Quintuple Date (Part 3)

“After you” Bruce said as he opened the door to the entertainment room with a flourishing bow.

Gwen released the breath she had been holding as they finally entered the entertainment room. Which in actuality did not take long at all as the entertainment was the second door in the hallway but to Gwen it had felt much longer as her eyes scanned every door in sight for signs of the sex dungeon. Hearing the door click shut behind her Gwen whirled around in a panic as she realized Bruce was now behind her. “Are you sure you are okay?” Bruce asked confused by Gwen's odd behavior. “You seem really jumpy tonight.”

“Huh, oh no I'm fine” Gwen answered mentally beating herself up for her inability to calm down. Get a grip Gwen. Bruce may have had sexy times with Lydia in the dungeon but that was her not you. Your just the older girl that works at his favorite store. He has no interest in someone like you. Resolving to put the Lydia night out of her mind Gwen turned back to the TV taking the massive size of it in properly this time. Gwen let out a whistle of appreciation as she took the beautiful piece of electronics in. “Whoa. We may have the same channels but your TV is still way better than mine. Eyes drifting to the left of the TV Gwen's vision caught sight of the massive collection of consoles hooked up and all thoughts of Lydia flew straight from her mind. Rushing forward to get a closer look and confirm what her she wasn't dreaming Gwen began to nearly drool at the impressive sight before her. “Oh my gosh! Is that a NES? And there's a Dreamcast! No way! That's a fucking Pong machine!” Gwen squealed as she stared at the system like it was the holy grail.

“Is that why you wanted the TV? Not that I'm against the idea of playing some games but I expected a more creative date idea from you to be honest.”

Broken out of her fangirling by Bruce's question Gwen turned away from the consoles and back towards him. “What? Oh no that's not what I want us to do at all.” Pausing Gwen turned back to the wall of systems with a hungry gleam in her eye. “Although...” After a moment of thinking Gwen shook her head and turned away. “No. Maybe next time. What I want is to share a show with you. Now give me the remote and sit.” After receiving the remote Gwen flopped down onto the couch next to Bruce and turned on the TV. “I discovered another season of Harem Hotel while I was flipping channels earlier” Gwen explained as she began to surf through the channels. “What I saw of it was actually pretty interesting and I thought as long as we're trapped here it might be a good idea to get an idea of what we're in for. Now if only I can find the channel again. There's a ridiculous amount of them on here.”

“You didn't memorize the channel of the show you wanted to share?” Bruce teased. The glare Gwen sent his way was not at all weakened by Kisala's cute face and Bruce decided to switch to a more helpful stance. “Maybe you would have an easier time checking the TV guide?” Bruce offered picking it up off of the end table next to the couch and holding it out to her.

“There's a TV guide?” Gwen said stopping her channel surfing. Taking the guide that may as well been a phone book from his hands Gwen began to flip through the guide. “Sally must be older than she looks to even know what one of these is. I think most young people these days barely know what cable is.” Both chucked at Gwen's joke before they jumped as a loud scream came from the room's speakers.

“DAMN THIS STUPID DOOR AND DAMN YOUR BITCH OF A DESIGNER!” Both frantically looked around the room in a panic looking for the source of the screaming until they finally realized it was coming from the speakers. Looking at the TV Gwen was shocked to see Jenny standing in the hallway her room was in beating on the door to her room with the putter she was meant to putt open her door with. As the situation sank in both broke out into a real fit of laughter at Jenny's antics. I must of stopped on Jenny's channel. Looks like she still hasn't got a hang of putting her door open. Once their laughter calmed down Gwen decided to leave the channel where it was while she looked for the right channel. Bruce seemed to be enjoying watching Jenny try and fail to sink her putt and she had to admit Jenny was pretty entertaining while she read through the guide. Finally Gwen came across a section in the guide dedicated to Sally's favorite seasons of Harem Hotel. Number 1 on the list immediately matched up with what Gwen's had seen.

