Ashley's Babysitter

[Jemina004]

Ash could hear baby music and the sounds of a toddler party in the den, but Emily led them into the kitchen instead.

"Please have a seat. Would you like some coffee?" Emily asked, motioning to the kitchen table.

"Yes, please. Do you have anything for Ashley, too?" Helena said, pushing a chair back from the table slightly before sitting down.

"Sure. Milk or juice?" Emily asked, opening the fridge.

"Milk, please. I don't want Ashley to get too excited." Helena said, pulling Ash into her lap.

"Sure thing." Emily said, busying herself at the counter.

Ash watched as Emily prepared two cups of coffee with a Keurig machine. While the liquid poured, Emily opened one of the counters and took out a bottle. Ash blushed as she filled the bottle with milk, then put it in the microwave.

"I hope you don't mind, my sister Lizzie loves warm milk." Emily said with a smile that widened as she looked at Ash directly.

It took a moment for Ash to realize that being in his mother's lap meant that his pink Pampers were on full display. Ash reddened once more as he tried in vain to conceal them. His actions only seemed to amuse Emily more, however.

Emily brought the two cups of coffee to the table, then went back for the bottle. She handed it directly to his mother, which dashed any tiny hopes that Ash had of at least being able to hold the bottle himself. After taking a moment to make sure it wasn't too warm, Helena popped the pacifier out of Ash's mouth, set it on the table, and inserted the rubber nipple of the bottle in its place.

Ash was quite used to drinking from a bottle now. Helena paid much more attention him than before, but she still had her column to write. Ash knew his mother wrote for a women's magazine but had certainly never seen the magazine itself. This meant that Helena saved time where she could. More and more, it meant that time-consuming meals for Ashley were replaced with formula that contained all the vitamins and nutrients he needed. He had unwisely thrown a minor tantrum the first time it happened, which meant that his liquid meals would be given in bottles from then on. And after the first time he had tossed the bottle to the floor, it meant that Helena would hold the bottle with Ash securely in her lap, just as he was now.

Ash wasn't feeling particularly hungry or thirsty but by force of habit, he immediately began suc-king. Warm milk trickled into his mouth, which made him swallow. The process repeated itself without Ash's conscious effort and Emily smiled again as she saw Ash accepting the milk from her baby sister's bottle.

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Emily and Helena then began talking. They appeared very comfortable with each other, and Ash noticed that his mother seemed to be treating Emily as an equal. Ash had to agree, considered that when she babysat for him, Ash had treated Emily as possessing just as much authority as his mother.

Ash himself was very much aware of the fact that Emily's estimation of him was going down by the second as Ash continued to drink from the bottle. Emily may have thought of Ash as an overgrown toddler beforehand, treating like he was four or five, but he had the feeling that this was cementing her view of him as more akin to a two-year-old.

Ash sighed inwardly as he kept swallowing the milk, knowing that he really couldn't do anything about it. That was when someone new entered the kitchen, someone Ash had never met before.

The girl looked to be about eight, and the resemblance between her and Emily was clear. They had the same dark hair and green eyes, though her hair was cut shorter in a bob. She was dressed more tweenishly, in capris, a sky blue t-shirt and wearing light makeup. She seemed to have a more aggressive air, however.

"I am *not* watching Lizzie again, Em! The deal was..." The girl said loudly, only trailing off as she noticed Ashley.

"This is Ashley. Say hello, Claire." Emily said quickly, giving a warning look at her sister.

Claire looked as if she wanted to burst out laughing, but the warning look from Emily, not to mention the raised eyebrows of Helena, made her tamp down on it. Instead, she took in Ashley's snowy white toddler dress and exposed pink Pampers with an only slightly mocking smile. If Ash had any luck at all, he would have finished drinking the bottle before Claire came in. As it was, he had to endure several more seconds of suc-king on the bottle in front of Emily and Claire before it was empty.

Though Emily had already made an introduction for him, Ash tried to say something to Claire as Helena removed the rubber nipple from his mouth. His luckless streak continued, however, as Helena immediately popped his pacifier back in.

"Hi, Ashley! I was just going to say that Emily needs to watch the toddler party since we had a deal to switch off every hour." Claire said, turning her attention to her older sister.

Emily sighed and stood up from the table.

"Mrs...I mean, Helena. Would you like me to show you the deck behind the house? That's where the parents are hanging out. Claire can take Ashley to the party in the den." Emily said brightly.

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Helena looked doubtfully at Claire, who quickly put on an angelic smile. Apparently, it covered up for her previous behavior since Ash's mother stood up and set him down in front of her. Ash looked up at Claire nervously since, to his further embarrassment, the eight-year-old girl was two inches taller than he was.

Claire gently took Ash's wrist at the exact spot his mother would use and led him from the room. Ash went along reluctantly, having wanted to spend more time with Emily. But Emily had only called Ash's mother to invite him to her little sister's party. Maybe Ash was only an afterthought for her. He glanced back to see if Emily was watching him, but her attention remained on Helena. Had she decided that Ash was beneath her notice now? He would have to keep wondering, as Claire quickly took him out of the room.

