Under Mommy's Control: Foundation
ACT 2
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.
"Anything?~"
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 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"
