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.

It was odd, usually the more he talked about his pathetic life, the less interest a girl showed in him. Amanda was different, though. She smiled, encouraging him to talk and drawing out the most unlikely details in the process. The depression he’d been dealing with since moving, the pit in his stomach that formed whenever he started to feel truly lonely. The fear that, even if he found his soulmate, that he would be such a wreck that she wouldn’t want anything to do with him. He’d had counselors and shrinks in the past less capable of pulling out that kind of information about him, but she just had a way about her. She made him feel comfortable, at least while she wasn’t trying to make him uncomfortable.

Toward the end of dinner, once they finally started talking about the events that had lead to their meeting, she leaned back in her chair, kicking off a heel and running a stockinged foot up the inside of his leg.

“So why don’t we talk about the little accessory you’re wearing for me tonight,” she said, her toes moving up his leg until they barely tickled the crinkly diaper over the top of his crotch. “I think it’s fair to say,” she continued, pushing with her foot and massaging his quickly growing cock through the material, “that you enjoy this.”

He let out a low moan, the blush in his cheeks a war between arousal and embarrassment. As Amanda’s toes continued to knead at his cock, arousal eventually won out.

“How often do you wear them?” she asked.

He shook his head, battling to maintain control over himself. “Never,” he said, “I mean, I always wanted to but…”

“But what kind of girl wants a guy who likes to wear diapers?” she finished for him.

He shrugged weakly, then moaned as her foot pressed a little harder, bending his cock.

“I’ll tell you what kind of girl wants a guy like that,” she said, rubbing her foot back and forth, “The best kind,” she whispered conspiratorially. Then she moved her foot away, tucking it back into her heel and finishing with her meal. Steve found it hard to concentrate for the rest of dinner, though, his cock staying rock hard almost the whole time.

When they finally finished the server asked them if they’d like the dessert menu. Steve politely refused, while Amanda’s response was a more enigmatic, “Thank you, no. I have enough sweets to keep me busy already.”

The restaurant was blessedly dark, so as they left Steve was pretty sure no one noticed how bulgy his pants were. Except Amanda, of course. She noticed immediately, one eyebrow arched high at him as she took in the obvious erection, making him blush profusely. The little smirk that touched the corner of her mouth said it all as she lead him back to her car by the hand.

Instead of getting into the driver’s seat, however, she lead him to the back passenger door,  opening it and slipping inside, then pulling him in after her. At least she had parked in a dark part of a relatively abandoned parking garage.

As he ducked inside and closed the door behind him he felt a wave of nervousness wash through him, making him queasy. “I don’t know,” he started, “Maybe we shouldn’t…”

“Shh,” she held up a finger to his lips, cutting off his objections, “I told you if you were a good little boy I’d have a present for you.” She moved her finger, replacing it with her lips and the lightest of kisses. “Do you want it?” She asked.

He struggled to answer for a moment, his mind spinning wildly. Somewhere he found the answer he was looking for and nodded dumbly, making her smile.

“Good boy,” she cooed, sending shivers up his spine, “Now come here.”

She changed position so that she sat reclining in the back seat and moved him between her legs, his back to her front. He could feel the soft fullness of her breasts through his shirt, though that was a secondary concern to the hands busy with his belt buckle. It didn’t stand much of a chance, though, as the belt fell open with the light clang of metal on metal. His breathing hitched as she reached for the zipper of his pants, the button popping with no effort, almost like they wanted to come off.

With calm, efficient fingers she worked his pants down until they were about mid thigh, exposing the diaper with the erection beneath it for the first time.

“Oh,” she said in mock wonder, “What a lovely gift you’ve brought me.” Her hands slithered downward, one stopping at his stomach and rubbing soothing circles there as the other dove further, it’s fingers slipping under the waistband of his diaper before the whole hand disappeared.

Steve gasped as he felt her soft palm grab hold of him. “Relax, baby,” she cooed quietly, “Just let me make you feel good.”

