Chapter 36

Intrigued by Katy’s thrilling tale of easy fortune, Lisa couldn’t help but feel a twinge of envy. She glanced over at Josh, her fifteen-year-old son, who was engrossed in his own game on the couch, his thumbs dancing across the controller with surprising agility. Normally, Lisa would steer clear of any ‘easy money’ offers, but if Katy and her son could win money, why couldn’t she and Josh? After all, knowing that her son had inherited her competitive drive, she knew they could conquer any challenge. Spending the day bonding over some video game sounds like just what the two of them needed.

Lisa cleared her throat. “Josh,” she began, a hint of excitement in her voice, “What do you say we give this game a shot?” Without waiting for a response, she grabbed her phone to call the number Katy had left for her.

With a mix of curiosity and anticipation, Lisa and Josh stepped into Room 234 of the Gladison Hotel. The air was thick with a faint hint of something sweet, like fresh strawberries. Their eyes fell upon the two tripods standing tall on either side of the king-sized bed, each with a camera lens pointed towards the center. On the bed, neatly placed, were two black eye masks and a sleek electronic tablet. Lisa’s heart skipped a beat as she noticed the debit card nestled between them, the prize that had brought them here today. Her gaze drifted to a yellow square stuck to the corner of the tablet, the words ‘Read Me First’. She picked it up, feeling the weight of the cardboard in her trembling hand, and read aloud the instructions printed in bold, all-caps letters: “To begin the challenge, both participants must first acknowledge the rules provided. Good luck!”

With a gasp of disbelief, Lisa’s eyes widened as the notification on the tablet confirmed the transfer of $10 to the debit card. “Josh,” she whispered, her voice shaking slightly as she passed the device over to him, “They’re serious. We just made $10 for doing nothing!” His eyes lit up with excitement as he scanned the rules. It seemed simple enough – stay in the room for eight hours, winning money on their card for tasks completed.

Obeying the instructions, Josh and Lisa carefully placed the black eye masks over their eyes. “It’s like we’re going to a masquerade ball,” Lisa quipped, trying to ease the tension. Josh managed a nervous laugh, his heart racing. Continuing to follow the instructions, Lisa spoke, “Cameras On”. They watched as the red lights on the front of the cameras lit up on each of the cameras. “Cameras Off”, and the red lights turned off.

They each took a deep breath and toggled the cameras on and off a few times, the red lights blinking in response. With a sense of newfound anonymity, they felt a strange mix of vulnerability and freedom. The tablet beeped, displaying a message that read, “Identity Protection Activated. Masks are on. You may now begin the challenge.” The sight of another $10 added to their total on the screen was the final push they needed to dive into the unknown. They were ready to conquer the day and, hopefully, leave with more than just memories.

The next set of instructions led them to the desk. With their eyes still covered by the masks, Lisa’s heart raced as she felt for the drawer and pulled it open. Inside lay two boxes of small, electronic devices with the words ‘Mom’ and ‘Son’ clearly marked. She handed the box marked ‘Son’ to Josh, and with trembling hands, they each applied the enclosed sensors to the designated areas of their chests. Lisa let out a small gasp as the sticky adhesive felt cold against her skin. Were these some form of an EKGs?

The tablet emitted a gentle beep, followed by the words ‘Synchronizing’. They exchanged puzzled glances, the air thick with uncertainty. Was this part of the game or had they made a mistake? Despite their apprehension, the thrill of the challenge overrode their doubts. They waited, the only sounds in the room the muffled rustle of fabric and the soft purr of the air conditioner. Then, a second beep resonated, and the tablet screen updated with a message, ‘Sync completed’. A few seconds later, another beep, ‘Mom Connected’. A few seconds after that another beep, ‘Son Connected’. When they both sat back down on the bed, they saw where another $10 had been transferred.

