Simon’s Much Needed Regression (part 2)
January 1, 2025Jake Goes on an Apology Tour (Part 2)
January 2, 2025
Brenda walked briskly into the living room, her face determined and more than a bit agitated. Her son, Jake, sat on the couch, his eyes wide with terror as he clutched the edges of his pink skirt. The fabric was soft against his trembling hands but felt like fire against his skin. His cheeks were flushed, not just from embarrassment but from the sheer humiliation of the situation. Brenda’s voice cut through the air like a whip.
“Up, Jake. We have some apologies to make.”
Jake winced as she grabbed his arm and yanked him to his feet. He stumbled, nearly tripping over his Mary Janes. His blouse was also pink, with frills at the collar, making him feel even more girly. Jake’s heart pounded in his chest as he thought about the cherry-covered cotton panties underneath the skirt. He had never felt so exposed in his life.
“Mom, please,” he begged, his voice barely above a whisper. “This is going too far. Please, don’t make me do this.”
Brenda glared at him, her eyes cold and unyielding. “No, you absolutely will. You embarrassed those girls and disrespected them, even if they don’t know it yet, and now you will apologize to each of them. And I mean properly apologize. Understood?”
Jake nodded quickly, his throat dry. He knew better than to argue. His mother had always been strict, but this punishment was beyond anything he could have imagined. She had caught him red-handed, his phone recording the sight of Mrs. Thompson’s daughter bending over in her backyard. The underskirt photos he’d taken of other girls his mom found after that didn’t help.
Brenda led him to the door, her grip firm on his arm. “First stop, the Thompsons’. Get moving.”
Jake shuffled out of the house, his legs feeling weak with shame. The sun was high, casting a bright light over the neighborhood. He couldn’t imagine a crueler setting for what he was about to endure. As they approached the Thompson’s house, he saw Mrs. Thompson watering her garden. She looked up as they walked by, her eyes widening as she saw Jake in his outfit.
“Brenda, is everything alright?” she asked, confused.
Brenda’s smile was more of a grimace than anything. “We’re fine, thank you. We just need to talk to your daughter for a moment.”
Mrs. Thompson nodded slowly, still eyeing Jake with confusion and suspicion. “Alright. I’ll go get her.”
As they waited on the front porch, Jake’s anxiety grew. He could hear footsteps approaching, and then the door opened wider to reveal Emily, Mrs. Thompson’s daughter. Her eyes widened as she took in Jake’s outfit, and a slight smirk played on her lips.
“What’s going on?” she asked, looking between Jake and her mother.
Brenda stepped forward, her voice calm but stern. “Emily, Jake here has something he needs to say to you.”
Jake’s mouth felt like sandpaper as he tried to speak. “I… I’m sorry, Emily. I shouldn’t have done what I did.”
Emily raised an eyebrow, clearly enjoying the spectacle. “And what exactly did you do?”
Brenda stepped back, giving Jake no choice but to continue. “I… I used my phone to look up your skirt without your permission. I’m really sorry.”
Emily’s smirk grew wider. “Sorry? Why don’t you show me what you’re wearing under there? Maybe that’ll help me believe you’re actually sorry.”
Jake’s eyes shot to his mother, pleading for help, but Brenda simply nodded. “Do as she says, Jake.”
With shaking hands, Jake lifted the hem of his skirt, revealing the white panties beneath. Emily’s eyes gleamed with satisfaction as she leaned in closer, getting a good look.
“I bet you’re sorry you have to do something like this if nothing else. But think before you try to pull something like that again next time.
Jake let the skirt fall back into place, his cheeks burning with humiliation. “Yes, Emily. I won’t do it again.”
Brenda patted his shoulder lightly, though it still felt heavy somehow. “Good. Now, let’s move on to the next house.”
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Aunt Brenda
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