Under Mommy's Control: Denied

Climbing up onto the bed, Jaime turned on the uneasy footing of his soft mattress, with his jeans tugged down around his thighs. He couldn't wait any longer. He needed it inside of him now!

He slowly bent down into a squat, and let out a soft coo when he felt the slick surface touch his cheeks, and then slide between them. He clenched down instinctively when it touched his tender hole. He was no longer a virgin to silicone, but this beast still scared him. As his cheeks clenched around the plug, he could feel it's exotic texture, and fantasized about how it would feel inside of him.

Jaime took a deep breath, and willed himself to relax. His cheeks loosened, and he felt the tip of the plug press a little deeper into his asshole as it slowly began to spread across it. The ridged surface clung to the folds of his pucker, and he could feel it tugging slightly around the edges. Releasing his breath, Jaime pressed down on his thighs, and began to push the plug home.

"Hah-ah-ah-ahhhhh~"

Jaime didn't even try to hide his moans as he began to stretch his ass around his new toy. Each time a ridge or a nub slipped over the ring of his anus, he let out a gasping moan that he prayed his Mother couldn't hear. Despite the risk however, he kept pushing down, desperate to fill the void inside him.

As he pressed on, he felt a layer of saliva being pushed along the surface, as his hole got stretched tighter and tighter, and hungrily gripped the plug. Every aspect of it got more and more pronounced, more apparent, more intense, until Jaime found himself at a precipice. He could feel the sting of his pucker, strained as far as it had ever been so far, and he had to take it further.

Rhythmically, Jaime started breathing in and out, like a woman giving birth. With every breath he could feel himself slowly sliding up and down on the plug, gradually getting deeper and deeper. Every time he slid down, he could feel his locked updicklette twitch, another jolt of precum leaking out through the tip of the cage.

"Jaime?!"

A sudden sharp intake of breath at his Mother's call was all it took. He felt himself slip over the event horizon, the widest part of the plug, as gravity and momentum did the rest. With a wet slapping thud he felt the plug seat itself inside of him, mashing into his prostate like a thrown football. Jaime's cock ached against the confines of his cage as another fat dollop of pre was forced out of him.

"Ooohhhhhh..."

He could feel all of it, seated inside of him. It was like a piece of him that was missing had finally been reunited. The ridges and nubs and girth seemed to fit perfectly inside of him, as his stinging answers tightly gripped around the base. He... just needed a minute, and then he'd be back with his Mommy to watch the movie. His M-Mother!

...

Sandra meanwhile was sipping her wine and smiling deviously to herself. The comments section was going wild over Jaime stretching his ass around that monster, and donations were pouring in to buy him bigger and more exotic toys. She'd set up the shot to show multiple camera views, so you could see the expression on his face and his asshole stretching around the plug. People were posting about how thick they thought he could go, how much they wish they had access to his ass, and even a few expressing admiration for him as their own role model. One commenter even said how much they'd be willing to pay for the plug after Jaime was done with it. He was becoming quite the spectacle to his fans~

She'd had to restrain herself quite a lot to keep herself from fingering herself right there in the living room, but she wasn't sure that even a Sissy like Jaime wouldn't have been able to tell. Instead she slowly enjoyed her wine and watched the camera feed, taking delight in watching Jaime struggle to stand and pull up his borrowed undies and jeans. Little did he know that he'd taken a full 20 minutes to seat that plug in himself, which had also given her plenty of time to plant an empty wine bottle on the couch and set up a few donation goals on her livestream account.

She'd started off with only a few dozen people from the BDSM board that Jaime had been looking at, but with the videos and streams she had been posting, she was now up to almost 800 followers, many of which were more than willing to donate funds to ensure more content. Sandra had set up some donation tiers where contributors could suggest outfits, choose toys, and if they donated enough, select hypnosis tracks to guide his development. That was only for the high rollers however, and she'd retain the option to veto.

As she waited for Jaime she watched as the bar to the first goal quickly filled up, and outfit suggestions quickly filled in. Every donation of $25 dollars got to submit a suggestion for a later poll, and some of the suggestions were already quite scandalous. Video game and anime cosplay suggestions, the usual assortment of waitress, schoolgirl, and maid uniforms, one for a woman's business suit, and even one suggesting a full latex encasement bondage suit. Now that would be something!