With the ‘Mom’ and ‘Son’ devices securely in place, Lisa and Josh sat cross-legged on the bed, the tops of their faces still shielded by the masks. They reached for each other’s hands, palms damp with a mix of excitement and nervousness. The tablet’s AI voice, smooth and detached, began to ask a series of simple yes or no questions, starting with the basics: “Does Mom like the color blue?” “Does Son prefer chicken over pizza?” Each question prompted a giggle or a murmured response from the other, as they leaned closer together, their bond growing stronger with each shared secret revealed. The tablet’s voice seemed to grow more intimate, the inquiries shifting to their personal tastes and preferences. The cameras remained steadfast, capturing their every move, yet the masks provided a surprising sense of intimacy, as if they were whispering secrets in the dark. Another beep, another question, and with every answer, the tension grew less and the anticipation gre more. Despite the innocence of the questions, a charged current flowed through their joined hands, hinting at the deeper.

As the tablet’s AI voice announced the end of the first hour with a gentle ding. The words ‘Break Time - 15 minutes’ followed by a reminder, ‘Turn cameras off before removing masks’.

“Okay,” Lisa said with a relieved smile as she watched the red lights dim as she spoke, “Cameras off”. Lisa reached up to remove her mask, “I don’t know about you but I have to pee.” Josh followed suit in removing his mask, and he was soon exploring the room they now occupied. In the drawer of the bedside dresser Josh finds a box labeled, ‘Treats for Mom & Son’. It was a box of protein bars and small bottles of apple juice.

With their masks off, Lisa and Josh shared a knowing smile over the ‘Treats for Mom & Son’ box. They each grabbed a protein bar and a bottle of apple juice, savoring the sweet taste that seemed to fuel their excitement for the next round of challenges. The timer on the tablet counted down from 15:00 to 0:00, the digits changing color from a warm red to a cool blue as it reached zero. They munched on their bars and sipped the juice, the crunch of the protein mingling with the soft murmur of their voices. “So, what do you think is next?” Lisa asked, her eyes sparkling with curiosity. “I don’t know, but I’m definitely up for it,” Josh replied, his voice filled with the excitement of a teenager on the cusp of adventure. They chatted away, sharing their favorite moments from the past hour and speculating about the mysteries that lay ahead in the game. As the timer reached the end of the break, they placed their empty wrappers and bottles aside, their eyes drawn back to the tablet, ready to continue their quest for the ultimate prize. Ready to to resume their game, they took a deep breath in unison and replaced their masks, the fabric whispering against their skin as the game’s grip tightened around them, leading them further into the unknown depths of this intriguing challenge. “Cameras On”.

With the red lights on once again, the game continued. They sat back down on the bed, the plush comforter beneath them enveloping them in a false sense of security. The AI’s voice grew softer, the questions more probing, delving into their personal lives and desires. Lisa felt a warmth spread through her cheeks as she admitted to a secret crush from her past, while Josh revealed his ambition to travel the world. Each confession earned them more points, the debit card balance climbing steadily

The first half of the next hour saw the game taking a more intimate turn. The AI’s voice grew softer, the questions now centering on their unique mother-son bond. “Do your friends find your mother attractive?” the tablet prompted. Josh’s cheeks flushed hot beneath his mask as he felt his mother’s hand squeeze his tightly. He swallowed hard before responding, “Well, yeah, she’s pretty.” The voice responded, ‘Yes or No’. Josh sat up a bit straighter, looking directly into Lisa’s eyes, ‘Yes, my friends find my mom very attractive.’ This time it was Lisa’s turn to blush.

The tablet’s AI voice continued, this time with a question aimed at Lisa, “Has Mom ever noticed her son’s friends looking at her in a way that suggests attraction?” Lisa’s breath hitched as she felt a warmth spread through her. She had noticed, of course, the occasional lingering glance or awkward stumble over words when her son’s friends were around, but she had brushed it off as adolescent shyness. With the false sense of anonymity the masks provided, she took a moment to consider the implication of the question. She squeezed Josh’s hand gently, feeling the tension in his fingers as she whispered, “Yes, I’ve noticed.” The room grew quieter as the reality of their situation settled in, the air thick with a newfound tension that was both thrilling and unsettling. The debit card balance on the screen ticked upwards again, the cold, digital numbers seemingly mocking the intimate dance they were being led through. Yet, they remained seated, bound by the invisible chains of the game, their masks a flimsy barrier to the truth that now lay exposed between them. The cameras, ever present, recorded their every reaction, the red lights showing their silent approval.

