Under Mommy's Direction Ch. 08

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A Sissy Son struggles to come to terms with his changes.
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Part 8 of the 8 part series

Updated 06/09/2023
Created 08/29/2019
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Sandra milled about the kitchen, keeping dinner warm for when Jaime finally built up the courage to come eat. She had let Jaime take all the time he needed to shower, get dressed, and make sure he'd gotten all the cum off of his face. Seeing the shock in his eyes when she had mentioned that "moisturizer works best after you've showered" while his face was still plastered with his own cum had been almost too fun, and she had struggled not to let out a knowing smirk at the moment. The sheer wall of embarrassment must have been incredible, and just thinking about it made her rub her legs together in excitement.

It was still no excuse for leaving his phone behind while he showered. A Sissy needs to always be at the back and call of their Master or Mistress, and Jaime was going to have to learn that the hard way. As she pulled dinner from the oven, she spotted Jaime out of the corner of her eye, tentatively peering around the corner into the kitchen. She turned away from him, smiling to herself, eager for what was sure to me a supremely awkward dinner for her Sissy Son.

...

Jaime had spent his time in the shower frantically scrubbing his face, desperately trying to wash off all the evidence, and his shame. If he had brought his phone with him, his Mommy would have heard the mix of deep breaths and pathetic attempts to reassert his masculinity.

"I'm not a Sissy... I'm not a SIssy... I'm not a Sissy..."

Jaime slid down the shower wall, sitting down on the floor and hugging his knees to his chest as the water rained over him.

"I'm just doing what Mommy says... She's threatening me... She could ruin my life... I'm just pretending for her... I'm not a Sissy inside..."

Jaime hung his head down, and stared at his little dick, locked away in that pink chastity cage, the perfect symbol for the state of his masculinity. Trapped beneath a veneer of pink, but still a man inside. Or so he thought. As he stared at his locked up clitty, he heard his own voice in his head.

"Little Sissy slut..."

Those were his words, his thoughts, his admissions.

"No..."

Jaime could feel tears welling up in his eyes. He was about to break into sobs when he heard his Mother's voice. He straightened up, listening for her at the door when he realised this voice was also coming from inside.

"Jaime~ Jaime~ Can you hear me?..."

The voice faded. It was distant and echoing inside his mind, but it was unmistakable his Mother's voice.

"I want you to do something for me Jaime, something that..."

His Mother's voice trailed off into murmurs and silence, as Jaime strained to concentrate.

"I want you to resist Jaime. I want you to keep fighting, no matter..."

Try as he might he couldn't hold onto her voice, as her words drifted away, only able to focus on the beginning. But he wanted to hear them all. Her voice was almost hypnotic, and he found himself hanging onto every word.

"I want you to do this...because... I don't want you to become a Sissy..."

Her voice faded in and out this time, Jaime catching words in bits and pieces. But he heard it, deep inside him. He had to resist. He had to fight it. His Mother had always been there for him; a widow, a single parent, a working Mom. She had carried him so far, he couldn't let her down now!

Jaime felt a swell of emotions. Shame, confidence, humiliation, courage. He could endure, he could play out through Mommy's abuse, but he would stay strong for his Mother. She believed so much in him, it would break her heart to see what he'd become. His Mother spoke to him one last time.

"You were born to be a Sissy."

"Born to be a Sissy..."

Jaime mouthed out the words, but his consciousness didn't register them. They struck right to his core as he fell away and his conditioning took over. As he stood to his feet, he ran his hands along his legs, feeling for any stray hairs that might have grown back, touching up his smooth body with the razor his Mother kept in the shower.

He stopped out of the shower, remembering what his Mother had told him just before, and applied a moisturizing layer of baby oil to his body, making it shine and gleam as he ran his hands down his curvy butt. He wrapped himself up in his bathrobe, and made sure to pick up the bikini he'd worn in here.

Gracefully he walked to his room, hung up the bikini on its hanger, and began to get dressed. He laid out his outfit on the bed and it was only then that Jaime's consciousness pulled itself back up, unaware of what had happened. Jaime stared down at the clothes he'd laid out.

Blue jeans, a grey t-shirt, white tube socks, and his first pair of panties. His first stolen pair. His Mother's pair. White, with pink trim, and a little pink bow on the front. The ones that had started all this.

