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Chapter 106
by
vanillathunder
What do the girls pick out for Kylie to wear on her hot date?
Figuring out "Kylie's" second date attire
As if Kyle had any say in the matter, he nodded and was quickly shepherded upstairs to the bedroom, where Melissa, Darla and Robin were deliberating on what would be appropriate attire for the date.
“I think we ought to go sexier. Something tight that shows off her curves, especially that ass!” Darla remarked.
Sitting down on the bed, Kyle blushed, not believing he even had an ass to show off.
“No, we’ve got to go more feminine on this one, show Greg that she’s a girly-girl at heart,” Robin added.
“Girls, are we forgetting that we have an advanced supercomputer that can generate algorithmically perfect outfits designed specifically to make sure Kylie looks as sexy and girly as possible?” Melissa interjected. “MARCI?”
“Yes, GUEST USER: MELISSA?” MARCI responded.
“Tonight is Kylie’s second date with Greg, and she needs to look her best, can you assemble some outfits that he’ll like?” Melissa asked. “Cross reference with any relevant data you have from the last date.”
“Certainly, Melissa.” MARCI responded.
“Don’t I get a say in all this?” Kyle asked.
“Of course you do, but later.” Melissa replied in an assuring tone.
“MARCI, Kylie’s looking to get lucky tonight!” Darla shouted. “Make sure Greg has easy access to her!”
“Noted.” MARCI chimed.
“Darla!” Kyle hissed.
“Don’t worry, I gotchu, girl!” Darla giggled.
The walls were abuzz with activity while the trio turned their attention from the closet back to Kyle.
“Okay, now that we’ve got MARCI on that, it’s time to discuss the game plan.” Robin said.
“Game plan?” Kyle asked.
“Yeah, so we can make sure that Greg gives you everything you need tonight. And vice-versa.” Darla replied with a smirk.
“Yeah, about that, I was thinking that maybe I should be taking things slow. This is moving a bit too fast for me…” Kyle started.
“Too fast? Oh, honey, you’re going the speed limit at most, especially with guys like these. Any slower and they’ll lose interest.” Melissa jumped in.
Kyle felt a rare burst of confidence as Melissa spoke. They were so engaged in ensuring that he found a boyfriend that he hadn’t really registered that none of them seemed to have boyfriends currently. Why was he the exception?
“But I don’t see any of you with boyfriends or going on dates! Why am I the only one doing this? It feels like you’re just using me as a doll to live out your vicarious fantasies!” Kyle snapped.
“Oh, girl, been there, done that,” Darla said. “Bought the t-shirt, not very impressed with it.”
“So you want to have a bunch of meaningless flings with random guys and make out at parties before moving on to the next one?” Robin asked.
“What? Of course not!” Kyle replied indignantly.
“Exactly, you want something meaningful! And didn’t you tell us that this is your first experience dating?” Melissa said.
“Well, yeah, but…” Kyle started.
“We’re just trying to make sure that you get the full experience! It’s better to do all of these things with your first boyfriend rather than some guy at a party who you’ll never see again. Does that make sense?” Robin said.
“I guess…” Kyle sighed.
“Then it’s settled. Now, we can discuss tonight’s plans. Remember, if the situation ‘arises’, you know what to do.” Darla added.
MARCI chimed and Kyle groaned at both that and the terrible pun. The girls continued to discuss tactics while MARCI did double-duty assembling outfit choices and compiling the discussions into programming for when the time comes to use the skills.
After a bit more time, MARCI chimed aloud, alerting the girls that their outfit choices were ready to choose from. Melissa, Darla and Robin quickly swarmed the screen outside the closet and started to pick their favorites from the no doubt comprehensive list that they wouldn’t let Kyle even glance at.
“Ew, not that one!” Darla grimaced.
“Nope, nope, ooh, that’s cute!” Robin exclaimed.
“I like these… Oh, and the shoes on that one are great!” Melissa added.
After a few minutes of deliberation, the girls had narrowed it down to two choices that they liked. And finally it was time for Kyle to add his two cents to the discussion, although he knew it was really just the illusion of choice, since he’d be wearing a sexy, uncomfortable outfit regardless of what he “chose”.
“Okay, which one do you like better? This one? Or… this one?” Darla asked as MARCI brought out two outfits on hangers.
The first option certainly fit Robin’s request for girly while also having enough inherent sexiness to likely satisfy Darla’s desire for showing off his body, even despite it being looser and more flowy. This outfit consisted of a ruffled lace-up sundress with spaghetti straps and a pair of square-toe block heels, both in a very bright and feminine pink. The dress was tight around the waist and flowed out, but wasn’t quite long enough to cover up his legs, which would be set off nicely by the heels, which showed off his still immaculate pedicure.
The second option was little more than a white cropped button up tank top with a red, short, pleated skirt and a pair of black heeled sandals. As much as Kyle disliked the pink of the first outfit, it at least left more to the imagination. And the block heels would provide more stability while walking, so Kyle could avoid needing a knight in shining armor.
“If these are my only choices, I guess I’ll choose…” Kyle started.
Does Kyle choose the sundress and heels or the crop-tank, skirt and heels? Or does he somehow demand a different outfit entirely?
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The Chronicles of Miss-chief
An anthology featuring stories about gender bending adventures!
An anthology featuring stories about gender bending adventures!
Updated on Jul 25, 2025
by BHCP2
Created on Feb 21, 2020
by vanillathunder
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