Ashley's Babysitter

[Jemina004]

"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.

[Jemina004]

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.

[Jemina004]

"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.

[Jemina004]

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.

[Jemina004]

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.

[Jemina004]

“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.

[Jemina004]

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.