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.)
Sophie moaned behind her gag, shifting as much as her restraints allowed in her over-sized 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 well punished 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 her, 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, then 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 escaping 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 it’s 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, over-sized 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 as her Mommy moved behind her, hands going to the strap on her gag and pulling it loose. 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, eyes taking in the smeared makeup and mascara tear stains that covered her cheeks.
“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 in to help with your accessories.”
“Thank you, Mommy,” Sophie said, but if she 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, 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 be 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.
Pulling it down, she realized with some dismay that it barely covered her backside while she was standing upright. If she needed to bend over, it would ride up far enough that you’d be able to see just about everything, and the panties her Mommy had picked out would do little to obscure the fact that she’d been given a good spanking recently. Her cage would also be on display, a fact she was sure hadn’t escaped her Mommy.
There was no sense in arguing, though. She would just get herself into trouble again, and the last thing she wanted was to get spanked in front of the man she was supposed to cook dinner for tonight. That would be a humiliation Sophie wasn’t sure she was ready to deal with.
It didn’t take her long to finish pulling on the little clothing remaining, garters and socks slipping on easily, though the panties did feel a little snug over her sensitive coinpurse, and they kept riding up to give her a wedgie that she had to continuously work to keep from exposing her bruised backside.
Looking down beside the dresser, she saw her Mommy had also picked out a cute little pair of cream colored flats for her to wear. Stepping into them, she looked at herself in the mirror above the dresser, taking in the full view for the first time. Aside from her slightly wet and wild hair, you’d have been hard pressed to find a better picture to put in the dictionary next to the word “sissy”.
Taking one last look to make sure she hadn’t forgotten anything, Sophie walked to the door, sticking her head out into the hallway.
“I’m ready, Mommy,” she called out, listening hard for a response.
“I’ll be right up, baby girl,” she faintly heard her Mommy say from downstairs.
Ducking back into the room, Sophie looked around, making sure there was nothing out of place before taking up position to wait by the dresser. It was only a few seconds until she heard her Mommy’s footsteps coming up the stairs. She took a deep breath, hoping her Mommy would like what she saw.
Sophie laced her fingers, fidgeting nervously as her Mommy came around the corner, now wearing a very flattering floral sundress. She stopped dead in her tracks when she saw the sissy in her pretty pink dress for the first time, a smile blooming on her face.
“Oh, sweetheart,” she said, voice airy, “It’s perfect.”
Sophie blushed at the compliment, dropping into a cute little curtsy so she wouldn’t have to meet her eyes. “Thank you, Mommy,” she mumbled shyly.
Her Mommy took her time strolling across the room to her, admiring the way the dress hugged her tightly in all the right places. It was ever so slightly shorter than she’d intended it to be, but as she looked her baby girl up and down, she decided that was more of a happy accident than anything else.
“I could just eat you up,” she said with a wicked smile as she slowly circled the scantily clad sissy, lifting the dress in the back to see the way her panties fit, the silky material snugly gripping her bottom and accentuating the fullness of her backside. “Victor is going to love you in this.”
Sophie’s mouth went dry. She’d really been trying not to think about the fact her Mommy wasn’t the only one who’d be enjoying the view tonight.
“Now,” her Mommy said, “Let’s finish getting you ready so you can go start dinner.”
Grabbing Sophie by the arm, Mommy moved her so she was facing the mirror above the dresser. Moving off to the side, she grabbed a slightly too-short chair and set it down behind Sophie, who carefully lowered her still sore bottom onto the hard wood of the seat. Opening up one of the dresser drawers, her Mommy pulled out a heavy old hairbrush that doubled as one of her favorite spanking implements and a medium length of light pink ribbon.
Using firm hands, Mommy ran the brush through Sophie’s hair for a minute or so until it lay perfectly flat, then grabbed the ribbon and used it to tie through Sophie’s hair, creating an adorable little bun on the back of her head with highlights of the ribbon poking through in a tight pattern that ended in a bow reminiscent of the ones on her socks.
Sophie watched in quiet amazement as her Mommy worked her magic. She always enjoyed doing Sophie’s hair, and Sophie was happy to have her do it. It was one of the few rituals they had fallen into that they both seemed to like.
With a few more tweeks, she finally seemed satisfied with how it looked. Nodding in approval, the corner of Mommy’s mouth quirked up in a little smile as she looked over her handiwork.
“Alright, sweetie,” she said, gently squeezing Sophie’s velvety smooth shoulders as she drew the sissy to her feet, “Let’s get your other end ready too.”
Sophie nodded meekly as her Mommy opened another dresser drawer. Inside was an assortment of anal toys that would make a professional dominatrix jealous. Every size, shape, and material you could think of was represented in some way. Taking a moment to think it over, Mommy grabbed a rather large cock-shaped buttplug. The material was similar to many of the sexflesh style toys she was so fond of, and the way it was tapered would ensure it stayed firmly seated in Sophie’s bottom while keeping her ready for something larger should the need arise. Grabbing a small bottle of lube with a pump nozzle, she seated herself in the chair Sophie had just vacated.