Amanda smiled to herself as she took Steve in her hand. It wasn’t big, but it wasn’t really small either. Maybe a touch below average, she decided, but wonderfully sensitive. Steve gasped and moaned under her touch, his slight frame shaking as her soft fingers worked magic like he’d never felt before. Amanda felt her smile deepen, he was like putty in her capable hands.

It took no time at all for her to have him on the edge, her expert digits teasing him in the most delicious ways, making his breathing ragged and causing his crotch to hump up at the air. Already, though, she had a good sense of his tipping point, bringing him to the very brink before tapering off and letting his excitement lull just enough to deny orgasm before starting to tease again. The first time she did it he whimpered like a whipped puppy.

“Hush, baby,” she breathed in his ear, her teeth nibbling on his lobe, “Dessert is meant to be savored. We don’t want it be over too soon, do we?”

Her hands were hard at work in opposition to her words, her fingers caressing around the the tip of his cock, making it jump and dribble pre-cum. The slickness it added to her fingers just drove him more wild, pushing him close to cumming again, but once more she backed off, her fingers barely making contact until the imminent threat of ejaculation was past before taking up their task again.

“Please,” he groaned up at her, his mind afloat in a desperate desire for release.

“Please what?” she asked, running her fingers all around it.

“Please let me cum,” he begged, eyes wild with need.

“Hmmm,” she seemed to consider it while continuing to tease him, “I guess I could let you, but you aren’t doing a very good job of asking.”

“What do you mean,” he gasped as her fingers wisked over his most sensitive spots.

“Well, if you wear diapers and get called baby, and I’m the one in charge, doesn’t it seem right that you have to call me Mommy?”

That statement sent a jolt through him, her fingers helping as well, driving him insane. “OK,” he moaned.

“OK, what?” she pressed.

“OK, I’ll call you the thing…” he said, trailing off unconvincingly.

Amanda laughed, slowly removing her fingers from his cock, but leaving her hand in his diaper, “Nice try, but this time get it right.”

Steve’s crotch humped up at her hand, but she kept from touching it until he started to whine. “Please,” he tried one more time.

“You know what you have to say, baby,” she said, coaxing him with her silky voice as she ran a single finger from the bottom of his cock to the tip, making him shudder, “All you have to do is beg Mommy.”

With his head as mixed up and confused as it was, begging was much easier than he imagined it to be. “Please,” he whimpered, “Please let me cum, Mommy.”

He’d have felt a chill crawl up his spine if he could see the grin on her face when he said it.

“Of course,” she cooed, her hand taking firm hold of his cock and slowly working it, “But only because you’ve been such a good baby boy today.”

With long, slow strokes she coaxed him to the edge, holding him there mercilessly close to release without letting him go. Finally, as he swore his head was going to explode in anticipation, she grabbed hold and started firmly jerking.

“Cum for Mommy,” she whispered, the combination of voice and touch pushing him over the edge with a whined gasp as rope after rope of cum was squeezed painfully from his balls, filling his diaper with the gooey mess. He clutched at Amanda’s dress, leaning back into her as she continued to milk him dry, making sure every drop had squirted out.

“What a good boy,” she said softly into his ear as his shaking slowed, “Did you enjoy cumming for Mommy?” Her fingers ran lightly over his shrinking member, caressing the skin and making him moan.

He was still breathing too hard to answer, but eventually his fingers began relaxing their death grip.

“I’m sorry,” he said, face coloring slightly.

“For what, baby?” Amanda asked, curiosity plain in her voice as her hand continued to manipulate his shaft.

He shrugged, humiliation surging through him. “I don’t know, I guess I thought you’d be disappointed, you know, because of how fast I came. I didn’t even get the chance to do anything for you.”

He sounded so genuinely distraught that Amanda couldn’t help but giggle a little. As she did, he turned away, his expression becoming pouty as he started to physically pull himself away from her.

