Under Mommy's Control: Enhanced

Under Mommy's Control: Enhanced

ACT 2

Chapter 3

Sandra woke up early. She had specifically set her alarm 30 minutes ahead so she wouldn't have to worry about Jaime waking up while she was still there. She didn't want to give him that opportunity, the chance to face her and partially come to terms with what had happened last night.

Pretending to be drunk, pretending to fall asleep, all just to lure Jaime in, to keep him off guard, and to give him a way to mentally justify what happened next. Cupping the smooth skin of his waist, sliding her hand across his perfect girly ass, jamming her fingers into the fat plug he had stuffed inside of him; if she'd actually been as drunk as she pretended, then she probably would have completely forced herself upon him.

Instead she had let him do it, let him think that he was taking advantage of her, using his own unconscious Mother for his own sick perversions. And just when he was about to achieve his long denied release, she stole it away from him. He didn't deserve that yet. Sandra had plans for his first 'Sissygasm' and she was going to make sure it was a formative event for her little Sissy Son.

As she got dressed and crept through the house, she carried her heels so as to not make any more noise than necessary. A quick check of the webcams showed that he'd never made it back to bed, so Jaime was most likely still curled up on the couch, wrapped up in a blanket of his own shame and self loathing. Sandra passed through the living room, and took the chance to lean over the back of the couch to see if he was there.

Curled up in the fetal position, his hands wrapped around his knees, she saw Jaime. She could see the dried streaks down his cheeks, the crust under his nose, and he looked like a mess in general. He'd been ugly-crying, clearly distraught over last night. Sandra grinned. He'd be so vulnerable today, so defeated. She was going to use that, take advantage of it. She wasn't going to give him a moment's reprieve as she dragged him deeper and deeper.

She quietly crept over to the TV, and yanked out the USB she'd slipped in last night. No need for Jaime to read any more of that she thought to herself, and maybe if he was clever enough he'd investigate. Now he'd just think he was even more of a hopelessly lost Sissy pervert, taking advantage of his dear old Mother.

Sandra turned back to Jaime, and watched his raspy breathing for a minute, then slowly leaned down even closer, putting her mouth right next to his ear and whispered in the husky voice she used on the phone with him as Mommy.

"Mommy loves you Jaime, you're going to become the perfect little Sissy Son for her~"

Then quick as an arrow she licked his earlobe, and gave it a bite. Jaime immediately started to stir in his sleep as she straightened herself out and headed out the front door. Sandra hopped into her heels as she shut the door behind her, and chastised herself. She'd only had these panties on for 5 minutes as she was already leaking into them.

...

Jaime heard a door slam, and began to stir from his restless slumber, scratching at his ear and stretching out on the couch. As he arched his back a shiver went through his body as he felt the plug inside of him grind over his prostate, squeezing out another drop of precum into his panties. He let out a soft moan before he could catch himself, and quickly covered his mouth.

That was the front door right? Was his Mother still home? Jaime looked down at himself in the clear morning light. Without the cover of darkness it was clear how girly he was dressed. There were no illusions that these were women's clothing, no doubt that he was openly crossdressing. A pang of shameful panic crept through him as he wondered if his Mother had already seen him, if she was still here.

Slowly and cautiously, Jaime pulled himself off from the couch, the plug shifting inside of him with each subtle movement. As he straightened his legs to stand, he could also feel how wet his panties were. They were soaked as if he'd spent the entire night leaking into them after he had...used? Molested? Raped his Mother?

The memories of what he'd done last night came crashing back to him all at once, watching the movie, his Mother getting drunk, her hands on his ass, on his plug, and him using her while she was passed out to try and... Jaime clenched his eyes shut. That wasn't him! He wouldn't do that! He loved his Mother, as a good Son should! It was Mommy's fault, it was... it was those subtitles! On the movie! Another one of Mommy's tricks to make him do things! He needed to get a grip, control himself, and his constant pent up arousal!

Quickly Jaime flipped on the TV and brought up the streaming service. The movie was still there half finished, and Jaime quickly put it on. But whatever brief hope he had were dashed when the french audio played, and completely normal french captions played underneath. He swapped through all the different subtitle options, looking for anything. German, Spanish, even Hindi. Nothing.

