Meeting Mommy

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."