“Aww,” she said, drawing him closer and turning his chin so he had to look her in the eyes, “Hush, baby. Of course I’m not disappointed. In fact,” she said, pulling her hand out of his diaper, cum strung to it in a couple of places as she raised it to her mouth, licking it clean while staring into Steve’s eyes, “You behaved perfectly, and I got exactly what I wanted.” She savored the taste, a wicked grin spreading over her face, “See? I knew I already had dessert picked out.”

Removing her hand from her mouth, she grabbed him by the back of the neck, pulling him in for a kiss. He melted into her grasp, his whole body still limp from his incredible orgasm. As she pushed her tongue into his mouth, though, he could taste some of his cum on it. He moved to back away in disgust, but Amanda’s grip was tight, easily holding him in place as she continued her exploration of his mouth. He struggled for another brief moment before giving in. It wasn’t so bad, really. At least not while her tongue was in his mouth at the same time. He felt his recently drained cock give a twitch in response.

Letting go of him, Amanda broke off the kiss, leaning back and taking stock of the young prize nestled in front of her. He leaned back into her, his weight comfortable as she ran her hands gently over his shoulders and neck, making him groan.

“See how nice things can be when you just give up control?” she breathed in his ear.

He could only nod in agreement as her strong fingers worked deep knots out of his neck, shuddering slightly whenever Amanda decided to suck on an ear or nibble on his nape.

They spent several minutes like that, Amanda’s only goal being to make Steve more comfortable with the position and the kind of submissiveness he’d fallen into, or been dragged into, depending on how you looked at such things. As Steve’s head started to get heavy, his eyelids drooping, Amanda gently shook him.

“Did Mommy tire out her baby?” she asked, a faint hint of teasing in her voice.

She had, though, Steve thought to himself.

“Well, if you liked that,” she said, her expression hungry again, “Mommy has all sorts of fun games to play. Some take a little getting used to and might be a tad... uncomfortable at first, but that’s all part of the process.”

Amanda’s voice sounded rather ominous to Steve and it was a toss up whether the thought scared or excited him more. The little thrill that ran through his tummy suggested excitement might be winning out. She ran a finger down his cheek and along his jawline, drawing him into another quick kiss before breaking it off.

“I think it’s time we left,” she said, sliding him upright and opening the door of the car. As she stepped out, Steve realized what a mess he was and started to fiddle with his clothes.

“Ah ah,” Amanda scolded, wagging a finger at him, “Come here.” With a firm grasp she locked her hand around Steve’s wrist, dragging him out of the car with his pants still around his knees, showing off his diaper to the world. He looked around nervously, trying to cover himself up from anyone who might be passing by, but Amanda slapped his hands out of the way, grabbing his clothes and straightening them out.

Steve was on high alert, but the garage was quiet, and the way she had parked meant that they were pretty well secluded as they stood between the car and a wall with deep shadows all around. Lastly, the way Amanda had her back to the rest of the garage actually did a pretty good job of sheltering Steve from any prying eyes that might have been there. They would see a woman helping a man try to look his best, not a young man who had just been utterly dominated and dressed like a toddler by an older woman.

She rebuttoned his shirt, smoothing it down to sit perfectly before finally pulling up his slacks to cover the diaper. As she buttoned them up and resecured his belt, he could feel the sticky load inside squishing around, making him grimace a little.

“What’s the matter?” Amanda joked, “Dirty diaper?”

He responded with a blush, his eyes sinking to the ground under her scrutiny.

“Don’t worry,” she said casually, “Mommy will get you changed once we get back to my place.”

Steve’s cock jumped at that. He hadn’t even considered the possibility of going home with this woman, but it seemed she had every intention of simply stealing him away.

“We’ll need to stop back by your place first, though, since I don’t have the appropriate materials in your size.”

The drive back to his place was very quiet. Steve was torn. Did he go along with this woman he’d just met who was moving at an incredible pace, or did he want to throw on the breaks and catch his breath? He cast furtive glances at her as she drove, trying to unravel his feelings about the whole situation. Finally he decided to make a pro’s/con’s list, just to see what it looked like. The pro’s were quite numerous and beneficial. Companionship, someone who saw and cared about him, and then of course there was the sex angle, though Amanda had basically guaranteed a continued freakshow of naughtiness if he chose to move forward. The con’s list was a bit barren: people would think he was weird if they found out. Still, there was something that held him back.

