The Faire, Part 50

by: Lady Lucia | Story In Progress | Last updated Feb 9, 2024


Chapter 36
The Faire, Part 44

Part 44


Cassidy briefly hesitated, before nodding. “Umm, okay.” She didn’t want to risk the successful delay she had achieved, especially since this seemed like Elena’s way of compromising. Arguing would potentially undo things and lead to the bathroom trip that Cassidy was going out of her way to avoid. 


Surprisingly, they didn’t head up to Elena’s bedroom like the diapered girl expected. Instead, she was led the opposite way by her hand to a flight of carpeted stairs that took them to a furnished basement. Rather than trying on some of Elena’s old clothes, the bossy babysitter informed Cassidy that they were going to check out the costume boxes in the storage room off to the side. After all, Cassidy clearly enjoyed dressing up like a cute fairy. That meant she would like trying on other costumes. 


Cassidy awkwardly stood in the middle of the basement as Elena pulled out two large bins from around the corner. Not consulting Cassidy in the selection process, Elena proceeded to dig through the first box until she procured a baby blue dress. “Ooh, I forgot about this! I went as Alice when I was around your age. Pretty sure I was taller than you back then, but I bet it will mostly fit.”


Similar to the fairy costume Cassidy had been convinced to ‘temporarily’ put on earlier, the dress Elena was holding up looked simple and childish rather than the sexy and form fitting costumes older girls tended to wear. However, she wasn’t about to complain. Putting on a costume meant no longer being naked save for the subtly sagging diapers she was stuck in. 


Elena decided that it would be easier to help Cassidy into the dress, rather than letting her do it herself. With a playful yet firm, “Arms up,” Elena waited for her to comply. 


Since Cassidy’s chest had been on display more or less since she was dropped off at Elena’s place, the directive for her arms wasn’t nearly as daunting as it could have been if Cassidy was still covering herself. That is, until she actually raised them. The motion caused her boobs to almost completely flatten out, making her look even smaller than normal. 


While Elena didn’t comment on the image, a quick downward glance and a small smile was more than enough to show that she noticed the change. “Now hold still, Cassie. This will just take a minute.” She stepped forward with any hesitation while adjusting her grip on the light blue dress until she was holding it near the hem. Pulling it over Cassidy’s head with very little gentleness or finesse, to the point where the soon to be costumed girl was worried that her hair was going to look atrocious by the time all was said and done, Elena eventually worked the outfit past her neck while pausing here and there to guide Cassidy’s arms through the appropriate holes. “There,” Elena nodded, once the dress was loosely sitting on Cassidy’s body, “Now, let’s just . . . ” She spent an extra minute fussing over the skirt and then the upper sections of the costume as she worked to fit it as best as she was able on the blonde’s petite frame. Rounding things out by attempting to smooth a few wrinkled spots with her hands, not very successfully due to how many years the dress had probably been folded up in the costume box, Elena dusted off her hands and stepped back with a smile. “Perfect! And you even have the hair for it. I had to wear a wig!”


Cassidy gave herself a cursory look, immediately skeptical as to how ‘perfect’ she actually looked as Alice. Without a bra on, the cut of the dress wasn’t doing her small mounds any favors. At least the skirt was long enough where the diapers were fully covered. Of course, now that she was thinking about it, something like that was only so helpful when the only other girl present was already aware of her mortifying underwear situation. 


Halfway aware, anyway. 


“Well, what are you waiting for?” Elena asked, “Dress-up is only fun if you show off your outfits. Try walking around, Cassie. Give me a twirl or two. A smile couldn’t hurt, either!”


Reluctantly going along with the first suggestion while hoping that would be enough for Elena to forget about the latter ones, Cassidy paced forward a few steps. As usual, she was way more focused on trying to look natural while walking around in dirty diapers than she was paying attention to how Elena’s old costume felt on her. That was the main reason why Cassidy was moving about the basement; every second spent doing an awkward fashion show was another second Audrey had to return. 


Elena wasn’t going to make it that easy, unfortunately. “Twirl, Cassie,” she insisted, “That’s what you’re supposed to do when you’re wearing a pretty dress.”


Quietly sighing to herself while facing the opposite direction, Cassidy turned enough for it to technically be considered a twirl. Though there was no risk of the diapers being exposed as the skirt slightly flared in response to her movements, she still briefly cringed at the prospect. Regardless of the recent reminder to herself that Elena was fully aware of them, Cassidy was still worried on instinct now that she was wearing clothes again. 


“How about a smile?” Elena added on, “Make it full of wonder! Come on, Cass. Aren’t you excited to be doing your very own fashion show?”


Not even a little bit. But Cassidy was clinging to her latest thought about doing whatever it took to run out the clock. So she pursed her lips into a smile that was more awkwardly demure than the enthusiastic kind of expression Elena was pushing for. 


*Click*


Elena’s phone definitely hadn’t been in her hand when Cassidy had last checked. Yet it seemed to materialize just when the costumed girl looked like she was fully posing for the lens, and the fact that the volume was on made it that much more of a surprise. “There you go,” Elena said, “Wow, you’re so cute.”


Cassidy gasped. “Elena!” she exclaimed, “Delete that!” The last thing she needed was yet another immature picture of herself out there. Because if Audrey had posted the first without asking, she could potentially do the same with whatever Elena sent her. 


“Umm, what did you call me?” Elena frowned.


That- that was so not what was important at the moment. Which was exactly why Cassidy didn’t waste time debating it. “Ms. Elena,” she corrected herself. Leaning into the ‘respectful’ thing, she also begrudgingly shifted her demand into more of a polite request, “Please delete that?”


“But why? Don’t you want to see how you look? There aren’t any mirrors down here. Besides, this way you can check out all your outfits later, so you know which ones you want to borrow later. I don’t mind lending this stuff out, but I can’t just send you home with all of it!”


“Just . . . Just delete it, Ms. Elena. Okay?”


“How about this?” Elena said. She placed a hand on her hip, “Let’s try on a few more, and take at least one picture of each. Then I’ll delete all of them after we look through them and you decide which one is your favorite.”

“But-”


“No ‘buts,’ Cassie. I could just keep all these adorable pictures, I guess.”


“No!” Cassidy hastily replied. Now that she had shown her hand, not to mention how Elena clearly knew what buttons to push anyway, she said, “What’s next . . .?”


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End Chapter 36

The Faire, Part 50

by: Lady Lucia | Story In Progress | Last updated Feb 9, 2024

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