With trembling hands, Jaime pulled them up his smooth legs, the sensation of them on his skin causing him to shiver and shudder. After promising himself that he'd resist for her, the taboo of wearing his Mother's panties had only become more exciting. If she ever caught him, ever found out. She'd be so disappointed, so ashamed of him.

"Excellent choice Sissy~ If there's one pair that your Mother knows is missing, it'll be those~"

Jaime almost jumped out of his skin at her voice coming from his cellphone. His eyes darted around the room, stunned that he'd forgotten how she could, hear and see everything he did in here.

"Aw, did you forget about me Sissy? You left me here all alone~ That's not what a good Sissy is supposed to do~"

Jaime began to stutter and stammer out excuses, fumbling over his words

"Tut tut, Sissy, I don't want to hear excuses! You'll find out what happens when you don't behave yourself after dinner~ Besides, I think I hear your Mother calling you~"

Jaime tilted his head in confusion when he heard his Mother's voice calling down the hall.

"JAIME! Your dinner is getting cold!"

"C-Coming!"

Jaime's voice trembled out the words as he looked back to his phone. She was beginning to know more about what was going on inside his home than he was. Jaime tugged up his jeans and pulled on his t-shirt, and grabbed his phone, before hesitantly heading for dinner, his panties and chastity cage rubbing with each step..

...

Sandra waited patiently for Jaime to enter the kitchen as she pretended to not to notice him lingering in the doorway. She fiddled with the pots on the stove until she heard the scooch of him setting into his chair. Stifling a growing smirk, she twirled around with a plate of food and a loving smile.

"There you are! Been spending too much time cooped up in your room lately sweetie, it feels like we haven't talked in ages!"

Sandra leaned in deep over the table as she set down Jaime's plate, giving him an ample view down the front of her blouse. She braced herself on his shoulder as she did so, gripping him firmly and passively holding him in place. She'd even swapped out her sandals for heels so she could tower over him and make him feel small. After what must have been an eternity for Jaime, she stood back up and released his shoulder, watching him slink down further into his seat with an all too obvious flushed look on his face. Sandra held her sweet loving expression and pretended not to notice his obvious discomfort.

She watched as Jaime mumbled out some excuse, not listening to his words, but watching his body language. He'd never been confident or sure of himself, and after all he'd been through so far, he'd only gotten more and more submissive. She cut her food and pretended to listen as he rambled on about what he'd been doing this week, looking for a job online, eying some university prep courses, etc. etc. Sandra interrupted him.

"Ooh, I'm glad to see you're looking forward to university! Your first real chance to go out in the world, spread your wings, become a man..."

Sandra let her voice trail off into uncertainty as she watched Jaime's expression fall. It was almost as if she'd snuffed out one of the little candles of hope inside of him that outside of his relationship with Mommy, others might see him as a real man. She put on an apologetic face and cooed to Jaime.

"Oh no sweetie, I didn't mean it like that~ You've been living at home all your life, and had Mommy here to help you all the way. When you go to University I won't be there anymore and you'll be able to fully blossom into who you really are~"

Jaime let out a noticeable flinch at her use of the word "Mommy" and she watched as his eyes darted down to the phone in his pocket. Sandra decided to push the issue.

"Once you're there you'll be able to have all sorts of new experiences! You'll meet new people, go to parties, have all sorts of adventures~"

Jaime' expression started to rise with the thoughts of all the possibilities that University might bring. It was almost adorable to watch his face light up with hope and potential before she went in for the kill.

"And when you're there you might even meet that special someone~ Someone to settle down with, make a life with, face the world with~"

Jaime nodded in agreement.

"Just promise me when you do, that you'll introduce me sooner rather than later. I want to make sure you're falling for the right sort of girl..."

Sandra couldn't hide her mischievous smirk as she let the next few words pass from her lips in a husky whisper.

".. or guy~"

The mortified look on his face was too much. It was almost as if she'd slapped him right across the face as his mouth hung open slightly as his eyes looked down. She could see his whole body trembling.

Sandra set her cutlery down on her cleared plate and stood up, her chair breaking Jaime's train of through with a loud squeak across the floor.

"You'll have all sorts of possibilities in University sweetie, just try not to forget your loving Mommy~"

And with that she stood up, dropped her plates into the sink and leaned over her son, giving him a smooch right on the forehead.

