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Chapter 108
by
vanillathunder
Where is Greg taking Kyle for their date? Maybe an intimate picnic on the grass? Or maybe dinner with his family? Or an event at his country club?
An intimate picnic on the grass
“My place to have a picnic on the grass.” Greg finished.
Of course, Greg was the master of understatements, because while Kyle had gotten used to huge mansions over the past few days, Greg’s family apparently dwarfed Melissa, Robin and Darla in terms of magnificence. As Greg’s car pulled up to a large gate, it opened and inside sprawled a palatial estate with rolling green hills, a hedge maze, and a large mansion capping it all off in the middle.
“Woah…” Kyle’s jaw dropped.
“It’s pretty amazing, although we don’t have an advanced AI to take care of us, so I think your uncle still has us beat…” Greg chuckled.
“Trust me, MARCI isn’t all she’s cracked up to be…” Kyle muttered under his breath.
Greg didn’t seem to notice the comment and kept driving until he reached a meadow behind the house under the shade of a large oak tree.
“And we’re here!” Greg grinned as he put the car into park.
He quickly unbuckled himself and got out of the car, rushing to the other side to open Kyle’s door, and help him out of the car. Still on the road next to the grass, Kyle took a step into the grass, before realizing that the heels he was wearing were not conducive to walking through grass, as the heel began to sink into the dirt.
“Mistress, I advise that you remove your shoes before walking on the grass, as injury may occur.” MARCI stated.
Thankful for the go-ahead to remove the dreaded heels, Kyle knelt down to try to unbuckle them, while Greg reached into the trunk of the car and pulled out a large picnic basket. Having some difficulty, Kyle wasn’t finished when Greg walked up with the basket.
“Oh, I probably shouldn’t have kept this a surprise so you’d have worn different shoes.” Greg said, bashfully. “But it’s all right, I’ll guide you through.”
Greg held out his arm, which Kyle hesitated before taking, but realized he could just unbuckle the heels while sitting, which might be easier. Greg led Kyle across the grass to the tree and left Kyle leaning against it, while Greg started to set up the blanket, unfolding it and splaying it across the grass.
“This place is beautiful…” Kyle found himself muttering. Despite everything, this meadow was immaculate.
“Thanks, I’d hoped you’d like the place.” Greg smiled. “Take a seat while I get everything ready,”
Greg helped Kyle down onto the blanket and Kyle started to unbuckle the heels, clenching his toes to relieve the pain he was already feeling from walking in them.
“I decided to go for a traditional picnic, I hope you don’t mind. So I’ve got some cold cut sandwiches, potato salad and fruit salad.” Greg said, as he started taking tupperware containers out of the basket.
“Wow…” Kyle’s mouth began to salivate at the spread of food that he knew MARCI wouldn’t be happy about later.
“And, I lifted this out of my parents’ cellar so we could have some fun…” Greg chuckled as he pulled out a bottle of wine.
“Wine? But we can’t…” Kyle started.
“I won’t tell if you won’t,” Greg smirked.
Given the week he’d had, Kyle had no problem taking a glass of wine after Greg had poured it and quickly draining it, letting out a resounding sigh when he finished it.
“Woah, looks like you were thirsty…” Greg remarked.
“Oh, uh, well…” Kyle didn’t really care what Greg thought, but it probably wasn’t a good idea to make himself out to be an alcoholic. Especially when he was being perceived as a girl. Greg seemed nice, but Kyle knew that appearances could be extremely deceiving.
They sat in silence for a few moments as Kyle nibbled on his sandwich. Greg turned to Kyle and smiled.
“You look beautiful tonight…” Greg said, looking down into Kyle’s eyes.
As Kyle looked up at Greg, he started to get lost in his eyes. Those gorgeous, ocean-blue eyes that would drive any girl wild, and his rugged chin, and the way that his pecs glistened in that one Instagram photo…
Shaking his head, Kyle tried to fight off the thoughts, little did he know that MARCI had been inundating him with subliminal messages imbued to cause just such a reaction. If Kylie wanted a boyfriend, she’d need to stop sabotaging herself, and this was the first step. And the wine was releasing his inhibitions just enough that he would let MARCI’s programming seep into his normal behavior.
“So, Greg… You play lacrosse, right? Tell me about that!” Kyle said, **** to change the subject.
