Meeting Mommy

With a last sniff it seemed like the little one had finally finished crying. Laying facedown on her little girly comforter on her little girly bed, Sophie, formerly Steve, ran a hand lightly over her tender backside, fingers gingerly probing the more painful spots, trying to judge how long it would be before she could sit down comfortably again. She bit her lip, making a face as she tasted the mascara that had run down her face during the punishment process. It would be a little while at least before sitting was something she wanted to do again, her Mommy had made certain of that. Fitting, considering laziness and generally being unproductive were the reasons cited for the evening's festivities.

As she felt around her bruised posterior her fingers delved further between her cheeks, their tips barely making contact with the puffy raised ring of her "pussy", a quiet whimper escaping as she flinched back from the almost unbearable soreness of having been used like a proper girl should be. Mommy had used her Punisher, a foot long monster nearly as thick around as her wrist. The constantly enema'd state of Sophie's rear-end had made the process as simple as adding lube and pressure. Lots of pressure. The restraints had rattled wildly during the initial insertion into her already well punished bottom, though the gag in her mouth had kept her from verbally protesting too loudly.

Looking much like a regular baby's pacifier except for the insertable 7" dildo to suck on, it did a great job of keeping little mouths busy instead of crying or complaining. That meant the room had been mostly quiet while she was breaking Sophie in, with the sounds of restraints being pulled against, quiet whimpering, and mommy's soft cooing being the loudest activities taking place.

Mommy was always very encouraging, even during punishment. Maybe especially during punishment. Even while Sophie had been firmly planted over her mommy's knee earlier that night, her bottom on fire from the wood-backed hairbrush cracking into it at full force, there had been nothing but positive things to say.

"You know I hate to have to do this to you, Sweety, but it's for your own good," she would say, her hand or hairbrush cracking against Sophie's bare skin for an unbearable duration of time while her Mommy's face was split by a grin that could give a nutcracker envy.

Sure, Sophie could have tried struggling, but between the cuffs locked onto each of her limbs and the surprising strength hidden in her Mommy's slight frame, she had tried to play that game before, and had found herself to be the spectacular loser of that particular struggle time and again.

So when Sophie's Mommy had picked her up from her babysitter with that angry look on her face, she had known what to expect when she got home and had mentally prepared herself for it. Unfortunately there wasn't much you could do to stop a sound spanking from being just as unpleasant as it was supposed to be. She'd been taken inside and Mommy had immediately put her into the corner of her playpen, a room that doubled as her Mommy's office.

On one half of the room were bookshelves with heavy books, filing cabinets filled with important papers and a computer set up on a sturdy wooden desk. On the other side a sturdy playpen had been constructed, one designed to be inescapable when certain ropes and props were used to help make Sophie feel especially helpless. Four cuffs, less than five feet of rope and a pair of special mittens were all it took to reduce a perfectly self sufficient young man into a mewling baby, and Sophie's Mommy reveled in making her feel that way.

Rarely was Sophie allowed to walk or stand, her Mommy instead preferring to keep shortish lengths of rope tied between her collar and ankle cuffs to keep her floorbound. Near the beginning of their relationship her Mommy had found her much more easily managed in such a state, and so kept her tied in at least some way most of the time. It had proven useful earlier when Sophie had tried to flinch away at the sight of the wooden hairbrush waiting for her on her Mommy's chair.

"Oh, no," she had said, her stern voice chastising the little girl while lifting her face to make eye contact, "You've earned that brush, and now you're going to take it... and probably something else too."

Sophie's eyes had pleaded, showing a desperation known only to those who have had their backsides blistered by a strict but loving Mommy. Especially one as adept at her craft as this one. Unfortunately it'd had the exact effect she'd expected it to... none. Mommy had just smiled, her wolfish grin making Sophie's butt clench in anticipation as she was carefully pulled up into position. Sophie's dropseat pajamas were opened, exposing her big baggy diaper to the world. Mommy had performed a quick inspection to make sure her little girl didn't need a change before being dealt with and, finding everything in order, pulled the straps on the sides to remove the diaper completely, exposing Sophie's bare bottom.

