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Chapter 42 by LordScissorsXIII
Bruce May Owe Jenny an Apology Later
Jenny's Date (Part Three)
(I would like to preface this by saying that the art generator really hates Risky. I understand the picture in this chapter doesn't really match Jenny's outfit but I still decided to use it as it at least looks similar to Risky and is mainly there to help show how large her chest is now. If these not quite right Risky picture bother people I'll stop using them so let me know.)
It took everything Bruce had to keep a straight face and not stare. Jenny's breasts had at least a cup size by now, her face was flushed, and she kept squirming in her seat. I guess that's what 13 rounds of Mario Kart full of loaded questions will get you. “Are you sure you're okay?” he asked. “Your driving is getting worse and you keep breathing heavy.”
“For the last time I'm fine” she snapped. Another slight increase. “Stop worrying about me and focus on the race.”
Right now Bruce was both happy and sad that Jenny seemed to have stopped wearing the skull part of her top. On the one hand the sight of those increasing melons spilling out of the skull would be a sight to behold, but on the other hand if she was wearing it she would have noticed her increase when they became to big to fit in the skull comfortably. Coming in first again he quickly turned his gaze back to Jenny to see her reaction.
“Mmmmm” came from Jenny. She had her lips pressed tightly together to keep the moan from escaping her mouth but couldn't stop her legs from moving as she tried to suppress the pleasure.

Time for a final push Bruce thought. “Hey Jenny.”
“Y-yeah? What do you want?”
“I was thinking about making the next race interesting. How about a wager?”
Jenny's eye twitched. “I don't see any reason for something like that” Jenny said nervously. “Normal races work just fine right now.”
“Just hear me out” he said. “I noticed that you're still only wearing one shoe. I was thinking you could wager your remaining shoe. If you win I'll convince Sally to give you your other shoe back.”
“I-um-how do you even know she'll agree to that? The bet wouldn't be fair if she didn't agree so no deal.” Jenny looked relieved to have found an out to the bet.
“That sounds super fun” a voice said from behind Jenny. Jenny slowly turned around to see Sally behind her.
“What are you doing here?” asked a nervous Jenny.
“My ears were burning and I just had to see who was talking about me. And I just so happened to overhear your fun sounding bet. I'd be more than happy to wager the shoe Jenny threw at the master on your next match.”
All her outs gone Jenny felt her compulsion kicking in again. “Fine” she finally said sounding defeated.
“I'll even let you pick the course” Bruce said. “May the best racer win.”
Jenny immediately went for the course she knew Bruce was the worst at. Toad's Turnpike. The very same track she nearly won on at the tournament if not for Sylvia's interference. They may have made it easier since the N64 but Bruce is still notorious for running into cars. I can win this.
As the race started it wasn't long before Bruce started driving into cars. Unfortunately for Jenny she wasn't doing much better with her very high state of arousal distracting her. Still as they entered the final lap Jenny was taking the lead and had a banana peel for protection. I can't believe it. I'm actually going to win!
“Say Jenny, I was wondering” Sally began to say.
Ignore her. She's just trying to distract you thought Jenny.
“Have you noticed that your breasts have grown by about 1 and a half cup sizes?”
What? Jenny thought. No, wait. Ignore her. That doesn't even make sense. Unable to help herself Jenny glanced at her reflection in the glass of one of the game cabinets. Wait. THEY ARE BIGGER. Head shooting down to look at her now enlarged chest Jenny didn't even notice as her character careened straight into one of the vehicles on the track. Hearing Bowser's crash cry she looked back up to see Bruce zoom past her and over the finish line. As the race ended she felt herself hit by another wave of pleasure. It's taking everything I have at this point to not shove my hands down my pants right now.
“Aww, you lost” Sally said with false sympathy. “But that means you lose the bet which means this now belongs to Bruce.” As she finished her statement Jenny's shoe disappeared from her foot and reappeared in Sally's hand.
With the loss of her shoe Jenny was hit by another wave of arousal as the protection of her shoe was lost. I can't take it anymore. Unable to resist the unbearable amounts of arousal that had built up in her over the night anymore, Jenny's hands shot down into her pants and started going to town on her pussy. One hand massaged and pinched at her clit while the other pumped her fingers in and out of her lower lips. Oh mercy that feels good.
Bruce watched on with rapt attention, not expecting Jenny to break down this much but definitely not complaining about it either. Sally meanwhile casually walked over to a trophy cabinet that had some of the trophies Bruce had won in it. She opened it up and placed Jenny's lost shoe on an empty pedestal as if to rub it in the girl's face that she had lost it to Bruce.
As Jenny continued to masturbate in front of them she managed to stammer out a question. “Wh-why are my b-boobs so big?”
“Oh, because of your secret transformation of course” Sally said with a giggle.
“Tr-trans-sformation?”
“Yup.”
Pinocchio Tits- Lying comes to Risky as easily as breathing. From now on whenever Jenny lies her breasts will grow. Admitting the truth will undo that lies growth (Pirate Queen)
“When d-did I get that?”
“It's Bruce's secret transformation. Each week he gets to pick one of you to get an extra transformation that you won't know about until I decide to give it to you. I gave you yours as soon as you entered the master suite. Speaking of then I still haven't punished you for losing a VP for being late. Let's do that now, shall we?”
Pinocchio Tits- Lying comes to Risky as easily as breathing. From now on whenever Jenny lies her breasts will grow. Admitting the truth will undo that lies growth. Caught in the Lie- If someone calls Jenny out on her lie and declares what it is before Jenny her chance at undoing that growth will be lost.(Pirate Queen)
“You have g-got to be kidd-ding me.” Jenny was having trouble focusing as she approached her climax. Having already been very worked up it didn't take her long to reach an orgasm. She screamed out as her body shook as the crotch of her pants turned dark. She slumped back against the couch drained of energy.
Masturbated for the Master + 3 VP First Bonus X 2
Bruce couldn't believe his eyes. He had just seen something he didn't think he would see even in his wildest of dreams. I just watched Jenny masturbate.
As she began to recover Jenny tried to reflect on all the lies she told over the course of the night. “What all did I lie about? Um, I lied about my terrible luck. I really am quite unlucky.” Her breasts shrank back down a little. “Yes! Let's see, what else.”
“You lied a lot about not caring that you were losing the competition” Bruce chimed in.
Jenny glared at him. “What did you do that for? Most of my lies tonight were about that. You did that on purpose didn't you?” Bruce said nothing but just smirked at her in response. “Wait a minute. You've been goading me into lies all night. You set me up.” Grabbing the controller she had been using Jenny reared her arm back to throw it at him. As she went to throw it she saw her shoe in the trophy case and remembering last time course corrected and instead chucked it at the wall. Glaring at him for a minute she stormed out of the room loudly declaring that she was going to bed.
Bruce followed her back out into the main room to see that she had taken a bunch of pillows and was using them to form a wall in the middle of the bed. “My side” she said pointing at one side. Pointing at the other she declared “your side.” She then threw herself under the sheets and turned away from him.
Bruce chuckled to himself as he went to change into a pair of sweatpants. _Jenny is always fun to watch. _Crawling under the covers on his side of the bed Bruce closed his eyes for the night and started to drift to sleep.
A Bad Night For Jenny but At Least She Finally Starts to Climb Out of Her Hole
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Harem Hotel
A reality show to alter reality
A reality show in which contestants compete for one lucky man or woman's affections, and are changed until they can.
Updated on Jun 19, 2026
by legolus
Created on Jan 9, 2022
by AliC
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