Flaunting Fashionista (i) and a Random Event

Cindi eventually decided on Flaunting Fashionista since it sounded fairly harmless. After pressing the option, however, a pop-up appeared.

Random event triggered: Instant Upgrade! Flaunting Fashionista will be immediately upgraded to level (ii). User may choose to play a bonus game for the chance to negate the upgrade along side the usual reward of removing a punishment. However, a loss will result in the upgrade proceeding as well as one of the two remaining punishments being randomly applied.

Would you like to play the bonus game?

"That's not fair..." Cindi whispered under her breath. She hated these kinds of random events, they're so annoying to deal with. Her dislike for the gimmick wasn't going to stop her from trying though. She began the level to find that it was the same as the one she had just played. That meant she had a decent chance of winning! She was playing through, mirroring her last game with slight tweaks to fix the mistakes she made. She was so close to winning, she had it!

"Alright that's enough. Sleep, now!" Katy snatched Cindi's phone from her hand and locked it, prematurely ending her game. Cindi begrudgingly let Katy have her way, she did need to let her help after all. She snuggled under the sheets and closed her eyes as Gem Ladies displayed new text behind the locked screen.

Bonus game failed! Flaunting Fashionista will now be upgraded to level (ii) (described below) and a second punishment will be randomly chosen from the remaining options. Selecting... Passionate Debts has been applied as the random punishment. Thank you for participating in the random event!

Flaunting Fashionista (ii) - User gains a strong compulsion to wear fashionable or cute clothing with a slight compulsion to wear sexy clothing. Plain clothing is seen as boring by the user and they will consider them itchy if worn. Additionally, user will derive enjoyment from showing off outfits to others.

"Quick, quick, get up! I forgot to set an alarm and we need to move fast so we aren't late!"

Alex awoke with a start to the sound of the woman yelling at him. He somehow recognized her voice as someone named Katy but he couldn't remember how he knew that. His eye opened groggily as he was forcefully dragged out of bed, not yet fully awake. He felt Katy tug and his head as if pulling something out of his hair and drag some kind of clothing off of him over his head but he couldn't register what it was. The noises of Katy's hurried actions got a little distant for a moment and Alex finally started to take in his surroundings.

He was in a girls room that he had never seen before though for some reason he knew it to be Katy's. How had he gotten here? Why wasn't he at home? Did he just get lucky with this Katy that he seemingly knew? And why was she in such a rush?

Katy then came bursting back into the main bedroom from her walk-in closet, "Sorry I wanted to get your opinion on it but we don't have the time so I had to pick for you." She dropped a bundle of clothes into Alex's arms.

Alex glanced up at her from the pile she had handed him, the look of confusion on his face clear as day, "W-wha-"

"Look I already told you we don't have time," Katy interrupted him hastily, "So that means you have to do as I say and you can't complain, got that? Now go get changed!"

She shoved Alex into the bathroom and he began to sort through the items he was given. Pink panties and a grey virgin killer sweater dress which included an open back and a sizeable boob window. Looking at the outfit, Alex noticed that his nails had been painted pink at some point. He couldn't complain, however. He wasn't allowed to. As he removed his current underwear, not even noticing that they were panties as well, he could not believe he was doing this. At least it's a cute outfit, he thought to himself. In fact if it weren't for the panties he'd probably have no issue with the sweater itself since it looked so fashionable. As he shimmied the dress to rest properly on his curves he noticed just how smooth his skin felt. It was a strange sensation but he wasn't allowed to complain so he dealt with it. He felt incredible exposed between the window in the fabric showing off his puppies and the short length nearly revealing his ass but in the end that was the price that needed to be paid to look good, and besides Katy told him to wear it and he had to do as she said. Before leaving the bathroom Alex noticed his hair was wavy and cascaded down his shoulders as opposed to his usual straight hair. Again, he couldn't complain so instead he returned to Katy.

"Oh you look even better than I imagined!" Katy, now dressed in a casual yet attractive blouse and skirt, ran up to hug Alex as he left the bathroom. "Tell me, what are your thoughts?"

"Well I definitely can't complain," Alex giggled, content but not exactly pleased with what he was wearing.

"I knew you'd like it," Katy smiled, missing the implication behind Alex's words. "Alright it's time to go but first you need to put these on. I checked your shoes earlier and we are luckily the same size. What a miracle!"

Katy placed a pair of strappy silver heels at Alex's feet. They looked to be 3 or 4 inches tall. Alex grimaced slightly, even if they were fashionable shoes he really didn't want to wear high heels. Despite his hesitance he still put them on, no complaining after all.

Once the heels were securely on his feet Alex had his wrist grabbed by Katy and she dragged him out the door into the halls of the sorority. How the hell had he ended up in a sorority last night? Had he been drinking again? He couldn't remember anything involving **** but it seemed to be the only reasonable explanation. Eventually Katy had brought the pair to their destination, a large gathering of the sorority sisters in the backyard of the sorority house surrounding a relatively large yet still clearly budgeted stage.