As she read through the comments and suggestions, she could see out of the corner of her eye, Jaime slowly sneaking down the hallway. She could tell from here how stiffly he was walking, and even in the dim light could see his face flushing red. She set down her phone and got herself into character.

"Jaaaiiimeee~ what took you so long! I've been waiting aaages for you!"

Sandra picked up and waved around an empty wine glass to punctuate her supposed inebriated state. She could see the look of discomfort on Jaime's face seeing her like this, but she knew he wouldn't refuse her.

"Hurry up and come sit down! I wanna see how the movie ends!"

Jaime could only offer up a diminutive apology as he quickly scooted over to the couch, and tried again in vain to sit on the far side. Sandra wasn't having any of it however, she wanted to have him up close and personal for what she had planned. She reached over for him again, this time taking a much more aggressive squeeze of his ass as she dragged him in, like a spider would with a fly caught in its web.

"No more getting up, you hear me Jaime? Your ass belongs to me tonight and I want it planted in that seat right next to me!"

The look on Jaime's face as she claimed ownership of his ass was a treat all in and of itself, and she gave him another squeeze before letting her hand slide up and rest on his hip. She slipped a finger beneath the trim of his borrowed hoodie, and let it rest along the top of his jeans. His skin was almost red hot, like his entire body was blushing. He was so stiff and uncomfortable at her touch, it was so adorable.

"Relaaax Jaime, it's just your Mommy~"

She forced herself to look away from what was certainly another blushing fit, as she grabbed the remote and resumed the video. There wasn't any dialogue in this part of the movie, just some artsy landscape shots and pensive looks. Still, she kept Jaime on edge, hiking up his sweater slightly and sliding her fingers along his exposed hips. He shuddered at her touch, and in turn she felt a shiver of lust course through her every time he let out a soft moan that he hoped she didn't notice. Soon enough however the characters started talking again, and her custom subtitles resumed.

She can tell Sissy.

Anyone could.

She knows what you've been up to.

She knows what you're wearing

She knows what you've got inside of you.

With each subtitle Sandra pulled Jaime up against her tighter and tighter. And with every new line she could feel him squirming, trapped in her grasp, trying to find a way to escape. Throughout this she continued to feign her ignorance, and even poured herself another glass of wine.

She knows you're a Sissy.

She knows you're a dildo stealing, cross dressing, caged little Sissy.

She thinks you're pathetic.

She'd throw you out on the street if she could.

You're garbage beneath her feet.

Sandra could swear she felt Jaime muffle a sob. She squeezed tighter, closing her trap around him.

She thinks you're a coward.

Lying, hiding, fooling yourself.

Every time you pretend you're a man in front of her, she sees right through you.

Jaime let out a soft gasp. It took every ounce of willpower Sandra had not to slide a hand into her pants. But she had other plans. With a dip of her head Sandra let her wine glass fall, as she laid her head against the arm of the couch, and almost closed her eyes, keeping them squinted open enough just to see the screen.

Stop lying to yourself.

Tell the truth.

You're a Sissy.

Stop lying to your Mother.

Tell the truth.

You're a Sissy.

Jaime was starting to hyper-ventilate. Reading those lines, wearing those clothes, being plugged, being locked away, being trapped in his Mother's grasp. He hadn't experienced anything yet. She let her hand slide down his hip, letting out a soft yawn as she pretended to sleep. Her fingers found the top of the heart shaped pockets on his girly jeans, and then slipped inside.

...

Jaime was panicking. Was this real? Did she know? Was the text really there on the screen? His eyes darted between the TV and his Mother. She looked like she was fast asleep.

You're a Sissy.

Jaime shuddered in her grasp as her warm fingers slipped off his exposed hip, and back over his jeans. He let out a breath of relief, until he had to suck it back in as her fingers found his pocket.

She knows.

Then he felt it. Her fingers sliding in, and slipping under the waistband of his boyshorts. These jeans didn't have any pockets! They were just slits that went right to his ass! He nearly jumped out of his skin as he felt his drunken Mother gliding her hand over his freshly lotioned ass, but he couldn't force himself to move. He felt petrified as her hand went where no Mother's hand should.

You're a Sissy.

