Dinner Date with Mommy Pt. 01

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Part 1 of a sequel to Meeting Mommy. Sissy fun abounds.
5.3k words
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Part 1 of the 4 part series

Updated 06/09/2023
Created 11/18/2018
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This is Part 1 of an update on the sissy Sophie and her cruel but loving Mommy, Amanda from the story Meeting Mommy (https://www.literotica.com/s/meeting-mommy)

It contains numerous perverse and offensive themes that I'm sure you'll all eat right up.

This story includes the following: Femdom, strap-on, implied forced-bi and cucking, enemas, butt plugs and anal play, feminization/sissification, spanking, CBT, humiliation, chastity, bathroom use desperation, and domestic servitude. (I may have missed a couple of things.)

Enjoy!

Part 1

Sophie moaned behind her gag, shifting as much as her restraints allowed in her oversized crib. She was as sore as she could ever remember being, her bottom still red hot from the spanking Mommy had given her before putting her down for her nap. That was the least of it, though.

Tied spread eagle on her tummy in a cute little baby doll dress and matching panties, bottom raised by a pair of pillows, Sophie tried to maneuver into a more comfortable position to relieve some of the throbbing pain from her abused little coinpurse. Trapped tight in her chastity cage, it had made the perfect target for her Mommy to discipline when she'd started being difficult.

A miserable tear slipped from the corner of her eye as another wave of agony rolled through her abused little orbs. Even without the ability to touch them she could feel where there would be at least light bruising for several days. Mommy had been merciless as she grabbed them in a single hand and stretched them down so she could freely wield a short piece of incredibly supple leather about the length of her palm, smacking it down hard enough to make Sophie squeal and struggle to get away as she covered every inch of skin on her most sensitive bits with bright red welts.

She remembered as her Mommy had stood behind her in jeans and a loose fitting sweater, lecturing as she worked the mini-strap all across the vulnerable flesh.

"The next time I tell you that you're going to do something, I don't want to hear anything from you but a sweet little, 'Yes, Mommy,' do you understand?"

Sophie had been gagged then too, unable to do anything but cry as Mommy continued to punish her for her disobedience.

"You liked Victor well enough when we met him for lunch the other day," Mommy had said, giving Sophie's aching sack a particularly hard swat, making her pull futilely at her restraints as she struggled to get away. "Though I suppose that was before you knew we'd been talking for a while," her Mommy had mused to herself.

"Regardless, you should really have seen this coming," she said, setting down the strap for a moment and running delicate fingers over Sophie's thoroughly punished scrotum, eliciting a groan from the poor girl. "Because while Mommy loves having her sweet little baby to play with," she closed her fist around the tender flesh and squeezed, the bound sissy's squealing and crying doing nothing to stop her as she continued, "She still needs a real man around on occasion to help keep her satisfied."

Sophie sobbed with relief as her Mommy let go, the aching feeling radiating all the way into her tummy, making her feel nauseous.

"And you, young lady," her Mommy had said, picking the strap back up, "Are going to help, whether you like it or not."

The conversation had lasted for several more minutes, her Mommy detailing all the things she and Victor had discussed. Not just his interest in Amanda, but his curiosity about Sophie as well, which had come as something of a surprise to the little sissy. When they had all met for lunch, Sophie had been allowed to dress like a man, or as close to a man as she was ever allowed. Beneath her jeans and buttoned up shirt she wore lacy garters and panties that framed and complimented her cute little chastity cage quite well. Other than that, though, lunch had been largely uneventful. They'd had a nice, vanilla conversation and Sophie had even been allowed to contribute, occasionally answering innocent questions from Victor.

Of course Sophie realized now that the purpose of the lunch was to meet with Victor and gauge his receptivity to the idea that the woman who was interested in him had a submissive sissy that she'd like to involve as well.

As her Mommy continued to tell her about all the things she and Victor had talked about without her, it seemed that she'd found just the right man. She'd told him all the humiliating ways she had trained her sissy. The cute little dresses and makeup she was forced to wear, the too-small chastity cage that dangled between her legs as a permanent fixture, plus the spankings, enemas, diapers, and hours upon hours of practicing with strap-ons, teaching the squirming little slut to hold still and take huge cock in whichever hole her Mommy desired. She'd also promised Victor that her baby girl would gladly do all of that for him and more... with a little incentive, of course. Mommy seemed pretty excited about it, too.

