Chapters tagged crossdressing

Getting ready for an outing 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...

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Get outfitted 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...

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Ash puts it on 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...

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Getting out on the town 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...

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An orange dress with red flats (Regular Ashley Outfit) 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...

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Ash puts the wig on 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...

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2,167 Views

Talking with mom 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...

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Delia is fine with this 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...

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Makeup and Nails 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...

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Taking it easy 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...

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