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=> Topic started by: Jemina004 on June 19, 2017, 01:53:52 PM

Title: Ashley's Babysitter
Post by: Jemina004 on June 19, 2017, 01:53:52 PM
"Ashley! Come down here for a moment!" Ash's mother called from downstairs.

Ash winced at hearing the girly version of his name that his mother loved to use. Despite constant efforts to get her to call him "Ash", she determinedly explained to her son that Ashley was a perfectly fine boy's name, and to just accept it because that's the name she chose for her darling boy.

Ash put down the Harry Potter book he had been reading. (The first one, as his mother decided that the ones past that were a little too mature for him to read alone) and checked to see if his pull-ups were wet. He had a bed-wetting problem that he just couldn't beat, and wore full diapers every night. Occasionally he would even wet himself accidentally if he spent too long playing a game or watching a movie. After the first few times it happened, his mother wanted him diapered whenever he was home, but he persuaded her that pull-ups were sufficient. Fortunately, they were still dry.

The 14 year old boy who had yet to hit a real growth spurt hastened out of his room and walked down the stairs to talk to his mother. He got down to the living room and saw she was dressed up quite a bit. His mother's long blonde hair was tied in a very classy up-do, and she was wearing an emerald green A-line dress with matching heels. She was just putting on her earrings and smiled at her son.

"I'm heading out tonight, honey. I know Aunt Sara was supposed to watch you tonight, but she can't make it. And I can't find any of the usual sitters on such short notice." Ash's mother explained apologetically.

"Oh." Ash answered nervously.

Most 14 year old boys would be glad to get a night to themselves. But Ash had a tendency to get scared when he was alone, and the last time they had tried it, Ash called his mother in a panic because of some noises he thought he heard in the basement. She called off her date and came back to check on him, but there was nothing wrong. After that, she always made sure he had a babysitter.

"So I had to get creative. You remember Emily right? You were such good friends when were you were both little." Ash's mother said with a smile.

"Yeah?" Ash answered slowly, wondering where this was going.

"Well...I called her mother and asked if Emily could come over tonight." Ash's mother said with some hesitation.

"Mom!!" Ash exclaimed. Emily was the same age as him!

It was true that they used to be friends. But that was when they were both little kids and they had long since stopped hanging out. Now Emily was a very popular girl that Ash had a big crush on. Emily had long, silky black hair and boobs that put the most girls her age to shame. She was on the track team, and the gymnastics team, and the volleyball team. Meanwhile, Ash had never even gone to middle school. His mother had decided that it would be best if she hired a private tutor for him after he finished elementary school.

"Don't worry, I didn't ask Emily to be your babysitter or anything. I just asked her if she wanted to keep you company for tonight, until I came back. She said she'd do it!" Ash's mother said brightly.

Ash groaned but didn't otherwise complain. His mother never listened to him anyway, and had a tendency to treat him like a petulant toddler if he didn't go along with her ideas. Besides, a small part of him was happy to pay the price of being hugely embarrassed in front of his crush if it meant he wouldn't be alone in the house all night.

The doorbell rang and Ash's mother hurried to answer it. Ash himself stayed where he was and fidgeted awkwardly. There was nothing he could do to save himself from the situation, and could only be thankful for the fact that the loose shorts he was wearing might conceal his pull-ups. He could run upstairs and take them off before Emily could get the chance to find out, but would wetting himself in front of her be any better? He had a tendency to pee without thinking about it when he was nervous, and he was definitely going to be nervous tonight.

After hearing the door open and some expected "Hi's", Ash thought he heard whispering. He crept closer to the door and only caught the tail end of whatever his mother was telling Emily.

"...here's my number, I'll call later tonight. Ashley's bedtime is 9 o'clock sharp. Make sure he takes his bath by 8:30." Ash's mother whispered.

So much for not being his babysitter. Ash sighed and decided to pretend like he didn't hear anything. If Emily kept up the charade that she was just there as a friend for awhile, it would make it a little easier on him.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 19, 2017, 03:17:45 PM
Ash's mother and Emily walked into the living room. He was immediately struck by just how pretty, and tall, she was. Emily's long black hair fell halfway down to her waist, and she was wearing a halter top and a denim skirt. What looked like 4 inch heels made her tower over Ash even more. They were both 14, but a neutral observer might guess her age to be 16, and would probably think he was 12, or more likely 10. After all, he had yet to really hit puberty, and Emily looked almost like a young woman.

"Hey Ashley. It's been awhile." Emily casually remarked.

"H-Hi Emily." Ash stuttered in response.

"Okay sweetie, have a good time with your friend! I'll be home later tonight I think." Ash's mother told him before she pulled him into a hug and kissed him on the cheek.

His mother picked up her purse and walked over to the door, pausing before leaving to give Ash a little wave, which he returned halfheartedly. After the door closer, he turned to face Emily. She was looking at him curiously. In particular, she was looking at his lower half.

"Are you wearing diapers?" Emily asked him slowly.

Ash turned red as a tomato. He had no idea what to say. Lying was the obvious choice, but it would be a very feeble lie indeed. The shorts he was wearing didn't conceal anything after all. And in the time he was standing there, paralyzed with indecision and looking right at Emily's increasingly amused face, his bladder let go. The warmth spread throughout his crotch, and he prayed his pull-ups wouldn't leak. He also prayed that Emily couldn't figure out that he was wetting himself at this very moment, but somehow it was always obvious to others. Both his mother and Aunt Sara could always tell.

"Oh my god, you are. That's so...adorable." Emily finished with a very amused giggle.

Ash stood there, blushing until his bladder was fully empty. He tried to come up with something to say to salvage the situation, but nothing would come. Eventually he just blurted out what he was thinking.

"Please don't tell anyone!" Ash begged.

"Well I don't think anyone would believe me if I did. Don't worry, sweetie, I'll keep your secret." Emily said with another giggle, pressing a finger to her lips.

"Do you need to be changed? Your mom didn't say anything about it, but I change my sister's diapers all the time, so I'm sure I can change yours." Emily offered with a genuine smile.

Ash groaned inwardly but gave a shy nod as a response. The alternative was sitting in wet pull-ups all night and probably getting a rash. Besides, how much more humiliated could he get?

"Come with me then, sweetie." Emily said, taking Ash's hand and leading him upstairs.

Ash opened his mouth to tell her where his room was, but realized it was a moot point. Only one room had block letters attached to the door spelling out "Ashley" in alternating blue and pink colored wooden blocks. His mother had put those on his door when he was a baby and adamantly refused to take them off, saying they were just too cute to ever remove. Emily opened the door and led Ash inside his own room.

"Well, this is cuter than I expected." Emily said with an appreciative grin.

Ash's room was more akin to a 8 year old boy's than a 14 year old's. A 8 year old with gender issues in particular. There was plenty of pink to go along with the blue. The posters on the walls were of Disney TV movies starring more girls than boys. His mother kept a very close eye on the media he was allowed to consume, and the TV in his room was kept on the Disney XD channel, with the channel buttons removed and the remote control stored in his mother's room. She would occasionally switch it to the regular Disney channel for a particular show if Ash begged her enough, but only after his mother DVR'd it beforehand to make sure it wasn't too mature for him.

His bed was a canopied affair that was at least a more gender neutral white, but still undeniably girly. Yet that was not the most embarrassing part of his room. It was the white changing table in the corner, where his mother diapered him every night. She was an expert by now at diapering him comfortably and securely, but whenever she let him try to do it himself, it was always either way too tight or way too loose. Ash suspected that his mother didn't try too hard to teach him how to do it, because she only let him try it himself every so often.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 19, 2017, 03:45:14 PM
A cliffhanger no longer! This is the next part.

It was here that Emily led him. Ash stood there in front of the table awkwardly in the absence of his mother's practiced efficiency. So he let out an embarrassing squeak as he felt Emily pull down his shorts. A few seconds afterward, he felt Emily sliding his wet pull-ups down as well. Ash stepped out of them and covered his pen-is shyly. He was never embarrassed about being naked in front of his mother anymore, but this was different.

"Okay sweetie, up on the table." Emily motioned with a smile.

Ash laid down on the changing table, still covering himself with his hands. Emily shook her head and pulled Ash's hands away, exposing his hairless pen-is. Despite his mother's earnest efforts to shield him from learning anything about sex, he knew that boys his age had hair down there, and their pen-ises that were definitely bigger than they were when they were kids. But Ash's was exactly the same size as it had always been, and though he looked carefully every once in awhile, he didn't have a single hair down there. On the few occasions where he mentioned this shyly to his mother, she had assured him that everyone grew at different speeds and he was perfectly normal.

"That is just the cutest thing ever." Emily said with another giggle.

Emily got some baby wipes from the case on the table and began wiping Ash's pen-is with them. His little pen-is started to get hard, which sometimes happened when he was wiped. His mother never gave any sign that she noticed or cared, and so Ash didn't care either. Besides, it was so small that it in no way prevented his mother from diapering him. But Emily evidently cared.

"Oh wow, it got a little bigger. I thought baby ones didn't do that, but I guess you're not really a baby, huh?" Emily remarked, curiosity sparkling in her eyes.

Ash blushed again and found his gaze drawn away from Emily's face to her chest. Emily had an impressive set of boobs that rivaled most grown women, and she hadn't finished growing yet.

"Like what you see, huh? Well since I guess you're showing me, I can show you." Emily said with a laugh.

Ash's breath caught as Emily pulled off her halter top. She was wearing a very sexy white push-up bra. Not quite as lacy and expensive as the ones he knew his mother sometimes wore, but still very mature. Ash longed for Emily to unhook her bra and showing her bare boobs, but he was going to be disappointed.

"Sorry sweetie, I don't think you're big enough to handle these. Just enjoy the view you have, okay?" Emily said teasingly.

Ash's pen-is was harder than he could remember it ever being, but he was too shy to start touching himself in front of Emily. Sometimes he would touch his pen-is for awhile in bed, but while it felt nice, he'd eventually get bored and do something else. Now though, his attention was fully on his pen-is, and he squirmed uncomfortably on the table.

"Want me to touch it, sweetie?" Emily asked happily, moving to touch Ash's pen-is before he'd even nodded.

If Ash was squirming before, it was nothing compared to how he much squirmed after Emily started stroking his very short length with two fingers. Her fingers moved up and down faster and faster, and it was only a few seconds before Ash felt his pen-is spasm and an incredibly warm and pleasurable feeling from it. But Emily wasn't stopping and his pen-is felt more sensitive than it had ever been.

"Stop, please!" Ash begged desperately, as the stroking caused him increasing discomfort.

"Oh, did you just...oh. Sorry sweetie, I know boys are sensitive afterward. But they usually shoot stuff out when they finish. I guess you're not there yet. Maybe someday." Emily said with an amused laugh.

"Okay, back to business. I know you were wearing pull-ups, but those almost leaked. I think you need a full diaper." Emily said, returning her focus to changing Ash.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 19, 2017, 05:13:34 PM
Another chapter! I hope people are enjoying this.

Emily used a small amount of baby powder on Ash before looking at the available diapers that were stacked up next to the changing table.

"Hmmm. Spider-man. Wreck-it-Ralph, I think? Plain white...oh my god. These are perfect!" Emily exclaimed, holding up one of the pink diapers that Aunt Sara preferred to use.

"Disney princess pampers? These are absolutely adorable. Let's try this Anna one, okay?" Emily said excitedly, holding up a riotously pink diaper with Anna from Frozen on it.

Ash frowned unhappily but said nothing as Emily lifted his butt to slide the diaper underneath him. In less than a minute, Emily had taped him securely into it.

"Looks like it fits you perfectly. I thought maybe a girl's diaper wouldn't fit right, but I guess you're not big enough for it to make a difference." Emily said, a teasing note returning to her voice.

"And look, there's flower buds on the front. I think they bloom if you wet yourself. Isn't that amazing, Princess?" Emily asked Ash earnestly.

"Princess?" Ash asked, frowning.

"I know, I know, you're a boy. But boys can be princesses too. Especially if they're wearing princess pampers." Emily said with a giggle.

Ash squirmed uncomfortably, feeling his pen-is starting to harden again. But now that it was securely encased in his diaper, there was nothing he could do about it.

"Okay Princess, now that that's out of the way, you can have some playtime." Emily said lightly while grabbing Ash's hand again.

"Wait, can I put shorts on again?" Ash asked with a bit of a whine in his voice. He really didn't want to walk around in just his diaper.

"I don't think so, Princess. Unless you have something just as adorable to wear over them. Do you?" Emily asked with interest.

Ash's eyes flicked over to the closet, where his mother kept some of the girly clothes Aunt Sara would sometimes bring. This did not go unnoticed by Emily, who walked over to the sliding doors and opened them.