“Found it” Gwen cheered triumphantly. “Harem Hotel: The Beautiful Therapist and the Depressed Author. I think you are really going to like this. Lot's of sexy girls. And don't even bother to try denying anything to me. I've sold you basically every video game you've gotten since you were 13” Gwen teased as she began flipping to the right channel. Bruce and Gwen both settled in to watch as the show opened up to a scene in a therapist's office.

Seventeen? Candy angrily questioned in her head as she stomped her way through the halls of the hotel. Realizing she couldn't get into her room on her own with her arms still bound and her having seen Sylvia wonder off in a daze she decided to just wonder around for a bit. As she wondered she decided to check the tally in her head of the total of yesterday's orgasms confident that she could easily hit the quota as the number would be one at most if not zero. Appallingly she was not even close to the correct number. We were literally all bound to each other yesterday? How is the number that high? I thought there might be one since I was fairly certain that Gwen orgasmed at least once in that ball pit but no matter how sensitive she is now there is no way she did it seventeen times. I was really counting on that low number considering my own sensitivity is on an uptick because of this stupid transformation upgrade which I'm 90 percent sure that bitch Lydia is behind. Well there's no way I'm hitting that number since Sally skipped half the day and my arms are still bound. Which I guess is at least one upside to Sally moving the challenge sooner. Once the round is over I can finally get rid of these ropes. As she continued to wonder the halls Candy couldn't help her mind drifting back to that seventeen and the origins of the high number. Seriously did one of the pairs just spend all day getting each other off? I'd blame Jessica and her ridiculous libido but she's way too awkward to do that with one of the other's. This train of thought continued to plague Candy's mind as she stalked the halls of the hotel.

Nikki gripped her controller tightly as she sat curled up on the couch as she frantically tried to kill Marluxia before that stupid doom counter hit zero. She had her legs folded up and pressed as close to her chest as she could holding the throw pillow she had taken from the couch against her chest protecting her modesty as best she could. “And that's **** number 1” Bruce said unhelpfully from his chair near the couch. To Nikki's surprise after Bruce had switched the game to her saved data, which was on here for some reason, Bruce had plopped down in a big recliner chair a bit away from the couch instead of next to her. Claimed that since they were trying to recreate her stream he should be set up where he could see both her and the TV at the same time.

I'm so sure it's for the authenticity and has nothing at all to do with me being naked Nikki thought sarcastically. Seeing as she only had an hour Nikki wasted no time starting the fight up again. Thankfully I had all that practice doing this right before I got kidnapped. I may have lost the bet that time but I'll succeed this time.

“Man for a first attempt you sure got close though. If you can keep up that kind of performance up you might actually beat all thirteen in the hour.”

“Naturally” Nikki bragged enjoying the praise. “I almost succeeded when rusty. Having gotten all that practice recently there's no way I can lose.”

“Oh? Someone's confident aren't they? Speaking of since we're recreating the steam and all does that mean the stakes of the bet are still on?”

“What? No of course it isn't. The bet is for chat to pick the next game I stream if I lose and last time I checked I'm stuck at a psycho hotel and not streaming. Plus seeing as your one person and not chat I get no extra engagement or any benefit from wagering with you at all.”

Bruce sighed. “I guess that's true. I don't really have anything to offer you if you w...” Bruce stopped mid-sentence as a small circle of swirling blue and orange energy appeared next to his face. Nikki screamed as an arm began to stretch out from the small portal and poke Bruce in the cheek with a small piece of paper. Nikki didn't even notice poor Sora get comboed to **** as Bruce reached up and took the paper from disembodied arm. As Bruce read the paper the arm waved at Nikki and then sank back into the portal which vanished as soon as the arm was gone. Bruce smiled as soon as he finished reading the paper. “I think I now have something to offer in the wager” Bruce said smugly. Turning the paper to face Nikki was stunned to see the contents. On the paper was a picture of Sally in some kind of slutty teacher's outfit. More important was the bold text next to her.

Principal's Pass- This pass is usable when the holder would take part in a round of transformations. The holder instead of taking part in a transformation vote may instead choose another harem member and they will receive a second set of transformation options in the holder's place. Good for one use.

