Kyle ends up with the cropped tank, skirt and heels

“If these are my only choices, I guess I’ll choose…” Kyle started.

Kyle hesitated, he didn’t want either option and was starting to have doubts about the dress. How was he about to choose a dress for himself? He was supposed to be a man! And men don’t wear dresses, no matter how cute they may be. Between MARCI and the girls making decisions for him these past few days, he’d been way too submissive. He had to stand up for himself!

“You know what? I don’t think I like either of these,” Kyle stated plainly.

“You don’t?” Darla asked.

“No, let me take a look at that screen!” Kyle used this new burst of confidence to stand up and walk over to the screen at the closet and flip through outfit choices.

The girls found Kylie’s newfound interest in her clothes to be strange, given how clueless she usually was, but decided that this was a good sign that she was starting to pick up on their cues. While Kyle did that, Robin’s phone pinged with a text, a response to one that she’d sent to Chrissie, asking for her opinion on Kylie’s outfits.

“Well, Chrissie says that she thinks Greg would like the second one best. A shame though, I like the sundress.” Robin shrugged.

MARCI chimed at that remark and while Kyle had just about managed to construct an outfit with sensible shoes, pants and not a stitch of pink anywhere, the screen suddenly froze as he tapped the confirm button.

“No! What’s wrong?” Kyle demanded as he fruitlessly tapped the button with his manicured finger.

“New information has been added to my databanks. Your intent to impress Greg will be achieved with this outfit. Commencing dressing sequence.” MARCI stated.

“No! Stop it, you stupid computer!” Kyle moaned as the arms seized him and pulled him into the bathroom to begin the process.

Over the sounds of the mechanical whirring and the water, the girls didn’t hear much of Kyle’s complaining, but he was certainly giving MARCI string after string of expletives as he was washed, re-styled, and dressed in the outfit that Kyle never would have chosen for himself in a million years. But hey, at least it wasn’t pink, right?

Stumbling forward in the heels, Kyle looked at himself in the mirror, his makeup having been immaculately done, with shiny kissable lips and dark inviting eyes. His hair had been restyled to match his outfit, brushed out straight, although with some volume to it. Kyle also uncomfortably adjusted because he was wearing a tight white strapless bra underneath the tank top, and a white thong underneath the miniskirt. The black heeled sandals, which featured just a strap over his toes and an ankle strap, also featured a stiletto heel, sure to **** Kyle to take short mincing steps the entire night.

“Fab-u-lous!” Darla exclaimed.

“Greg is going to go nuts for you tonight!” Melissa added.

“Selfie time!” Robin beamed.

And so Kyle got **** into an impromptu photoshoot as the girls **** him into all sorts of seemingly suggestive poses for posting on his burgeoning social media accounts.

The only saving grace was the fact that they didn’t make him send any photos to Greg, wanting to preserve the surprise.

That ate up some time, and a few hours later, Kyle was standing in the foyer with a purse hanging from his shoulder as the girls chattered on about what he should be doing on the date.

“You’ve got this, girl.” Darla beamed. “Can’t wait to hear all about it in the morning!”

“Have fun,” Melissa said, giving Kyle a reassuring hug. Or at least a hug that Melissa thought was reassuring, in practice it made Kyle even more nervous.

*DING DONG*

“Mistress, Greg has arrived. Shall I let him enter?” MARCI asked.

Kyle simply shrugged, which MARCI took as a yes and the door slid open, revealing Greg, carrying flowers and wearing board shorts and a short-sleeve button down shirt.

“Wow…” Greg’s mouth dropped open. “You look incredible! And I look… underdressed.”

“No, you look great, doesn’t he, Kylie?” Darla chimed in.

“Uh, yeah…” Kyle said.

“Anyway, uh, these are for you.” Greg held out the flowers, which Kyle reluctantly took into his manicured fingers.

But just as quickly, MARCI grabbed them out of his hands and into the air.

“I’ll put these in a vase. They’ll look lovely on your end table, Mistress.” MARCI stated.

“Well, that’s one way to accept them, I guess.” Greg chuckled. “I’ll never get used to MARCI.”

“You can say that again…” Kyle muttered.

“Shall we go?” Greg asked.

Kyle looked back towards the girls, who gave him an encouraging smile, and then back at Greg. There was no way he was getting out of this, so he just had to bide his time until it was over.

“Yeah, let’s go.” Kyle said, and followed Greg out of the house.

Greg opened the door of his car once more to let Kyle in, and he struggled to sit comfortably with his thong riding up his ass.

Greg opened the conversational floor with some small talk and pleasantries, complimenting Kylie a few times and asking about Chrissie. Kyle gave answers as best he could, with MARCI’s prompting making sure that he was being an attentive date.

As Greg kept driving however, Kyle began to wonder what Greg had planned, as they didn’t head towards the nearby city center, instead they were cruising along a highway heading deeper into other suburbs and gated communities.

“Where are we going?” Kyle asked.

“Well, I wanted it to be a surprise, but since we’re almost there, I’ll tell you.” Greg replied. “We’re going to…”