Chapters tagged crossdressing

by Katnaace

Chapter 36

Even with the family as it was, Caroline could still see room for improvement. More specifically in her son - Max. For some reason, thoughts of him had hung over her mind since the family reunion. Heck, she could use a similar method to the one she used on Carol. "Do you really...

by Katnaace

Chapter 37

Skipping her way towards Littleroot Town proper, Cara took a moment to examine her surroundings. Her disguise had held up so far, but there was no telling what curve balls that people might throw her way if she wasn't careful. "This is so exciting." Cara thought and cracked a wi...

by Katnaace

Chapter 38

"Yes, actually." Cara announced and sauntered over to the counter. She had an exact thing in mind here. Whether or not the antique store had what she needed, remained to be seen. "I'm looking for retro clothes like the ones I'm wearing right now." The woman at the counter nodded...

by Katnaace

Chapter 39

Taking a moment to think her options over, only one place came to mind - the perfume store. While his hair definitely needed a retro touch-up, she had a feeling that was something her mothers wanted to do that as a mother-daughter outing. Perhaps with May as well. While still adj...

by Katnaace

Chapter 8

Leading Carla out of the walk-in closet, May shifted her focus over to a vanity. Sitting Carla down in front of there, she dug into the drawers. "Hold still, Carla." May barked and got a thumbs-up from her 'mother'. Tempted as she was to look directly into the mirror, she was go...

by Katnaace

Chapter 7

Heading over to her closet, May took care in opening it up. Inside, what looked to be a mix of regular clothes and contest outfits stared back. "For now, June, let's go with my regular clothes." May explained and Ash nodded. Watching her reach in, out came a set of bra and panti...

by Katnaace

Chapter 9

With that now done, May and June sat on the bed. "Now that I look like your sister, now what?" June inquired and watched her sister bring a finger to her chin. While she had a couple ideas of what she wanted to do, right now, they needed to get June into the right mindset. "You...

by Katnaace

Chapter 6

Staring in, Ash was met with Iris's outfit. "Huh." the trainer thought and stripped out of his clothes. Throwing them off to the side, Ash had a feeling that Iris was likely to dispose of them once they got to their final destination. At least, he hoped that she would. Starting...

by Katnaace

Chapter 7

Letting out a sigh, Ivy stepped out of the bushes. Taking a moment to calm her nerves, that was easier said than done here. By no means impossible, it would certainly be a chall- "Oh my." Iris greeted and Ivy's cheeks went red. Thought immediately cut off, it took everything for...

by Katnaace

Chapter 7

Now on the bed, Ash got to work stripping down. With the door closed, he had more than enough privacy to not worry about freaking someone out. Once he had done that, the trainer threw the clothes off in one corner. Then came the matter of waiting for Lusamine to return. Thankful...

by Katnaace

Chapter 12

Taking a moment to think it over, an idea came to Delia. Part of her wasn't sure why she didn't think of this yesterday. Perhaps because this was spur of a moment. Yeah, that was probably it. "How would you feel about getting to play with people your age, Ashlee dear?" Delia inq...

by Katnaace

Chapter 8

Tempted as Ash was to take the test, something about getting into the Officer Jenny uniform felt right here. "I would like my uniform first." Ash answered and the Jenny led him down the hall. Coming to a stop at the first door on the left, she opened it up. Inside, a room fille...

by Katnaace

Chapter 7

Throwing all caution to the wind, Ash stripped out of his current clothes. While Lopunny hadn't provided him with the proper undergarments (sadly), he thankfully had a couple pairs of panties from his other crossdressing misadventures. With that out of the way, his attention tur...

by Katnaace

Chapter 8

Taking care to get used to his heels, Ash took care to head for the front door. Trying to make as little sound as possible, that was quite a challenge right now. "Ready to do this?" he called out, waiting a moment for Lopunny to catch up. Finding them at his side, a low 'lop' wa...

by Katnaace

Chapter 6

Taking a moment to look over his options one more time, Ash eventually pulled a hanger off. In one of those dry cleaning bags, was an orange dress with red flats. A wig sat at the bottom of the bag, but it wasn't completely necessary for the outfit. Didn't stop Ash from pulling t...

by Katnaace

Chapter 7

Taking a second to think it over, Ash pulled the wig out. Within, he was met with his wig cap. Pulling it out, the trainer got to work fitting it onto his head. Pulling his hair in, he got to work getting the cap on. While initially odd, it started to feel familiar to him. "I sh...

by Katnaace

Chapter 8

Ash spun around, Delia now standing before him. Leaving to his mother to find out right away. "I just wanted to change things up. That's all." Ash answered, a sense of melancholy coming over his body. Could his mom not see the way that he felt right now. Or had those thoughts ne...

by Katnaace

Chapter 9

Delia let out a sigh. Part of her didn't want to believe that her son wanted to be a girl. But she was not a heartless person (in her eyes). "I will allow it..." Delia started and watched her daughter perk up ever so slightly. Was she really prepared to hear what she was about t...

by Katnaace

Chapter 10

"Ashley, would you mind if I touched up your makeup and did your nails?" Delia inquired and watched her daughter perk up once more. "I would love that." Ashley answered, trying her best to make the words sound feminine. Rough and fake, Delia knew she had her work cut out for her...

by Katnaace

Chapter 11

Leaving Delia's room, Ashley made a beeline for her room. She didn't know why exactly that was the first place that came to mind, it just was. "Where did I leave that diary?" Ashley thought and opened a drawer up. Peering inside, she was met with blue journal decorated with a fl...