"Just imagine, sweetie," Mommy had said, finally releasing her ruined little coinpurse, leaving the sissy to collapse in relief as she tried to choke back her sobbing, "You're finally going to put all that training we've done to good use. And once he's had his fun with you, Mommy gets her turn."

She'd walked around with her phone in her hand and held it low so Sophie could see it through tear distorted eyes. It showed a picture of a man from his strong jawline down to the tops of his knees. Sophie had recognized one of the tattoos on his forearm from their lunch, identifying the man as Victor. He wore no clothes in the picture, showing off well-muscled arms arms with a strong barrel chest and a thick, dark mat of manly hair across it. He sported a tight stomach as well, the outline of abs barely visible, reminding Sophie of one of those firefighter models you might see on a calendar.

Of course those models didn't usually go naked on the bottom half as well, but even if they did, Sophie doubted it would have been even half as impressive as what she'd seen right there. She'd blinked hard to get the tears out of her eyes, making sure she wasn't seeing things, but the image stayed the same, showing Victor's enormous flaccid cock reaching all the way down to the middle of his thigh, impossibly girthy for being so limp.

Mommy must have seen the look in her eyes, because she laughed as she pulled her phone back to look at it again, "I know, right? I told him someone must have accidentally misplaced a Pringles can."

Sophie had shivered, her Mommy running a soothing hand over her bare shoulders.

"Don't worry, sweetie. I know it looks scary, but you've taken strap-ons that big before. It shouldn't be too uncomfortable, at least physically speaking. Of course I'm sure there'll be a short period of mental adjustment as you get used to the idea that a real man is going to hold you down and pound that dirty little pussy of yours until your cummies squirt out. Afterwards he'll keep going until he fills you up with his hot, thick seed, but then that's all part of the fun. Well... for me, anyways."

With a wicked giggle, her Mommy had turned to leave the room, reminding Sophie that she had better get some rest since she'd be back in a few hours to let her up to cook dinner. With a flick, she'd turned off the light and closed the door behind her, leaving Sophie in the dark to writhe alone in misery. Sleep escaped her for all but the briefest of moments as the ache between her legs would jolt her back awake when she moved too much, even with her restraints still tight.

With no clock in the room, Sophie had no way of telling how much time had passed, though another little problem started to rear its head before too long. Still dressed in her baby doll dress and panties, her Mommy hadn't bothered to diaper her up before leaving, and that started to become something of an issue as Sophie realized she was going to have to pee really badly, and soon. Naturally her crib was lined so little accidents like that wouldn't be too unfortunate an incident, but if she got her dress all messy and soggy her Mommy would probably give her another good spanking before dinner, and with her backside already in such a sorry state, it wouldn't take much to have her bawling her eyes out again.

Feeling a phantom twinge in her already well punished bottom, Sophie decided that was something she really didn't want, so she did the only thing she could; she grit her teeth on the gag in her mouth, and clamped down hard on her bladder, and did her best to make sure she didn't leak.

Time seemed to stretch out and go on forever, all thoughts of sleep abandoned as the urge to go potty would hit hard, leaving her shaking with the effort of holding it back before it hit her again, even harder than before. By the time her Mommy walked back in, little tears of desperation had started to slip from her eyes as the impending accident loomed over her. She almost sobbed with relief as her door swung open, the sudden light momentarily blinding as it flicked on so her Mommy could get her up.

Sophie's legs shook with effort as she watched her Mommy cross the room from the corner of her eye.

"Aw, what's the matter baby?" Mommy's voice was equal parts sympathy and mocking. "Do you need to go potty?"

Sophie nodded her head as hard as she could, pleading with her eyes as she did so.

"Just another few seconds, sweetie. Be a good girl and hold it for Mommy," she said as she reached the crib, hands efficiently untying the knots that held her baby girl in place.

As her hands came free, Sophie reached down, trying to will her bladder to stay strong as her Mommy continued to untie her. It didn't take long before all the restraints had been removed, though when she tried to push herself up she found her limbs were uncooperative, still stiff and weak from being tied for so long. Her Mommy giggled at her little struggles.