"Now be a good little boy and clean up after Mommy. She's had a long day and is going to enjoy a nice lie down~"

Sandra walked out of the kitchen, leaving Jaime behind with his thoughts as her heels clicked down the hallway.

...

Jaime slinked back into his room, his Mother's words still swimming around inside his head. He could hear her saying the words, and everytime his mind replayed it, she got more and more dismissive, more condescending, more degrading. By the time he had finished cleaning in the kitchen it had felt like she had been calling him a little Sissy. Not a real man, a faggot.

The more Jaime thought about it the darker his thoughts went. Did she know? Did she know about the panties? The dildo? Did she know that was cum? How long had she known? Jaime let out a desperate sigh as he threw himself onto his bed and buried his face into his pillow. He just wanted to cry. To break out into sobs and have this all be over. Jaime gritted his teeth, gripping handfuls of sheets as he tried not to break out into tears.

"No! She doesn't think that..."

His Mother loved him! She supported him! She said as much... she'd just never actually... seen him be a man. He'd never had a girlfriend... He didn't have any real muscles... And maybe... Maybe following Mommy's directions was beginning to affect him outwardly.

Jaime thought hard as he felt swallowed back a sob. He hadn't complained at all when his Mother had told him to clean up the kitchen. He'd been doing the laundry, and more chores around the house at his Mommy's insistence. Maybe she'd been conditioning him to listen to women? Could that be a thing? Could it have happened so fast?

He sniffled as he thought more about it.

"I want you to resist Jaime."

His Mother's voice echoed in his head again, telling him to fight it, to keep strong, resist.

I want you to keep fighting..."

"You were born to be a Sissy."

Jaime slammed a fist into the mattress. This was all so confusing! So many thoughts and impulses that he'd never had before! He knew he needed to resist, to hold on, for himself, for his Mother. But still... There was another voice. It had started off quiet, but it was getting louder.

It wasn't just Mommy telling him to do things. Part of him wanted this, to do what she said. And it was wanting more and more. It started with the panties, tasting his cum, but those had just been thoughts, suggestions. They were becoming urges... He was losing control...

"Having a tough time there Sissy?~"

Jaime buried his face deeper into his pillow. He couldn't deal with this right now.

"You still need to be taught a lesson Sissy~ Can't have you being so forgetful, even if you are Mommy's little airheaded slut~"

Jaime winced at her words. Being called a sissy was bad enough, but he was being attacked from so many angles now.

"Chop, chop Sissy! I'm being very lenient with you right now, but I will not tolerate any more failures."

Mommy's voice turned cold and stern at the end of her statement, a gentle prodding that turned into a dire threat. Jaime rolled over, his eyes red and puffy, desperate to let out a stream of tears.

"Poor Sissy, having such a rough day and still needing to be punished. Mommy promises this won't hurt too much~"

Jaime failed to take much solace in her words.

"At the bottom of your big box of goodies that Mommy bought you, there is a box full of all sorts of punishments and lessons for naughty Sissies who don't listen to their Mommies. Inside there will be all sorts of boxes, but I want you to take out the large brown envelope."

Jaime nodded as he scooted over on the bed, and threw the covers off the box that he had so haphazardly tossed on after his Mother came to his room. There were still all sorts of numbered boxes, but as he shifted them around he found another box in the corner with the word 'Punishments' written on it in black sharpie. Jaime swallowed hard.

Opening the box of punishments, he wasn't granted any insight into what potential pains might lie in wait for him, as they were all packaged as well, but he did spot the large brown envelope right away, and not willing to spend any more time with his Mommy contemplating him going through these punishments, he quickly closed the boxes, and set it on ground on the far side of his bed, hidden from sight of his bedroom door, and hopefully out of his Mommy's mind.

"You can open it Sissy~"

Tearing open the top of the envelope, Jaime peered inside only to see not much of anything. All he saw was a strange triangular sheet of what looked like black plastic. He dumped the contents onto his bed and investigated it more. It was a black triangle of what looked like a gel or wax, sandwiched between two sheets of thin clear plastic. Jaime looked over it puzzlingly.