As they pulled up in front of his apartment Amanda put the car into park and looked over at him.

“You’ve been awfully quiet since we left dinner,” she said, looking over at him, “Anything you want to talk about?”

Steve feels like his heart is in his throat when he finally manages to speak up, “Um, I’m not sure I should be staying at your place tonight.”

Amanda’s expression didn’t change, but he could see the disappointment reflected in her eyes. “That’s OK,” she said, the same disappointment barely leaking through into her voice, “These kinds of games aren’t for everyone.”

“It’s not that I didn’t like it,” Steve corrected her, probably just a touch too fast, “It’s all just so… odd. I don’t really know what I’m supposed to do, or how you expect me to act or…” He sighed, face sinking into his hands, “My head is such a mess right now that I don’t even know what turns me on anymore.”

A light touch on his hand brought his eyes back up to face a gently smiling Amanda.

“Don’t tell me what you don’t know,” she said quietly, taking his hand into hers with a squeeze, “Tell me what you do know.”

Steve took a deep breath, “I know I’m tired of being lonely. That I hate my life the way it is now. That I would do almost anything to find an existence that fits me the way I wish it would.” Then, shifting in his seat with a sour look on his face he added, “And that the mess I’m sitting in is kind of uncomfortable.”

The way she laughed at his last comment made him blush fiercely, but it was a good natured laugh, not meant to belittle him, and he felt his own smile poke out a little in return.

“And…” he said, looking anywhere but at Amanda as he continued, his voice becoming very soft, “That I could probably use some help getting changed out of it.”

There was silence in the car for a long moment and Steve chanced a glance up at Amanda, who was studying him intently, a little smile playing at the corner of her lips. Then, without a word, she flipped the ignition on her car, killing the engine, and popped her door to step out into the cool night. Steve watched her walk to his side of the car, the tight dress hugging her every curve as she walked through the lamp light. After getting his door open, she held out her hand for him to take. He hesitated for just a moment before grabbing it and letting her help him out of the car. A firm push shut the door behind him as he stepped out, and with Amanda still holding him by the hand he was quickly escorted to his place, him indicating which door was his by pointing from behind her. She took the key from his hand, flipping the lock with a quick turn and threw the door to his tiny world wide open.

Clothes were scattered all around the small space, casualties of trying to pick out an outfit earlier that night. There were a couple smaller piles of dirty clothes in a corner, and the sink had a few dishes that needed washing in it, but it wasn’t terrible for not expecting company.

Amanda, however, did not look pleased, her eyes taking in every messy detail. She even ran a finger over the top of a window frame on the wall, tsking as it came away covered in dust.

“Sorry,” Steve said weakly, “I haven’t had much reason to clean up for company lately… or ever, really.”

As she finished looking the place over with a critical eye, Steve could feel her attention move back to him. He shrunk under the weight of her hard stare, a feeling almost like vertigo forming in his stomach. After a few long seconds he heard her sigh.

“Cleanliness, it seems,” she said pinning him in place with her gaze, “Is a trait that must be properly encouraged. It’s something you’ll want to pick up quickly, because trust me when I say that dirty little boys are not welcome in my home, and I have ways of dealing with them that ensure bad habits end quickly.”

Steve swallowed hard, seeing a much stricter side of Amanda than he’d experienced yet.

“It is pretty late, though, “ she continued, “So I’m not going to make you clean it now. However,” she stepped close to him, almost nose to nose, surprising Steve as he had to look up almost an inch to meet her eyes, “If this place isn’t spotless the next time I visit, I’m going to make you a very sorry little boy, and if the walls in this place are anything like the ones in my old apartments were, every neighbor for blocks will hear it. Do you understand?”