She'd sat there for a few minutes, hands idly kneading and molesting the bare bottom laying across her lap. She would run her fingertips over the skin, barely making contact and sending goosebumps up Sophie's spine before spreading her cheeks with one hand and gently massaging her rosebud with caresses from the other. After a few minutes of this Mommy would raise her hand high in the air and bring it down with a resounding slap onto her baby's bottom, the impact jiggling her rear end and leaving a bright red handprint clearly outlined. Then her hands would go right back to their ministrations, making her little charge wiggle and whimper between swats.

And she lectured the whole time. "You know Mommy only wants what's best for you, Baby," she would coo, "That's why we have to break all these nasty habits." Followed by the sharp report of flesh on flesh and a pitiful cry from behind the gag.

Once the ivory skin of Sophie's backside had started to turn crimson her Mommy's hands tended to wander a bit more, sometimes going between her legs, though this was the worst kind of teasing to Sophie as she felt her Mommy's fingers gently fondling her swollen testicles. The two orbs were at least double their normal size, the product of cruel teasing and denial. Add that to the cage that prevented any kind of erection and it made the whole experience that much worse. Sophie had gone almost three months now without release, her Mommy only letting her out of the cage occasionally to be washed in firms hands and under strict supervision. Recently she'd needed to start icing Sophie down to get her erections back under control after her cleanings. She took a special kind of pleasure from that process as she would hold an icecube to the head of Sophie's penis while she writhed and bucked to get away from the terrible cold until the whole thing went limp.

Of course, that was part of the process of creating a little girl. You had to remove the penis aspect from their sexual orientation and replace it with something else. In her case, due to her Mommy's preferences, it was simply a different penis. For most of a year Sophie's Mommy had been training her pussy, starting with small plugs and eventually working up to "Mommy's cock", a pink 10" jelly dong that she enjoyed burying in Sophie's mouth or throat whenever she felt like it.

Most days didn't go by without Mommy's cock making at least a perfunctory appearance, and Sophie had long since learned to take it at a moment's notice without being warmed up first. Mommy's strap-on technique wasn't exactly rocket science, either. She would squirt some lube on the dildo, a little between Sophies cheeks, and then line up for a nice steady push. It didn't matter how hard Sophie cried, begged, or struggled, once Mommy's cock was on its way in, nothing stopped it. She delighted in her little girl's struggles and wailing as inch after inch of jelly dong disappeared up into the reluctant girls bottom until, with a delighted coo, she buried it in to the hilt, praising Sophie for being such a good girl as she did so.

Looking down at were her jelly dong entered its favorite tight hole, Sophie's Mommy would savor the feel of her baby's clenching pussy. If she wasn't gagged by that point, Sophie usually started an adorable mewling as every inch of fake cock was ground firmly into her, loosening her up and getting her ready for her hard fucking. A few minutes of that treatment and she would start the milking process. Mommy knew her baby wanted to cum, what little girl didn't want to, but she was determined to teach her little girl to cum the "proper" way. By taking hard cock in her tight pussy until she felt raw, and then some. Mommy really loved to power-fuck her little girl, pulling almost all the way out before slamming back in, and the worse behaved her little girl had been, the harder she fucked. Sometimes, like today, her little girl even needed something extra to help her be really good. Doc Johnson's 12" behemoth served to fill that role, and her hole, perfectly.

The insertion process tended to be more involved, with the pushes being slow incremental increases designed to eventually wear down any amount of clenching or natural tightness. She would push until Sophie's struggles became truly frantic before pulling back just a touch, then pushing in hard to that depth again and going a little further. Sophie's legs would kick against their restraints in protest, tears of pain and humiliation streaming down her face, but Mommy would not be denied.

"What a good girl," she would breathe in Sophie's ear as she worked the toy in, her teeth nibbling on a tender neck or ear, "That's right, take Mommy's cock. All the way in. Shhh, no tears, baby."