"Have fun, sweetie!" His mother called over his shoulder.

Claire was walking faster than Ash was used to. He had difficulty keeping up. The Princess Pampers he was wearing was causing him to waddle, and the sky blue sneakers that Claire had on were easier to walk in than his own white Mary Janes. The swishing sound of his diaper was quite loud, and Ash was aware that Claire was looking him over. He couldn't keep the tiny skirt on his toddler dress from showing his diaper at this pace, try as he might.

Ash didn't know how much Emily had told her, if anything, so he knew that Claire would most definitely be curious. As they walked, Ash could hear the sounds of the party getting closer, but Claire stopped in the hallway before reaching the den.

"So, how old are you? Five, Six?" Claire asked, before realizing Ash's mouth was full.

Claire popped the pacifier out of Ash's mouth as he briefly thought about the fact that everyone seemed to have control over Ash's pacifier except for him. He had no idea what to say, however. He couldn't admit that he was really 14, and every time Ash had tried to lie in the past, it was a dismal failure.

"Well? Can you even talk?" Claire said, frowning at him.

Ash could indeed talk, but he was so intimidated by the eight-year-old girl in front of him that he couldn't find any words to say. Claire shook her head and popped the pacifier back into Ash's mouth.

"Guess not. I'll come up with a story for you then. You're Ashley, a five-year-old girl who can't talk and wets her diapers. You do wet them, right?" Claire said, a mocking tone entering her voice.

[Jemina004]

Claire flipped up the tiny skirt on Ash's toddler dress to get a clear look at his Princess Pampers. Ash, who was shakily slightly at this point, felt his bladder let go. He could do absolutely nothing as he was wet his Pampers under the gaze of an eight-year-old that looked, acted, and seemed far more mature than he was. The flowers on the front of his diapers bloomed at once and removed any doubt as to what was happening.

"Wow...I guess you do. I should probably find Em...but..." Claire said, a mischievous look on her face.

"I'll change you instead." Claire said, her eyes twinkling with delight.

Ash did not like this suggestion. He didn't trust Claire to not make fun of him on the changing table, and Ash had been hoping that Emily would rub his pen-is as she changed him. Ash frowned and shook his head quickly.

"What? You don't think I can do it? I've changed Lizzie before, you know." Claire said, putting her hands on her hips.

Ash shook his head again but was aware that he had very little ability to stop Claire. If Claire took his wrist again and decided to change his diaper, he could do nothing about it. The pacifier stopped him from saying anything, and once again, the idea that he could take it out was simply beyond his ability to comprehend. Ash could see Claire beginning to dismiss his head shakes and was resigning himself to having his diaper being changed by an eight-year-old when Emily came around the corner holding his mother's diaper bag. Ash had never been gladder to see her.

"Why didn't you take Ashley to the party?" Emily asked Claire, once again treating Ash as if he was too much of a baby to bother addressing directly.

"She wet herself, look!" Claire said gleefully, still holding the skirt of Ash's toddler dress up.

Ash reddened as Emily finally looked at him, well, at the front of his Pampers, at least. She smiled as she saw the blooming flowers, but once again did not bother speaking to Ash.

"Okay, okay, give her here. I'll change her." Emily said, holding out her hand and not bothering to correct Claire's designation of him as a girl.

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"Wait! I want to do it." Claire said, frowning and taking Ash's wrist.

"But you hate changing Lizzie." Emily said, looking curiously at her.

"Yeah well...that's boring." Claire said, a bit of a blush entering her face.

"I'll tell you what, I'll change Ashley, but you can watch, okay?" Emily said, stepping forward to take his hand.

"Fine!" Claire said, letting go of Ash's other hand.

Ash did not think this was fine, as the chance of Emily stroking his pen-is was much lower now if Claire would be watching. But the pacifier he was suc-king on was not only keeping him from speaking, but it seemed to indicated to Emily that she didn't need to bother explaining herself to him directly. Conversation was only for those that could communicate in return, like Claire or his mother, apparently.

Ash sulked as he let Emily lead him away from the party and toward another room. Not that she noticed. Instead, Claire was the only one giving him attention. She noticed his unhappiness but was apparently too excited by the prospect of seeing Ash's diaper get changed to care. Emily opened the door and led all three of them into a small room in the hallway.

It was immediately apparent that this was Lizzie's room. The walls were painted light pink and there was all manner of toys strewn across the room. Two large objects dominated the room. One was a pink crib, the other was a changing table. As Ash was looking around, he felt Emily lift him up onto the table.

Emily had unpinned his diaper with a practiced efficiency that rivaled his mother. In no time, Emily had slid his diaper off, leaving his tiny pen-is exposed. Claire looked at it with wonder, giggling with sheer excitement.