It had been all him. He'd taken advantage of his own Mother, and why? Because he needed to cum? Because he was locked up in this infernal cage? Jaime pressed his hand to the front of the jeans he was wearing, feeling the hard plastic shell of his chastity cage, and the cool dampness of his soaked panties. He needed to get these girly clothes off, have a shower, get a grip. He turned to head back to his room and the plug shifted in his ass again as well, squeezing his prostate inside of him and forcing out a wet groan of begrudging pleasure. He needed to get this plug out...

Jaime slowly snuck back to his room. As he passed the dark and empty kitchen, he caught the time on the stove out of the corner of his eye. 8:30, his Mother had already left for work. Had she seen him? Did she go right past? Jaime could only guess and hope that she'd assumed he was in his bed, and not checked the couch.

Back in his room he felt the many watchful eyes of Mommy on him as they watched through the cameras shed forced him to install. She hadn't said anything to him since yesterday afternoon, but that woman his Mother had mentioned at dinner... Jaime pulled the baby blue hoodie off over his head, its delicate softness caressing over his perky nipples as he took it off. They'd gotten so sensitive lately, and his regular clothes felt so rough against them.

No more boy clothes.

He pulled down the tight fitting jeans, thinking about the heart shaped "pockets" in back, that in reality just gave unhindered access to his pantied ass. But they hugged his hips so well, and showed off curves he didn't know he had.

Embrace femininity.

Now he stood almost naked in the centre of his room, wearing nothing but his Mother's workout underwear. Black boyshorts with a magenta trim waistband. He hadn't had the chance to wash them first, they had still lighty smelled of his Mother's sweat and deodorant. Now they were soaked from his locked dripping clitty and smelled of sex.

You need to wear panties from now on.

Jaime hesitated as he slipped his thumbs into the waistband. Wearing these felt so right. Like he was meant to, supposed to, needed to. Even taking them off to shower felt disappointing and wrong.

Once you feel the soft material cradling your little clitt, you'll never be able to wear boys underwear again.

He'd tried going commando yesterday, but it was just so uncomfortable, everything felt so rough on his soft bare skin. He'd already destroyed and thrown out all his boys underwear for Mommy, and he'd worn all of his Mother's panties already. Jaime bit his lip, knowing the answer. He'd have to do laundry. Something about that felt more... real than just wearing them. Like it was a part of him now. Part of his life now, routine. Jaime tugged down his underwear and let them fall to his ankles, exposing his pink chastity cage, and the black henna tattoo that labeled him a "SISSY." It hadn't faded in the slightest, and was still as bold and vibrant as the day he'd been tricked into steaming it on.

You're a Sissy forever, and there's no going back.

Jaime clenched his forehead. He kept getting these micro-headaches, brief flashes in his head. Probably brought on by stress, but they were getting worse it seemed. And with every flash he seemed to get a wave of arousal.

You're a Sissy

A wave of pleasure.

You're a Sissy

A wave of bliss~

Jaime pulled his hand away and looked back down at his locked up clitty. He was breathing heavily now, and his dicklette was leaking a strand of precum that was now sticking to his thigh. God he was so horny, it felt like he hadn't cum in forever. He brought his finger down to his thigh, and ran it through the stream of precum, wiping it up with his finger.

Good sissies savour cum.

Mindlessly he brought it up to his lips, puckering them up for a kiss as he pressed the tip of his dripping finger against them. He pushed, holding his lips tight for a moment, before letting the finger slip through and slide over his tongue, tasting himself on it.

A good sissy doesn't waste a single drop of cum, and good sissy savours it.

Jaime hungrily sucked on his finger, desperately trying to lick every last drop of himself off. Each taste setting off another flash in his head, another wave of arousal, pleasure, and bliss. Every flash sent a spasm in his body as his ass clenched around the plug, and his clitty twitched in its cage.

Good sissies savour cum, good sissies savour cum, good sissies savour cum.

...