Sophie couldn't help it though. It hurt. And it was humiliating. And she hated it... sometimes. If she were being honest with herself, she could barely think of a time when it didn't excite her at least a little. She'd been curious about her switch side for quite some time before meeting her Mommy by accident at the store. Mommy had been in the baby aisle, not because she needed anything but because she loved all of the cute little toys and had been reminiscing about having one to play with. Sophie, Steve then, had always been curious about diaper play and had finally worked up the courage to go buy himself some.

With Halloween coming up, he had planned to play it off as a joke, like he intended to wear one to a costume party, then throw the rest away. He probably would have done it too, but his Mommy, a total stranger then, had been standing in the way. With a polite cough he had asked her to move, quickly grabbing the package and moving to walk away, afraid to make eye contact or speak any more than that.

"Those are going to be a little big on you," Mommy had said quietly as Steve started to walk away, stopping him in his tracks. Reaching up she grabbed a different pack, handing it to Steve while removing the one in his hands and putting it back.

"Much better," she said with a smile, "Those will hug tight enough that you shouldn't leak."

"Oh, no, it's not like that," Steve stuttered, "This stuff, it's just for a costume, I don't use it or anything."

She gave him an appraising look from head to toes, her eyes taking in the slight frame, baggy clothes and long, unkempt hair. He was a rather pretty boy, she concluded, a knowing smile playing on her lips, "Of course not, sweety."

Steve felt himself go scarlet as this woman inspected him, and he knew she wasn't fooled by his weak lie in the slightest. He just wanted to get out of there. Panicked, he tossed the package back onto the shelf and started to bolt away.

"Hold it," the whip crack of the woman's voice stopped him in his tracks, though he couldn't bring himself to turn around. The sharp click of heels sounded on the ground behind him, followed by the crinkle of packaging. When she moved around in front of him she had the pack of diapers in her hand, reading the back idly.

She turned to squarely face him, looking him in the eye, "Didn't you want to buy these?" It seemed like a simple question, but the way she asked it seemed like it implied a whole lot more.

Steve looked away, his deep blushing speaking more loudly than his voice was capable. She smiled at him. "It's OK," she said quietly, stepping closer and running a hand over his cheek, "Even if you don't want them anymore, I'd like you to have them."

Steve tried to think of something to say, but she just turned away, taking him by the hand, and led him to the front of the store. She checked out, paying without the clerk blinking an eye, and just that fast they were in front of the store, her handing Steve his first bag of diapers since he'd been big enough to get out of them. He'd practically trembled with nervous excitement, but tried to contain himself in front of the woman.

"Er, thank you," he said quietly, eyes locked on the ground with the bag held awkwardly in one hand.

The woman laughed, a pretty tinkling sound, "So polite, too."

Steve had been trying to find a way to excuse himself when she saved him the trouble.

"Unfortunately," she said, "I have to get back to work." She appeared to be genuinely disappointed. "However," she added, holding up a card, "I think this is a conversation that we should continue at some length."

Steve looked up and met her eyes after looking at the business card. Amanda Walls: Image Consultant. There were several different numbers on the card, but she pointed to the one at the bottom.

"That's my personal phone number," she said, pulling it out of her purse to illustrate, "And very few people have it. Even fewer have permission to use it."

"Cool. Like an exclusive club?" Steve joked weakly.

She stared at him for a moment, her blank face slowly resolving into a rather feral grin, "Sure, sweety. A very exclusive club." There was a hunger in her eyes that scared Steve, but that curious part of him stuck its nose out.

"So... like when should I call you, or text you, or whatever?" He said, trying hard to be casual.

She studied him again for another moment, "You aren't busy tonight, are you?"

Of course he wasn't, and she didn't wait for him to finish anyways.

"Good," she said, "Now you're going to go home and put one of those on," pointing at the bag at his side, "And then you're going to send me a picture of you in it."

Steve's mouth worked soundlessly for a moment.

"No arguments?" Amanda asked, "Good boy. Now get going. I'll be waiting on that picture."

As she turned and guided him back into the parking lot she also landed a hard swat on his rear, making him jerk upright and walk away with a very embarrassed look on his face. Glancing over his shoulder he saw Amanda sauntering away, a predatory grin on her face.