“Well?” Bruce teased. “Do you want it?”

Of course I want it Nikki thought as she stared at the paper with desire visible in her eyes. After seeing some of the transformations some of the others got I'd offer damn near anything to get my hands on that. Wait. Keep calm. Don't seem too eager. “Well I suppose that would be an acceptable offering. Depends on what you would want me to wager” Nikki said unsuccessfully trying to keep the want out of her voice.

“Hmm” Bruce mused to himself as he put on an exaggerated thinking look. “Well, I do so love your attire this evening. What say you that if I win you repeat the look for our next date?”

A few moments passes as Bruce's offer sank in in Nikki's mind. WHAT? Nikki mentally screamed as her face turned even redder than it already had been.

Akane slowly rolled over as she lay content passed out in her bed. She wore a small smile on her face as she happily replayed the fun evening she had with Bruce in her dreams.

Luanne stared dumbfounded at her reflection in the bathroom mirror. After screaming Luanne had immediately bolted for the nearest door in the suite. Thankfully for her it had turned out to be the bathroom. Locking the door behind her Luanne had taken a few moments to calm down before trying to properly take stock of her current appearance. Her hair was as smooth and shiny as if she had gotten a professional to do her hair at a fancy salon. Looking closely she barely managed to notice that she was wearing makeup but it was so expertly applied that she had to nearly press her face against the mirror to see it. Noticing a pleasant smell in the room Luanne was confused since she was in a bathroom and couldn't find an air freshener. After a minutes search she realized that the pleasant smell was coming from her. Finally running out of things to check with a sense of dread Luanne turned her attention to the outfit she was wearing.

Can I even call this an outfit? Luanne thought as she checked herself out in the mirror. This is the most scandalous outfit I have ever seen. It gives the illusion of covering everything important but only just. Sure my breasts are covered in the front but the coverage on the sides is basically nonexistent and with how big my breasts are now that's a lot. Speaking of lack of coverage this thing doesn't cover my back at all. The only fabric back there is covering my butt but it might as well not with how little fabric there is. The only thing properly covered is my vagina but the sweater is so short I could show it off at any second if I don't move carefully. And of course that psycho maid didn't give me any underwear.

Luanne was broken out of her thoughts by a soft knock at the door. “Princess. You've been in there for a while. Are you okay?”

Speak of the devil. “No I am not okay” Luanne whisper yelled through the door. “I woke up to find out I'm dressed like some kind of slut in front of my childhood friend that I haven't seen in a decade.”

“Can I take that to mean that you intend to hole yourself up in the bathroom and ignore your date Princess?”

“Yes that is exactly what I am going to do. I am not coming out until you bring me some proper clothes.” Luanne smiled triumphantly when she heard Kirumi sigh on the other side of the door.

“In that case Princess I have **** but to come in.”

“And just how do y...” Luanne had to take a quick step back as Kirumi phased right through the door and stepped into the bathroom. “Oh. I guess I should have seen that coming with everything else you're capable of.”

“Now let's get this problem settled so that you can go out there and have a nice date with your master. Do you have a problem with the preparations I did for your date Princess?”

“Yes I have a problem. Your help is terrible. First you buy me this terrible transformation that has me groping myself every five minutes and now you dress me up in this, this...”

“It is called a virgin killer sweater princess” Kirumi explained passively.

“Thank you. This awful virgin killer sweater. Why on earth would you think any of this is helpful?”

“I put a lot of thought into the things I bought for you Princess. Firstly everything I bought was to help you better appeal to the master which based on his reaction has worked out brilliantly. Secondly all of my purchases were carefully chosen to fit in with your fetishes of exhibitionism and humiliation.”

“My fe..I don't ha..what are you talking about?” Luanne sputtered. “I have no such fetishes. As embarrassing as this is to admit I'm a virgin. A week ago people were more likely to ask me where my parents were than to ask me on a date.”

“I'm afraid you are mistaken Princess. Your fetishes have no connection to you being a virgin and our research is very thorough. Even if you are unaware of your fetishes I can assure you that we are not.”