“Come on, baby girl,” she said, patting her lap, “Time’s wasting.”
Taking care to keep her dress smooth, Sophie knelt beside her Mommy and gently lowered herself over her lap.
“Good girl,” Mommy said, gently rubbing and patting her sensitive bottom before lifting her dress and sliding her panties down to the middle of her thighs.
Sophie could feel her Mommy shifting around, the sound of lube being pumped and spread across the large toy loud in the quiet room. A few moments later she felt her Mommy’s hands prying her abused cheeks apart, lube slickened fingers working over her tight hole for a second before she felt one start to push inside. Sophie whined softly at the sudden insertion, her Mommy ignoring her as she added another finger, twisting and thrusting ever deeper as she went to help work the reluctant rosebud open for the large toy.
Sophie licked her lips as her Mommy’s strong fingers continued their uncompromising exploration, her vigorous digits occasionally sliding over the tickle spot deep in her bottom, making her groan and push her bottom up for more. The movement didn’t go unnoticed.
“Is my baby girl feeling like a needy little slut today?” Mommy teased her, fingers purposely fluttering over the sensitive area for a moment, eliciting more moans from the sissy. “Don’t worry, I’m sure we’ll find some way to scratch that itch for you tonight.”
Removing her fingers, Mommy pushed the toy up to her entrance, the head prying her tight hole open ever so slightly.
“Relax, sweetheart,” she said, one hand working the toy in little by little as the other alternated prying her cheeks apart to make the insertion a little easier.
It wasn’t the biggest toy her Mommy had used on her, not by a long shot, but it still felt huge as her bottom reluctantly opened up to accept the rude invader. Taking shallow breaths and whining occasionally, Sophie did her best to keep her bottom relaxed as her Mommy finally pushed the toy in past the widest portion and her bottom started draw the large plug in on its own. With a whimper, Sophie felt the toy slide home, the base pressing firmly against her bottom cheeks.
Grabbing the base in a firm grip, her Mommy slowly pulled the toy back out, making her gasp as the widest part popped back out. Giving the clean plug an appraising look, she decided the slut had done a good enough job getting herself cleaned out. Pressing the toy back against her tight hole, she gave it a hard push and twist, forcing it in hard enough to make Sophie cry out.
“There,” she said, pulling Sophie’s panties back up so they would help hold the toy in place and patting her bottom reassuringly, “That wasn’t so bad, was it?”
“No, Mommy,” Sophie replied, voice timid as she pushed herself back into a kneeling position, shifting uncomfortably as she became accustomed to the lewd intrusion, her bottom pulsing seemingly at random around the thick cock.
Suddenly her Mommy tsked, drawing Sophie’s attention to a shiny little trail of cum just below the hem of her sundress that must have leaked out of her cage while her Mommy was getting her ready.
“Clean that up,” she said, voice brusque.
“Yes, Mommy,” Sophie squeaked, quickly leaning in to lick the mess off of her thigh, the salty taste extremely familiar to her. She was always required to clean her messes with her tongue after being milked, and after so long in chastity, it seemed like she leaked more now than she had ever squirt as a boy.
Leaning back, Sophie allowed her Mommy to inspect her cleanup job. Nodding in approval, her Mommy stood from the chair, straightening her dress as she did so.
“Alright, sweetie, I’d say you’re just about ready for our little dinner date.” Her Mommy looked at herself in the mirror, smiling confidently at what she saw. “Now get to the kitchen and get to work. Our guest will be here in about an hour.”
“Yes, Mommy,” Sophie said, standing up and giving her Mommy a meek curtsy before shuffling out of the room, her discomfort evident as her tight little hole slowly adjusted to the toy.
Watching her dolled up sissy leave out of the corner of her eye, Amanda let a sly smile touch her lips. She had high hopes for their date tonight. The smile turned into a wicked giggle as she remembered the picture of Victor she’d showed Sophie and the poor girl’s frightened reaction.
High hopes, indeed.
End of Part 1
Thanks for reading, and remember check out my other dirty stories here or on fetlife! Most of Part 2 is already written in my head, I just need to sit down and clack away on my keyboard for a few hours to make it a reality. Check back soon for more, and don't forget to share the love, you filthy pervs. <3
Meeting Mommy (Femdom/sissy fun) - Prequel to Dinner Date with Mommyhttps://fetlife.com/users/3383439/posts/2530734
Consequence and Compromise Part 1 (Femdom, power exchange, cunnilingus) -https://fetlife.com/users/3383439/posts/3959807
Zoey's Basement Transformation (Femdom/sissy/bi fun):
Part 1 - https://fetlife.com/users/3383439/posts/2533455
Part 2 - https://fetlife.com/users/3383439/posts/2545709
Part 3 - https://fetlife.com/users/3383439/posts/2552717