Under Mommy’s Control: Foundation

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Under Mommy’s Control: Foundation


Chapter 4

“0… too late Sissy. I just hit send~”

Jaime’s whole world stopped as he heard those words. She sent them. All the things he’d done to avoid this, digging himself deeper and deeper, and she just hit send. His mind raced over the events of the last few weeks; the crossdressing, the dildos, the chastity, evidence of any single one of those being sent to his Mother would ruin his life.

“I warned you Sissy, time and time again. You talked back to me, and now ignoring my calls? No, that’s not anyway to treat your Mommy~”

Jaime just laid on the floor in defeat, every possible scenario playing out in his head, none of them ending well for him. There was no way in hell he wasn’t getting kicked out at the very least, more likely everything would be aired publicly. His Mother was a sweet woman, but when scorned he had a vicious streak.

“In thirty minutes when your Mother sees that email, life as you know it is going to end, Sissy~”

Jaime’s swirling storm of anguish halted for a minute.

“T-thirty minutes?”

“Well of course Sissy, your Mother is at work right now, in a meeting to be exact. I can see her from the hallway.”

“Y-you can see her?”

Jaime’s suspicions had come true. She had made contact with his Mother at work. Mommy was finding all sorts of ways to sink her claws into his life, and his Mother was no exception.

“Don’t sound so surprised Sissy, did you think I would go through all the effort of compiling the evidence of your transgressions to hold over your head, and not ensure that I’d be able to witness the aftermath?”

Jaime winced as Mommy tittered to herself over the phone, her laugh cold and cruel.

“I can’t wait to see the look on your Mother’s face when she sees what I’ve sent her, I even arranged to have her one-on-one for coffee after~”

Jaime strained his brain as he thought through the situation. Thirty minutes, one on one. There was a chance! Jaime pulled himself up off of the ground and grabbed his phone.

“Mommy w-wait!”

There was an expectant silence on the other end of the line.

“I-if you’re meeting her one on one, y-you can distract her! You can get her phone and delete the email!”

Jaime’s plea was met with another burst of cruel laughter.

“Oh, and just why would I do that Sissy? I have no use for disobedient little boys who don’t listen to their Mommy.”

Jaime steeled himself through her mockery and stammered out his plan.

“I kn-know her phone password! I-if you can just get a hold of her phone, you can access her email and delete before she sees it! If you c-can do that then…”

Jaime’s voice trailed off and went soft.

“… then I’ll do anything.”

There was silence on the other end.


Jaime could feel another knot twisting in his stomach. Even with this as his only choice, he could feel like it was a mistake.

“A-anything, Mommy.”

Sandra’s mind was running wild with possibilities. She hadn’t been expecting this kind of possibility, but this morning had been full of surprises. She needed to do some set up, but she already had the perfect plan for Jaime. A few tweaks to her schedule, some phone calls, and a favour from a friend, and everything would be set up.

Sandra took a breath and cleared her throat, and then pressed unmute on her phone, adopting her husky, sexy, ‘Mommy’ voice.

“Just remember then Sissy, you asked for this. You begged me for this opportunity~”

“Yes Mommy…”

Sandra squirmed in her seat, the resignation in his voice hitting all her buttons. She composed herself, and built up her voice, ensuring that each word was dripping with honeyed venom.

“You’ve been hiding inside for too long Sissy. It’s finally time we take you out into the real world~”

Sandra paused for a moment, waiting for any sign of dissent, before continuing.

“And quite frankly, I’m tired of the one doing all the work to help you live out your secret fantasies. So you’ll be going on a bit of a hopping run.”

She could hear Jaime let out a low whimper, clearly beginning to regret his decision, but too scared of the consequences to speak up.

“I will take mercy on you though Sissy. You won’t have to wear those clothes you stole from your Mother.”

A sigh of relief.

“Instead, you’ll be wearing new stolen clothes. You’re going to steal some of your Mother’s sexiest lingerie. The sexiest set you can find.”

Jaime winced.

“I want you to find the set that you can best imagine your Mother getting fucked in. I want you to picture as best you can what your own Mother would look like in that outfit, and her getting fucked by a real man in it~”

Jaime let out a soft groan on the other end.

“You’ll be wearing those under your ugly boy clothes while you’re out there in the real world~”

Jaime’s mind was already starting to form a picture of his own Mother in his mind, seeing her dressed up in her usual formal karataş escort business attire.

