Under Mommy's Control: Foundation

"Now the top."

Choking back half a sob, Jaime lifted up his hoodie, careful not to catch it on his Mother's bra. Pulling it over his head, he let him fall beside him into a heap with his jeans. The quiet sound of it hitting the ground was the only thing he could hear other than the distant hum of thee warehouse ceiling fans. Then her voice pierced the silence

"Such a sexy outfit for such a timid little thing~"

Then he felt her.

She pressed herself up against him, her hands wandering over his body, poking at his breasts, tugging and the top of his stockings. Two fingers tucking into the band of his panties traced their way in from the side, until the bumped up against the hard plastic of his chastity cage.

Mortified, it took everything Jaime had within himself not to break into tears. He felt both of her hands pressed up against the exposed parts of his thighs, and then he jumped when he felt her hot breath on the bare patch of groin above his panties, and framed by the suspenders. Her could feel her eyes, reading each letter of the black henna tattoo that he'd steamed into his crotch, her warm moist breath enunciating each and every letter of the word.

"S I S S Y"

Tears started streaming down his cheeks, but he kept his eyes clenched shut. He felt her fingers once again in the band of his panties, and the fabric being tugged down over his cage, bearing more of his secret shame to her. He felt a strand of presumably stretch from the moistened panties, and then snap back, dangling from the tip of his cage. He felt a finger, pressing against the tip, and then rolling back and forth. Her hands left his thighs.

What started as tears were now full on sobs. His chest heaved with each choked gasp of breath, and he worried that the sound of his breakdown alone would attract more than enough attention for someone else to investigate.

Then a finger pressed against his lips, and the tip of it pushed into his mouth and across his tongue. Jaime could taste the familiar salty tang of his own precum. The tasted somehow seemed to calm him, as he let out a final heaving sob, and began to merely sniffle as he suckled the pre off her finger while she cooed to him.

"Shshshhh little Sissy. It's all okay now. I understand why you're here."

A sudden shove sent him reeling back, and the dusty armchair caught him as he fell forcefully into it. His eyes snapped open from the fall, only to immediately be covered by the cashier's hand as she stepped over and straddled his lap, sitting across his thighs and facing towards him.

"I know it's scary right now Sissy, but you're gonna close those eyes, and then I'm going to dry those tears. After that, I'll help you out with what you came her for."

All Jaime could manage was to croak out the softest "ok" while he closed his eyes behind her hand. It soon left his face, and was replaced by a moist cloth that dabbed at his eyes, and down his cheeks. He'd calmed down a bit now, and with his eyes shut was suddenly more attentive to the feeling of her straddled across his lap. The warehouse air was cold, but he could feel the heat of her thighs transferring into his. Her shapely ass wasn't heavy, but the weight of it on top of him made him feel safe, secure, protected. The one thing that Jaime didn't notice however, was that despite having a porcelain skinned goth girl sitting across his lap, her pussy mere inches from his crotch, his clitty was passively soft within its cage.

"There there, all better now Sissy~ now just hold still, and let Big Sister work her magic~"

Jaime was about to ask what she meant, but then he felt the cool kiss of something against his lips. It slid across the surface, one way, then the other, his bottom lip, then the top. Jaime's mouth parted into a soft gasp as he realized what she was doing.

Then her hands were on his cheeks, her fingers rubbing a cool cream across his face, working it into the nooks and crannies around his nose and eyes. A pad came next, patting all over his face, only to be opposed by something moist that came in dabs.

A brush tickled his cheeks, and almost made him sneeze before a finger was quickly tucked under his nose. All throughout this process, Jaime was in shock, unable to move or react, in part due to fear, in part due to an undeniably curiosity of what the result would be. A soft pad pressed over his eyelids, and then he felt his lashes being tugged on, one set at a time.

The whole process seemed to fly by in an instant, but then suddenly, he felt a weight lift up off his lap, and the sound of smug accomplishment.

"Mmhmm, just as I thought. All you needed was a little TLC~"

Jaime just sat there, too afraid to move his face, his eyes still pressed shut, until he felt her hand on his thighs again.

"Open."

Jaime didn't truly know what he had expected to see, but it wasn't this. In front of him was a mirror, reflecting back his face. But instead of some garish caricature of a whore, or a visage like a painted doll, Jaime was shocked to see that his face looked almost positively... normal. No red lipstick, no dramatic eyeshadow, no nothing.

It took a few moments for his eyes to take everything in, but that's when he realized. He wasn't looking at the normal face of your average boy, but of your everyday normal... girl.

Embrace femininity.

In a vacuum, looking at just his face in the mirror, Jaime could swear that it was a girl staring back at him. He reached up to touch his cheeks, before a hand darted in and stopped him.