“Oh well, you know, my school is the two-year reigning champ of the county, I’m the goalie, which some say is the most important position on the field.”
“I bet, you’re the last line of defense after all…” Kyle gushed, hoping this would be enough to keep his mind off of anything romantic. “Tell me about your strategies!”
Greg started to prattle on about lacrosse, and try as he might to focus on the technical sports terms that he surely knew, Kyle’s mind kept shifting downwards.
“Dammit,” Kyle thought. “Stupid MARCI, stupid girls, I can hardly ignore it when it’s all they ever talk about…”
He tried to focus on things other than the thong riding up his ass and Greg’s package, like the lipstick stain he left on the wine glass. Just another reminder of the feminine web he was trapped in.
“Want another drink?” Greg held out a refilled glass to Kyle, breaking him out of his thoughts.
In response, Kyle sputtered and accidentally waved his hand into the glass, knocking it back and spilling the contents directly onto Greg’s clothes.
“Oh my god! I’m so sorry!” Kyle immediately grabbed a napkin and began to blot at the spill, immediately realizing that in his hurry, he’d gravitated directly to Greg’s crotch.
“It’s okay, really, it’s just a little spill.” Greg said.
Pausing, he looked worriedly into Greg’s eyes, his hands resting squarely on top of Greg’s member, which was straining through the board shorts he wore.
“Unbutton his shorts.” MARCI ordered.
Normally, Kyle would have ignored that until he was **** to comply through “corrective measures” but between the ****, subliminals and his general nervousness of the situation, he followed the instructions without a second thought.
“Woah, are you sure about this, Kylie?” Greg asked, sitting up slightly.
“Now unzip his shorts.” MARCI instructed.
This time, Kyle had a slight bit of trepidation, Greg’s comment having temporarily overridden the autopilot.
“Unzip his shorts, Mistress. Failure to do so…” MARCI was cut off as Kyle began to unzip the shorts.
Doing so gave Kyle a view of Greg’s boxers underneath his shorts, and the outline of Greg’s dick through the boxers was clearly visible. Looking at Greg’s engorged member, Kyle’s eyes nearly bulged out of his skull. Sure, he thought his own temporarily trapped one was at least average, but Greg’s was something else! He’d probably need both hands for that! That is, if he intended on doing anything of the sort, which he didn’t. He needed to fight MARCI’s conditioning, or the buzz from the **** or whatever this was! Kyle tore his gaze away to look up at Greg, who had a look of concern on his face.
“Listen, Kylie, you don’t have to do this if you don’t want to. I know what your friends are like, I know what Chrissie is like, but you seem… different. We don’t have to jump into any of this until you’re ready.” Greg insisted.
Gosh, he was such a gentleman, everyone else was trying to **** him to do things, the girls were forcing him to go on dates, MARCI was forcing him into these sexy outfits, even Sam was forcing him to keep living this nightmare instead of fixing it, but Greg was the only one who cared what Kylie wanted… what Kyle wanted. Between both dates, Greg had never been anything but kind to her… him. There had to be a way to show his gratitude to Greg.
As Kyle ran through the situation in his head, his hands had a mind of their own, quickly getting Greg’s penis out of his boxers, where it stood fully erect. Kyle stroked it for a moment, wiping away a drop of precum that had leaked out.
MARCI had determined a psychological profile for Greg, based on his social media accounts, her recordings of his interactions with Kylie and testimony from Kylie’s friends, and had determined such: Greg was a kind, caring potential partner, hyper-masculine and athletic, but also very intelligent. He wouldn’t take advantage of Kylie, but once Kylie provides her consent, he will have no problem taking a dominant hand in their relationship.
“Are you sure about this?” Greg asked, taking Kyle’s free hand in his.
“Say yes,” MARCI instructed.
Kyle wanted to say no, of course he did, but he couldn’t deny the… curiosity that he felt. Not to mention the feeling of his own trapped member stiffening inside the prosthetic. Why was this turning him on? But he didn’t necessarily have to do anything with his mouth, he could just use his hands, that’s how MARCI had started the training anyway, he could save the rest for the next date.
Wait, why was he even entertaining this idea? Could he fight MARCI’s programming? What was Kyle going to say? As Kyle opened his mouth to reply, even he would be surprised by what came out.
How does Kyle respond?
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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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