"Oh. My. God. This is so incredibly cute!" Emily exclaimed, pulling out the pink nightie Aunt Sara had bought for him a couple of years ago.

Ash sighed but didn't attempt to dissuade Emily from putting it on him. She took off his t-shirt and then she slipped it over his head. It was pretty tight, and the skirt didn't cover his diaper at all. The short skirt was intended to make changing a diaper easy, and that fact that it was a little too small for him made it so that his pampers showed almost as clearly as before.

"Wait wait, I need to take a picture of this." Emily said with glee, taking her cellphone out of her pocket.

Ash had no choice but to watch as his crush immortalized his humiliation by taking picture after picture with her phone. As embarrassed as Ash was, he also felt a tinge of jealousy. His own cellphone could hardly be called that, as it was heavily modified by his mother. It was loaded with Disney music and little kids games, with no ability to use the internet and could only send and receive calls from his mother's phone as well as Aunt Sara's. (The only exception being 911)
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 19, 2017, 09:15:33 PM
New chapter! Not sure how much I'll keep writing but these still a few to come regardless.

"Okay sweetie! We have a little time before I make something for you to eat, so what do you want to do?" Emily asked him.

Ash honestly didn't know what he wanted to do, so he gave a tiny shrug. Emily frowned and shook her head, and for a second Ash thought she was mad at him. But it seemed that it was directed at herself.

"Never give a toddler an open-ended choice, dummy." Emily instructed herself under her breath.

"Okay sweetie, I see Candyland over there. Do you want to play Candyland, or do you want to play with your horsies?" Emily asked, motioning to the pony figures arranged on a small shelf on the wall.

Ash felt a little insulted, but then realized she was right. Now that his choices were boiled down to two, it was much easier to choose.

"Um, horsies." Ash answered, embarrassed.

"Good choice, sweetie. Sit down on the floor and I'll get them for you." Emily instructed lightly.

Ash sat down on the floor and watched as Emily gathered up the pony figures he had collected over the years and spread them out in front of him. For the first few minutes, he felt incredibly self-conscious about playing with them under Emily's watchful eyes. But eventually he lost his self-consciousness and started using his imagination to create a big fancy ranch for them, and only looked up from his toys to see that Emily was sitting on his bed, texting someone. He thought about asking her a question, like about who she was talking to, or what time it was, but he found that he didn't really need to know. It was much easier to go back to playing and to simply trust that his babysitter would take care of him.

"Alright sweetie, it's time for dinner." Emily said to Ash.

Ash looked up to see that the sunbeam coming from the window had shifted position on the wall, and after glancing at the unicorn clock he had on the wall, Ash was surprised to find that 45 minutes had passed with him sitting on his tummy on the floor. He had been completely lost in his play world, and Emily no doubt found it very amusing to watch him neighing and making clip-clop noises with his tongue as he played with the ponies.

"Kids have such great imaginations." Emily said with a smile, reaching out to grab Ash's hand.

Ash got up, feeling his tummy rumbling and wondered what Emily would make him for dinner. He was eager to head down to the kitchen, but Emily wasn't ready to go yet.

"Wait a second Princess, I need to check your pampers." Emily instructed, with a tone that was remarkably similar to his mother's when she wanted him to do something specific and he wasn't focusing.

Emily lifted the skirt on his nightie and examined Ash's front closely. He hadn't wet himself during his lengthy playtime, but that was only because his bladder was empty before and he'd had nothing to drink. Ash thought about telling Emily this, but knew it would be a waste of time. His mother never bothered to take his word for it when she wanted to check if he was wet, so why should Emily be any different?

"No flowers?" Emily said, mostly to herself as she moved her hand to check Ashley' dryness with her hand.

Ash squirmed at the feeling of her hand over the front of his diaper, and felt his little pen-is growing hard again. But evidently, it was too small and his diaper was too thick for Emily to tell.

"Good job, princess! Let's go!" Emily said with a fake tone of excitement that his babysitters tended to use with him.

Ash let himself be led downstairs by his babysitter and reflected on how relaxed he was now by comparison to before. Emily had seen everything there was to see about him, and he had nothing left to hide. Maybe that was better than constantly trying to act his age with people he didn't know.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 19, 2017, 11:45:48 PM
As they were heading into the kitchen, Emily slowed down a moment. She thought for a second, then turned around to look at Ash.

"Do you have a highchair, sweetie?" Emily asked mischievously.

"N-No I don't!" Ash protested weakly while looking away from his babysitter.

In truth, there was a highchair in the kitchen, but it was folded up and was slipped into the gap between the refrigerator and the dishwasher. Since he was always undersized for his age, his mother had him use it until he was almost 8 years old. Emily didn't know that, but Ash had the complete inability to lie convincingly. He didn't know exactly what gave him away, but whenever he tried to lie it went over like a lead balloon. And so it was that Emily looked at Ash with deep skepticism.

"Hmm, let's take a look then." Emily said shortly while leading Ash into the kitchen.

Ash fidgeted awkwardly while Emily looked around in the kitchen. It only took her a few seconds to find the folded up highchair, and she pulled out it of the gap with a satisfied air.

"What do we have here, princess?" Emily asked Ash, looking at him directly.

"A highchair." Ash mumbled, looking away.

"Toddlers lie a lot, sweetie, so I'm not upset. But you need to try to be more honest with me in the future, okay?" Emily asked him, using a measured, even tone very similar to the one Ash's mother used on the occasions where she needed to lecture him.

Ash nodded quickly and watched as Emily set up the high chair, then came closer when Emily gestured for him to do so. She lifted the tray in front of the highchair and Ash sat down on it. Emily then lowered the tray and locked it in place. To Ash's surprise, he was still able to sit in it fairly comfortably.
 
Emily tested the tray part of the chair to make sure it would keep Ash secure, then walked over to the refrigerator. There was a digital lock on the handle which prevented Ash from opening it himself. When he was a little kid, he used to be a bit chubby. His mother had bought the locking refrigerator years ago to control the amount of calories her son consumed. But even after she slimmed Ash down successfully, she kept the lock on the handle. Ash didn't mind. He trusted his mother to feed him correctly. He didn't even bother to try to see what combination Emily entered to open the fridge.

Emily then checked some of the cabinets. These were not locked, but there was no need to lock them. The food there was all packaged and required cooking. Ash had no idea how to cook anything, as his mother had forbid him from ever touching the stove.

"Hmmm. What do you think sweetie, chicken nuggets or macaroni and cheese?" Emily asked him, holding up the two packages in her hands and once again making sure to limit his choice to one or the other.

"Um, macaroni and cheese." Ash answered shyly.

Ash would never admit it out loud, but he was glad that Emily was so quick to pick up on the fact that he had a very hard time making a decision himself. He was so used to his mother simply deciding for him. Being asked to choose between two options was a little challenging by comparison, but he found he could do it.

Ash watched in awe as Emily whipped up the macaroni and cheese with ease. He would have been scared of the hot burners himself, but Emily seemed to have no fear. After only a few minutes, she poured the macaroni and cheese onto a plate and sat down at the table next to Ash. She speared some macaroni and raised the fork up to Ash mouth.

"Open up sweetie!" Emily instructed in a sing-song voice.

"I-I can do it myself." Ash stammered in response.

"I don't want you to get your cute little dress dirty. Now open up." Emily instructed again, her tone becoming a little sharp at the end.

Ash recognized that tone from his mother and it signified a lessening of patience. He opened his mouth immediately and Emily was quick to insert the fork into his mouth. She waited until Ash's mouth closed and withdrew the fork, then gave him time to chew and swallow. Emily then speared more macaroni and repeated the process. Ash fell into the rhythm and in no time, the plate was empty.

"All done! Now let's see what we have for you to drink." Emily said with satisfaction as she got up from the table.

"Grape juice or apple juice?" Emily asked as she looked in the fridge.

"Grape juice!" Ash answered a bit of excitement. He was quite thirsty and his mother generally gave him milk afterward and reserved juice for earlier in the day.

"Grape juice it is. But I don't want you spilling anything." Emily said as she rummaged through one of the lower cabinets.

"Aha! This'll be perfect!" Emily exclaimed, holding up a dusty sippy cup.

Ash blushed slightly as Emily washed the cup, then poured a small amount of grape juice in the cup before fastening the lid. She placed it in front of Ash and watched as he grabbed the handles on each side before raising it to his lips. He knew he looked like a toddler doing this, but he was just doing what came naturally. The sweet taste of the grape juice was more important than listening to Emily giggling anyway.

"No more spills! I should mention it to your mother that you liked using your sippy cup." Emily said lightly.

Ash blushed again and waited for Emily to wash the dishes. He wished he could get up from the highchair, but he knew that wasn't going to happen. The lock on the highchair required some strength to open it, and even though Emily manipulated it easily, he wasn't sure he could. Once she was done, she walked over to Ash and unlocked the tray so that he could get up from his highchair. After he stood up, Emily immediately raised the front of his skirt and examined the front of his diaper once again.

"Still nothing! I'm impressed, sweetie! I definitely thought you'd be wet by now." Emily exclaimed as she ran her fingers over the front of Ash's pampers.

Ash squirmed and was on the verge of asking his Emily if she would touch his pen-is again when she led him into the living room.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 20, 2017, 01:55:26 AM
Next chapter!

"We have 30 minutes before your bath time. How about we watch a show?" Emily asked brightly before leading Ash to sit down to the floor in front of the couch.

Ash waited patiently for Emily to turn on the TV and select something she decided was okay to watch. After a minute or two, she selected an episode of Yo Gabba Gabba. Ash was quite excited to see this show, as his mother had decided that some of the musical guests might be too mature for him.

After less than a minute of watching, Ash had crept forward to lay down on his tummy in front of the couch and was entranced. He was vaguely aware of Emily sitting on the couch behind him and texting, but he was too preoccupied to give much thought to his babysitter.

It was only when they went to a commercial and Emily switched to another channel, this time a very boring one meant for preschoolers that his trance was broken.

"Emily! Can we please please go back to Yo Gabba Gabba? Please?" Ash begged, using a whiny-but-not-too-whiny voice that worked well at getting his mother to relent just a little bit.

"Once the commercials are over. Those things are all intended to get toddlers excited and begging their parents for new toys, and I'm sure they'll work on you." Emily answered with a smile before getting up from the couch to check Ash's diaper again.

"I see someone wet their pretty pampers!" Emily exclaimed in genuine excitement.

Ash blinked and realized that yes, he had wet himself without even knowing it. He was so into the show that he never felt his bladder release. He blushed as Emily easily flipped him over onto his back and examined his front.

"Look, sweetie! Flowers!" Emily said with amusement, pointing down to the flowers that had bloomed on the front in response to his wetness.

"I-I didn't mean to!" Ash said sheepishly, more worried that she would insist on changing him then and there and he would miss more of Yo Gabba Gabba.

"I know sweetie, babies never do. But that's why they have to wear pampers." Emily said with a giggle.

"Can we please watch the rest of the show first, Emily? Please please please!" Ash begged.

"Don't worry, princess. It'll be time for your bath when the show is done, so we can wait." Emily said with a sympathetic smile.

Emily used the remote to turn back to Yo Gabba Gabba. Ash returned his focus to the show, but noticed that Emily hadn't sat back down yet.

"I'm going start running your bath, sweetie. So don't worry, I'll be right back, okay?" Emily told him in a reassuring tone.

Ash nodded and acted like it was no big deal, but inwardly, he would have been a little nervous if Emily left him alone without saying anything.

It was a few minutes before Ash became dimly aware that Emily had returned. By now the show had his full attention however, and he watched it happily until the end. When it was over, Emily turned off the TV and got up from the couch. She took Ash's hand and gently pulled him up until he was standing. Emily led Ash upstairs to the large bathroom where he took his baths. By now, Ash was squirming in discomfort from the cold wetness of his diaper and was eager to get into the warm bath.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 20, 2017, 04:38:31 PM
As Emily lead him into the bathroom, Ash immediately noticed that Emily had used some of the bubbles that his mother put in the bath once a week as a treat for him. He felt a tinge of pleasure at the thought of playing with the bubbles as Emily pulled the nightie over his head and took off his wet pampers. He shyly covered his pen-is once more as Emily led him into the bath.

"Don't worry, sweetie. The temperature's mild. I know babies have very sensitive skin." Emily said with a smile.

Ash blushed and blew a few bubbles into the air as Emily picked up a washcloth and added a generous amount of the baby soap his mother used. The fact that his mother insisted on giving him daily baths with the same baby soap she'd always used on Ash had kept his skin very soft and smooth. It was something that Emily noticed immediately.

"Wow, I give baths to my 3 year old sister and her skin isn't even as soft as yours." Emily remarked with surprise.

