Ash becomes Ashley
It all started when Ash and Dawn met up with two of Ash's old friends, Misty and May. Brock had some business back in Pewter City, so Ash and Dawn were seeing him off at the airport when they met up with the two. Misty, May and Dawn had already met a couple of times before so there was no need for introductions. After some talking the four decided to travel together for a while until Misty had to go back to Kanto and May to Hoenn. In the mean time they made their way to a nearby forest, where they made camp for the night.
That night Ash was really tired so he went bed early. But the girls weren't all that sleepy yet so they stayed up chatting. During the conversations, Misty brought up the time when Ash cross-dressed in order to get into the Celadon Gym. She figured they would just laugh it off and move on to the next topic. Instead both May and Dawn brought up the times he cross-dressed with them. Except for the time with Dawn, when he wore a milk maid outfit, they agreed that he looked a lot like a girl. It was then that they decided to see how much of a girl he could look like.
The next morning Ash woke up feeling refreshed, never expecting what was going to happen to him that day. As soon as everyone was ready they headed out. "Man those three sure are acting weird today," thought Ash since they kept looking at him and giggling. He shrugged it off and they went on their way. The girls said that they wanted to do some shopping and since Ash didn't mind, the group headed for the city. First they went to a couple of dress stores looking for a similar dress to the one Misty mentioned the night before.
It was an orange dress with a blue bow at the top of the chest. Finally at the second store they found one that was identical. They bought some cute panties with Pikachu on the front and a couple of bras to go with them. Ash didn't see any of this because he was waiting outside. They went to some other stores and bought things they planned on using on him including a couple of other outfits, some makeup, pink nail polish, a blonde wig, a pink hair ribbon and other accessories. When they were done they decided to go to a hotel and show him their surprise.
"What?! Where did you get that dress? I haven't thought about that in years!" Ash said in complete shock looking at what they picked out for him. "C'mon Ash no one else will see besides us," Misty said giving him the cutest look she could. "Please?" both May and Dawn pleaded. Surprisingly Ash agreed without much of a fight so the girls went to work.
First they sent him to the bathroom to put the panties on. When he came out they put the bra on him and had him put on the dress. Then they put the wig on him and went to work, each of them working on a different part of him. Misty started working on his nails while May started tying the ribbon in his wig and fixing it. Then Dawn started to work on his makeup. Soon, after Misty finished his toe nails, they added some white anklet socks and orange shoes to match the dress. They added an orange purse and the look was complete.
They stood him up and before they showed him his reflection they just had to admire their work. "He's much too pretty to be called Ash," Dawn said. "You're right, 'she' needs a new name," said May. Then Misty chimed in, "How about the name he used last time he wore this outfit, Ashley? Is that ok with you?" she asked Ash. He wanted to see himself first to see how he looked, and then he would decide if the name fit.
So he walked over to the mirror and they unveiled it, since they kept it covered in order to keep his look a secret from him until it was finished. Ash couldn't believe his eyes! He thought he might look a bit like a girl but not completely like one! "Ok, I guess Ashley is appropriate," 'she' said in disbelief. "Yay!" the three screamed. They spent the rest of the day having Ashley try on a bunch of outfits they bought for her.
A few days later, Ash and Dawn bid farewell to their friends as they left for home. Ash had not yet gained enough confidence to go out in public as Ashley yet. So Misty and May went on their respective planes and headed home. Brock wasn't back yet as he still had another week in Kanto. So Ash and Dawn left and continued on their journey. Later that day the two didn't feel like camping out they got a hotel room. Then Dawn asked Ash "would you like to try on another dress?" He thought about it for a moment. "Well let me see it first," he responded. Dawn grabbed a bag and pulled out what looked to be her contest dress!
"Isn't that the dress you wear at your contests?" Ash exclaimed. "It looks like it but this one's your size," Dawn explained. "Ok I'll wear it," said 'Ashley' excitedly. "Great! Let's get ready to change, Ashley!" Dawn said helping Ashley remove her jacket. "Sure, Dawn let's get started," she responded with a big smile on her face.
