It's the Halloween season, so what better time for a story about a sissy caught in a trap?
"I'll get you boys!" The woman yelled, dashing down her steps to give chase to the troublemakers who had just egged her house. How she hated how Halloween made all the boys into pranksters. It was still afternoon! The trick or treaters were not even out in force yet!
Chasing them to the fence, she could not help but grin eagerly when one of them stumbled just enough for her to catch up and grab him.
"We'll see what your parents have to" she turned the struggling boy around and saw his near adonic face. Why was such a beautiful child such a bad boy? It was time to have some fun, she decided. "You know what, I have something else in mind for you, my dear." Taking him by the wrist, she dragged the hollering boy into her house.
"Hey, let me go, lady!" Jake yelled as she closed the door.
"Nope. You're going to do a bit of community service for me."
"What?"
"It's either that or we involve your parents." The boy paused.
"What kind of community service?" His mind raced as he imagined having to rake the woman's enormous yard.
"You're going to hand candy out to trick or treaters. My house is very popular, after all."
"Is that all?"
"Yep." The woman's smile made it clear there was something she was not saying.
"What's the catch?" You are, she thought.
"Well, I get to pick your costume." She thanked fate that exactly what she needed was by her sewing chair. "I need you to promise that you will wear exactly what I give you to wear, no questions asked."
"I promise."
"What do you promise?" She murmured.
"I promise to wear exactly what you give me to wear?"
"That's right." She smiled to herself. "Here you are." She handed him the neatly folded outfit, his nose wrinkling as he saw how pink it was. "Go on. Scoot."
* * *
Jake sighed as he looked at his reflection in the mirror. She had given him a full ballerina outfit and he felt ridiculous in tights, slippers, everything a ballerina wore. He remembered seeing his cousin's recital and she wore exactly this, he felt like. He fingered the skirt in distaste. There was something especially feminine, he thought, about how the skirt was see-through enough to show the bottom of the leotard. It seemed to flaunt the fact he had had to take his boxers off to put all this stuff on.
"I can't do this." He muttered. He was about to undress when the door opened.
"Oh, don't you look precious!" She purred.
"I can't do this!"
"You promised." She reminded him. "And I doubt you want me to call your parents while you're dressed like this." She looked him up and down. "Here." She tied the strings at the front of the leotard into a proper bow. "And for your hair"
"Ow!"
"It needs to be a tight bun. This is your costume, remember?"
"Yeah, yeah." He growled.
"Just think. If you hadn't thrown those eggs at my house"
"I know."
"Alright, so you'll stand by the door and give out one piece of candy to each trick or treater."
"What if someone recognizes me?"
"You'll be honest." She replied mildly. "Hi, my name's Jake and I'm my mommy's pretty little ballerina tonight."
"Mommy?"
"It's just pretend." She teased, brushing his cheek with an expertly manicured hand. "And that's only if someone outright says you're a boy, okay?"
"Fine." He felt like he was getting in deeper and deeper.
"Take your position, my delicate little rose." She smiled as he stood by the door. "And what's your line?"
"My name's Jake and I'm my mommy's pretty little ballerina?"
"Such a good memory!"She praised. "But be more peppy about it."
"Isn't this a bit much?"
"It's just harmless fun, Jake." She turned and left him to his duty. Something had been bothering him, however. Had he told her his name?
As the trick or treaters began to arrive, Jake realized that they cared more about the candy than the ballerina boy handing it out. He would have almost relaxed, but his legs got progressively colder and colder as the autumn wind swept through his tights.
"Oh," the woman said when he mentioned it during a lull. "You just need to get your blood flowing. "Here, do a few of these." She demonstrated a pliƩ. He did his best impression. "Keep at it, my pretty little ballerina." She smiled approvingly as he kept trying, but only out of sight of the trick or treaters. She disappeared into the other room, cleaning up his discarded clothes. He would not need them anymore, she thought as she eyed his boxers with distaste.
The clock in the hall chimed and she hurried out to see Jake still practicing pliƩs, the bowl empty. She clapped her hands.
"Very good, my wonderful little ballerina."She said. Jake blushed.
"So, I'm done now?"
"Yep. I don't think any more trick or treaters will come." She took his hand in her own, smiling at him. "You did very well."
"Can I go get changed now?"
"Of course. Let's get you into your nightie. It's time for Mommy's pretty little ballerina to go to bed."
"What?" He tugged at her hand even as it tightened around his. "Let me go."
"I know you want to stay up, but it's bedtime, sweetie."
"You're crazy, lady!" She frowned and gave the boy's bottom a swat. He had four layers covering it, from the skirt to the leotard, tights, and panties, but they were all whisper thin and the smack was quite firm. He yelped.
"Who are you?" It only took two more swats to get the panicked boy to say his line.
"Mommy's pretty little ballerina."
"That's right, young lady." She pulled him toward the bedroom. "Now, we're going to get you into your nightgown and you're going to have a good night's sleep. In the morning, it'll be back to being Mommy's pretty little ballerina, I assure you."
"But... I'm a boy." His eyes widened as he saw the pink bedroom she had brought him to.
"Yes, you are." She agreed. "But you'll be mommy's pretty little ballerina all the same." She smiled gently down at him. "In the morning, we'll sign you up for lessons and you'll spend all day every day fully immersed in ballet and pretty things so that you become mommy's pretty little ballerina, inside and out." Jake could not believe his ears.
"You can't."
"What choice do you have?" She asked as the wind began to howl outside. "Try to get home in your ballerina outfit? Naked? You'll freeze."
"Where are my clothes?"
"I have a whole closet of clothes here for you. Outfits galore for mommy's pretty little ballerina." She smiled as he took in row upon row of frilly, feminine outfits. "Remember, you promised to wear exactly what I give you to wear"
"But"
"You didn't expect that promise to last forever?" She smiled at him. "Such a pretty little thing like you, you never even thought of that." She brushed his cheek and smiled. "Don't worry. Mommy's here, here to make sure all you ever have to think about is how you're mommy's pretty little ballerina." She turned to the closet to grab his nightie, the first of many. He would resist, fight, but what could he do? He was a pretty little fly, caught in her web.
The End
Betty Pearl's Sissy Stories 20.1
Topic: Mommy's Pretty Little Ballerina (Read 9039 times)
