Simon’s Much Needed Regression (part 1)

The kitchen table was a battlefield of scattered cards, snack crumbs, and red solo cups. Brenda stood triumphantly, her arms crossed over her chest, a smug grin plastered on her face. Across from her, Simon slumped in his chair, his eyes wide with disbelief.
“I can’t believe you lost,” Brenda said, her voice dripping with amusement. “You were so sure you had it in the bag.”
Simon shook his head, still trying to process what had just happened. “This… this isn’t fair. You cheated!”
Brenda raised an eyebrow, her grin widening. “Cheated? Please. I played by the rules, Simon. You’re the one who couldn’t keep up.”
Simon clenched his fists, frustration bubbling inside him. “Fine. What do I have to do now?”
Brenda’s eyes glinted with mischief. She reached into the drawer beside her and pulled out a neatly folded diaper. The sight of it made Simon’s stomach churn. He knew what this meant.
“Remember the bet?” Brenda asked, holding the diaper up for him to see. “Loser has to wear a diaper all day long. No exceptions.”
Simon’s face flushed with embarrassment. “Brenda, come on. This is ridiculous. You weren’t serious about that!”
Brenda shook her head, her expression firm. “No way. A bet’s a bet, Simon. Now, let’s get this over with.”
Simon hesitated, his pride battling his desire to escape the humiliation. But Brenda was relentless. Her eyes locked onto his, daring him to back down. Finally, he sighed in defeat.
“Alright, alright,” he muttered, standing up and undoing his belt. “But you better not tell anyone about this.”
Brenda chuckled as she approached him, her hands deftly working to remove his pants. “Oh, Simon. Don’t worry, your secret’s safe with me.”
Simon winced as she slid his underwear down, exposing him to the cool air of the room. He felt utterly vulnerable, his cheeks burning with shame. Brenda didn’t waste any time, quickly unfolding the diaper and positioning it underneath him.
“Just relax,” she said softly, her fingers brushing against his skin as she securely taped the diaper. “It’s not as bad as you think.”
Simon groaned, feeling the weight of the diaper pressing against him. It was humiliating, but there was nothing he could do about it. Brenda stepped back, admiring her handiwork with a satisfied smile.
“There we go,” she said, patting his bottom lightly. “All done.”
Simon fumbled with his pants, pulling them back over the bulky diaper. The sensation was foreign and uncomfortable, making him feel like a child again. He avoided Brenda’s gaze, his embarrassment deepening with each passing second.
“Now, don’t you dare take that off,” Brenda warned, her tone playful yet firm. “A bet’s a bet, remember?”
Simon nodded, too ashamed to speak. He hurried out of the room, desperate to escape the humiliating situation. Walking through the house, he couldn’t help but notice how different it felt to move with the diaper between his legs. It restricted his movements, making everything awkward and clumsy.
By mid-morning, Simon began to notice a strange sensation creeping over him. His thoughts felt foggy; his mind sluggish. He struggled to focus on simple tasks, and the increasing brain fog made it incredibly hard to concentrate. Panic set in, as he knew something was wrong, just not what! Do you think he’ll find out what’s wrong? Click right here to read and find out!

Mommy Brenda

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