"No touching. It's a natural look, and I won't have you ruining my hard work after 30 seconds. Now get dressed, and be careful with the hoodie."

Silently and in shock, Jaime did as he was told, tugging up his jeans, gingerly putting his hoodie on over his head. But at every opportunity he stole a look back to the girl in the mirror. As he donned more and more of his male clothing, the effect seemed to become subdued, until he was fully dressed, and it almost didn't look like he was any different at all.

No more boy clothes.

But he knew. He knew that once the facade of his boy clothes was stripped away again, she'd be there, staring back at him.

"Are they your Mother's?"

His eyes torn from the mirror, Jaime found himself facing the goth cashier once again. Her expression seemed so much warmer now, her piercing green eyes now welcoming and accepting.

"Y-yes... I'm just... borrowing them..."

She leaned in, putting her hands on his shoulders, and her mouth by his ear.

"You mean you stole them~ Don't worry little Sissy, Big Sister won't tell a soul. You just have to promise me one thing..."

"Wh-what's that?"

"That you'll be a little Sissy forever~"

...

Sandra got the ping on her phone just as she was helping to load the last trash bag into the back of the crew's truck. It was Jaime, addressed to Mommy. He picked everything up, and now just needed a ride home. With a smirk, she dispatched the rideshare she had on standby to his location. If she timed it right, she could do a couple laps around the block, and be back just as he was arriving, that out to speed him along before he had the chance to look around and notice anything was amiss.

She signalled the crew leader, and handed him a wad of bills in an envelope. This sort of work was best done under the table, no paper trail to follow should anything go awry.

With that she strutted back into the house to give it a final once over. She went through each and every room, to make sure everything was as it should be. Then she checked to make sure all the windows were open, and as she left through the front door, she deliberately left it slightly ajar.

Checking her phone, she could see that Jaime was only 10 minutes away, so she sent him as text, as his Mother, not Mommy.

"Hey sweetie, there's an issue with the power at work, so I'll be home early, see you in 15."

...

Jaime was pulled out his daze of staring at his reflecting in the rear view mirror from the back seat of the rideshare. He glanced at the message on his phone, and then quickly flipped to rideshare app. He was 10 minutes from home, he might just beat her!

The last minutes seemed to drag on, but finally he arrived at home. His Mothers car wasn't in the driveway, but she couldn't be far. He ran around to the back of the van, and grabbed the heaps of bags that he'd stowed. The last ones he'd picked up, the cosmetics, were by far the heaviest.

Desperately eager to do it all in one trip, he filled his arms and dismissed the driver. He dashed up to the door, cursing under his breath that he'd have to fish his keys out of his pocket. The door was open.

Only taking a moment to pause and contemplate if he'd left it open when he left, he shouldered through, leaving the door wide open behind him. As he made his way down the hall, his nostril flared and he felt a breeze. All the windows were open, and did he smell... paint?

Through the open front door he heard the scrunch of tires entering the driveway, she was home! Jaime had to make the final mad dash to his bedroom, he could stash everything in his closet, hide it behind his clothes, and sort through it later!

He pushed through another open door, leading to his bedroom, and tossed all the bags onto his bed. He swung around to the closet and flung the door open.

...

It was empty, All save for the outfit he'd pilfered from his Mother's closet.

...

Jaime looked over at his dresser.

He reached out and pulled open a drawer.

Empty.

Another.

Empty.

Drawer after drawer, Jaime went through his dresser, looked under his bed, empty, empty, empty, nothing!

Running around to the other side of his bed, he yanked open his nightstand drawer, and was faced with the panties he'd stolen from his Mother, his pink dildo, and that monsterous buttplug.

It was all gone.

Every scrap of boys clothing except for what he was wearing, was gone.

Even Mommy's box of "gifts" was gone.

A call came down the hall.

"Hello Jaime, sweetie, I'm home!~

.....

Thank you all for reading my latest chapter in Jaime's descent. It took a little longer than I'd hoped, but I'm glad I was able to get something out for you all to enjoy. Jaime has been pushed once again to take another step, but at least this time he found someone who seemingly is willing to legitimately help him on his journey.

So just as before, use the comments section or send me feedback to let me know how much of a little Sissy Jaime is and how you'd like to put him in his place, or how much you wish it was you. Now that the ball has started truly rolling for him, I'm able to open the story up in a way that will allow me to incorporate much more of your feedback. So if there's anything you want to see Jaime wear, do, see, or have done to him, let me know. This story can be as much a product of your filthy imaginations as it is mine, so let the ideas flow, and let's see where it takes us.

Thank you kindly~

Mommy's Hypno Sissy