Sandra put her car into park, and took a cursory look at her surroundings before taking out her phone and opening the camera live stream. She was behind a dingy strip mall that was only a block away from her house. As much as she loved her new office that she'd set up to manage the technical side of what was rapidly becoming a lucrative livestream, for some things she needed to be close to home. Confident that she had the privacy she needed for now, she looked back down to her phone

Jaime was still in his room, mindlessly sucking on his finger, no doubt having licked a fresh drop of precum off of it. After a few minutes of that she watched as he finally snapped out of his daze, and quickly grabbed the bottle of pink pills in a vain attempt to deal with his arousal. She stared intently as twisted open the bottle, plucked out a pill, and swallowed down the garish capsule. Jaime's body stiffened, clenching down on itself tightly, before letting out a soft shudder and relaxing again. Sandra smiled, content in the fact that these pills were already becoming routine for him. But then Jaime stood there for a moment. She curiously watched as he futilely tried to scope out the cameras in the room, before palming the bottle in his hand. Sandra zoomed in on her screen to get a better view.

Sandra's expression turned from a smile to a grin as she saw him fumble the bottle in his hands, rolling out a few more pills as screwed the cap on. Again, with all the subtlety of a fire truck, he scanned the cameras in his room again as he tried to determine if he'd been seen. He kept his fist closed as he went over to his closet, rummaging through where he'd hidden his Mother's panties, before bundling them up in his arms.

"It's about time that Sissy did some of his laundry" sniggered Sandra as she watched him carry the pilfered panties out of his room for a wash, along with the concealed capsules. Sandra felt a pang of disappointment as his round boi butt sauntered out of the room, and out of sight of her cameras. If only she'd managed to arrange things one day sooner...

...

Jaime slammed shut the lid of the washer and set the dial to 'delicates.' A weeks worth of panties was hardly worth doing as its own load, but he couldn't risk them getting mixed in with the rest of the laundry his Mother had him doing. Pulling on the knob, Jaime heard the whoosh of water beginning to fill the basin, reminding of the shower he so desperately needed.

Jaime pattered back down the hall to the bathroom, his bare feet feeling cold on the hardwood floor as he walked through the house stark naked. He hadn't bothered to throw on shorts or a t-shirt. His Mother wouldn't be back until this evening, and he frankly just didn't feel like it. It wasn't that he was feeling particularly like he wanted to be nude just that... He didn't want to wear those clothes right now. Having felt how nicely some of his Mother's clothes had fit him, he realized how uncomfortable boy's clothes were. Maybe that's why girl's fashion was so much more expensive? Better quality and more comfy?

As much as he mused on the subject, he couldn't really distract himself from the current source of discomfort for him. The thick plug that he'd forced inside of himself in a moment of weakness had been dominating him since he'd woken up, throbbing in a dull aching pain as his ass stretched and clenched around it with every movement.

The lube he'd used last night had dried up over the night, and now it was stuck fast inside of him. A long relaxing hot shower would go a long way towards helping to free his anal intruder, but he'd prepared a contingency plan. Relaxing his clenched fist he stared down at the 5 pills he'd managed to smuggle out of his room, hopefully without notice. They must have been some sort of muscle relaxant, because they helped him with the painful morning erections that strained inside his cage, but when he'd taken the one this morning in his room, he'd realized that his entire body seemed to loosen up. Maybe they could help him relax enough to remove this aching buttplug without too much difficulty...

Jaime shut the bathroom door behind him, turning the lock out of habit. This bathroom was one of the few places he could still feel safe. No risk of his Mother barging in on him, and more importantly, no cameras. Mommy didn't have eyes on him in here, but he was dreading the inevitable call so he needed to be quick. He'd snubbed her yesterday, stood up for himself, and for a day had felt a weight lifted off of his own shoulders. But the perversions she'd forced him into were taking their toll on him, and he dreaded to think of what she had in store for him next, and the punishment he was sure to face.

Pushing back the building feeling of woe, Jaime focused himself in the moment. He twisted the shower knob and tested the water. He'd need it hot to help him relax, and set it as high as he could stand it. He rummaged around under the sink for the baby oil he'd need to help lube up, and set the pills on a little tray atop the toilet tank that he could reach from the shower.