Mommy’s tone suddenly shifted.

“You have 15 minutes. If you’re not fully dressed up in a suitable set of your Mother’s best lingerie by then, you will know the consequences. You begged for a second chance and now you have it. Do not disappoint.”

And with that Jaime heard a click and the line went dead, stirring him out of his daydreaming. He didn’t have time to fantasize! He raced out of his bedroom and down the hall to his Mother’s. He tore her underwear drawer out of the dresser and dumped it on the bed. He didn’t have time to be careful, he’d have time to clean it up after.

Rapidly, he started sifting through the piles of underwear, sorting out the cotton and satin and grabbing all the lace panties and bras to find matches to. His Mother’s underwear drawer wasn’t nearly as organized as she was, and Jaime could feel the clock ticking for every second that he spent digging through the pile, scanning it for a set that matched.

Finally Jaime found a bra and panty set that matched. Quickly he ran over to the mirror and held it up over his clothes, to get an idea how it would look. The pantiy’s black frills outlined dark lace panels that showed off as much as they hid. Even with both sides of it over his crotch Jaime could still see the bright pink of his chastity cage through the translucent lace. Jaime closed his eyes.

He pictured his own Mother once again, standing in the mirror opposite him, replacing his reflection. She was taller than him already, but wearing heels in his mind’s eye, she seemed to tower over him. The authority radiating off of her in her dark blue business suit as she stared down at him with her stern expression.

Jaime shivered. If there was one thing that everything he’d experienced had taught him, it was that he clearly had a thing for authoritative women… Jaime swallowed, his throat was getting dry.

Slowly, he imagined piece after piece of her outfit disappearing. First her jacket, revealing the white blouse underneath, his Mother’s chest heaving out slightly now that it was no longer constrained by the jacket. Slowly, he mentally unzipped her pencil skirt, letting it fall down around her ankles. He pictured her stern expression turning into a sneer as her own Son mentally stripped her down.

Jaime’s heartbeat increased as she pictured his half naked Mother, her lingerie only covered by the tails of his blouse hanging over her panties and hiding her bra. Jaime bit his lip, as button by button he undid her blouse, revealing her collar bone, and then lower and lower, showing off the top of her cleavage, her breasts, until finally the shirt vanished, and his Mother stood in front of him, wearing only the lingerie he’d picked out, and her heels.

Jaime’s vision still towered down at him, sneering in disgust as he ogled her body. Her long slender legs, her luscious curves, her amples breasts…

Jaime’s eyes widened, and then looked down at the bra he was holding to his chest, with its D sized cups hung empty in front of his chest. Quickly he unfolded it, and pulled the straps around his back. He didn’t even have to clip them together before he realized how much it didn’t fit him. Staring up in the mirror he stared at a scared little boy play dress up with his Mom’s clothes, and the bra looked terrible on him, empty and misshapen. Jaime’s eyes darted to his Mother’s alarm clock. It had already been 10 minutes!

Jaime started to feel a knot of panic forming in his throat. He dug through the pile of bras he’d set aside, all of them far too large for him. What was he going to do? Should he stuff it? Then it’d be visible through his boy clothes! Maybe he could stretch and safety pin it around his back? The stretched bra looked terrible and distorted!

Jaime spun and sat back down on the bed, his head in his hands. 4 minutes left. Peering up from his hands, Jaime stared at the photos on his Mother’s nightstand next to the alarm clock. There was one of his graduation, his grandmother and… his Mother’s wedding photo.

His Dad wasn’t in the picture, but that’s not what caught his eye. It was his Mother’s bust. She was so much younger, gorgeous in his pristine white dress, and her subdued bosom gave off a sense of innocence. She was also less curvy, slimmer, more his body shape.

“I want you to find the set that you can best imagine your Mother getting fucked in”

Jaime replayed Mommy’s instructions in his head. Her bridal lingerie, on her honeymoon… There couldn’t be a set of lingerie that she was more likely to have… fucked in…

3 minutes.

Jaime dashed to his Mother’s closet, remembering all the boxes of old clothes she’d tucked in the back. He tore open their tops, searching for what he needed. The first box? Old dresses. The second? Retro jeans. Third? No. Fourth? No! Jaime yanked box after box out of his Mother’s walk-in closet, making a mess around him as the spilled and dumped karataş escort bayan their contents. One box left. It was labeled. ‘MY WEDDING NIGHT.’ Jaime grabbed the box and ran to his Mother’s bed with it, and ripped it open.