"Come on, then, baby girl, let's get you out of there before you have to clean up after yourself and make dinner."

Mommy wrapped a firm hand around Sophie's upper arm, leveraging her up into a sitting position before helping her down from the crib, still holding onto her arm as her legs swayed uncertainly beneath her. They took small steps toward the bathroom, Mommy's strong grip helping keep her upright as she turned on the light, revealing the two toilets in the room, one normal and the other a pink, oversized training toilet.

Mommy helped lead her over to her sissy potty and shimmied her panties off before easing her down on top of it, making sure her little cage was pointed straight down. Letting go, Sophie practically collapsed on top of it. Barely able to hold herself in a sitting position, her Mommy moved to steady her from behind. Amanda's hands went to the strap on her gag and unsnapped it. Sophie breathed a heavy sigh of relief as the gag was pulled free, working her stiff jaw as she did so.

"Thank you, Mommy. May I go potty now?" Sophie asked, looking up at her Mommy as she walked back in front of her.

"You may," she said, crossing her arms as she stared down at the pathetic sissy on her cute little training seat.

Sophie groaned as she was finally allowed to relieve herself, the feeling almost sexually gratifying after being made to hold it for so long. She couldn't remember ever having to pee so badly, her shoulders giving little shudders occasionally as the stream eventually started to thin. With a final sigh, her head slumped forward, exhausted from the ordeal as she finished humiliating herself on the little potty.

"Better?" her Mommy asked expectantly.

Sophie nodded tiredly without looking up, "Yes, Mommy. Thank you."

Her Mommy crouched down in front of her, taking her chin and raising it so she could look at the sissy's face. Her eyes took in the smeared makeup and mascara tear stains that covered Sophie's cheeks with a critical gaze.

"Good," she said, "Because you have a lot of work to do before Victor gets here in..." she looked over at a clock on the wall, "Two hours."

Her Mommy stood up and walked to the door of the bathroom, giving instructions as she did so.

"I want you washed and fresh, inside and out. When you do your makeup, I want you to take your time with it, because if I have to come in here and do it for you, we're going to take it off the hard way. Am I clear?"

"Yes, Mommy," Sophie replied meekly, eyes downcast.

"I'll leave your outfit out next to the crib. Let me know when you're done putting it on and I'll come help with your accessories."

"Thank you, Mommy," Sophie said, but if Amanda heard the sissy's reply, she didn't acknowledge it as she left the bathroom, leaving the door hanging wide open as she did.

With a pained groan, Sophie peeled herself off the potty, feeling finally returning to her legs as she used the nearby sink to push herself into a standing position. With short, shuffling steps, she walked to the shower and turned it on, making sure the temperature was right before moving to the bathroom closet and pulling out the traveling shower bag her Mommy had put together for her.

Inside were all kinds of fun toys. Butt plugs, dildos, a sturdy harness for strap-on play, nipple clamps, a couple of spanking implements including a cruel little pink lexan paddle with holes drilled in it, lube, condoms, a few pairs of waterproof cuffs, and an enema kit.

Grabbing the enema kit, Sophie left everything else where it was. By the time she got back to the shower, the water was piping hot, just the way she liked it. Setting up the enema kit was simplicity itself. It was one of those open top kinds where you just secured it underneath a running water source and voila, instant infinite enema at whatever temperature you like to set your water to.

It only took a few seconds to get the kit set up the way she wanted. Turning away from the shower, Sophie peeled off her baby doll dress and grabbed a hanger out of the bathroom closet, carefully hanging the garment up before walking to where her Mommy had tossed her panties on the sink to hang them with the dress as well.

With everything set to go, Sophie took a moment to look at herself in the mirror. Her hairless body still looked foreign to her, even after almost a year of being kept as her Mommy's sissy baby girl. The diet and exercise plan she'd been on had worked wonders with her physique, slimming her down and making sure any muscle she developed was long and lean instead of bulky. Her flexibility had also grown by leaps and bounds, and she could now stretch in ways that would have once seemed impossible to her.

She took a closer look at her chest, looking at the little bee stings that her breasts had started to turn into. Apparently her Mommy had been giving her low doses of hormones for some time, though when she actually worked up the courage to ask her about it, her Mommy had assured her they were well below the threshold of physical change and were simply intended to make certain parts of her anatomy more sensitive.