Her voice cracked hard, like a thunder peal over a prairie, sending shivers through him as he eagerly nodded agreement.

“From now on when I ask you a question in private you will answer to me as Mommy. Do you understand?” The hard cast of her features matched her voice perfectly as she loomed over him, pressing the point home.

Steve felt himself bump into the wall behind him as Amanda backed him into it, her eyes never breaking contact as she faced him down. He’d never felt so small as he did at that moment with that scary feeling in his stomach, but for some reason it made squeaking, “Yes, Mommy,” just a little easier.

Apparently appeased with how cowed he looked, Amanda’s stern countenance softened considerably, a smile touching her lips again as she reached out to run a hand over his cheek.

“Good boy,” she purred, the hand running along his cheek pulling back to grab him firmly by the chin, “Now hold still so I can get you changed. No fussing.” She pointed warningly at him at the last part before grabbing him by the lapels and pulling him away from the wall.

“Stand up straight,” she said, correcting his posture with a sharp smack on the back of a thigh just below his diaper, making him jump.

One hand reached down to gingerly rub the spot as Amanda stood straight in front of him, her hands going to the buttons of his dress shirt, but as she undid the first one it popped off right in her hand. With a sigh she took a closer look at the shirt, especially around the collar where some of the material was starting to fray.

“How old are these clothes?” she asked, rubbing some of the fabric between her fingers.

“I don’t know,” Steve said with an embarrassed shrug, “A few years?”

“Well,” Amanda said, giving him her diagnosis, “This shirt is a gonner. Where is your garbage?”

“But I like this shirt,” Steve whined, “It’s one of the only nice things I have to wear.”

Amanda raised an eyebrow at him, “Sweety, this stopped being ‘nice’ a while ago. Clothes wear out, it happens.”

Steve felt himself flush with shame. “Look, I just can’t afford to replace it, OK?” he snapped, his tone much more waspish than he intended for it to be.

The stoney look that appeared on Amanda’s face let him know that he was suddenly treading on very thin ice. He immediately started backtracking, stammering in his haste.

“I-I’m sorry,” he said, eyes wide, “It’s just, I can barely afford food, and rent, and bus costs to get to work. I don’t really have many nice things and this is,” he looked down at the frayed material of the collar and the busted button, a sad look passing over his face, “was one of them. Just one more disappointment, I guess.”

Amanda felt her heart go out to him. Considering the cut and material of the shirt, it had probably cost him a couple’s days work to afford at a minimum wage job. Closely eyeing his slacks for the first time, she discovered they were in a similar state of disrepair, and far too big, as well. Even his belt looked well worn.

She took a deep breath, trying to hedge her expectations just a little. This was all very new to him, and she could tell that he was obviously intimidated by her, but she could also see him trying to do his best to obey her. She would just have to coax him along slowly.

With a quiet sigh Amanda reached back out, making Steve flinch a little, but it was only to continue unbuttoning his shirt. As the last button came undone, she walked around him, drawing the garment off as she did, then took it to his closet to hang up. As she turned back around she took the opportunity to study his bare upper body. He was what you might call skinny/fat. Not overweight, but not in shape by any stretch of the word, with only a small tuft of hair extending up out of his trousers, ending well below his navel. He looked a little like an underfed scarecrow with spindly limbs. Moving behind him, she trailed a finger lightly across his shoulders.

“Sweety,” she said quietly, mouth close to his ear as she ran her hands over his back, “It’s not that I’m disappointed in you. I’m disappointed that you don’t expect better from yourself. But it’s OK,” she said, sliding her hands down around his sides to reach his belt, “I know how to help with that.”

She stepped on the heels of his shoes, pushing forward gently so he would pull out of them. With a final zip she opened his slacks, the large garment easily falling off to the ground even past the diaper. A quick tug and she had pulled the pants off of his legs, hanging them up as well and leaving Steve in nothing but his diaper and socks.

Walking to the closet, Amanda pulled out a towel and a washcloth, then moved back to the bed, pushing the package of diapers off to one side and laying the towel down in the middle.