Emily got up and looked at the medicine cabinet next to the sink. An entire shelf was reserved for the products Ash's mother used on him, and she scanned it with wonder.

"Baby lotion, baby moisturizing cream. Well, now I know why your skin is so soft. Oh my god, I recognize this. This is a rectal thermometer!" Emily said with glee, raising it in the air.

Ash blushed very deeply and looked away from Emily. She giggled for a bit, then looked at Ash with a little more sympathy. Her laughs died down and she put the thermometer back.

"Well, maybe next time." Emily said with a kinder air.

Emily picked up the baby lotion and looked at the direction tab. Ash could have told her how his mother used it, but decided to let his babysitter figure it out. She read it out loud with a smile on her face.

"'For use after bathing to soften your baby's skin'. Sounds fun!" Emily announced, smiling.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 20, 2017, 04:41:33 PM
That was a little short, so here's the next part!

Emily returned to the tub and lathered up the washcloth again. She began the process of bathing Ash, but this was a different kind of bath than Ash usually had. His mother was very efficient at bathing him now and had it down to a science. But Emily seemed intent on washing him slowly and thoroughly.

She used the washcloth behind Ash's ears, his neck, his chest, under his arms, and then moved down to his legs, starting with his toes. Ash blushed more and more as Emily traveled further up his legs, moving the washcloth past his knees and up his thighs. Ash's little pen-is was quite hard at this point and he was looking forward to Emily touching it. But first she decided to make sure his butthole was squeaky clean. Ash squirmed in the bath as she pushed a finger behind the washcloth into his butt, then worked it slowly from side to side.

Ash was relieved when Emily moved onto his tiny balls. She moved the washcloth gently over them and grinned when she felt how small they still were.

"Boys shoot out stuff from their pen-ises, but the stuff is made here. Except these aren't making any yet. Maybe in a few years, sweetie." Emily said with a teasing tone.

Emily then moved the washcloth over to his pen-is, but very softly and slowly. Ash wanted her to touch it like she had before and whined at the unsatisfying contact.

"Do you want me to keep being your babysitter, sweetie?" Emily asked while keeping up the teasingly slow pace of her touching.

"Yes!" Ash immediately answered.

"Well, you'll need to tell your mommy that you want me to babysit you again." Emily instructed slowly.

"I will! I will!" Ash said quickly.

"And you'll have to make it more fun for me. I like dressing you up in cute girly clothes. Ask her to buy you more dresses." Emily said with a smile.

"O-Okay!" Ash agreed readily. He would have agreed to practically anything to get Emily to touch his pen-is like she did before.

"And tell her you love the color pink. You want everything pink; your diapers, your dresses, your room, everything." Emily said, grinning as she began to stroke the very small length of Ash's pen-is.

"O-Okay! Please, Emily!" Ash begged in his best whine.

Ash squirmed in the bath as Emily finally began to stroke his pen-is in a satisfying way. She used two fingers to cover Ash's pen-is with the washcloth and moved them up and down quickly. In less than 10 seconds Ash felt his little pen-is spasm and gasped at the very pleasurable feeling from it. But if Emily understood that his pen-is had gotten too sensitive after that, she gave no sign because she didn't slow down.

"Please stop, stop!" Ash begged in a tone that was far different than his earlier whine.

"Oh, did you finish, sweetie? It's a little hard to tell." Emily said with a laugh as she raised the washcloth to show there was nothing on it.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 20, 2017, 09:48:29 PM
New chapter!

"Now that that's out of the way, it's time for some shampoo." Emily said lightly as she grabbed the baby shampoo off the side of the tub.

"It says "No more tears", but I want you to keep your eyes closed anyway, okay sweetie?" Emily instructed as she uncapped the bottle.

Ash closed his eyes immediately and squirmed slightly at the cold feeling of the shampoo gel being poured onto his head. The feeling of Emily's fingers lathering the shampoo into his hair however, was much more pleasant.

"Your hair is so soft, sweetie. Why don't you grow it out? You could have long blonde hair just like your mommy." Emily said encouragingly as she continued to lather Ash's hair.

Aunt Sara often said the same thing to Ash. She would brush his hair and bemoan how short it was. Maybe growing his hair out wouldn't be such a bad thing.

"Okay, sweetie, time to rinse." Emily said as she stood up.

Ash still had his eyes closed tightly, but he recognized the sound of Emily taking out the detachable shower head from above him. After a second or two, a warm jet of water fell on his head to rinse the shampoo away, aided by Emily's fingers. Soon his hair was free of shampoo and the jet of water had stopped, but Ash kept his eyes closed until Emily said it okay to open them.

"All done, sweetie! You can open your eyes now." Emily instructed him warmly.

Ash opened his eyes to see Emily standing up in front of the tub and holding up a fluffy white towel. She motion him to stand up and step out of the tub, which he did quickly. Emily then wrapped him in the towel and picked up a separate one to start drying off his wet hair. Ash wrapped himself in the towel gratefully as the water on his body began to cool. After drying his hair, Emily then rubbed the towel over every inch of Ash's body. After he was completely dry, Emily dropped both towels into the hamper next to the sink. Ash was no longer wet or cold, but he still naked in front of Emily and quickly covered his pen-is with his hands.

"Let's try that baby lotion, shall we?" Emily said to Ash, her eyes twinkling.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 20, 2017, 10:40:05 PM
Ash fidgeted as Emily opened the bottle of lotion and poured some of the creamy liquid onto her hands. His mother only used the lotion once a week, and in fact had just used it on him last night. But he doubted Emily would be dissuaded from wanting to use it on Ash herself.

Emily spread lotion onto Ash's cheeks and forehead and worked in it gently with circular motions. She did the same with his neck, his shoulders and his arms. Ash's chest and tummy were already very soft, so she skipped them. She turned Ash around and applied the lotion to his back, but skipped his butt. Because of his diapers and frequent application of baby powder, Ash's butt was as soft as any real baby's. She then rubbed more lotion onto his legs.

The feeling of Emily's fingers rubbing in the lotion was pleasant, but the closer her fingers got to Ash's thighs, the more his pen-is responded. Ash decided to beg Emily to touch it again. After all, once he was diapered again, he wouldn't get another chance for a long time.

"Emily, can you please please touch my pen-is?" Ash begged in his best whine.

"Again? I just rubbed it a few minutes ago." Emily said with a shake of her head.

"I know, but it's sticking out again." Ash said blushingly, removing his hands to show that his pen-is was indeed hard.

Emily smiled wryly and squeezed out more lotion onto her fingers. She reached down to grasp Ash's tiny pen-is with two fingers and slowly stroked it. Ash gasped as the heavenly feeling of Emily's fingers combined with the creaminess of the lotion.

"If you want me to touch it in the future, you can't call it a pen-is anymore. Babies have pee-pees, understand?" Emily said with a teasing note in her voice.

"Y-Yes!" Ash said blushingly.

"So, what do you want me to touch?" Emily prompted.

"M-My pee-pee!" Ash answered immediately.

Emily grinned and quickly began to stroke Ash's pee-pee until he gasped and whined for her to stop.

"Please Emily, it's too sensitive!" Ash whined loudly, prompting Emily to quit.

"It's so adorable how you can't shoot anything. But it fits. Boy juice is needed to make babies, but you're a baby yourself. And babies can't make babies." Emily said with a grin as she grabbed Ash's hand.

"Alright sweetie, it's 9 o'clock. That's a pretty late bedtime for a baby, but that's something I'll talk to your mommy about." Emily said, considering.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 21, 2017, 12:11:00 AM
Next chapter! The story will "end" in a little bit, but I'll probably just continue it in this thread. Why not?

Ash let himself be led out of the bathroom. Although he was still naked, Ash didn't mind. His mother always led him to out of the bathroom naked to his room in order to diaper him and put him to bed.

As soon as they entered the room, Emily led Ash over to the changing table. After he laid down on it, Ash had the sense to not bother covering his pen-is. She immediately selected another pink diaper for Ash, this time with Jasmine on it. She paused to apply baby powder to him, then slid the diaper underneath his butt and had it taped securely in less than 30 seconds.

"So, does your mommy use anything else to make sure you don't wet your bed?" Emily asked inquisitively.

"Um, I use rubber pants." Ash mumbled as he pointed to a drawer on the dressed next to his changing table.

Emily walked over and opened it. She rummaged through the drawer until she found what she wanted, which turned out to be his one pair of plastic pants that was pink.

"Rubber pants? These are rubber panties, sweetie. Look, they have ruffles along with the leg holes!" Emily said with a grin.

Emily walked back over to the table and worked the rubber panties up Ash's legs until they were snugly covering his diapers. Ash would never admit this to anyone, but he had a hard time sleeping without them. He just didn't feel secure without their snug presence over his diaper.

Emily then took her time in selecting another nightie for Ash to wear. She held up a purple one with quite a bit of lace around the edges, and a small sunshine yellow one that had an even shorter skirt than the one Ash was wearing before. Both had been purchased and added to his closet by Aunt Sara.

"Which do you like better, princess?" Emily asked him, holding one in each hand.

"Um, purple." Ash said quickly.

Emily nodded in agreement and brought the purple nightie over to Ash. She quickly slipped it over his head and helped Ash put his arms through it. Emily then stepped back and looked at the overall effect.

"So. Adorable. I'm going to take a picture, and I want you to smile this time, okay princess?" Emily instructed him while she took out her phone.

"Say Cheese!" Emily told him, raising the phone in front of her.

Ash gave a shy smile as Emily took several pictures of him. He could only hope that Emily was taking them for her own private enjoyment, but knew he had no way to prevent her from sending the pictures to anyone she wanted.

"Okay sweetie, hop into bed." Emily instructed him, motioning toward Ash's white canopy bed.

Ash got up from the changing table and walked past Emily to his bed. He thought he heard a click sound and turned his head to see Emily taking another picture, this time focusing on his rubber panty-covered butt. The skirt on the nightie he was wearing did not cover much of anything, unfortunately. One more picture captured Ash's blushing face as he realized what was happening.

"Sorry sweetie, but this is just way too cute not to take a picture of." Emily said lightly as her fingers moved quickly across her phone.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 21, 2017, 02:11:13 AM
Ash pouted as he climbed into his bed. Emily put her phone away and walked over to tuck Ash in. She smoothed the covers and then sat down on the bed.

"Your mommy said she's not coming home until later tonight. Between you and me, I think she made a friend. A guy friend, I mean. But I shouldn't say any more. I don't think that's the kind of thing babies should hear." Emily said, the teasing note in her voice returning.

Ash didn't mind this knowledge. His mother often went out on Friday and Saturday nights and didn't come back until way past his bedtime. Aunt Sara was usually the one watching him on those nights. Ash didn't think his mother ever brought men home, but he was always fast asleep anyway. They were never there in the morning, at least.

"By the way, I don't know if you're mature enough to call her 'mom'. I think calling her 'mommy' would be better. What do you think, sweetie?" Emily asked lightly.

"O-Okay, Emily." Ash answered. He knew by now that questions like weren't really questions.

"I'm sure she'll like it more. Want a bedtime story, sweetie? It's a few minutes after your bedtime, but I think we can squeeze a quick story in." Emily said with a smile.

Ash nodded. He really did like it when his mother read him a story before bedtime, and he was worried Emily might not. He watched as Emily walked over to the bookshelf and read the titles.

"'How Do Dinosaurs Say Goodnight', 'Bear Snores At Night', ooo 'Goodnight Moon'. My sister loves this one." Emily said as she pulled the book from the shelf.

Ash blushed a little as she selected a book his mother hadn't picked for a long time, but he didn't complain.  Emily sat down on the edge of Ash's bed and started reading.

"In the great, green room, there was a telephone. And a red balloon. And a picture of a cow, jumping over the moon. And there were three little bears, sitting on chairs. And two little kittens, and a pair of mittens." Emily read in a soothing, rhythmic tone.

Ash's eyes began to droop. He was usually asleep already by now, and Emily's relaxing voice was making him very drowsy.

"And a little toy house, and a young mouse. And a comb, and a brush, and bowl full of mush. And a quiet old lady, who was whispering, hush. Goodnight room. Goodnight moon. Goodnight cow jumping over the moon. Goodnight-" Emily said, dropping her voice a little after each sentence.

Ash didn't get to hear the rest of the book, because he had gone to dreamland.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 21, 2017, 08:49:36 PM
"Good morning honey!" Helena said as she raised the blinds in Ash's room.

Ash blinked in the sudden sunlight, then sat up and rubbed his eyes. He always glad to see his mother after one of her late nights. But he forgot that he was still wearing the purple nightie Emily had put on him the night before.

"Honey, is that the nightie Aunt Sara bought you?" Helena asked with curiosity.