Running a light finger over one of her nipples, Sophie shuddered. It certainly seemed to be working. Between the hormones and the chinese cupping set her Mommy used on her nipples, some days it felt like if she played with them enough, she could nearly reach orgasm, though her Mommy always stopped her before that point. She felt her locked up clitty give a little jump at the thought before she sighed and grabbed a box of makeup wipes to remove her ruined mascara and lipstick. Her Mommy didn't buy her the waterproof kind, since she liked see Sophie cry it off while she was getting punished, so it only took a few moments to get the majority of it off.

With a glance at the clock, Sophie hopped in the shower, hands busy as she washed her face and shoulder length hair. With her outside taken care of, Sophie grabbed the nozzle of the enema kit, squatting down so there was more gravity-fed water pressure as she inserted the small piece of plastic and released the lock on the hose, hot water instantly flooding her tummy as she squeezed tight to hold it in until she felt full. Locking the hose again, Sophie stepped carefully out of the shower, bottom cheeks held tight together as she maneuvered to the regular toilet, enemas being one of the few times she was ever allowed to use it, simply for the sake of easier clean up.

With a low moan, Sophie relaxed, the water flowing out of her in a loud torrent. It took almost a minute before she was sure it was all out, carefully standing back up and checking to see how dirty she was before flushing the toilet. Her Mommy kept her relatively clean most of the time, so there wasn't much filth to remove, though just to make sure she repeated the process two more times, making sure the last time there was nothing but clear water. Finally satisfied that she was clean enough to pass one of her Mommy's inspections, Sophie jumped into the shower one last time, removing the enema kit and placing it aside. Using soapy hands, she made sure to get into every nook and cranny, flinching slightly as she ran slick hands over the abused orbs dangling between her legs.

As she rinsed off the last of the soapy residue, Sophie turned off the water and stepped out, grabbing a giant fluffy pink towel from the rack nearby and meticulously drying herself off. She ignored the enema kit hanging over the shower curtain bar. Her Mommy had taught her to leave it out for a few hours and give it time to dry out. She'd put it away tonight before bed after making sure there was no moisture left inside to grow into mildew.

Using the towel to wipe the condensation off of the mirror, Sophie looked at herself once more. Her face was a clean slate again, ready to be made up into the cute little sissy her Mommy expected her to be.

Opening one of the sink drawers, Sophie pulled out her very own makeup kit. While she wasn't overly familiar with makeup brands, she knew enough to know that her Mommy hadn't skimped when it came to quality. The little bag held hundreds of dollars worth of makeup, and Sophie had been drilled for countless hours in its use, her Mommy standing behind her with a strap or paddle as she applied mascara and blush too many times to keep track. Lip liner, lipstick, eyeshadow, she could even use concealer like a pro now. Pulling up a magnifying mirror, Sophie let out a tired little sigh and got to work.

It took her nearly fifteen minutes to get things exactly the way she knew her Mommy would want them, the coloring subtle and subdued but still slutty with model-quality thick, dark eyelashes. Carefully placing all her things back in the bag, she glanced in the big mirror and quickly worked her hair into some semblance of order. Knowing her Mommy would probably want to do it herself, she left it loose but manageable.

With a sigh, Sophie knew she was as ready as she would ever be. Turning, she grabbed the hanger with her dress and panties on it and made her way back to her crib. The light was already on in the room, the outfit her Mommy had chosen prominently displayed on the dresser. Sophie stopped to put her dress back in the closet before moving over to see what had been picked out for her.

Swallowing hard, she picked up the new dress her Mommy had bought her. It was a stunningly pink halter top affair that looked like it would be more comfortable on an old Barbie than on a real person. Beneath the dress was a pair of matching panties with garters and a pair of long light pink kneesocks that had cute little bows at the top.

Sophie groaned inwardly. The outfit her Mommy had picked out really would look adorable on her, making her look more like a slutty porcelain doll than the man Victor had met for drinks. She could already imagine the man's expression the first time he saw her. She blushed deeply, trying to push the thought away as she moved to slip into the slightly too-small dress.

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