“Sit,” she said, patting the towel. Steve moved very slowly, his arms doing a poor job of covering his mostly naked body. As he moved to the bed, though, Amanda went to the sink, turning on the water and running the washcloth under it until he could see steam from the heat start to fog up his mirror. As he sat down he could clearly feel the mess in his diaper and was grateful it would soon be gone, though as he stared at Amanda’s back, he felt himself flush in embarrassment. He was about to have his diaper changed by a very attractive woman who seemed to be enjoying the whole scenario even more than he was.

With a flick Amanda turned off the water, squeezing most of the excess out with a quick ring, though from the way she held it you could tell it was nearly scalding hot. Steve swallowed hard as she moved back to the bed, his nervousness plainly showing. As she reached him, Amanda went to her knees, one hand rubbing over the material of the diaper before reaching for the velcro straps. First one, then the other, both opened with the reverence of a christmas gift. Amanda hummed quietly to herself as she pulled the material down, cooing as his member came into view.

“Oh my,” she exclaimed, “What a big mess in baby’s diaper. Someone must have been feeling very needy.”

Steve felt himself flush again and look away, but Amanda laid a hand on his thigh, rubbing softly. “Shh,” she said, “It’s OK, Mommy will take care of you.”

Taking the hot cloth in one hand, Amanda slowly worked her way down from his waistline, using it to loosen up all of the dried semen matting down his pubic hair. Steve groaned as the cloth made contact the first time. It was hot, but pleasantly so, and the way she used it to gently clean him had his member starting to react in no time.

Amanda was quick to comment. “So needy again already?” she asked with a giggle. “What a little handful you are,” she said, completing the double-entendre by taking his cock in her hand with the washcloth and wiping it with soft strokes. Steve gasped, muscles clenching tight as she did.

“I can just tell,” she continued, “That even if I change you now, if we don’t take care of this little problem before I leave,” she bent his hard shaft to the side, eyeing the member critically, “then you’ll just end up with another dirty diaper right after I’m gone.”

Steve wanted to deny it, but with how hard she had made him, and all the dirty things she had put into his head, she was probably right on target. He doubted he could last five minutes after she left before he broke down and did the deed himself. The situation seemed to delight her, though.

“Alright,” she said, leaning back, “Get on your hands and knees and stick that bum out. Quickly,” she snapped, and Steve hurried into position, turning himself over and sticking out his backside as far as he could.

Taking the washcloth once more she started to wipe gently at his coinpurse before moving farther up over his perineum, and finally between his bum cheeks, making him gasp and flinch.

“Hush, baby,” she said, one finger working the cloth over his sensitive rosebud as the fingers of her other hand started to lightly stroke his shaft, “Just relax and let it happen.”

And he tried, he really did, but the sensation was just so alien. He’d thought about maybe trying anal before, but had never gone further than a couple of pokes or a little rubbing. As Amanda’s expert fingers did their work he could feel his bottom wiggling back and forth under the attention.

A sharp slap on the backside and the firm order to, “Hold still,” quieted his rustling a little, but he just couldn’t hold completely motionless. Regardless, it seemed to be enough as Amanda continued without another interruption. Steve could feel the firm pressure of the cloth slowly starting to loosen him up and sink in a fraction of an inch or so. As it reached that depth she twisted her wrist sharply, thoroughly cleaning the little hole in a manner rough enough to make him jump and whimper.

“Good boy,” she praised him, patting his bottom lightly as she laid the washcloth down beneath his cock, her voice sultry as she added, “Now let’s see what Mommy can do to make her baby feel better.”

Reaching into her purse she pulled out a small bottle of lube. With the pop of a cap, she squirted a fair amount into one hand, then closed the bottle and dropped it onto the bed incase she needed it again. Rubbing her hands together to warm up the cool lube, she reached out a gentle finger and brushed the cool clean skin of his just-washed anus, tickling as she did so.

