Disable your Ad Blocker! Thanks :)
Chapter 18
by
Dayeandknight
what happens next?
To Nora's Clothing Store
The elevator's aggressively inoffensive music played as Ashley's head throbbed. He looked down at his bag of items, brow furrowed in confusion. He couldn't understand why he had taken the pills when it was so obvious that they were meant for women. He was a guy, it didn't make any sense at all.
Pikachu was in a haze of his own after being subject to Hypno's ability. He was doing his best to shake it off but wasn't having an easy time of it. Everything in him was telling him that something was wrong, that Hypno was dangerous. Hypno wasn't his enemy but he was still causing Ash to act weird, even if he was only tying to help her. He glowered at the oblivious Pokemon, trying to summon the will to jolt him but he just couldn't bring himself to fight him anymore.
Hypno bounced with joy at how well everything was going since they got to town. His Ashley was remembering herself and her new pikachu was finally settling down since he had the heart to heart with him earlier. He knew it would take time but he hoped they could become friends soon. There was so much to learn about battling from such a strong pokemon.
The elevator doors opened once they got to their floor reveling store after store. They walked together, new clothes on their agenda. Much to Hypno's dismay, Ashley kept going to stores that normally held his preferred but every time he picked something up, it just didn't feel right. They just weren't...cute. Ashley was getting really frustrated at his own thoughts, forcefully handing the plain t-shirt back on the rack.
“Sorry guys, this was a bust. It doesn't look like we are going to find anyth-” Ashley cut himself off in mid thought, pausing as they exited the last clothing store when he spotted something that caught his eye.
In the window of another shop was an a simple blue dress hanging loosely over a mannequin. Ashley couldn't understand what it was about it that held is interest like it was but he had a hard time pulling his eyes away from it. Taking a few steps backwards he looked up to read the name of the store.
“Nora's” is said in stylized purple letters. It was the place the rude lady told him to go to back at the bath house, he remembered. From the look of it, it was a woman's store, which wasn't something Ashley had any interest in visiting. Even so, his eyes drifted back to the dress. Hypno took Ashely's hand and began tugging it, attempting to lead him inside.
“It wouldn't hurt to just look,” Ash relented though uncomfortable.
A bell chimed, announcing the entrance of the trio, which alerted Nora to their arrival. Nora's voice projected out from the back of the store, informing them that she would be with them momentarily. Hypno wasted no time in pulling Ashley over to a rack of skirts he thought might be to taste while Ashley took in the sight of various shoes lining the left wall and undergarments lining the right. He felt uneasy surrounded by so many feminine garments and started to consider leaving.
“I'm so glad you came, Ash was it?” Nora grinned, stepping out from the back room.
“Ashley...”
“Oh, yes. Ashley. I remember now,” she lied.
“Um...I'm not really sure-” Ashley began to explain why he had to leave but was interrupted.
“What to get? Don't worry, I have an eye for this kind of thing. Come along,” She said taking his arm into her own.
Ashley couldn't get a word in edgewise as Nora lead him to a chair and had him take off his shoes. She sized his feet then pulled out a tiny notebook and made a note of it. She then stood him up and very quickly produced measuring tap and got his sizes. She pulled him over to the wall of undergarments, which was making Ashley feel uneasy. She grabbed a matching pair of panties and a bra, both with a small bit of lace.
“The bra should help, I think you will be pleasantly surprised.”
“Help with wh-” Ashley was interrupted buy another tug of his arm.
His pokemon followed as he was yanked back and forth across the shop while Nora held different articles of clothing up to Ashley's body. His face grew flush with embarrassment at everything that was happening and tried to bring this experience to an end.
“Hey, I don't think-”
“Your right, green isn't your color.”
“No I can't wear-”
“You're right, we should show off your legs.”
“Look, I just looking for something to wear tonight.”
“What's happening tonight?”
“I have a da...dinner. I'm going to dinner.”
“Dinner, huh? With a boy?” She smirked.
“Well, yes...but.”
“Oh, I know just the thing!”
Ashley's arms were filled with a slow growing pile of women's clothes which soon became too high for him to see passed. He was lead into a large changing room, stumbling along as he blindly followed. Everything was taken out of his hands and placed on a bench inside.
“You start getting changed into one of the selections and I'll get you some shoes to try. We will find you something perfect for tonight, I promise,” Nora said, closing the door as she left the trio along with the clothes.
What happens next?
Disable your Ad Blocker! Thanks :)
Crossdressing Stories
A collection of separate stories that all involve guys ending up in dresses
A collection of separate stories that all involve guys ending up in a dresses
Updated on Feb 22, 2026
by Dayeandknight
Created on Feb 1, 2018
by Dayeandknight
- 5,858 Likes
- 2,187,937 Views
- 929 Favorites
- 620 Bookmarks
- 384 Chapters
- 73 Chapters Deep
- All Comments
- Chapter Comments