Ash immediately blushed and remembered exactly what had happened last night. How Emily had told him to tell his mother he wanted more dresses and girly stuff. Ash didn't have to do it or necessarily wanted to, but he really did want Emily to babysit him again.

"Yes mommy, I picked it out." Ash said with embarrassment.

Helena's eyebrows rose at hearing 'mommy', but a second later she smiled. Ash remembered how sad she was when he switched to 'mom' a couple of years ago. Maybe he should have kept calling his mother that in the first place.

"You did, huh? Well, Aunt Sara was right, you look really cute in it. Now come here honey, let's get your diaper changed." Helena said, motioning for Ash to come to the changing table.

Ash climbed out of bed and walked, or to be more accurately waddled, to the changing table. He always wet himself several times during the night and his diaper was quite heavy now. This was usually very routine for him, but Ash found himself blushing as his mother lifted the skirt on his nightie and examined him.

"Are those the rubber panties Aunt Sara bought you...and the diapers she bought too?" Helena asked Ash with surprise as she worked the tight rubber panties down his legs.

"Um, yes mommy. Emily said they were cute so I picked them." Ash mumbled shyly as he stepped out of the rubber panties.

"I see. Well, they are. I didn't know you liked them so much, honey." Helena said, sounding as if she was thinking about something.

Ash waited for his mother to un-tape his wet diaper, then he laid down on the changing table. He watched his mother throw it into his diaper pail, and shivered slightly as his clammy skin was exposed to the air. Helena  began cleaning him with baby wipes and his little pen-is became erect at once. His mother gave no sign that she cared, but things had changed for Ash since the last time. He blushed again and squirmed on the table, wishing very much that Emily was here to touch his pen-is again.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 22, 2017, 08:53:41 PM
"Stay still sweetie. I'm almost done." Helena instructed absently, looking at the stacks of diapers on the changing table.

"Okay honey, do you want one of your regular diapers, or one of the ones Aunt Sara bought?" Helena asked, holding up a Wreck-it-Ralph diaper in one hand and a Tinkerbell diaper in the other.

"Um, Tinkerbell." Ash mumbled, fidgeting on the changing table.

Helena thought for a moment, and then nodded to herself. She tossed the boy's diaper back onto the pile and brought the Tinkerbell diaper over to Ash. In less than 30 seconds, she had applied baby powder to his bottom and had him securely diapered once more. She then pulled the purple nightie Ash had worn the night before over his head, leaving him naked except for his pink diaper.

Helena went over to the closet and took out the small yellow nightie that had been hanging up there. Without bothering to ask if Ash wanted to wear it, she slipped it over his head. Ash fidgeted a bit in the tight nightie, but didn't otherwise complain. His mother stepped back and looked at Ash warmly.

"You look completely adorable in that, honey! I'll have to pick up some more dresses for you later then, if that's what you want." Helena said with a smile.

Ash nodded quickly. If Emily was ever going to touch his pen-is again, it would probably only happen if he was wearing something girly like this.

"Alright honey, how about some breakfast?" Helena asked him brightly.

Ash got up from the changing table and tried to walk out of the room, but his mother quickly grabbed his hand in order to lead him out herself. Ash was surprised for a moment, but then let his mother lead him downstairs just like Emily would.

When they got to the kitchen, Ash stopped worriedly. Emily hadn't put away his highchair. It was still sitting at the kitchen table.

"Honey, I couldn't help but notice that your highchair is out. Did you use it last night?" Helena asked him pointedly.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 22, 2017, 11:05:19 PM
Ash blushed and nodded. He tried to think of some explanation, but his mother didn't seem to want one. She simply scooped him up in her arms and deposited Ash in the highchair. Helena then locked the tray securely.

"I'm surprised you still fit in it. But I'm glad you do, honey. Now I don't need to worry about you wandering off while I'm making your food." Helena said with a satisfied air.

Ash squirmed a little in the chair but wasn't sure how he felt. Without Emily there to capture his attention completely, Ash could actually think about other things. On one hand, it was a little distressing to be stuck in the highchair. It wasn't uncomfortably tight, but he could neither pull himself out or work the tough latch on the tray. But he also felt kind of safe and snug.

Ash's thoughts were interrupted by a gentle ringing sound. He recognized it as the ringtone for his mother's phone. Helena paused her efforts at the counter, took her phone out of her back pocket and looked at it. She then pushed a button to enable speaker phone and sat it down on the counter.

"Hi Sara, how are you this morning?" Helena asked while going back to making what looked like oatmeal for Ash.

"I'm good, Helena. How is little Ashley?" came the chipper voice of Aunt Sara.

"He's right here. He's wearing that cute little yellow nightie you bought him, if you can believe it." Helena answered, looking at her son with a smile.

"Oh my god, is he? I have to see it!" Aunt Sara exclaimed excitedly.

"Okay, give me a second." Helena said, picking up the phone and pointing it at Ash.

"Give Aunt Sara a smile, honey!" Helena instructed, speaking directly to Ash for the first time.

Ash smiled shyly and his mother took a picture. It was only after the picture was taken that he realized he was sitting in the highchair with his legs open with his pink diaper clearly in view. Ash shut his legs immediately afterward, but the photo was already taken. A few seconds later, Aunt Sara received it on her phone.

"Ashley looks so incredibly cute! I wish I was there!" Aunt Sara said with glee.

"Well, maybe you can be. You can take him shopping later. Ashley seems to like some of the girly stuff you've brought over, but there's not much of it." Helena said, putting the finishing touches on Ash's oatmeal.

"How about this afternoon? I know the cutest little store to bring him to!" Aunt Sara said with definitely interest.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 22, 2017, 11:48:46 PM
"Sounds good! Let me give Ashley his oatmeal." Helena said as she picked up the bowl as well as Ash's favorite plastic spoon.

Helena placed the oatmeal on Ash's highchair. Ash made a face at it. Oatmeal was not his favorite and he could usually get his mother to make him something else if he turned his nose up her first effort. But apparently not today.

"You're not going anywhere until that bowl is empty, sweetie. I'll be back in a little bit, and if you haven't eaten it, then I'll help you finish, okay?" Helena said evenly.

Helena then opened one of the cabinets at the counter and pulled out of one Ash's old bibs. He made another face at that, which his mother ignored.

"I don't need a bib!" Ash mumbled resentfully.

"I'll tell you what, honey. If you finish your oatmeal and your bib is spotless, you won't have to use it next time, okay?" Helena offered.

Ash nodded because he knew it was best to just accept any deal offered by his mother. He could never get her to give ground, and if he refused, she would just do it anyway. At least this way Ash could try to avoid having to use it again.

Helena tied the bib to Ash's neck and kissed him the top of his head before walking out of the kitchen. As she left, Ash caught the first part of what she was saying to Aunt Sara.

"I met the hottest guy last night.  Yeah, the one I wanted to dance with last time. You know that bra and panty set I got at Bloomingdales? Well,-" Helena said excitedly as her voice faded.

His mother talking about lingerie made him think of seeing Emily's boobs covered by her sexy bra. The memory of it made his little pen-is react, but he couldn't touch it himself. Now that he thought about it, Ash wasn't sure when he would get the opportunity to do it. Beforehand, he could pull down his pullups and touch it in secret if he wanted to. But now he was securely diapered almost all of the time. And when he wasn't, it was because his mother was changing him or bathing him. Maybe he could try after bedtime, but he usually fell asleep very quickly and didn't wake up until morning.

Ash shook his head to clear it. He just had to get Emily to babysit him again soon, that's all. In the meantime though, Ash needed to eat the bland oatmeal that was currently sitting right in front of him.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 23, 2017, 01:16:14 AM
New chapter! This proves that you should never throw out a playpen even when the child supposedly gets too old!

Ash shook his head to clear it. He just had to get Emily to babysit him again soon, that's all. In the meantime though, Ash needed to eat the bland oatmeal that was currently sitting right in front of him.

Ash started to spoon it up while he wondered where his mother had gone. He could hear sounds of her moving something, but his highchair faced away from the living room and he couldn't twist himself enough to see anything. The only thing he could do was eat his oatmeal quickly. A little too quickly, as it turned out.

After about 5 minutes, Ash was done. His mother hadn't come back though, and he was getting a little worried. Ash decided to call out and get her to come back.

"Mommy? Mommy, I'm done!" Ash called.

"Okay sweetie, I'll be there in a second."came his mother's voice from the living room.

Ash fidgeted in his highchair for a few more seconds before his mother returned. He was eager to get out of the chair by now. So eager that he had forgotten about making sure not to get any on his bib.

"Good job on the oatmeal, honey! But I see that you got a little on your bib. Oh well, that's what bibs are for!" Helena said with a smile as she took it off.

Helena unlocked the tray and scooped up Ash again. He expected to be let down, but instead his mother carried him into the living room. And waiting for him in there, right in the middle of the room, was his old playpen.

"Mommy! I don't need a playpen!" Ash whined and squirmed in his mother’s grasp.

“Shhh. Mommy needs to do some housework and I’ll feel better if I know where you are. But don’t worry, it’ll be fun. Look, I brought some of your old toys from the closet!” Helena said brightly.

His mother had indeed brought some of his old toys out. They included his blocks, his toy xylophone, some stuffed animals and the dolls Aunt Sara had bought him when he was 10th birthday. Even now, Ash was embarrassed to remember unwrapping the Bratz dolls she bought him, only for them to be confiscated by his mother as she thought they were too mature for him. So instead, Aunt Sara bought him three American Girls dolls; Willa, Emerson, and Ashlyn.

Helena deposited Ash inside the playpen and looked down on him warmly.

“Have fun, honey! You can play until lunchtime. If you get tired and want to nap, or you need to be changed, call for me. I’ll just be in mommy’s room with the door open.” Helena instructed him with a smile.

“Wait mommy, Can I have some juice?” Ash asked hopefully.

“Oh that’s right! I totally forgot. I’m sorry sweetie. I’ll be back with some apple juice.” Helena said, surprised at herself.

Ash was barely able to see his mother return to the kitchen. His playpen was unusually tall. Even standing up, the top of it was even with his neck. The sides of it were smooth and he wasn’t very good at climbing. Ash doubted he could climb out even if he really wanted to.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 23, 2017, 03:21:21 AM
New chapter once more!

Helena came back with Ash’s apple juice, but in a container he wasn’t expecting. It was a sippy cup, but one even more childish than the one Emily had given last night. It was shaped like a sippy cup, but had a soft nipple that required him to suc-k on it to get any juice out.

“Here you go, honey. I saw the sippy cup in the sink and I was going to use that, but you might knock it over in there. With this, you can’t spill it at all!” Helena told him brightly as she handed the babyish sippy cup to Ash.

Ash blushed at the cup, but decided that he was thirsty enough to use it anyway. He immediately began to suc-k on the rubber nipple and was rewarded with the taste of apple juice. Helena watched Ash fondly for a few seconds, then left the room.

He suc-ked and drank until he was no longer thirsty, then Ash dropped the sippy cup on the floor to see if nothing really would come out. Just like his mother said, the juice could only come out of the rubber nipple at the top.

Ash played around with some of the toys a little bit. It was surprisingly fun to make different sounds on the xylophone with the soft baton. But he quickly went over to the dolls. He knew the stories for all of them from the little booklets that came with the dolls.

Ashlyn was the princess of the bunch. She had long dark brown hair and skin that was the same shade of hot cocoa his mother would sometimes give him as a special treat. She wore a pink tiara and a pink tutu and was secretly his favorite.

Willa loved animals and her clothes reflected that. She wore ladybug-colored boots and a pink-and-red top that had cat whiskers on it. Willa’s hair was in pigtails and was the exact same color of blonde as Ash’s hair. Aunt Sara had naturally assumed that Willa would be his favorite, but Ash was scared of most animals.

Emerson was a dancer and had maybe the prettiest clothes of them all. Her skirt and top were a combination of purples and pinks and red. She had long dark hair with pale skin and reminded Ash of Emily. By the time Aunt Sara gave him the dolls however, Emily was way too mature to want to play with them.

Ash quickly started to have fun pretending all 3 of them were friends and were having a sleepover. They would tell each other stories and brush each other’s hair and watch TV shows that Ash’s mother wouldn’t allow. He was having so much fun that he didn’t notice that more than an hour had passed. The only reason he noticed anything at all was that his mother had returned to check on him.

“Having fun, honey? I just need to see if you have to be changed. Lift your skirt up for mommy.” Helena instructed him.

Ash blushed and lifted his skirt. It occurred to him that he should look to see if he had wet himself without knowing, and was surprised to see the flowers on the front of his diapers had bloomed.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 23, 2017, 03:15:49 PM
“Come here, honey. I’ll change you real quick.” Helena told him, holding her arms out at the edge of the playpen.