Steve gasped, then moaned as her other hand closed tightly around his very erect penis, starting slow downward strokes like you might see a farmer use to milk a cow.

“Oh, god,” he whispered, the tickling feeling at his backdoor becoming more pleasant the longer she stroked him. However, as she started to slip her finger in, he did whine just a little. A sharp smack from her free hand quieted him down quickly enough, though, and soon Amanda had her middle finger in up to the first knuckle. She wiggled it around, making him groan.

“Please,” he started to beg, but stopped, not know what he wanted to beg for. To take it out, to put more in? His head was a whirlwind of pleasure and confusion.

Amanda didn’t seem to have any problem interpreting though. “That’s right,” she said, a wicked smile on her lips, “Beg your Mommy for more.”

Steve felt the finger being pushed deeper and wiggled his bottom in protest, earning himself another, harder slap. “Don’t you dare move,” Amanda’s voice dripped with unspoken promises of harsh punishment.

And so Steve sat as still as he could, face dropping down to the mattress and wailing quietly into the comforter as Amanda gently but firmly finished inserting her finger.

“There we go,” she said, voice syrupy-sweet, “See, that’s not so bad, is it? All that fussing just for a little finger.”

Steve’s toes curled as she started to wiggle her finger around inside, jumping as he felt her rub against something sensitive.

The sensation was bizarre, and Steve started to get nervous.  “I… I don’t know if I like this. It feels so...” he gasped then, feeling Amanda’s finger touch that same spot inside again.

“Shh,” Amanda said, running a comforting hand over his back, “It’s only uncomfortable for a little while. Just relax.”

He tried, managing to loosen up a little bit, though each time her finger flicked over that spot it made him jump.

“What a sensitive little tickle spot you have,” she said after a particularly large jump, “I think it could use some attention.”

Her finger made light circles around the spot, rubbing over it gently and making Steve moan.

“What did I tell you,” she smiled, “Just trust Mommy and she can make you feel so good.”

Steve tried to think of something to say, but the pleasure shooting through him as she massaged that spot erased all thoughts in his head. As she resumed milking his shaft at the same time, he thought he would die.

“Look at all that baby juice leaking out,” she cooed, making Steve look back between his legs. A long stream of precum hung from the tip of his cock, growing in size every time he felt that tickle inside. “Sometimes babies can’t even wait for an orgasm to let their cummies go.” She giggled, laughing at some joke only she understood.

But even as he watched the cum leak out of him, Steve felt his need to cum, really cum, growing by leaps and bounds. Amanda must have noticed, because she decided to switch up her style, her finger inside performing long, slow strokes over the spot as her milking hand increased tempo.

Steve’s breath started to come in ragged gasps, his cock and anus both spasming from the attention they were receiving.

“Remember, baby,” Amanda reminded him sweetly, “Ask for permission.”

There, he felt it, the tingle deep in his tummy that let him know he wasn’t too far from climax.

“Please… please,” he whispered, hoping she would relent.

“Please what?” she teased, slowing her stroke and barely touching his tickle spot.

He moaned, face flushing with embarrassment as he broke down. “Please let me cum, Mommy.” It was barely more than a whisper, and all jumbled together, but Amanda smiled like the Cheshire cat anyways.

“What a good baby,” she cooed, “Of course Mommy will help you with your little problem.”

Steve almost fainted as he felt her finger return to his tickle spot, fluttering like a humming bird. A flick, a firm rub, then a gentle caress. His hips humped downward at the attention, though this time Amanda didn’t correct him, instead allowing him to continue humping down into her milking hand. She could tell he was already close. If the amount of precum hadn’t given it away, his panting and whining would have. With firm strokes she drew him to the edge of orgasm, holding him there for the briefest of moments before bringing him off.

Steve cried out as he came, the convulsions much stronger than normal, his cock feeling as though it would explode at the release. As he came, Amanda continued to play with his ticklespot, which had suddenly become even more sensitive, making his orgasm even more powerful.