Preparing himself for the sting of the steaming hot water, Jaime took a breath and stepped inside. The hot shower engulfed him, and his skin lit up with pinpricks of pain with every drop, but Jaime endured. Slowly but surely, his body acclimated to the heat of the shower, and Jaime's tensed shoulders relaxed as the heat began to sink into his body and soothe his muscles.

Jaime took the time to fully let go, turning his face up to the stream of water and letting the constant patter on his face wash away his stresses. His hands ran over his body, wiping down sheets of water as he rubbed himself, slowly massaging his limbs. He felt a prickle of stubble as he ran his hands down his thighs, and couldn't help but notice the razor he'd left in the shower out of the corner of his eye. He had to admit that he'd gotten used to the silky smoothness of his body, and he didn't want any more reasons to tempt Mommy's wrath...

The blade ran slickly across Jaime's soaking body, removing any traces of his body hair that was attempting to grow back. Up and down his legs, across his chest, and over his groin, Jaime quickly worked to return himself to a state of utterly smooth hairlessness. He had to carefully work his way around his chastity cage to ensure he got everything, but when he moved to shave his ass, the plug blocked his progress.

Jaime breathed in deeply and set the razor down. He couldn't put this off any longer. He reached around and gave the base of the plug a tentative tug. He could feel its knurled textured ridges gripping his insides, his anus clamped down tight around it, greedily keeping it in. God it was so big... Why did he do this to himself? Why was he so weak? Jaime tugged a little harder and felt it grind across his prostate, making him shudder under the stream of water.

He let go of the intruder and quickly popped the cap off of the baby oil, pouring a generous amount into the palm of his cupped hand. He reached around back with it and pressed it up around the plug, smearing baby oil all around the base, using his finger to work in around it, slipping them under the base of the plug and against his taught puckered hole. He spent the next few minutes applying as much lubrication as possible, wiggling the plug side to side in an attempt to force some of the baby oil further inside of him. Each bump and twist of the plug elicited another nudge onto his g-spot, another shiver of pleasure, or moan of bliss.

Jaime turned the heat of the water up. He'd gotten too used to it, and he needed it hotter. Biting his lip, Jaime tightly gripped the base of the plug and took in a deep breath, then relaxed. As he slowly let the air out of his lungs, with shaky hands he slowly pulled on the base. He could feel the fat shape inside of him slip and slide downwards, the lube having loosened it inside of him. But he only managed to shift it a half inch or so, before his ass clamped down and refused to release. As his body clenched he felt it suck the plug back up inside him, smashing it back against his prostate. A clear flow of precum was now leaking out of his caged clitty, which was now beginning to strain against the pink plastic.

Jaime took in a deep breath, and let it out slowly. He knew this wasn't going to work. He needed some help. With an outstretched hand grasping blindly from behind the shower curtain, he groped around the top of the toilet tank looking for the pills. He felt the rim of the tray and scooped up a pair of pills in his wet hand. With his eyes clenched shut from the water, he quickly popped them into his mouth and swallowed.

For a moment Jaime didn't feel anything. Literally nothing at all. It was almost as if his body had stopped sending signals to his brain. He stood there for what could only have been a few minutes, before he began to feel the warm water flowing down his body again. Slowly sensations came back to him. Then he felt a soft tingling emanating from his stomach. Whether it was the pills themselves, or something purely psychosomatic, he couldn't deny that it felt... good. As the tingling spread he found his muscles relaxing, and his eyes squinted open despite the stream of water on his face. As he looked down at his hands, he could swear he could still see the pills in his hand. Squinting more he could see that it wasn't the pills themselves, but that the pink dye had stained his finger tips. That the capsules had started to dissolve in the wetness of his hands.

"Oh no..."

Jaime yanked the shower curtain back and stuck his head out, the remaining pills still on the tray, but with pools of pink water spreading under them from his wet hand. He felt his body getting looser as the pills worked their magic, but would two be enough? He reached back to tug on the plug, but the stress of the situation was fighting back. He couldn't risk it. There was no way he'd be able to go back for more without Mommy noticing, he couldn't let them go to waste. He picked up the tray and tilted his head back, dumping the contents into his mouth and pouring in the pink stained water at the bottom.