Ashley's Babysitter

[Jemina004]

"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.

[Jemina004]

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.

[Jemina004]

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.

[Jemina004]

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)

[Jemina004]

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.

[Jemina004]

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.

[Jemina004]

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.