‘Has Son and friends openly discussed Mom’s attractiveness?’ Josh’s heart raced as the AI’s question pierced through the quiet. He and his friends have talked about his mom’s ‘attractiveness’, her big boobs, many times. But to admit it to his mom? Josh took a deep breath, the weight of the mask suddenly feeling much heavier. “Yes,” he murmured, his voice barely above a whisper. The room felt hotter, the mask sticking to his damp skin. He felt her hand tighten around his.

The tablet beeped, the balance jumping again. Lisa’s hand tightened around his, her pulse quickening as she felt a strange mix of maternal concern and something else, something she hadn’t allowed herself to consider before. Lisa couldn’t admit it, but this game was definitely leading them down a path.

With the start of the next half hour, the tablet’s AI voice took on a more provocative tone. “Mom, do you know what a milf is?” The word hung in the air, charged with a new kind of energy. Lisa’s grip on Josh’s hand tightened, but she managed to respond, “Yes, I do.” Her voice was steady, despite the heat that had started to build in her cheeks. “Son,” the AI continued, “do you know what a milf is?” Josh nodded, his voice thick with nerves, “Yes.” The room was silent for a beat, the only sound their synchronized breathing. Then, the final question, “Son, do your friends consider Mom a milf?”

Josh swallowed hard, his heart hammering against his chest. He knew what his friends thought of his mom; they had called her a milf before, but saying it out loud, to her, was a whole different ball game.

Josh felt his mother’s hand quiver in his, and with a heavy sigh, he decided to lie. “No,” he murmured, hoping his voice didn’t betray the truth. The room remained still, the only sound the hum of the air conditioning, until the AI’s cold, emotionless voice broke through the silence, “Inaccurate response detected. Lying is not allowed in this game. The truth is essential for progression and bonding. Please answer truthfully.” Josh’s hand reached up, remembering the sensors as Lisa’s squeezed his other hand even tighter. Her eyes boring into him through the fabric of their masks. Lisa and Josh now knew that the game was watching, listening, and judging every word.

Josh took a deep breath, knowing he couldn’t deceive this all-seeing force. “Yes,” he admitted finally, his voice cracking with embarrassment.

The room grew even more tense as the AI’s voice posed the next question, aimed directly at Josh, “Son, do you personally think of Mom as a milf?”

The implication of the question hit hard. Was his mom a mom that he’d like to fuck ... Its weight hung in the air, thick and palpable, making the silence seem to stretch on forever. Through the black fabric of their masks, Lisa and Josh could feel each other’s eyes on them, the intensity of the moment making it impossible to look away. The lie of a second ago felt like a lifetime, and now the truth was staring him in the face, demanding an answer. With a deep breath, Josh steeled himself and whispered, “Yes.” The room remained still for a moment, the only sound the erratic thumping of their hearts.

The tablet beeped, the AI’s voice now a seductive purr, “Mom, does being seen by Son and friends as a milf excite you?” Lisa’s chest tightened, the question hitting closer to home than any before. The truth was, she had always taken pride in her appearance, and the idea that young men found her desirable was a secret thrill she had never admitted to herself, let alone her son. With a quiver in her voice, she responded, “It’s ... flattering, I guess.”

“Incorrect response,” the AI chastised, its voice suddenly stern. “You must answer with ‘Yes’ or ‘No’. Does being seen by Son and friends as a milf excite you?””

Lisa took a deep breath, her heart racing beneath the mask. She didn’t want to lie, not now. Not after everything they had shared. “Yes,” she murmured, the word slipping out like a confession.

The tablet beeped, and the room filled with the sound of their hearts pounding in their chests. The balance on the debit card grew once again. The air was electric with tension, the unspoken truth now a current flowing between them. The masks felt heavier than ever, the darkness behind them seeming to amplify their vulnerability. The game had entered uncharted territory, and they weren’t turning back yet.

As the third hour began, the tablet’s AI instructed them to remove their tops. Lisa felt a jolt of apprehension, but the prize money was too tempting to end the game here. She glanced at Josh, who looked equally torn. Despite her reservations, she knew they had come too far to quit. They both nodded in silent agreement.

Soon, Josh was naked from the waist up and Lisa was just in her bra. Lisa wished she could go back in time and choose a less revealing bra. Given the thin fabric, Lisa knew she was practically naked.