Disable your Ad Blocker! Thanks :)
Chapter 105
by
vanillathunder
Do the girls show up to get "Kylie" ready for her date? Or does Kyle have some time to himself?
Kyle has some time to himself
With a start, Kyle sat up in bed, panting heavily. As he struggled to catch his breath, shaking the sleep from his brain, he found himself with very little memory of what exactly he dreamed about with each passing second. But knowing what his waking hours consisted of, he knew his nightmares were probably somehow worse. Steeling himself for what was to come, Kyle realized that with it becoming part of his daily routine, he felt less and less shame about it, even if it had only happened twice so far. But it was definitely the routine that was causing it and not Kyle actually liking it. Although one could argue that sexual release, in whatever form it takes, is nothing to be ashamed of at all. Even if Kyle was a man being **** to orgasm like a woman.
As the ball gag was secured in his mouth and MARCI began to get to work, it was all Kyle could do to focus on the situation in a coldly logical way, even as MARCI piped in simulated voice clips of Greg’s voice and showed images of him projected on the ceiling. But Kyle wasn’t attracted to Greg, couldn’t be attracted to Greg, however, with this much pressure and outside influence, he could hardly help what images and sounds were present during moments of intense pleasure, could he?
“Mmph!” Kyle exclaimed as he climaxed for the second time.
After being cleaned up, and showered, MARCI chose to dress Kyle, after putting his hair up in a messy bun, in a short pink bathrobe and a pair of fuzzy slide slippers, also pink (naturally), which also showed off Kyle’s still perfectly pedicured toenails.
“What? Run out of ideas, MARCI?” Kyle muttered.
“My systems show that you will not need to get dressed for your date for several more hours, Mistress. Would you prefer to change into your outfit now?” MARCI asked.
“No!” Kyle shouted. “I’m okay with this!”
“Very well, mistress. Your presence has been requested in the kitchen for breakfast, along with your brother at the request of your uncle.” MARCI said.
“Oh, okay.” Kyle said.
He made his way downstairs to the kitchen to find Sam, still in his pajamas, a far more masculine ensemble of t-shirt and flannel pajama pants, nursing a mug of coffee at the kitchen island.
“Hey,” Sam muttered. “Any idea what Uncle Mark wants us for?”
“I’ve stopped trying to figure out why anything is happening in this god forsaken place anymore…” Kyle grimaced. “Having fun with Chrissie? Or are you back with Kim?”
“Never hurts to have options,” Sam smirked. “Besides, I hear you’ve got options too. What are you, up to three now? Or so Robin tells Chrissie.”
“You know I don’t want any of this you…” Kyle was about to give Sam a piece of his mind when Uncle Mark walked into the room, fully dressed.
“Hey, kids! Glad you could make it, I’ve got some news to share with you. But first, I need my coffee. MARCI, the usual!” Uncle Mark exclaimed.
“Coming right up, Master Gladstone.” MARCI responded and a hot mug of black coffee quickly came out of a hole in the kitchen island.
“Can I get a coffee as well, MARCI?” Kyle asked.
“Certainly, mistress. I’ll prepare it according to your preferences.” MARCI responded, and after some buzzes and whirs, a plastic tumbler was produced containing what Kyle presumed to be the most accurate recreation of what the girls would have ordered for him at the coffee shop.
Kyle would have argued, but that was proving less useful by the day and maybe if he just accepted that this was how things would be until Sami and Amy returned with their passcodes, things would go smoother.
“What the hell am I thinking?” Kyle thought to himself. “I’ve still got to fight this!”
But before he could give himself more of a pep-talk, Uncle Mark jumped back into the conversation.
“So, as I explained last night, the company just made a huge acquisition, but because of that, I need to take a quick overseas trip. Normally I’d ask if you wanted to tag along, but this is just going to be purely business and it’ll barely be a few days, and I figure you’ve probably both got plans with your friends here.” Uncle Mark started, giving a slight smirk as he did, directed at both boys. “So I’ll be back Sunday night, but you’ll have to get along without me until then. And I’m leaving MARCI in charge.”
MARCI made an audible chime at that remark.
“Obviously she’s a computer, so she can’t do any harm to you, nor can she hold you against your will or anything like that, but if you have any problems, she’s authorized to handle them.” Uncle Mark said.
“But!” Kyle tried to argue.
“Don’t worry about anything, Kylie and I can handle ourselves.” Sam interjected. “Kylie’s got a hot date tonight anyway.”
“Just what I wanted to hear, Sam! And Kylie, be careful.” Uncle Mark said. “See you when I get back!”
And with that, Uncle Mark left the room, leaving Sam and Kyle alone.
“What was that for?” Kyle asked.
“What? You do, don’t you?” Sam replied.
“I’m gonna kill you!” Kyle went to grab Sam, but suddenly the doorbell rang out.
“Mistress, your friends have arrived. Shall I let them in?” MARCI asked.
“Have fun on your date, and Chrissie says Greg’s really looking forward to kissing you again!” Sam mocked as he quickly slipped out of the kitchen, much to Kyle’s consternation.
Trudging over to the front door, Kyle sighed as MARCI opened the door and the three girls came into the house.
“Kylie! It’s time!” Darla exclaimed.
“If Greg thought you looked good for Date #1, then he’s gonna get his socks knocked off tonight.” Robin added.
“Shall we head upstairs to get you ready?” Melissa asked.
It was going to be a very long day for Kyle.
What do the girls pick out for Kylie to wear on her hot date?
Disable your Ad Blocker! Thanks :)
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
- 6,620 Likes
- 1,308,401 Views
- 704 Favorites
- 572 Bookmarks
- 469 Chapters
- 110 Chapters Deep
- All Comments
- Chapter Comments