Naughty Boy’s Sissy Training! (Part 1)

“Stand up straight, young man,” Mommy Liz demanded, her voice sharp as a whip crack. “You’ve been nothing but trouble all week, and it’s time you learned some discipline.”
The boy, James, shifted uncomfortably under his mother’s stern gaze. His eyes darted around the room, avoiding her direct look. “I—I’m sorry, Mom. I didn’t mean to…”
“No excuses!” Mommy Liz cut him off, her hands on her hips. “You need to be taught a lesson, and I’m just the one to do it. Go to your room and wait for me. And don’t you dare come out until I come get you.”
James swallowed hard, feeling shame and apprehension as he trudged upstairs. The heavy footsteps echoed in the silent house, each step a reminder of his naughtiness. He stood by his bed, his mind racing about what punishment he would get.
Minutes later, Mommy Liz appeared, carrying two garment bags. Her expression was firm, leaving no room for argument. “Strip down completely,” she ordered, setting the bags on the bed.
James hesitated, his cheeks flushing red. “Mom, what are you doing? Please, I promise I’ll be good.”
“Too late for promises,” Mommy Liz replied coldly. “Now, strip. You need to learn that actions have consequences.”
Reluctantly, James began to undress, his hands trembling slightly. He felt exposed and vulnerable as he stood there in nothing, the cool air brushing against his skin.
Mommy Liz unzipped the bags, revealing an array of items that made James’s eyes widen in disbelief. The first bag contained three frilly pink, lavender, and grass green dresses. The second bag had more things on hangers: pastel nightgowns, petticoats, girly panties with matching bras, and thigh-high stockings. “What… what are those for?” he stammered, his voice barely above a whisper.
“For your training, of course,” Mommy Liz said matter-of-factly. “From now on, you’re going to learn what it means to be a good sissy. Evidently, the boy thing isn’t working out. It’s time to teach you some humility and obedience.”
She picked up the pair of lacy pink panties and held them out. “Put these on. And then we’ll start with the rest.”
James stared at the panties, his mind struggling to process this sudden change in his life. “Mom, please, I can’t wear those. They’re… they’re for girls.”
“Exactly,” Mommy Liz retorted. “And that’s the point. Do as you’re told, or the consequences will be worse.”
With a deep breath, James reached out and took the panties from her hand. He stepped into them slowly, the soft fabric sliding against his legs as he pulled them up. The satin felt foreign and humiliating, but he knew better than to say anything else.
Next, Mommy Liz grabbed the matching pink nightgown and held it up. “This too. You need to look the part if you’re going to play the role properly.”
James slipped it over his head, the fabric rustling as it settled around him. The nightie was smooth and cool and felt better than his usual cotton pajamas.
“Good,” Mommy Liz nodded, her expression softening slightly. Now, let’s work on your hair.” She pulled a brush and some ribbons from the bag and styled James’s hair into pigtails, tying them off with bright pink bows. What else will Mommy Liz make him do? Click right here to find out!

Mommy Liz

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