Ash waddled forward (he might have wet himself more than he thought) until he reached his mother. Helena scooped him up and carried him upstairs to his room.

When Helena reached the changing table in Ash’s room, she laid him gently down on it, then took a breath.

“Are you wetting yourself more, honey? It’s not a bad thing, but we might need to think about putting another changing table in the living room.” Helena said idly.

Ash squirmed as his mother removed his wet diaper and began to clean him with baby wipes. Once again his little pen-is hardened, and he decided to ask his mother again about it.

“Um, mommy?” Ask asked hesitantly.

“Yes, honey?” Helena prompted.

“Should my pee-pee be...bigger?” Ash asked while blushing deeply. Emily had told him he needed to refer to it by that name, after all.

Helena blinked and looked at Ash’s pen-is. She looked at it as if it was the first time she really saw it, and was unable to immediately suppress an amused smile. Then she remembered that Ash was her son and she should not make fun of him like that.

“Well, maybe. But it’s nothing for you to worry about right now.” Helena said lightly.

“But-” Ash started.

“Shhh. I think you need a nap before Aunt Sara gets here. I don’t want you getting tired and cranky when you go shopping with her.” Helena said with finality as she finished diapering Ash.

“I’m not tired!” Ash whined.

“I know you think that honey, but you need a nap. Just trust mommy, okay?” Helena said, scooping Ash up once more.

Helena moved the covers on Ash’s bed to the side and dropped him down onto it. She pulled the covers over him and kissed him on the forehead, ignoring the resentful look on his face.

“I’ll come back in a little while. Try to sleep, okay?” Helena said as she shut the door.

Ash kicked the blankets around for a moment and thought about getting up from the bed. He didn’t have stay in bed, but most things he could do in his room would make noise. And any noise would probably result in his mother coming to check on him. Ash was about to get up anyway when he yawned. His bed was actually feeling more comfortable by the second. Ash decided to close his eyes for bit and quickly fell asleep.

“Hello, Ashley!” came a chipper voice that woke Ash up.

Ash blinked and looked up to his Aunt Sara was standing beside his bed. She was a few inches shorter than his mother, who was fairly tall for a woman. In exchange, she was a little curvier. But she had the same blonde hair, the same color of eyes, and the same smile.

"Want to go shopping with me, cutie?" Aunt Sara asked him.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 23, 2017, 09:42:34 PM
In no time at all, Ash found himself being carried to Aunt Sara’s car. He had begged her to let him change into shorts and a t-shirt, but Sara flatly denied that. After all, what would be the point of changing into boys clothes when they were going to be shopping for dresses? The only somewhat boyish thing Ash got to wear was his white sneakers, but Sara assured him that they would fix that too.

Ash expected to have to sit in the back seat, but when Sara opened the car door, he saw a car seat placed there.

“Auntie Sara, I don’t need a car seat!” Ash whined loudly.

“Sorry honey, but I checked the state guidelines and you’re still a few inches too short to not have to use a car seat.” Sara said, strapping Ash in.

Ash felt constricted by the car seat, but it wasn’t very uncomfortable. The problem was that elevated him so much so that people in other cars could see him through the window. Well, Ash would just have to ignore them, that’s all.

“I had to borrow a friend’s car seat before I got here. Her little girl just outgrew hers on her 7th birthday. Lucky us, huh?” Aunt Sara said with a smile as she buckled herself in.

Ash fidgeted in the car seat as Aunt Sara drove down the suburban roads around their house. Sara noticed his silence and tried to engage Ash in conversation.

“I’m sorry I couldn’t be there last night, sweetie. But I hear your mommy got your friend Emily to watch you for the night. Did you have fun with her?” Sara asked, looking at him in the rear-view mirror.

“Yes, Auntie Sara. It was really fun!” Ash said earnestly.

“Oh, cool. But she wasn’t more fun than me, right?” Sara asked him with a pretend pout.

“Um, no Auntie Sara.” Ash said after a moment. In truth, Emily was a lot more fun than his Aunt, but he didn’t think she wanted to hear that.

“Hmm. I’ll just have to work harder to make it fun for you then, sweetie. What do you think about getting some ice cream after we finish shopping?” Sara said offeringly.

“Okay!” Ash said with excitement. It wasn’t exactly what Ash would have asked for, but ice cream was something he rarely got, as his mother tried to limit his sugar intake as much as possible.

“Good! Now how about we put in your CD?” Sara said as she popped it in.

The CD was full of Disney songs, and “Let It Go” led off. Sara began singing the lyrics and eyeing Ash in the backseat. Eventually he relented and started to sing them with her. It was surprisingly fun to do, and before Ash knew it, they had pulled up to a medium-sized store that had the name ‘Winkles’ in glittery writing. There were baby toys in the windows and tiny mannequins showcasing toddlerwear. As he watched, a woman walked in the door with a baby on her hip and a somewhat older daughter trailing her.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 24, 2017, 12:39:07 AM
New chapter! Winkles really does sound like a fun place to shop.

Sara got out of the car and went to open the backseat. After a second, she unstrapped Ash from his car seat and paused.

“Sweetie, do you want to walk in with me, do you want me to carry you?” Sara said, looking very much like she would prefer to carry him.

“I want to walk! Please, Auntie Sara!” Ash begged. He would look way more conspicuous being carried by his aunt.

“Okay, but let me know if you get tired.” Sara said with a tiny frown.

Sara grasped Ash’s hand and firmly led him into the store. As they entered, a young woman in a blue polo shirt and tight tan pants greeted them.

“Welcome to Winkles! All baby shoes are 50% off today!” The young woman said in a pleasantly excited tone. Her sales pitch was directed at Sara, so she didn’t immediately notice Ash.

“Hello...Lexi! I’m here with my nephew and we’re going to buy plenty of pretty dresses! Say hello, Ashley.” Sara said to Ash, reading the young woman’s name tag.

“Hi.” Ash said shyly as Lexi took in his appearance.

Lexi’s eyebrows rose at seeing Ash’s short blonde hair, yellow nightie and pink diaper. A second later however, she smiled at Ash and bent down to talk to him at his level.

“You want some pretty dresses, huh? You came to the right place!” Lexi said, grinning at Ash.

“The girl’s section is to the right.” Lexi said to Sara as she straightened up.

Ash led himself be led into the girl’s section, glad that it wasn’t as big of a humiliation as he thought it would be. Sara immediately ooo’d and aaah’d over the selection. She grabbed toddler dresses off the rack and placed them up against Ash. She seemed to reject none of them, and placed them, one atop the other, on her arm as she strode through the aisle.

Ash wasn’t paying very much attention to Sara however, as there was another family at the other end of the aisle. A mother was browsing idly and hadn’t noticed him, but her daughter, a cute girl with dark pigtails who looked to be about 6, was looking at Ash curiously. She was wearing a tiny t-shirt and a tutu and didn’t appear to need a diaper or pullups or anything. She drifted away from her mother and came closer to Ash, who was blushing and hoping that Sara would realize she had enough dresses for now. But both adult women were focused on shopping.

“Hi!” the little girl said excitedly to Ash.

“Hi.” came Ash’s shy response.

“I like your dress. Um, are you a girl or a boy?” the little girl asked with a whisper.

“Um.” was all Ash could answer with.

By now Sara had noticed the conversation taking place below her. She bent down and decided to help her nephew out a little.

“Ashley’s a boy, but he’s as cute as any girl. Don’t you think so?” Sara asked the little girl, who nodded immediately.

“Yeah!” she said excitedly.

“Megan!” the girl’s mother called from the other end of the aisle.

Megan turned around to head back to her mother, but not before looking back at Ash and giving him a friendly wave, which he returned at Sara’s urging.

“You made a friend! Aren’t you glad you came shopping with me, sweetie?” Sara asked him with a smile.

Ash nodded uncertainly. Megan seemed very nice and he thought he could be friends with her, but seemingly friendly girls had teased him before.

“I think I have enough cute little dresses here. Let’s go to the changing room!” Sara said, grabbing Ash’s hand to lead him there.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 24, 2017, 09:17:01 PM
New chapter! It's a bit long, but I think splitting it into two would make them a bit short. Oh well!

Sara led Ash into a changing room. Ash didn’t bother complaining, as he knew it was too much to hope for that Aunt Sara would let him dress himself. She pulled the yellow nightie he was wearing over his head, leaving him in his pink diaper.

Sara scanned the dresses she brought before selecting a lavender toddler dress that reminded her of Rapunzel’s dress in Tangled. She knew it was Ash’s favorite Disney movie and wanted to get him in a good mood. She slipped it over his head and helped put his arms through the sleeves.

“Look in the mirror sweetie! Just think, if we grew your hair out, you’d look just like Rapunzel!” Sara said with enthusiasm.

This remark brought a tiny smile to Ash as he pictured himself with Rapunzel’s long, long hair. He liked the color a lot and favored his Aunt with a pleased nod.

“Good, we’ll get it! Now let’s try this pretty green one, you like green, right?” Sara said as she held up a forest green toddler dress with lots of ribbons on it.

So it went with Sara alternately dressing and undressing Ash. She seemed to love everything she put on him. At first Ash would nod when he liked the dress too, then as he became more tired he would nod his approval every time in the hopes that they would get done faster. There were still half a dozen dresses to go through when Ash came up with a different plan.

“Auntie Sara, I’m tired.” Ash whined.

Sara blinked and checked her watch. They’d been in the dressing room for more than half an hour!

“I’m sorry sweetie. I know, let’s go buy some shoes. You can sit down while I put them on you.” Sara said kindly as she pulled a snow white dress with many ruffles off of Ash.

Sara put the yellow nightie back over Ash’s head and scooped him up. Ash sighed as she walked out of the changing room with him. Maybe he should have thought about this plan a little more. Sara walked past a woman with two young children, a boy and a girl, walking behind her. Both of them giggled at Ash but stopped quickly when their mother shushed them.

They reached the shoe section fairly quickly and Sara sat Ash down on a small bench there. She looked around for a clerk to help, but there was no one around. Sara simply grabbed a shoe-sizing instrument and found out Ash’s shoe size. He was embarrassed to find out that his shoe size was the same as an average 8 year old girl’s.

Sara went over to the 8 year old section and began pulling down boxes. She grabbed 4 of them before coming back, only to drop them on the ground before going back for more. Ash sighed again and swung his feet back and forth, as they didn’t quite reach the ground from where he was sitting.

Sara returned with 4 more boxes, as well as some pink ruffled ankle socks for him to wear. She took off his shoes and socks, and then put the much more girly ankle socks on him. It looked like he had tiny pink tutus on his feet.

The shoes Sara selected him for were a pair of shiny black Mary Janes, 3 pairs of tiny sneakers in pink, lavender, and white, turquoise sandals, and 2 pairs of pink and black ballet shoes. Sara was extremely entertained by putting the shoes on Ash’s feet, but Ash himself was quite bored. He liked some of the shoes, just like he liked some of the dresses, but Sara’s enthusiasm for it exceeded his by quite a bit. Once they were finally done, Sara seemed to read Ash’s mood.

“Want to go play a bit, sweetie? I have some more stuff to get for you and your mommy, but you can hang out in the play area now.” Sara said as she stacked up the boxes of shoes she planned to buy.

Ash nodded eagerly. He didn’t know what the play area was like, but it had to be more fun than shopping. Sara scooped him up once more and carried Ash out of the shoe section.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 25, 2017, 12:10:24 AM
New chapter! Megan is definitely the kind, mature friend every sissy needs.

The play area turned out to be surprisingly large. Plastic fencing was all around it.There was a huge dollhouse in the corner that was surrounded by a cluster of little girls. In the middle was a set of train tracks where a tiny plastic train went round and around. Two young boys were engrossed with it and gave Ash no mind. And in the corner, there look like a small ball pit filled with multicolored plastic balls. Sara dropped him just inside the gate.

“Have fun, sweetie! I’m going to pick up a few things your mommy might want to have. Be back in a bit!” Sara said loudly as she left.

Ash’s entrance into the play area did not go unnoticed. Thankfully, boys were still enthralled by the train, but the girls at the dollhouse were now watching him. Some of whom were whispering and giggling. Ash wanted to check out the dollhouse, but was far too intimidated to approach them. So he fidgeted and stayed where he was while the giggling increased.

Suddenly another girl appeared from the other side of the dollhouse. It was the nice girl Ash met before! Megan’s eyes lit up at seeing Ash and she wasted no time in coming up to him.

“Hi!” Megan said to Ash.

“Hi.” Ash said back shyly, feeling a sense of deja vu.

“Wanna play with the dollhouse?” Megan asked him brightly.

“Um.” Ash answered once again. He wasn’t at all sure the other girls would let him play there.