Staring back up at him, neatly folded, was a set of back and hot pink lingerie. Bold lace black borders, vibrant pink flower patterned panels, pink ribbon accents and black design motifs all worked in tandem to create an image of complete femininity and sexuality.

2 minutes.

No more boy clothes.

Embrace femininity.

He didn’t have time to think about it.

Jaime dumped out the contents onto the bed.

Bra. Panties. Stockings. Suspenders

He grabbed the panties and tugged them up his legs. They barely contained his cage, and were cut so lower his Sissy tattoo was on full display.

He pulled the bra to his chest, fumbled with the clasp. Once, twice, third times the charm!

The stockings, black nylons with a pink and black trim. They glode up Jaime’s shaven smooth leg, and he trembled the whole way.

One piece left. The suspenders. Jaime stepped into them, hiking them up his legs and stretching them over his hips. They sat high on his waist, creating a black frame of lace with his panties that perfectly highlighted his tattoo.

1 minute.

Jaime ran over to the mirror and stared at himself. She looked… Jaime caught himself. He didn’t have the time! He took his phone, snapped a photo, and sent it to Mommy, before falling back on the bed overtop the scattered pile of his Mother’s lingeries, breathing out a sigh of relief. Quickly looking to his phone, he saw the time. 15 seconds left. Jaime closed his eyes and relaxed.

No more boy clothes.

Embrace femininity.

Sandra on the other hand, was anything but relaxed. Seeing her Son completely dolled up in a full set of lingerie for the very first time was sending waves of arousal over her entire body. She could barely even tell that he was a boy! With his waifish form and curvy hips, from the neck down he looked completely feminine. Not even the tiny bulge of his chastity cage was enough to throw off the illusion unless you looked closely enough. It was well worth the price she’d paid for the rapid delivery to have it here so quickly.

Sandra wasted no time in posting the image for her early access supporters, and was immediately flooded by comment after comment from her thirsty followers. She wondered for a moment how many of Jaime’s secret fans were at work, but it never seemed to have an impact on the engagement to her new posts. It seemed that people were more than willing to make the time in their busy schedules to watch his sissy downfall. Speaking of which, she needed to tell him the next step down that path.

Jaime’s phone rang for an instant, before it automatically picked up and he was greeted once again by the familiar domineering voice of his Mommy.

“My, my Sissy, it looks like your Mother was quite the dynamo in her day~ Nobody wears something like that unless they’re truly looking to get fucked, and that goes doubly for you Sissy~”

Jaime scrunched up his face as he tried to bury his head deeper into the mix of his mother’s bedsheets and lingerie. No matter how much he knew he didn’t want to do this, that it was all her bidding, her words stung deep and lashed at his ego and rapidly failing sense of masculinity.

“Just imagine if she could see you now~ There would be no doubt in her mind who you truly were at heart. She’d know that you were feeling the exact same things that she did when she wore that outfit. When she dressed herself up like a slut, eager, ready, and practically begging for cock~”

Jaime grabs wads of bras and panties, and tried to drown out her words by stuffing them against his ears. His Mother was the only stability he had left, he couldn’t let Mommy take that away from him, poison his thoughts with her words…

“Enough about her though Sissy. Today is all about you~ Just as I said, now we’re going to take you out into the real world~”

Jaime’s hands fell from his ears as he began to take in what she was saying.

“You’re going out dressed like that, with the last veneer of your masculinity to hide it from the rest of the world. You can put only whatever pathetic scraps of your male wardrobe still give you comfort over top, and then you’re going shopping~”

Jaime’s head twisted out of the mess of fabric, his ear perched towards his phone.

“I’ve picked out an entirely new wardrobe for you, and its not coming to your door this time. You’re going to go pick them all up in person, with your secret hidden just beneath the surface. You can tell the shop clerks whatever lies you like, that they’re for your girlfriend, or your sister, or even a gift for your Mother, but you’ll know its a lie~”

Jaime could feel himself trembling, the very idea escort karataş of being out in public at all frightened him now, let alone with what he was wearing.

