Naughty Boy’s Sissy Training! (Part 3)

(part 2) They arrived at the mall, and it was already packed and bustling. James tried to keep his head down, but the whistles and laughs he heard let him know that people were looking at him. Mommy Liz led him inside, heading straight for a store with window displays filled with pretty garments. Some ladies were sitting on cushioned benches to one side, with the pretty clerks bustling about.
“Liz, who’s this sweet little thing?” one of them asked a middle-aged woman with a kind smile.
“This is my son, James,” Mommy Liz explained, her voice casual. “He’s been very naughty, so I’ve decided to teach him a lesson by dressing him as a sissy.”
The group chuckled, their eyes twinkling with amusement. “Oh, that’s quite the transformation!” another friend chimed in, her gaze sweeping over James with interest. “Can we help pick out some new clothes for him?”
Mommy Liz nodded, a pleased expression on her face. “Of course! It would be good for him to see how others perceive his new look.”
James stood there, feeling increasingly exposed as the group surrounded him, each picking out items they thought would suit him. There were skirts, blouses, even more, lacy panties, pantyhose, and stockings. The embarrassment was overwhelming, but he knew better than to protest.
One of the women held up a particularly frilly pink dress with puffed sleeves. “How about this one, dear? It would look lovely on you,” she cooed, smiling encouragingly.
James nodded weakly, his cheeks burning red. “Yes, ma’am,” he mumbled, accepting the dress from her.
As they continued to select outfits, the conversation turned to other aspects of sissy training. They discussed the importance of obedience and shared stories of their experiences with similar disciplinary measures. James listened silently, his mind racing with thoughts of what lay ahead.
After what felt like an eternity, they had amassed a pile of clothing items for James to try on. Mommy Liz thanked her friends for their help, and they agreed to meet again soon to check on James’s progress.
Back in the changing room, James stared at the pile of clothes, his hands trembling slightly. Mommy Liz helped him undress, removing the layers of feminine garments with practiced ease. She then proceeded to help him put on the new outfit they had selected: a soft cotton blouse, a knee-length skirt, and a pair of floral panties.
As she adjusted panties around his waist, Mommy Liz leaned in close, her voice low and soothing. “Remember, this is all for your own good, dear. You need to learn to behave properly; this is how we will do it. You’ll thank me one day.”
James nodded silently, his emotions a tangled mess within him. He felt trapped in this role, unsure how to escape or if he wanted to. As Mommy Liz finished dressing him, he looked at himself in the mirror, seeing a stranger staring back at him. The person he once seemed to be distant, fading further with each passing moment.
“You look perfect,” Mommy Liz declared, admiring her handiwork. “Now, let’s go show off our pretty sissy to the world.”
She took his hand firmly and led him out of the changing room and back into the bustling mall. James walked alongside her, his head held high despite the shame burning within him. He knew this was just the beginning of his journey, and the thought terrified and intrigued him. As they approached the exit, he couldn’t help but wonder what other surprises awaited him in the days to come.

Mommy Liz

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