"It goes over your crotch Sissy~ It's going to make sure you can never grow nasty pubes ever again. You're going to burn out those hair follicles, and have a beautiful silky smooth sissy crotch forever~"

Jaime let out a sigh, a mix of relief and of dread. A smooth crotch wasn't so bad, lots of men shaved their junk, but not being able to grow it at all? This was the first thing Mommy was telling him to do that was permanent, something that would stay with him forever.

"All you need is a hot wet cloth Sissy, as hot as you can get it. I want to be able to see the steam rising off it as you scald away your pubes~"

Jaime flinched at the wording, imagining his masculinity literally burning away.

"And you'll do it in here Sissy, where I can see you from all angles~ Now do as you're told, and go fetch that cloth."

Jaime dutifully got off his bed, peeking to see the hallway was clear first before darting into the bathroom. He let the water run for a full minute, until it was steaming up the sink and starting to fog up the mirror. He could scarcely hold the cloth as he wrung most of the water out, and took it back to his room.

"Looks nice and hot Sissy, now drop those jeans, lower those panties, and say goodbye to your thick and curlies~"

Jaime sat on the end of his bed and shucked his jeans down to around his ankles. He shimmied out of his white and pink panties, until they came to rest just above his knees. Jaime stared at his bare crotch, still smooth from when he had shaved it. He hadn't even started to grow anything back at all yet, maybe this punishment would hardly make a difference...

"No more stalling Jaime, or I'll call your Mother in here to watch."

The volume of the speaker turned up as his Mommy threatened to twist them to full blast. Hurriedly, Jaime peeled off the plastic backings, carefully centered the triangle on his groin, and pressed it down hard with the scalding hot wet cloth.

Jaime took in a quick breath of air as the sudden shock of burning pain turned into a steady fiery tingle. His knees clenched together as he quivered in pain, his hands still pressed down on his groin.

"H-how long do I-"

"Until I say."

Her response was quick and curt, and Jaime knew not to argue as the heat and pain started to slowly fade. For what felt like an hour but was only a few minutes, he struggled through as the heat diminished until it was a bearable throb.

"That should be good enough now Sissy. Peel it off slowly and lets see how it took."

Jaime lifted up the cloth and started to peel of the black waxy triangle, his sensitive groin send bolts of pain out as he pulled the sticky material away. Jaime closed his eyes tightly as he powered through it, finally feeling a sense of relief as he tugged away the last corner. As he opened his eyes he could see his computed screen was now filled with a camera feed from his room, and it was centered right on his groin.

In cursive black lettering, written across his now permanently silky smooth crotch were the letters S I S S Y. Jaime's head snapped down to look and he could see the word staring back up at him. SISSY. He'd been branded, titled, there was no denying anything if anyone ever saw that. Frantically and without thinking he took the cloth and scrubbed at it, hoping to wipe away the letters

"Oh Sissy, do you think Mommy didn't splurge a little on you for this? That's not some cereal box temporary tattoo, that's high grade black henna, and you just steamed it into your skin~ That's not going to fade for a long, long time~"

Her words sank into his head as he stared back and forth between his crotch and the screen, the bold black letters staring back at him, spelling it out, who he was, what he was becoming.

SISSY

SISSY

SISSY

Panic began to set in as Jaime realised he had lost control. He wasn't just listening to Mommy, hoping for a way out, or that it would end, or that she would lose interest. He wasn't under Mommy's direction, he was under her control!

SISSY

SISSY

SISSY

Jaime began hyperventilating, he couldn't catch his breath. He gasped for air as the word pounded in his head. He was in panties, locked in chastity, and was now branded across his crotch a Sissy. Jaime's head began to spin faster and faster as he struggled to focus.

SISSY

SISSY

SISSY

"It just finally clicked, didn't it Sissy?"

Mommy's voice pierced through his mental haze like an arrow, finding its mark in his fragile psyche.

"It's already too late. You can't stop any of this now. I own you now Jaime."

Jaime stopped hyperventilating. He stopped breathing all together. It felt like everything was on pause, except Mommy's words coming from his speakers.

"You will do as I say, we both know that. And you can try to resist inside, try to not let the things I make you do and feel not change who you are inside. But you will change. Slowly yet surely. I'm going to poke and prod and pinch at your weak little psyche, strip away all the illusions of masculinity, and rewire that soft little brain of yours until you're my perfect little SISSY!"

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