“This, this is slander” Luanne shouted.

“Can you honestly tell me Princess that you never got turned on when being treated like a child in public? That the embarrassment of the situation never got you going?” Kirumi paused for a moment before taking Luanne's incoherent sputtering as a go ahead to continue. “It seems that I miscalculated in my assistance Princess. We must first make you aware of your own fetishes before we can properly work on appealing to the master. So I offer you this deal. You will go out there and spend the evening talking with the master. If you can go the entire night without getting aroused, discounting any arousal directly brought on by your groping yourself, I will refund every purchase I made for you this round. Deal?”

That got Luanne's attention. Everything? Even the transformation? Luanne nodded so fast she looked like a Tifa bobble head. It will be embarrassing but totally worth it. There's no way I have fetishes like those. Kirumi opened the bathroom door and bowed as Luanne made her way out and saw Bruce sitting in a chair. She did her best to remain confident and not hide as he stared at her. _This will be an easy win_.

Once more Jessica found herself standing naked in front of the mirror in her bathroom. I still can't believe it. I keep expecting to wake up and find it all a dream but I really have become the hottest video game character I've ever seen. Reaching up to grab one of her breasts Jessica began to slowly knead the large mound of flesh. I didn't get to get off yesterday thanks to being bound to Jenny but today Alex is spending the night in the master's suite. That means there's no one to interrupt me and I can go as long as I want. Sorry Candy but since tomorrow's the challenge day you probably weren't going to make tomorrow's quota anyway. Jessica watched her reflection as her free hand began to move closer and closer to her eagerly waiting pussy. Time to break a record.

Alex sighed as she let the soothing waters of the shower rain down on her. She grumbled to herself as she began to lather up some soap. “I can't believe I'm stuck up here with Bruce while some kind of copy Bruce probably tries to **** himself on Daisy. I can't believe that girl ditched me like that. This rebellious phase of hers has been cute but now she's taking things too far putting herself in danger like that.”

As Alex began to wash the sweat from her body she felt a tap on her shoulder. “Excuse me but can you pass me the soap?”

“Oh sure.” Alex said calmly as she passed the person behind her the soap.

“Thanks” said the stranger.

Wait a minute Alex thought as she froze. Realizing what had just happened Alex whirled around to find a naked Sally beginning to lather up a loofah. Alex glared daggers while Sally hummed to herself as she finished. “What do you think you are doing?” Alex growled at the naked host.

“Showering, duh.” Alex's glare only intensified which just served to make Sally giggle. “Fine angry pants, we'll get straight to business then.”

“Business?” Alex questioned.

“Of course silly. You were late to your date and lost points as a consequence. Surely you remember what happens when you lose points while in the negative, right?”

Crap. “Punishment, right? Well bring it on you sadist. It's going to be hard topping that dress so bring it on.”

Sally sighed but continued to bath herself. “I don't enjoy inflicting these punishments you know.” Sally paused for a moment. “Okay I do enjoy it but not like this. Not when your just self destructing like this. Do you know what kind of awful things would have happened to you by now on basically any other host's show?”

“So what, I'm supposed to be grateful? Fuck that and fuck you.”

“See now that's the right attitude. Keep that up and you can do so much better.” Alex just raised an eyebrow at the excited airhead. “Oh. You meant that in the insulting way. That makes more sense I guess” Sally said with another sigh. Then a sadistic grin took over her face. “Well I've got something special for you this time. It seems just the threat of punishment isn't enough to keep you from self destructing so I'm going to give you some proper motivation. It's punishment time!” Sally cheered as she struck a pose.

Love the Dress – Alex needs some motivation. From now on any embarrassment she feels from her punishment dress will cause an equal amount of arousal. This effect is only active while Alex has a VP score of 0 or below (Punishment Tomboy Princess)

“Enjoy” Sally chirped as she vanished into thin air.

Alex paused for several seconds before throwing her loofah where Sally was a moment ago. “BITCH!”