Megan looked at Ash for a few seconds, then looked back at the dollhouse. She saw the girls there watching them and suddenly seemed to understand the situation.

“It’s okay Ashley.” Megan said as she grabbed Ash hand and pulled him along with her.

Ash let himself be dragged to the dollhouse and watched as Megan looked at the other girls almost aggressively until they turned back to play with their dolls. They reached the dollhouse and sat down at an empty corner of it. Once Megan was satisfied that no one was staring at Ash anymore, she smiled again and started to talk to him about the doll she was playing with.

It turned out to be a Bratz doll. Megan went on and on about her doll, which was named Jade. Jade had the same dark hair and pale skin that Megan had, and was dressed stylish to the point of being sexy. Ash felt a little bit of jealousy as Megan described how her mom bought her all of Jade’s accessories, but they were all at home. Ash’s own mother had banned the dolls from their house.

Megan seemed to notice Ash’s interest and stopped talking abruptly. She frowned for a second and fidgeted, then offered Jade to Ash.

“You can play with her, if you want.” Megan said almost mournfully as she held the doll out.

Ash quickly declined and found another Bratz doll sitting on the bed in the dollhouse room they were playing next to. No one else seemed to be playing with it, so he picked it up. Megan’s expression cleared as she hugged Jade to her chest in relief. A second later, Megan started to tell Ash all about the Bratz doll he was holding, whose name was Cloe.

Ash listened to Megan talk about Cloe, feeling relaxed for maybe the first time since he’d come into the store. Maybe too relaxed as it turned out, because he started to wet himself and couldn’t stop. Ash’s panicky look did not go unnoticed by Megan, who looked down at his diaper and giggled as she saw the flowers start to bloom. Ash was mortified and felt close to tears as he continued to wet himself in front of Megan.

Megan had noticed Ash’s distress by now however, and stopped giggling. She patted him on the arm softly and tried to calm him down.

“It’s okay Ashley. Don’t cry.” Megan said soothingly to him.

Megan got up and ran to the edge of the play area. She waved to the clerk (a teenage girl) who was idly watching them, while really reading a magazine. Megan eventually managed to get her attention however, and the clerk came over to the fence. Ash was worried Megan would loudly tell her that Ash needed to be changed, but it seemed like Megan was smarter than he gave her credit for. Megan motioned for the clerk to bend down, then whispered in her ear. A second later, the clerk looked at Ash and gave him a smile.

“Come here, sweetie.” The teenage clerk said, waving Ash over to her.

Ash got up, praying that none of the other girls could tell that his diaper was saggier than before. This time, his wish seemed to be granted as none of them paid him any attention. When he got to her, she bent down to scoop him out of the play area.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 25, 2017, 08:46:53 PM
“Is your mommy around? I can change you, but she should probably do it if she’s here.” the teenage clerk said, looking around.

“Auntie Sara is. She has hair like me.” Ash said shyly, aware that he was much more visible up in her arms.

“I see her. But she looks a little busy. Lexi’s helping her carry all the stuff she bought to the car.” the teenage clerk said as she hitched up Ash.

“I’ll just take care of it for her. Let’s go, sweetie.” the teenage clerk said as she turned toward the bathrooms.

“My name’s Jenna, what’s yours?” Jenna asked him as she walked.

“Ash.” Ash responded shyly.

The teenage clerk went right to the family changing room next to the larger bathrooms, but found it was occupied. She frowned and looked at the looked at the girl’s bathroom, and Ash suddenly knew where she would take him.

“Sweetie, I need you to keep your eyes closed, okay? No peeking.” Jenna said evenly.

Ash nodded and closed his eyes tightly. In truth, he was a little curious, but knew to do whatever an adult told him. Even if the ‘adult’ in this case was probably only a couple of years older than him.

Jenna carried Ash inside the girl’s bathroom. He hoped that it was empty, but immediately heard voices as they entered. Ash’s eyes were still closed tightly, but they seemed to belong to a woman and a young girl. The mystery of what they were doing was solved quickly as Jenna put Ash on a changing table. The girl was getting her diaper changed on the table next to Ash.

Jenna untaped Ash’s diaper and removed it smoothly. However, Jenna seemed to pause for a few seconds afterward. Ash blushed, knowing exactly what she was looking at. The situation might have passed if the little girl being changed next to him didn’t pipe up excitedly.

“Look mommy, his pee-pee is like baby Joshie’s!” she said with glee.

Ash could hear both Jenna and the other woman share a laugh together. Ash fidgeted and wished that his little pen-is wasn’t sticking up so much. Maybe they wouldn’t be so amused if it was soft. After a few seconds, he felt baby wipes on his pen-is and he squirmed desperately, wanting Jenna to touch it.

Ash could hear the other woman leaving and hoped that meant he could open his eyes. Ash knew he had to keep his eyes closed until Jenna said otherwise, or he would risk getting scolded. But Jenna said nothing, so Ash’s eyes stayed closed.

It was only when Jenna finished wiping and he could hear the crinkling of a diaper being pulled out that Ash decided to beg Jenna to touch him before he lost the chance completely.

“Jenna, could you touch my pee-pee? Please?” Ash whined desperately.

Ash’s eyes were still closed, so he didn’t know what expression Jenna had on her face. But she paused in her efforts to diaper Ash.

“I don’t think so, sweetie.” Jenna said with a laugh.

“Please! Mommy and Auntie Sara won’t do it!” Ash whined again.

“I should think not! But I don’t want to make a mess.” Jenna said doubtfully as she slid the diaper underneath Ash’s bottom.

“You won’t! My pee-pee won’t shoot anything! I promise!”Ash whined once more, feeling his chance slipping away.

“It doesn’t? Well...” Jenna trailed off as she brushed her finger across Ash’s little pen-is.

Ash felt hope in his chest and squirmed his hips around, trying to brush against Jenna’s finger. Jenna let him squirm on the table desperately for a little while, occasionally brushing her finger against Ash’s little pee-pee, then watching as he tried to move in that direction as if they were playing Marco Polo. All the while, she applied little sprinkles of baby powder on him. But eventually she got tired of the game.

“Sorry sweetie, that just proves that your pee-pee isn’t ready for that stuff. Now if you stay still from here on, I won’t have to tell Auntie Sara about this, okay?” Jenna said as she began taping up Ash’s diaper.

Ash whined loudly in frustration, then nodded his head. He didn’t want Aunt Sara knowing about this. She would undoubtedly pass it on to his mother, and Ash certainly didn’t want the scolding that would come from that.

Jenna picked Ash up from the table and carried him out of the girl’s bathroom. She noted with amusement that his eyes were still closed even after they left.

“You can open your eyes now, sweetie.” Jenna said with smile as she took Ash to the checkout counter.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on June 29, 2017, 10:51:42 PM
Jenna carried Ash to the front of the store, where Aunt Sara was conversing with another woman who looked vaguely familiar to him. After a second, he realized it was Megan’s mother. That had to mean Megan was close by. Ash looked down and saw Megan was holding onto her mother’s hand and looking around in boredom as the adults talked.

Megan's eyes lit up as she saw Ash in Jenna's arms. She tugged at her mother's hand and pointed at him with excitement.

"Look mommy! There's Ashley!" Megan said happily.

"Ashley had a little accident earlier. But he has a fresh diaper now." Jenna said airily as she passed him to Sara.

"Oh? I hope you thanked the nice lady." Sara said to Ash.

"...Thank you Jenna." Ash mumbled, feeling some resentment toward Jenna but not daring to express it.

"Don't mention it sweetie. I hope I see you again!" Jenna said with a smile as she walked back toward the play area.

"Megan said she wants to have a play date with you, honey! Isn't that right?" Sara said, looking at Megan.

"Yeah!" Megan agreed with enthusiasm, nodding her head more than was strictly necessary.

"We'll set it up later, then. Here's my sister's number." Sara said as she recited Helena's phone number to the woman.

"Alright! Say goodbye to Megan for now!" Sara said to Ash.

Both women smiled as Ash and Megan waved goodbye to each other. Sara then walked out of Winkles with Ash on her hip. As she opened the door to place Ash back into his car seat, Ash saw just how full the car was. The other half the back seat was filled with packages of diapers and  bags full of baby paraphernalia.

Sara strapped Ash in and then reached across from him into a bag. She fished a small item out of the bag, and it turned out to be a fuchsia-colored pacifier.

"I noticed you didn't have any pacifiers, honey. So I bought you a few to try, if you want to." Sara said pleasantly, holding the pacifier up to Ash's lips.

In truth, Ash didn't really want try it. But he knew Aunt Sara would pout if he refused, so he opened his mouth with an inaudible sigh. Sara smiled and popped the pacifier into Ash's mouth immediately.

"So cute! Alright honey, let's head home!" Sara said, shutting the door.

Sara started up the car and drove out of the lot, chattering away about the many dresses and shoes she'd bought. Truth be told, Sara had run up quite a charge onto her credit card, but she could never stop herself from buying things for her nephew.

Ash himself was barely listening. The more he suc-ked on the pacifier, the more relaxed and content he became. If it wasn't for the nap Ash had taken earlier, he would have been out like a light. Sara's voice faded into a pleasant buzzing as Ash dozed in his car seat.

It wasn't until they had returned home that Ash realized he never got the ice cream he was promised.



Okay! They'll be a short break both in real life and story life, and I shall pick it up in a week or two with either Megan's playdate or Ashley going to Emily's house to meet her little sisters. (I can imagine which one would be more popular.)
Title: Re: Ashley's Babysitter
Post by: Jemina004 on November 17, 2017, 01:17:19 PM
Ash was very happy to be standing outside Emily's house, despite the deep embarrassment he felt. When Ash pictured this, the 14 year old boy didn't imagine that he would be standing there in a snowy white toddler dress and matching white Mary Janes. Although his mother loved all the dresses that Aunt Sara had bought for him, this one was her favorite, and she adored the lace and ruffles that covered it. It was the outfit Helena would usually dress Ash in when they left the house. So when Emily called to invite Ash to her 3 year old sister's birthday party, he was not surprised to see his mother pull it out of the closet. Ash secretly liked the dress as well, though he had to deal with his mother constantly adjusting the large bow on the back of the toddler dress.

However, the dress was only one reason for Ash's embarrassment. It just barely covered the pink Princess Pampers he was wearing underneath. Emily was aware that he wore diapers, but Ash knew that it wouldn't be long before everyone inside found out he wore them too. Practically any movement on Ash's part meant that his diapers would peek out, and it was impossible not to show them whenever he bent over or sat down.

The third reason for Ash's embarrassment was his mother's grip on his wrist. Ash had a limited amount of freedom inside the house, but whenever they left the house, Helena made certain that Ash was safely under her watch at all times. When he wasn't in his carseat or stroller, his mother would carry him or at least hold his hand. At first Ash was annoyed at this, but he quickly began to feel safe and secure because of it. Though Ash wouldn't admit it, if he had been standing there without his mother's hand on his, he would have gotten scared.

The final reason for Ash's embarrassment was, ironically enough, making him also feel quite content at the moment. He was suc-king on the pink, jewel-toned pacifier Helena had popped into his mouth when they left the house. The pacifier had a soporific effect on Ash, and Helena made certain to use it whenever she felt that her son needed to relax. Before naps or bedtime, when Ash was already sleepy, giving him his pacifier would put Ash out like a light.

It was also useful for making stressful situations more manageable for him. Ash had to admit that he was quite nervous at the thought of seeing Emily again, and maybe his mother had noticed. He just wished she would take it out before someone opened the door. Technically Ash could have removed the pacifier himself, but the idea didn't really occur to him. Helena decided when to pop it in and when to pop it out. Ash's decision-making, already poorly developed, tended to be nonexistent when he was suc-king on his pacifier.

So it was that Ash was standing outside his crush's house in a white toddler dress, pampers, and suc-king on his pacifier as his mother rang the doorbell.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on November 17, 2017, 03:22:50 PM
Next part!

The door opened, and as Ash had both feared and hoped, Emily was there. The 14 year old looked quite stylish in an emerald green dress that was cinched around her waist with a glossy black belt. The black heeled boots she wore meant that Emily towered over Ash by more than a foot, despite being the same age. The outfit matched her long, dark hair and green eyes perfectly. Ash could only stare, and doubted he could have said anything even if his mouth wasn't occupied.

"Oh. My. God! You look so absolutely precious!" Emily exclaimed, taking in Ash's extremely girly and babyish outfit.

Ash reddened but could do little else. The pacifier meant that he couldn't talk, and Helena showed no sign of wanting to take it out. Ash had begun resigning himself not being able to speak when Emily boldly bent down and popped the pacifier out of his mouth.

"H-Hi Emily. I-I think you look really pretty." Ash stammered out, a little unused to talking.

