Ashley's Babysitter

[Jemina004]

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.

[Jemina004]

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.

[Jemina004]

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.

[Jemina004]

“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.

[Jemina004]

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.)

[Jemina004]

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.

[Jemina004]

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.