Amanda watched him shoot his load onto the washcloth she’d laid under him earlier, her fingers staying busy until long after semen stopped coming out. After another few seconds, Amanda finally released her grasp on his now shrinking cock, her finger popping out from inside him at the same time. Steve shuddered at the sensation, his whole body still shaking from the ordeal.

“Another mess,” Amanda tsked, “Where does it all come from?”

Steve looked underneath himself at the washcloth, a little surprised at how little there was on it. Sure, he’d had a fantastic orgasm earlier, but this one had been mind shattering. He’d imagined looking down and seeing he’d accidentally ejaculated out his spleen, but there was only a small puddle of the stuff in the middle of the cloth.

Folding up the little cloth, Amanda tossed it into the dirty clothes basket nearby.

“Now that that’s all out of the way, maybe we can finally finish getting you changed!”

Going back to the closet she grabbed the last clean washcloth and took it to the sink, preparing it just like the one before. This time, though, as she started to clean him with it, there was no protesting or wiggling, no erections, and no attitude. He laid with half his face down on the comforter, his head a tired tangle of confused thoughts as he let this woman who insisted he call her Mommy touch and clean him more intimately than anyone had in years.

As she finished wiping off all the slippery lube Amanda grabbed at part of the dry towel he was kneeling on and used it to pat him off. He offered no resistance as she grabbed his arm, pulling him up and pushing him back onto the bed so he was face up again. Grabbing the package of nearby diapers, she pulled one out, lifting both of his legs with surprising ease as she slid it under him. Reaching back into her purse she pulled out a small container of baby powder. Sprinkling some onto her hands, she started to spread it over his diaper area, soft hands rubbing gently over his freshly washed skin.

The gentle ministrations felt wonderful, but there was something about it that transcended his desire. Even as she ran light fingers over his now soft cock, he didn’t feel himself respond to her touch at all, at least not sexually. He just felt… comfortable. Like this had been a part of him that he just didn’t know about yet, and she had showed him how to find it. He did whimper, though, as her powdery fingers delved between his cheeks and anointed his little starfish, playing with it for a second and making him bite his lip.

“What a good boy you’ve been,” she cooed, finally pulling the diaper closed and strapping it firmly on.

Steve blushed a little, eyes downcast, “Thank you for changing me, Mommy.”

Amanda looked surprised for a moment, but the smile that blossomed on her face could have warmed the sun on a cold day. “Of course, baby,” she said, drawing his face up to her and placing a gentle kiss on his lips, “It was my pleasure.”

Steve started to say something when a huge yawn cracked his jaw.

“Is somebody sleepy?” she asked, running a warm hand over his neck and shoulders. After a tired nod Amanda pulled him up off the bed, drawing back the covers as she did so, then maneuvered him neatly inside, drawing the blankets up and tucking them tightly on the side.

She looked beautiful as she leaned over him, a little smile on her face as she reached down to move the hair out of his face and plant a soft kiss on his forehead.

“Good night, baby,” she said quietly, playing with his hair for a moment before moving to the door. She pushed it open, standing there briefly before saying, “Text me in the morning.”

“OK,” he replied, voice sleepy, “Good night, Mommy.”

As the door to his apartment had closed, Steve snuggled further into bed, a funny feeling in his tummy. It was always cold in the drafty little room, but that night, with the memory of Amanda fresh in his mind, he felt warm sleeping in his own bed for the first time in months.

Sophie snapped out of her daydreaming as she heard the sharp click of heels start down the hall toward her room. She whined nervously, her pussy convulsing. Mommy had promised her a very rough second round of anal to make sure she learned her lesson about being lazy.

The clicking stopped and Sophie looked behind herself toward the door, her eyes taking in her Mommy’s sleek body, naked except for the sturdy harness with the enormous strap-on sticking out of it. Her pussy clenched in anticipation.

“I hope you’re as ready as I am,” she said, a wicked gleam in her eye as she stalked toward the helpless girl. “I’m going to make sure this is the last time we have this conversation.”