It was obvious to Dawn that Ashley was really going to enjoy this as she helped her undress. When she was down to just her boy underpants, Dawn handed her a pair of pink panties and she went into the bathroom to put them on.
By now Ashley had noticed how different the panties felt then her boy underwear. They felt softer and more comfortable than those boxer shorts she normally wore. "Maybe I should start wearing these more often," she thought as she exited the bathroom. Once out, Dawn helped her put on a strapless bra.
"Is this okay?" Ashley asked as Dawn adjusted the bra. "Yeah it fits you just fine Ash, oops, I mean Ashley." Dawn stammered. "Okay, just checking." Before Dawn would put the dress on her, she insisted on doing Ashley's nails since the nail polish from before had been removed. So Dawn started on Ashley's nails, which had gained some length since last time. Once Dawn was done smoothing out some rough edges, she started applying the pink nail polish.
Once that was done, it was time for the dress. Dawn unzipped the dress and helped Ashley into it, since her nails hadn't completely dried yet. As she was zipping it back up Dawn said, "I'm sure this dress will suit you Ashley." "You really think so?" Ashley replied. "Of course it will. With a little more work you'll be very pretty." "Thank you Dawn, I hope I will."
Now it was time for the wig. Dawn carefully removed it from the box she kept it in. She put it on a foam head and brushed it out. She tied the ribbon into a bow in the wig and it was ready to put on Ashley. As she was putting it on her, Dawn commented, "you know it's great how you let me put you in this dress and everything." "Well I figured since you, Misty and May did this to me a few days ago, I figured what was the harm? Besides, I actually kind of enjoy doing this with you Dawn," Ashley said with a smile. Dawn was surprised but happy at what Ashley said. "Thank you Ashley, I'm enjoying this too! How would you like to do this more often with me? Before you answer I just want you to know, if you say yes then I'm not going to remove the nail polish when we're done. It's much easier if we leave them that way. So it's up to you whether or not you want to do this."
Ashley thought about it for a minute, after all she would have to keep the nail polish on even when she went back to being Ash if she agreed to it. Finally she made her decision, "Yes, I'd love to do this more with you. I don't care if I have to wear the nail polish as a boy; I enjoy doing this too much to say no!" Dawn was stunned for a moment but then she managed to say, "That's great Ashley! I can't believe how fast you agreed to that. Anyways we're almost done; all that's left is the makeup and the shoes. First, let's get your shoes on." She helped her put some white anklet socks, so she wouldn't mess up her dress. Then she added some pink shoes.
Now it was time for the makeup. First Dawn started with a light foundation. Then she added some blush, and while she was doing that Ashley asked her a question. "Dawn, do I look pretty yet?" "Of course you do Ashley, and you'll be even prettier once the makeup's done," Dawn replied. Finally, Dawn added some pink lipstick and the look was complete. Ashley was about to walk over to the full length mirror, when Dawn stopped her. "Hold on," she said. "I just have to get some pictures of you."
Dawn pulled out a camera and took a picture. "You look so pretty, Ashley." "Do you really think so?" Ashley replied. "Of course I do, Ashley. I wouldn't say it unless I meant it." "Thank you so much," Ashley replied as she curtseyed.
Dawn nearly fainted as she snapped another picture. She finally uncovered the mirror and Ashley finally got a good look at herself. Just like before she was stunned at how beautiful she looked. There was no way anyone could tell she was really a boy. "Dawn," she said, "would it be alright if I stayed like this until Brock comes back? We have other outfits that I can wear. I just feel so pretty right now, I want to stay like this for a while." "Of course you can Ashley. I'd love for you to stay like this."
So Ash stayed dressed as Ashley for the rest of the week. She even went out in public as Ashley. Just before Brock came back, Dawn and Ash put the Ashley clothes in a special storage facility. This way they could access them anytime they wanted with a phone call. They met Brock at the airport and things went fairly back to normal. Though without Brock's knowledge Ash wore panties under his clothes. So once in a while, whenever Brock left for any length of time, Ash would become Ashley again.