"Thanks, sweetie! But not as pretty as you do." Emily said with a smile.

Ash opened his mouth to speak, but couldn't figure out anything to say. The silence stretched for a few seconds, and by the time Ash thought of something, Emily had judged his open mouth to be a request to put the pacifier back in, so she popped it in his mouth. Ash made a fussy noise in response, but Emily's attention had shifted away from him.

"Hello, Mrs. Lowenthal." Emily said, extending her hand to his mother.

"Oh please, call me Helena." His mother said, shaking her hand lightly.

Emily bade his mother to enter, and Helena stepped inside, pulling Ash with her. Ash resented the fact that Emily's attention wasn't on him, but he was used to his kind of thing by now. Whenever they met people, they would always ooh and aah over Ash's cuteness. But after they were introduced it was time for conversation, and nobody expected Ash, in his toddler dress and suc-king on a pacifier, to contribute.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on November 17, 2017, 10:30:27 PM
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.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on November 17, 2017, 11:49:24 PM
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.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on November 18, 2017, 01:22:14 AM
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.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on November 18, 2017, 02:06:08 AM
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.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on November 18, 2017, 09:34:30 AM
"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.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on November 18, 2017, 09:10:23 PM
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.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on November 19, 2017, 01:51:53 AM
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.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on January 12, 2018, 11:47:08 PM
"Good morning, honey!" came the chipper voice of Ashley's mother.

Ashley blinked and tried to burrow beneath her soft pink blanket, but her mother wasn't having it. Helena brought down the side of Ashley's white crib and gently pulled the blanket off from over her. From the moment her mother had seen Ashley curled up in Lizzie's pink crib, she had immediately decided to get Ashley's own crib out of the basement. Ashley had been put to sleep in her old crib that very night, and had slept in it every night for the past six months, as well as her three hour-long naps per day.

At first, Ashley had complained, or tried to. While she didn't mind the crib, as it made her feel very secure, she loved her white canopy bed. But her mother paid her wordless protests no mind. Which was easy to do, considering that Helena kept Ashley's pink pacifier in her mouth almost all the time now. Only during feedings was the pacifier popped out of Ashley's mouth and Helena popped it right back in afterward. Even then, it was only during dinner between spoonfuls of baby food made from peas, carrots, sweet potatoes, or her favorite, bananas, that she was able to talk. Otherwise, the bottles of warm milk mixed with formula were just as effective as her pacifier at keeping Ashley's mouth occupied.

"Aren't you excited, honey? You have guests today!" Helena said, smiling down at Ashley.

Ashley realized that her mother was right. She didn't have a calendar in her room, but if Ashley had guests, it must be her birthday. Her 15th birthday, to be exact. Though judging from the fact that the toddler dresses Aunt Sara had bought for her still fit her well, she hadn't grown a centimeter since. That included her pee-pee, of course. Though Ashley checked herself often, she was still entirely hairless below her eyebrows.

Above her eyebrows was a different story, however. In the past six months, Ashley's honey-blonde hair had grown out considerably, and was now down to her shoulders, to the delight of Aunt Sara. Her aunt loved to give Ashley a bath in order to towel it off, brush it, and put it into a cute style. Sara never bothered consulting Ashley about what style she may have wanted, though. Ashley simply found her blonde hair in pigtails or a french braid.

It cemented the view of her as a girl to strangers. Before, when Ashley tried to dress like a boy, strangers just assumed she was a tomboy. Something about Ashley's big eyes, slight build, smooth skin, and nervous sweetness made people think she was a girl no matter what. And now, thanks to her toddler dresses and long hair, there was no mistaking it.

Her mother and Aunt Sara had been relentless in using female pronouns for Ashley. About a month into solely being referred to as "she" or "her", Ashley started to accept it. By now, her memories of hopelessly trying to dress and act like a boy seemed weird to her. Her mother said she was a girl, and as far as Ashley was concerned, her mother was always right. So that was that.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on January 13, 2018, 12:59:33 AM
Helena lifted up the front of Ashley's lilac-colored nightie to check her pink Pampers. She had wet herself during the night, several times in fact. But the snug plastic panties Ashley wore every night had done their job: Not a drop had leaked, leaving Ashley's nightie and her crib dry.

After six months of being diapered 24/7, Ashley no longer had the slightest control over her bladder. She tended to wet herself most frequently when she was deeply relaxed, such as when she was securely in her crib, or being fed with a bottle. Something about being in her mother's lap, suc-king contently on a bottle of warm milk that she was holding, caused her bladder to release. Of course, Ashley could wet herself at any time, which meant that Ashley was always kept in her Princess Pampers.

"Let's get you changed, honey." Helena said, lifting Ashley out of the crib.

Ashley obediently clung to her mother as Helena moved her from her crib to her changing table. Helena was extremely practiced at this by now, and shimmied Ashley's snug plastic panties down her legs in a trice. She tossed them into the wash hamper and untaped Ashley's diaper.

As Helena wiped her with baby wipes, Ashley was dimly aware that she had once found this embarrassing. But having her diaper changed by her mother was the most familiar thing in the world to her now. Ashley simply suc-ked on her pacifier and waited for her mother to finish. Her pee-pee got stiffer, of course. Though it wouldn't get any bigger, it did stiffen slightly when her diaper was off.

Emily had rubbed her pee-pee months ago, but that was the last time it had happened. Ashley had no chance at all to do it herself. The only time she wasn't securely diapered was when she was being changed, or in the bath. At both times, Ashley was under the close supervision of her mother, so she couldn't do it then either. And asking was out of the question, especially since Ashley was kept quiet by her pacifier.

The first few weeks were stressful. Her mother obviously didn't understand, and put down Ashley's fussiness to her deciding to be difficult. Eventually, Ashley was able to put it out of her mind. The desire to make her pee-pee spasm never left her, in fact, it subtly increased over time. But aside from certain instances like seeing her mother dressing up for a date, (Helena reviewed lingerie for a women's magazine, and had an entire closet full of bras, panties, garter belts, and stockings. She also took for granted the idea that Ashley didn't care if her mother showed up to check on her while she was wearing nothing more than a push-up bra and a pair of matching panties that she was writing about.) or talking with Aunt Sara about a man she had met, Ashley was able to ignore the feeling.

Before, Helena would make certain Ashley was out of earshot before she got into the juicy details, but now, her mother seemed to think any such conversation went over Ashley's head. Which wasn't to say that Ashley understood everything Helena said about sex, as she was quite sheltered. But Ashley understood enough to make her pee-pee stiffen considerably, with no hope at all of doing anything about it.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on January 13, 2018, 10:51:00 PM
"All done!" Helena said, taping up Ashley's new diaper.

Helena lifted Ashley into a sitting position. Ashley was quite used to this by now, so she lifted her arms automatically to make it easier for her mother to pull her nightie over her head. Clad only in her Princess Pampers, Ashley watched her mother pull open the closet and select a toddler dress for her. Helena pulled out two dresses: one was a lime green dress without much lace that was designed for movement, and the other was a sunshine yellow dress with plenty of ribbons. Ashley shyly pointed at the yellow one. Thanks to her pacifier, pointing was Ashley's main method of communication now.

"Yellow looks so pretty on you, honey. Good choice!" Helena said cheerfully as she put the other dress away.

Her mother slipped the toddler dress over Ashley's head. Helena smoothed it out, planted a kiss to the top of Ashley's head, then gathered up Ashley's hair. Unlike Aunt Sara, who loved to spend time putting Ashley's hair into complicated french braids, Helena had plenty of other things to handle with her daughter. She simply placed Ashley's honey blonde hair into two cute pigtails. Helena then picked Ashley up, with one arm under her diaper-clad butt. Ashley reflexively clung to her mother, realizing that it had been awhile since she had actually walked anywhere.

Recently, any time that Ashley needed to go somewhere else in the house, her mother had lifted her and carried her there. Just now Ashley had gone from her crib, to the changing table, and was now heading downstairs, all without even standing up, much less walking.

"You're going to look so adorable for your friend! I called Emily and asked if she could come for your special day. She said she'd try to make it, but that her mother would be bringing Lizzie for sure." Helena said to Ashley as she carried her downstairs to the kitchen.

Helena, always organized, opened the fridge and retrieved one of the bottles of milk she kept there. She popped it into the specially-designed bottle warmer Aunt Sara had purchased. In less than 30 seconds, it brought the bottle of milk to the perfect temperature for Ashley.

Her mother then sat down on a chair at the kitchen table. Ashley's highchair was close by, but that was only used for dinnertime. Helena settled Ashley down on her lap and popped her pacifier out, then set it on the table. Her mother then inserted the rubber nipple of the bottle into Ashley's mouth, who began suc-king at once. Warm milk filled Ashley's mouth, causing her to swallow, which caused her to suc-k more, and the process repeated without any conscious effort on Ashley's part. After six months of this reliable routine, drinking from a bottle was as natural as breathing to her now. Helena, for her part, had one free hand now. She took advantage of this by pulling out her phone and dialing someone while Ashley contently drank from her bottle.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on January 13, 2018, 11:49:01 PM
"Hello, Mrs. Carmichael? I'm calling to ask when you want to bring Lizzie over today." Helena said over the phone.

"I'm thinking a little before noon. And please, Helena, call me Julia." came the voice from the phone.

Their conversation progressed to more adult topics, and not the kind that Ashley had any interest in. She stopped paying attention to the phone call and simply focused on enjoying her milk. As Ashley kept drinking, her mother tilted the bottle higher and higher until it was nearly empty. Only when the bottle was drained was Ashley aware that the front of her diaper felt a little warm. Ashley had wet herself while she was drinking, but just a little. Certainly not enough to warrant a diaper change this quickly. Helena took the rubber nipple out of Ashley's mouth and wasted no time in popping Ashley's pacifier back in its place.

"Alright, honey. Time to play!" Helena said in the singsong voice she used to keep Ashley content.

Helena carried Ashley over to the living room, in the middle of which stood a playpen. She carefully lowered Ashley into it before planting another kiss on the top of Ashley's head.

"Have fun, honey. I'll check on you in a little while." Helena said, wiping her hands free of nonexistent dust before she turned to leave the room.

Ashley watched her mother go, trying to calm the feeling of nervousness that came over her whenever her mother was not right there to handle any possible problem. Helena turned to give Ashley a small wave, which Helena did whenever she had to leave her daughter in a room for any length of time. Ashley waved back, and only then did Helena leave the living room.

Ashley knew that even if her mother wasn't here, she could still see Ashley. A camera was placed on the ceiling light over her playpen, and Ashley knew that the video from the camera could be accessed with the press of a button on her mother's phone. The same was true for the night-vision camera above her crib, which meant that Ashley was never truly out of her mother's sight. Still, just the feeling of being alone made Ashley nervous.

Standing up for even this long was surprisingly tiring, so Ashley quickly sat down in her playpen. After months of usually being carried while inside or riding in a stroller while outside, Ashley wondered how far she could walk if she wanted to right now. It was mostly a moot point, considering her playpen was the only place where she had room to walk. And especially since everything in here was easily accessible from a seated position. Without really realizing it, Ashley found that using her hands and knees was an easier way of getting around the playpen than trying to stand and walk.

Ashley quickly found her dolls, Ashlyn, Emerson, and Willa. Lately, whenever she played with them, Ashley couldn't help but imagine they were her older sisters. The way they were dressed seemed more mature than Ashley felt, considering that none of them wore Pampers like her. Ashley liked to pretend that Ashlyn loved to brush her hair, while Emerson, the most Emily-like of the bunch, liked to tease Ashley. Sometimes she went too far, which caused Willa, who had the same color hair that Ashley and her mother had, to want to protect Ashley.

Ashley was dimly aware of her mother checking up on her every 30 minutes or so, but was too engrossed in her play world to pay Helena much mind. It was only when Ashley heard the doorbell ring that she realized that hours had gone by. She looked down to see that the flowers on the front of her pink Pampers were in full bloom. Ashley had wet herself once or twice more, and definitely needed to be changed.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on January 15, 2018, 02:15:52 PM
"Hello, Julia! This must be Lizzie. She's so cute." came her mother's voice from the door.

"Hi! And thank you. Say hi too, Lizzie." Julia said, in the same friendly tone as her mother.

"Hi." came the quiet but happy voice of a little girl, who could only be Lizzie.

Ashley crawled to the edge of her playpen and stood up, with a little difficulty, so she could see over the sides. Helena came into the living room, followed by another woman who was carrying a little girl. They walked right up to the other edge of the playpen and looked down at Ashley.

