but right now that is all I wanted. I sighed as I got back to the massive cleaning project.

The cleaning project dragged on, each menial task a reminder of my degradation. As I scrubbed the floors on my hands and knees, I couldn’t shake the images of my mother’s humiliation from my mind. The cloud drive pinged again, and I hesitated before checking it, dreading what new depravity awaited me.

Next Vid...

This time, the video showed my mother in the Inspector’s office, her makeup smeared and hair disheveled. Inspector Myers, a portly man in his late 50s, leered at her from behind his desk. “Well, well, Ms. Powers,” he chuckled, his voice dripping with lust. “I never thought I’d see you like this. But Steve assured me you’d be ... accommodating.”

My mother’s eyes were glassy, her movements mechanical as she approached his desk. “Yes, sir,” she murmured, her voice barely above a whisper. “Whatever you need.”

The Fire Inspector’s grin widened as he unzipped his pants. “I’ve always wondered what that smart mouth of yours could do besides lecture,” he sneered. “Time to put it to better use.”

As my mother knelt before him, I felt a sudden pang in my chest as the man barked, “Nu uh sweety turn around, all fours, I get vip access, whore” He bellowed chuckling as he ordered my mother around. It was one of the parents at the school she worked for.

My mother hesitated for a moment, her eyes darting to the door as if considering escape. But she knew there was no way out. With a defeated sigh, she turned around and got on all fours, her short skirt riding up to expose her vulnerable flesh.

Inspector Myers wasted no time. He grabbed her hips roughly and thrust into her with a grunt of satisfaction. “Oh yeah, that’s it,” he growled. “I’ve been wanting to do this for all year, you stuck-up bitch.”

I watched in horrified fascination as the Inspector ruthlessly pounded my mother, her body jerking with each brutal thrust. She bit her lip, trying to stifle her cries of pain and humiliation.

“Look at you now,” Myers taunted between grunts. “Not so high and mighty anymore, are you? Just another whore for us to use.”

The scene was depraved and yet I couldn’t look away. My cock strained painfully against its cage as I watched my mother’s degradation. I hated myself for my arousal, for the twisted part of me that craved to see more.

As Myers neared his climax, he grabbed a handful of my mother’s hair, yanking her head back painfully. “Take it all, you filthy slut,” he snarled, driving into her with increased ferocity. My mother’s face contorted in a mix of pain and unwanted pleasure as the Inspector reached his climax, filling her with his seed.

As Myers pulled out and zipped up his pants, he gave my mother’s rear a harsh slap. “Not bad, Powers. Maybe we should make this a regular thing.” He chuckled darkly as he left the office, leaving my mother crumpled on the floor, used and discarded.

The video feed cut out, and I was left staring at a blank screen, my mind reeling from what I’d just witnessed. The house suddenly felt suffocating, the weight of my humiliation and twisted arousal pressing down on me. I tried to focus on my cleaning tasks, but my thoughts kept drifting back to the videos, to my mother’s degradation, and to my own conflicted feelings.

As I moved to the living room to start on the carpets, my phone buzzed again. With trembling hands, I checked the notification, dreading what new horror Steve had in store for us.

Later that night.

That evening, I had barely just got done making the dinner Pamela requested. I was serving when the door opened. My mother looked exhausted following Steven and Pamela. I wanted to console my mother, but my mother had none of it. It felt she was waiting to take out a days’ worth of frustration right at me.

“Well, well, look who finally finished his chores,” my mother sneered, her eyes blazing with a mixture of anger and something darker. “Did you enjoy the show today, you little pervert?”

I stammered, trying to find words, but she cut me off with a sharp slap across the face. The sting brought tears to my eyes, but I dared not protest.

“On your knees, now,” she commanded, her voice dripping with contempt. I obeyed instantly, dropping to the floor at her feet. She circled me slowly, like a predator toying with its prey.

“You think you had it rough today?” she hissed. “You have no idea what I’ve been through. And now it’s time for you to pay.”

She grabbed a fistful of my hair, yanking my head back painfully. “Open wide, bitch,” she growled, shoving her fingers into my mouth. I could taste the remnants of her day’s activities, and my stomach churned with a mixture of disgust and arousal.

Steve and Pamela watched from the couch, clearly enjoying the spectacle. “That’s right, show him who’s boss,” Steve chuckled, clearly amused by the role reversal. My mother settled into her dominant role above me right away almost like she could not wait to really degrade me.

My mother’s grip on my hair tightened as she forced me to look up at her. “You think you’re the only one who can be humiliated?” she snarled. “It’s time you learned what it feels like to be truly degraded.”

With a swift motion, she yanked me to my feet and shoved me against the wall. Her hands roamed my body roughly, groping and pinching as I whimpered in a mix of pain and unwanted pleasure.

“Look at you, getting off on your own mother,” she sneered, her hand brushing against my caged cock. “You’re even more pathetic than I thought.”

Steve stood up, a wolfish grin on his face. “Why don’t you show him how it’s done, sweetheart?” he suggested, his voice thick with lust.

My mother’s eyes gleamed with a cruel light as she turned back to me. “On your hands and knees, now,” she ordered. I complied, trembling as I assumed the position.

She circled me slowly, her heels clicking on the hardwood floor. “You wanted to see me debased?” “Now you can see firsthand, come slut, start licking, start with my shoes” she commanded, her voice laced with contempt. I hesitated for a moment, overwhelmed by the sudden shift in power dynamics. My mother’s foot tapped impatiently, the sharp heel a silent threat.

“I said lick, you worthless worm,” she hissed, pressing her shoe against my lips. The acrid taste of leather filled my mouth as I tentatively began to lick, my tongue tracing the curves of her expensive heels. I could taste the grime of the day, a bitter reminder of her degradation and my own complicity.