"Maybe that's why they're called cougars," Steve reflected. It certainly felt like being hunted, at least. As he sat down into his car and put the package next to him he thought back to that knowing look in her eyes, the confidence, the way she had asserted her will over the situation. The thought gave him a thrill, like leaning over the edge of a tall cliff, or the feel of almost being caught doing something bad. Maybe being hunted wasn't necessarily a bad thing.

That thought kept repeating in his head, even well after he got home. His tiny studio made it hard to not look at the package sitting on the middle of his bed, but all he could do was pull the business card out of his pocket and contemplate. Did he really want to send a stranger the most embarrassing picture anyone would ever have of him? He'd run the card through his fingers so much that dirty smudges were beginning to show up around the edges, the corners curling slightly as well.

It was almost dinner time by the time he finally made his decision, stripping down and carefully pulling open the package. Grabbing a diaper, it took him a minute to find the best way to put it on, finally deciding to put it down and sit on it, then adjust the straps until if fit tightly. When he finally had it fitting right he had to admit, Amanda had been right, they were a perfect fit. Looking at himself in the full size mirror he felt something click inside. Taking out his phone, he snapped a picture prominently displaying his diapered dairy air, his shy smiling face barely visible in the background, and punched in Amanda's number to send it. He felt a wave of panic as his finger hit the send button, but it was too late now. He would just have to wait and hope she liked it.

What followed was one of the most nerve-wracking hours of Steve's life as he waited, eyes glued to his phone, for her response. Apparently it was acceptable, because the text he got back read, "What a good boy. How does italian sound, and where should I pick you up?"

That night as Steve left his apartment complex to walk out to Amanda's car he had been overly paranoid, eyes searching everywhere for the first person to point out the excessive bagginess of his pants, or how crinkly he sounded while walking. In subsequent texts Amanda had told him about the restaurant they were going to and how expensive everything was.

Steve had shamefully admitted to still being financially reliant on his parents for a lot of things, though Amanda responded in a very understanding manner, offering to pay for him that night if Steve would simply do her the favor of wearing the gift she had bought him earlier that day. It seemed like a fair enough trade to him. Free food for wearing something no one else would know about? That kind of program could feed college kids all over the country.

His enthusiasm started to wane, though, as he realized he didn't really have any clothes that could cover the damn thing. No matter what he wore you could tell that something was a little odd. Finally he chose a loose fitting pair of black slacks and an expensive button up shirt that had seen better days. Unfortunately, it was all he really had in the way of dress clothes anymore.

Stepping up to Amanda's car, he admired the sleek black Mercedes before opening the door and stepping inside.

"Well aren't you just adorable," she said as he leaned back into the seat, face heating up from the attention.

"Er, thanks," he managed to croak awkwardly, "You look really pretty tonight," he added after barely glancing at her. It was true though, she did. A tight red dress outlined every curve and sway of her body, highlighting the mature beauty of a grown woman versus the cuteness of the girls his age that he'd had so much bad luck with.

She leaned over the center console, pushing her arms together and intentionally putting her impressive cleavage under his nose. "There's that polite streak again," she said, "If you keep behaving so well," she reached out a hand, running it over his thigh, her fingers making small circular motions until they moved up, touching the border of his diaper beneath his slacks, "I just might have to give a you little reward." He jerked away slightly, face coloring bright red as she pulled back laughing.

"I may have been craving dessert all day," she said, eyeing him hungrily, "But dinner should be delightful as well."

And it was, kind of, in a tortuous sort of way. A few softly spoken words with the Hostess got them a nice quiet corner away from most of the other customers. She used the space to grill him. Family, friends, hobbies. The answers for each were kind of pathetic. Mom and Dad, divorced, rarely saw either, though they helped pay his bills out of guilt. No siblings. He'd moved to the city almost a year ago but didn't know anyone he considered a friend. Other than that he watched a lot of Netflix, was a prodigious reader, and worked his entry level job as a night shelf stocker in a local supermarket. He'd been in school, but with little to interest him he'd dropped out rather quick.