Ashley's eyes grew wide as she saw how beautiful the other woman was. She was like Emily, only instead of looking as if she was fast approaching womanhood, it was clear that she was already there. The woman had Emily's dark, shiny hair, brilliant green eyes, and was as tall as a model. It was obvious where Emily had gotten her very impressive cup size, as this woman had fantastic breasts. She was wearing a dark purple blouse that showed the outline of an oddly shaped bra beneath it. It took Ashley a second to realize that it must be a nursing bra.

"Here's my beautiful little treasure. She's the birthday girl today. Wave to Julia and Lizzie, honey. " Helena said, directing the last part at Ashley.

Ashley obediently waved to the woman, who was regarding her with a smile that included just a hint of amusement. Clearly, Emily had already filled Julia in with the details, or some of them. But seeing Ashley in her yellow toddler dress, which did not fully cover her Princess Pampers, must have been quite a sight. She had the same teasing but ultimately friendly look that she could remember Emily having as she gazed down at Ashley in her playpen.

"Oh, she's wet herself again. I'm going to have to change her real quick." Helena said apologetically, though the apology seemed to be directed at Julia and not at Ashley, about whom she had shared this embarrassing fact aloud.

"That's fine, really! Lizzie wet her pull-ups on the ride here, and I was actually going to ask you if you had a changing table." Julia said, hiking up her daughter on her arm.

"We sure do! Follow me." Helena said cheerfully, bending down to pick up Ashley.

Ashley, well used to this by now, lifted her arms up to make it easier for her mother to pick her up. Helena settled Ashley on her arm before heading out of the room, with Julia following her. As they both headed upstairs to Ashley's room, she looked over her mother's shoulder at Lizzie.

Lizzie had the same dark hair as Emily and her mother, Julia. Her eyes were more of a green-blue color, and she was looking at Ashley with quite a bit of curiosity. She was wearing a dress as well, and though it was definitely made for toddlers, it didn't have nearly as much lace and ribbons as the dresses Ashley had. They also completely hid what Julia had mentioned as her pull-ups earlier, which meant that Lizzie must be progressing toward being potty-trained. And of course, Lizzie did not have a pacifier in her mouth like Ashley had. The 3 and 1/2 half-year-old girl waved at Ashley, who waved back as her mother taught her to do.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on January 15, 2018, 04:28:53 PM
Helena opened the door to Ashley's room and placed Ashley down on her changing table. Her mother placed her off to one side of it so that there was room for Lizzie, who Julia had placed down beside her. Both women flipped the skirt up on the dresses of the toddlers on the table and got to work changing them. Ashley's diaper was not as easy to handle as Lizzie's pull-ups, but Helena's practiced efficiency made up for the difference.

"You're pretty good at this." Julia remarked as she took some of the baby wipes from the table.

"Well, my little princess wets herself a lot. I swear, she has a bladder the size of a thimble." Helena said, making use of the baby wipes for Ashley as well.

Julia's mouth moved into what might have been a smirk at the word "thimble". Ashley's pee-pee would have fit comfortably inside one, as Julia seemed well-aware of. Her pee-pee stiffened from the wiping, which still did not keep it from fitting into a thimble, but it did mean that Ashley wanted very much to ask Julia to touch it. Needless to say, she couldn't. Ashley's pacifier made that an impossibility. Lizzie did not have any such impediment, though.

"Pee-pee! She has a pee-pee!" Lizzie said, trying to point toward it.

Both women laughed and continuing changing them. Lizzie was done first and Julia picked her up, which meant that she got a much better view of Ashley, who was still on the changing table. Helena took her time in selecting a new diaper for Ashley. Her mother was about to decide when she picked up two of them and showed them to Lizzie.

"What do you think Ashley would like, sweetie? Elsa or Moana?" Helena asked, holding the two pink Princess Pampers up.

"Elsa! Elsa!" Lizzie said at once, pointing toward the Elsa diaper.

"Good choice! I think Ashley likes that too." Helena said, looking from Lizzie to Ashley, still on the changing table with her skirt flipped up and her pee-pee exposed.

Ashley nodded despite herself. Lizzie seemed very pleased at herself to have chosen the "right" one and clapped her hands as Helena bent down to put the pink diaper on Ashley. As Helena slid the diaper beneath her butt, Ashley knew that another chance for her pee-pee to get touched was gone, but she wasn't expecting it to happen anyway. Only if Emily arrived would it be a possibility. Her mother finished taping up the diaper and picked up Ashley once more.

"Let's go to the kitchen, shall we?" Helena asked, fixing Ashley's hair with her free hand.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on January 15, 2018, 10:10:01 PM
Ashley settled on her mother's arm, feeling more comfortable with a dry diaper. The hours had flown by quickly in her playpen, but her stomach reminded her how long it had been since her morning feeding. She was quite looking forward to more milk, even though it would probably mean getting fed in front of Julia and Lizzie.

Helena walked over to the fridge and took out another bottle of milk for Ashley. She was on the verge of putting it into the bottle warmer when she turned around to see that Julia had already sat down at the table. She had put Lizzie down in front of her on the table in order to free her hands.

"I hope you don't mind, but it's been awhile since I've fed Lizzie." Julia explained as she unbuttoned her blouse.

"Oh, not at all. I wish I had kept up with breastfeeding Ashley, actually. It can be a hassle to warm up bottles for her all the time." Helena said thoughtfully.

"I'm going to miss it when Lizzie gets tired of this. It makes me a whole cup size bigger." Julia explained as she pulled the flap to the side on her nursing bra on her right breast, exposing her nipple.

Julia picked up Lizzie from the table and settled her on her lap again. After some hesitation, Lizzie began to suc-kle from her nipple. Ashley squirmed slightly in her mother's arms, feeling distinctly jealous for some reason. Helena noticed this and looked at Ashley curiously.

"You know, it's not all that difficult to start the process up again. There are some pretty safe drugs you can use." Julia said, showing no discomfort at all.

"I've thought about doing that. I'm not sure it's worth the effort, though, if Ashley won't take to it." Helena said, shaking her head.

"Well if you want to find out, you can give her here. Lizzie doesn't drink much anymore." Julia offered.

Ashley squirmed in her mother's arms, wishing she had a way of communicating her interest more definitively. Helena was quite in tune with her daughter, however. She nodded and brought Ashley to the table, sitting her down in front of Julia.

Julia uncovered her left breast and exposed the nipple there. It was the first time Ashley could remember seeing an uncovered nipple. Unsurprisingly, her pee-pee stiffened in her diaper, but it was mostly hunger that was on her mind. Julia pulled her into her lap and popped her pacifier out, leaving her nipple right in front of Ashley. Ashley felt a little shy about this, but her empty stomach drove her to lean forward and starting suc-kling Julia's nipple.

Warm milk trickled into Ashley's mouth. It seemed like the absolute perfect temperature for her mouth. It was a little bit like her usual feeding, but it tasted sweeter. Something about the taste was very appealing to her, however, and she found herself suc-kling with more enthusiasm. Ashley quickly understood that a bottle was really just an imitation of a nipple, and the real thing was far more satisfying.

"Wow, she definitely likes it." Julia said, laughing a little at Ashley's enthusiasm.

It was then that the doorbell rang.

"That must be Emily." Julia said offhandedly as Lizzie stopped suc-kling.

"I'll answer it. Ashley is going to be so glad she made it!" Helena said cheerfully as Ashley heard her leave the room.
Title: Re: Ashley's Babysitter
Post by: Jemina004 on January 15, 2018, 11:05:37 PM
Ashley felt a little embarrassed about Emily seeing her being breastfed, but she wasn't entirely in control of herself right now. Her stomach was demanding more breastmilk, and Ashley continued to swallow the sweet, warm milk that trickled into her mouth, feeling like she couldn't get enough.

Lizzie, on the other side of Julia, seemed to have had enough, however. She pulled back and looked at Ashley curiously. Possibly she had never seen anyone else get breastfed.

"Ashley likes your milk, mommy!" Lizzie said with wonder.

"She does! Are you sure you've had enough, sweetie?" Julia asked.

Lizzie nodded. Ashley could hear pleasantries coming from the hall and knew it would only be a few seconds until Emily came into the kitchen. She had the vague desire to pull back like Lizzie had, but she simply couldn't. When Ashley was being fed, her body was firmly in control. The instinctive urge to keep suc-king was powerful, and her body wanted more breastmilk. So it was that Ashley continued to be fed from Julia's breast as Emily walked into the room.

"Emmy!" Lizzie said enthusiastically.

"Hi, Lizzie! And I'd say hi to Ashley too, except she seems a little busy." Emily said, her voice thick with amusement.

"Can you take her, Em?" Julia said, motioning to Lizzie on her lap.

Ashley couldn't see much from where she was, but she saw Emily pick Lizzie up from Julia's lap beside her. The milk from Julia's breast was running low, which meant that Ashley thought that Julia might end the feeding. But after Julia pulled Ashley off her left breast, she simply switched Ashley over to her right breast, the one that Lizzie had been fed from. Once more, Ashley's body was in control as she immediately began suc-kling again. Any embarrassment Ashley felt about Emily watching her was completely irrelevant to her body, which only cared about getting more milk.

"She really likes that, huh?" Emily said from behind Ashley.

"She really does. I'm going to have to talk to my doctor about starting up lactation again." Helena said.

Ashley could do nothing more than continue to suc-kle from Julia's breast as the women at the table began to talk among themselves. Even Lizzie got in on the conversation. Meanwhile, Ashley could neither speak nor see anything other than the D-cup breast that was continuing to deposit sweet milk into her insistently suc-kling mouth. The only thing Ashley could do was hope that her stomach would be full soon.

Ashley had to endure several more minutes of helpless suc-kling before Julia pulled Ashley off of her breast. Julia quickly popped her pacifier back in before handing Ashley back to her mother. For the first time today, Ashley could see Emily, who had gotten a very entertaining look at Ashley already. Emily was wearing a sky blue halter top and a daringly short skirt. She was regarding Ashley with a look that said that she was never going to forget the sight of Ashley suc-kling from her mother's breast like a helpless baby. To make matters worse, Ashley had wet herself once again. The flowers in the front of her exposed Pampers were blooming, and Emily knew exactly what that meant.

Despite her sense of keen embarrassment, Ashley was feeling tired now. She always napped after lunch, and her full stomach was causing her eyelids to drop. Helena, being aware of the time, stood up from the table with Ashley in her arms.

"The birthday girl needs her nap, I think. Wave bye-bye to everyone, honey." Helena instructed her.

"See you in a little bit, cutie!" Emily said, waving at Ashley.

Ashley obediently waved back at Emily and Lizzie. Her mother carried her from the kitchen and upstairs to her room. By the time Helena had deposited her in her crib, Ashley was practically asleep already. The last memory she had before falling asleep was her mother settling a blanket over her. Helena kissed the top of her head before raising the sides of Ashley's crib. She smiled at her daughter before leaving to rejoin the conversation in the kitchen.
Title: Re: Ashley's Babysitter
Post by: DanieBoy on May 20, 2018, 09:52:04 AM
I'm hoping that Jemina004 will add a few more words to this wonderful tale. I keep hoping and soon I know thatb she will add to it.
Patience is a virtue, at least that's what the saying is.
All the best to you and yours Jemina!
DanieBoy
Title: Re: Ashley's Babysitter
Post by: Sissy Poopsie on December 29, 2018, 12:11:00 AM
I just read this whole story again from start to finish.

It is a brilliant story and hopefully sometime maybe more will be added to it. Fingers crossed.
Title: Re: Ashley's Babysitter
Post by: Plateguy on June 06, 2019, 07:43:13 PM
I know it has been quite some time since the last installment, but I sincerely hope there will be more of this wonderful story.
Title: Re: Ashley's Babysitter
Post by: pierrylouys on January 14, 2020, 06:33:19 AM
Really hope someday this story can continue
Title: Re: Ashley's Babysitter
Post by: patticakes on November 15, 2020, 02:14:10 PM
I just re-read this story after many months, and still find it to be one of the best in terms of story line, realistic dialogue, (each character has a distinct voice), and descriptions throughout.  I am commenting today to move it up so that newcomers can readily see it and enjoy it as much as I and many others did when it was first published here.  I, too, wish that someday the writer will consider taking the story forward or going back to fill in certain parts of the timeline that were left out.
Title: Re: Ashley's Babysitter
Post by: sweet baby katie on September 13, 2021, 09:51:31 AM
This is one of my most favorite stories.  Well written.  Hits perfectly on all sissy baby themes.  It would be a treat to read more by this very able, and very tuned, in author.
Title: Re: Ashley's Babysitter
Post by: sarahpenguin on September 15, 2021, 12:56:34 AM
King of surprised he was not given new baby safe dolls given he was being treated like a very very tiny child who could not even walk much less crawl by the end of the story. The hero could have choked and died on any items of doll clothing by putting it his mouth to investigate what it tasted like. :)