"I knew she wasn't really a girl. But Ashley seems kind of like one." Claire whispered, giggling again.

"Hmm. Good question. I think Ashley might be too young to have an opinion. Her mom dresses her like a girl though, so let's go with that." Emily said, smiling at her sister.

Ash would have liked to have spoken up at this but could do nothing more than suc-k on his pacifier and squirm at the cold air around his pen-is. Ash had never been more conscious of the fact that he was entirely hairless below his eyebrows. Not even the tiniest follicle had even begun to sprout, and his pen-is had not changed an iota since he was six years old.

[Jemina004]

Emily took out some baby wipes and began wiping his pen-is with them. Ash's pen-is reacted predictably and got bigger. Well, it was stiffer anyway, it hadn't actually gotten any longer or thicker.

"Is that as big as it gets?" Claire asked, looking completely jealous of her older sister right now.

"Most pee-pees get bigger, but Ashley is still a baby. That's as big as it gets." Emily said, a teasing note entering her voice.

The fact that Emily had glanced at Ash's face for the first time since she watched him drink from a bottle gave him hope. He still couldn't speak, but he tried to plead as much as he could with his eyes. Emily raised an eyebrow in response. It was as if Emily had assumed he was too much of a baby to care about that now. He continued to squirm desperately, willing Emily to have mercy on him. Emily rolled her eyes, which initially disappointed him, but then Emily looked back over her shoulder to the diaper bag she had dropped on the floor.

"Claire, can you get one of Ashley's diapers? They're in the bag there." Emily said, nodding her head toward it.

Claire turned around and began rummaging through the bag. As soon as her attention was elsewhere, Emily began using two fingers to stroke his tiny pen-is very quickly. In seconds Ash was squirming in pleasure as his pen-is gave a slight spasm. Not even the tiniest drop came out to announce he had c-um, of course. Once again, Emily hadn't seemed to have noticed his dry orgasm, and Ash's pen-is began getting far too sensitive.

This had happened last time, but back then he had the ability to beg Emily to stop. This time, his pacifier was making that an impossibility. Ash squirmed harder and made fussy noises, but Emily ignored them. His only hope was that Claire would find his diaper and maybe that would get Emily to stop. But Claire was not making as much progress as he hoped.

"What kind of diaper? There's lots of Princess ones here." Claire said, still rooting through it.

"Which princesses?" Emily asked idly, not pausing the fast pace of her stroking.

"Ariel...Jasmine...Mulan...Rapunzel..." Claire listed slowly, supremely unaware of Ash's plight.

The sensation from Ash's pen-is had turned from warm pleasure to hot discomfort that approached pain. Now though, his pen-is was spasming constantly and the sensation seemed to be a combination of both. It didn't help that Emily's fingers were continually teasing and caressing the head of his pen-is without letting up in any way. Ash was distantly aware of his tiny balls rising and clenching again and again, as if they were trying to shoot something. But of course, he had nothing to shoot.

"How about you decide?" Emily said to Claire, knowing that she was causing Ash to orgasm countless times.

"Hmm...Rapunzel, I guess. Wait. Do you think one of Lizzie's diapers would fit her?" Claire asked idly.

"It might. Do you want to try?" Emily asked Claire while she grinned at Ash.

"Sure!" Claire said excitedly.

Ash had to endure a few more seconds of the extreme sensations coming from his pen-is before Claire put the diaper back in the bag and turned around. Emily stopped stroking him at that exact moment and Ash gasped with relief.

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He looked at Emily in amazement, but her attention had already shifted away from him and back to her sister. Claire retrieved one of the plain pink diapers that were kept in a small bag on the table. They looked quite small, but that didn't seem to dissuade Emily any.

After applying baby powder, Emily unwrapped the diaper, slid it up underneath his butt, and taped it securely. It was tighter than his usual diapers, but it wasn't all that uncomfortable. Ash could only blush again as he realized that diapers meant for a three-year-old girl could fit him.

Ash yawned slightly or tried to around the pacifier. He always felt tired after his pen-is spasmed, and the girls noticed immediately.

"She's sleepy! Should we put her down for a nap?" Claire asked excitedly.

"That's a good idea. Babies need their rest." Emily said, agreeing.

Ash didn't complain. His mother got her best work done when he was napping, which meant she put him to bed several times during the day. Lately, Ash had gotten used to it and could only go about four hours before wanting to nap. He had been very good about not getting out of bed, as not to give his mother any reason to bring his crib back up from the basement. But it seemed he couldn't avoid it here.

Emily picked him up easily and carried him to Lizzie's crib. She laid Ash down on the pink covers and removed his Mary Janes and frilly white ankle socks. She then twirled the starry mobile hanging above the crib so that it made gentle twinkling sounds. Ash felt his eyelids lowering further by the second, and curled up underneath the blankets as he quickly fell asleep. He didn't even hear Emily and Claire leave the room.