Meeting Mommy

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.