Jaime let out a whimper as her fingertips thudded against the base of the fat plug jammed in his ass, pressing it against the button inside of him. Oh god why did that feel so good? Did she hear that? Was she still asleep?

She knows.

His Mother didn't stir, her eyes shut, her mouth slightly open and drooling. She nudged the plug again, and let out a moan. Holy shit, he was leaking like a faucet. This was so fucking wrong...

You're a Sissy.

Then she stopped. Her hand didn't move, it just lay there, cupping his ass, fingers resting firmly against his plug. His clitty twitched. Oh god what was wrong with him.

She knows.

He needed it.

You're a Sissy.

He needed to feel it again.

She knows.

He couldn't help himself.

You're a Sissy.

Jaime could force himself to move and escape, but he couldn't stop himself from flexing his hips, and grinding the base of his buttplug against her fingertips.

...

As she felt his hips push back against her hand, Sandra moved her index finger just slightly towards the middle of the base of the plug. There was a reason it was so heavy. There was a reason it was so large.

She knows.

With a whirr, the fat plug in Jaime's ass began vibrating with the power of a cordless drill motor. Her finger pressed firm against it, driving it deep and hard against his faggy love button. Jaime's entire body shivered against hers, and he let out a long whine as she ground the rumbling plug inside of him. The intensity of the vibrations was set to grow stronger and stronger, and she found herself having to press firmer to keep it in place.

You're a Sissy.

...

Every panting breath out of Jaime's mouth was a loud desperate whine. He couldn't keep it together. He pressed his ass against his own Mother's hand, mercilessly battering the fat silicone knob against his prostate, forcing the vibrations deeper and deeper into his core.

"Haaannnhh... M-Mommy~"

She knows.

He could feel a pressure inside him building. A faint buzzing tingle behind his clitty. He'd only felt it in passing before, with the dildos, but this was unrelenting. The plug was now vibtrating in pulses, sending thunderous waves of pleasure through his body that broke down and the foundation of his resolve. He could feel himself letting go, getting louder, pressing harder against his Mother's hand.

You're a Sissy.

He couldn't stop himself. He didn't want to. It felt like he'd been caged for ages, like he hadn't orgasmed in ages. With each pulsing wave he felt himself getting closer, closer to release, closer to an orgasm.

She knows.

"Oh god!"

You're a Sissy.

"I'm gonna cum!"

She knows.

"I'm a Sissy and I'm gonna cum!"

You're a Sissy and she knows!

"I'm going to have a sissygasm!

His Mother yawned.

...

Sandra pressed her fingers hard into the base of the plug and held down the button. The vibrations stopped. She shifted in her seat and then quickly drew her hand out of her Son's pocket, dragging her fingernails along his smooth perfect bottom, before throwing them over her head and letting out a loud overly dramatic yawn. She held it for a moment, watching Jaime out of the corner of her eye, waiting to see if he made a move. He'd gone white as a sheet and was curled up looking down at himself. His skiing shone in the light of the TV, wet with sweat, and he was breathing in quick, rapid, shallow breaths.

"Oh my goodness Jaime, just look at me! A glass of wine or two in the evening and I'm useless~"

Sandra let out a little titter as she drew her hands back into herself, taking a moment to breathe in the smell of her Son's ass on her fingers.

"I think I need to head right to bed, otherwise I won't be able to get up in the morning!"

She reached over a tousled Jaime's hair with the same hand she so enjoyed molesting him with. She didn't wait for a reply from him.

"You can stay up and finish the movie if you'd like. Obviously if I fell asleep at couldn't have been enjoying myself very much~"

And with that Sandra wobbled off, still pretending to be a little drunk. With her back to her Son, she couldn't resist bringing her fingers up to her lips, and giving one of them a suckle, savouring the flavour of his boipussy on them. She was going to finger herself raw tonight. No wasting time setting up Hypnos, no carefully watching him fall asleep. Tonight was all about her. Jaime could sleep on the couch for all she cared

Thank you all for reading my latest chapter in the destruction of Jaime's fragile masculinity and his Mother's growth into becoming a sexual predator. It has been a long time coming that Sandra got to have her way with him a little, and I know how excited some of you are for more~

As always I love reading your feedback and comments, and I love reading about new idea that you have regarding poor little Jaime. It always warms my black little heart.~

Thank you kindly~

Mommy's Hypno Sissy