“But enough talk Sissy~ I’ve already called you a rideshare. It arrives in 5 minutes. You have that long to get dressed, be out front, and ready to go. And then next time you contact me, you had better have everything I’ve sent you for, otherwise I send your Mother this newest photo, alongside with letting her see the others I’ve already sent. No if’s, ands, or buts!”

Mommy’s cruel laugh filled the room as Jaime cursed himself for digging himself deeper once again.

“And remember Sissy, you begged me for this~”

And with that the line went dead.

Jaime pressed his face deeper into the mattress, and let out a groan of frustration. How far was she going to take this? How far would she go? Was there any hope of keeping this all a secret, or was he just adding fuel to the fire? Jaime pushed himself up off the bed, he didn’t even have the time to question it.

Looking at the mess on his Mother’s bed, he winced knowing he couldn’t even clean this up before leaving. He rushed to his room and grabbed the hoodie and jeans he had been wearing yesterday. Sliding them up his legs, he noted how much more comfortable they were, how the nylons shielded him from the coarse denim. He shivered slightly as they rubbed against his bare legs over the jeans. Pulling over the hoodies, the bra protected his nipples against the rough cotton fabric, slighting tugging on them as the bra shifted on his chest.

No more boy clothes.

Embrace femininity.

Looking to his mirror, Jaime confirmed that he looked just like your average guy, with only his nervous eyes betraying the potential of his secret. Quickly he headed for the door, got his shoes on, took several deep breaths, and went outside.

Sandra watched the location tracking on the rideshare app. She watched the car approach the house, stop, and then drive off, head off for the high-end mall downtown. As soon as the car left the neighborhood, she switched over to her contacts and scrolled through her recents.

“We’re good to go… Yes… We’ve got a couple of hours before he comes back, but we have a lot to get done… I’m headed there now. I’ll unlock the door, and then we can get to work… yes.. Perfect… see you all soon~”

She hung up the phone and started her car with a flourish, her giddy mood betrayed by the wide grin across her face. It had taken far too long to get Jaime out of the house during this whole experience, and she’d needed a bit of help to get everything she wanted done. She was pleasantly surprised what favours she could get in exchange for being a part of Jaime’s transformation. Discounts, irregular work hours, specialty requests, and all it cost her, or Jaime that is, was something she’d make him do eventually anyways.

Sandra pulled into her driveway, unlocked her front door, and headed straight for Jaime’s bedroom. Boyish blue wallpaper, masculin bedspread, and reeking of body odour. A renovation was in order, but it was going to be extra work for the reveal she wanted.

Oh well she thought. No rest for the wicked~

Jaime fidgeted in the back seat of the sedan and anxiously looked out the windows to see where he was taking him. The driver hadn’t said a word to him when he picked him up, and started driving immediately once he was buckled in. Every so often he’d look back at Jaime through the rearview mirror, almost as if he knew…

Jaime’s thoughts were interrupted however when the car made a quick turn, and rolled up to an unfamiliar shopping centre. The driver again, didn’t say a word, but watched through the mirror Jaime slowly exit the car, and stepped out to his destination.

Jaime stood outside of an anchor store at the upscale mall downtown that he’d heard of, but never been to. The large box shaped building loomed in front of him, its glass display windows showing the latest in women’s fashions; dresses, suits, casualwear, accessories, you name it. Staring up the facade of the building, in large, bold, dark red lettering, was the name of the store.


Jaime didn’t have long to appreciate the pun, as his phone pinged with a text. He’d been half expecting to have Mommy dictate her directions to him aloud in public, but instead, he was presented with a simple list of instructions.

‘Sissy, you have several pickups to make at your newfound temple of femininity. All the order’s have been placed under your name, just let them know who you are, and that you have a pick-up.

The store is a bit of a maze, and I’d hate to lose you to temptation in there, so I’ve made you a handy list to guide you along.

Casual Wear: 3 bags
Professional Wear: 1 bag
Formal Wear: 2 bags
Undergarments, Sleep Wear, & Swimwear: 5 bags
Cosmetics & Accessories: 3 bags

Once you are finished send me a photo of yourself and all of the bags, and I’ll dispatch your ride.’

That was it. No threats or bargains, just a simple set of instructions. Go in, get the bags, go out. Easy peasy, he thought to himself. Jaime steeled himself, walked forward, and entered the store. Sliding glass doors yielded before him, as he strode into the vestibule.

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