Upon entering the crowd Katy waved to the woman standing on stage signaling her to begin, "Ladies, ladies! I'll need you all to quiet down. All four contestants have arrived so it is time to begin! As you all know the first of the three challenges is a runway modeling with a slight twist. Each of our lovely contestants will have to model a single outfit as best they can all while dealing with this." The woman raised a small plastic cylinder and the crowd erupted into fits of giggling. "That's right. Each one of them will be equipped with a vibrator as they walk the runway. The challenge here is to be as elegant and beautiful as possible while resisting an orgasm. Our panel of senior sisters will be judging each performance however the scores will not be revealed until all challenges have been completed. Good luck ladies, now come and take your places!"

"Wow, this seems like it'll be one hell of a show," Alex mused imagining pretty girls stumbling down the walkway from the **** of their arousal.

"This is just the start," Katy replied, glad that "Cindi" seemed to be enjoying herself, "Just wait until round 2. That one is the real party. Now come on, you need to get in line."

Katy led Alex to the side of the stage where three other girls were waiting. Two of them clearly didn't want to be here, their appearance had the bare minimum effort put into it and their faces clearly lacked any enthusiasm. The third was definitely invested by comparison, she wore a flowing yellow off-the-shoulder summer dress that perfectly complemented her tanned skin and long dark hair.

"It's nice to see that there'll at least be some competition here," The girl in the summer dress approached Alex, "These other girls seem to have just been bribed to come. I'm Vanessa, by the way." She stuck out her hand to Alex.

"Oh, um, Alex." He shook her hand in response.

"Well nice to meet you Alex, and may the best of us win. I'm looking forward to the challenge." Vanessa turned and got onto the stage, apparently the first to walk the runway. She did a good job at looking natural, strutting and posing on the walk forward but she unfortunately stumbled a bit on the way back.

"Damn it," She swore as she reached under her skirt and pulled out the vibrator, "I was almost perfect but then my knees had to buckle under me." She handed the vibrator off to the next girl and then patted Alex on the shoulder, "Good luck."

Before Alex could ask what she meant she was already leaving. Both of the following girls did terribly compared to Vanessa, neither could walk straight and one of them even fell over before the halfway point. Alex was having fun watching the poor girls struggle until the vibrator was unceremoniously passed to him.

"Wait, wait, wait. I can't do that!" Alex began to panic realizing he was expected to go out on stage.

"Oh come on," Katy turned to him, "It's way too late back out now. Besides, don't you remember our deal? You have to do this."

"Alright fine!" Alex relented, suddenly resolute with what he had to do. Lifting the skirt of his dress he maneuvered the vibrator into his ass.

"Now listen to me, I'm gonna give you some last minute advice." Katy gripped Alex's shoulder's tightly, "All you have to do is walk like normal. I've seen the way you strut your stuff, you're a natural! Just focus on walking and posing and whatever you do, resist the urge to finger yourself." Katy gave Alex a playful pat on his butt as he was ushered on stage.

Alex's heart was pounding in his chest as he began to sashay down the makeshift runway, which certainly wasn't helped when Katy switched on the vibrator remotely. He seductively swayed his hips without even thinking between different poses, each more suggestive than the last. Somehow he was autopiloting his way through despite the growing pleasure he was feeling as the vibrator massaged his prostate. In fact, he was enjoying himself. All the eyes on him were like endorphins being sent directly to his brain. He could feel himself swelling to full mast as he became rock hard until finally, at the end of the runway without making a single mistake, he came.

The vibrator switched off and Alex dutifully pulled it out of his ass as Katy ran over to him, "O M G! You were perfect out there! You definitely won the first round, no doubt!"

"Thank you so much," Alex was ecstatic, "How can I ever repay you?"

"Oh shut up, that was all you," Katy replied, believing that Alex was referring to the results of the challenge, "All you need to do for me is win the second round too. Put on a show that even a seasoned slut would blush at! Speaking of which the next challenge is being revealed now."

The announcer woman from before was back on the stage, speaking to the crowd once again, "What a way to end it, huh? She certainly did well! Moving on to the second round we have the most scandalous of the challenges. As the most popular sorority on campus, Theta Theta Theta expects its members to be experienced and skilled sexually so for this round the contestants will need to preform a faux blowjob on this dildo," She pulled an unrealistically large pink dildo from behind her back to reveal to the crowd, "Joining the panel of judges for this round is Alpha Alpha Alpha's very own head, William!"

Will jogged into view from his hiding place and immediately took note of "Cindi", giving her a wave. While Alex wasn't sure who this William guy was he decided to return the wave so as to not be rude.

"Listen up," Katy snatched Alex's attention away from Will, "The order is reversed this round so that means you go first. Get out there and rock their world!"

"Of course!" Alex was more than willing. It didn't matter that he was about to suck a dildo in front of dozens of people, he had to do it for Katy! He owed her and he wasn't about to be the type of person to flake on debts. He was going to man up and suck that rubber cock like a slut!

The second Alex was on stage he dropped to his hands and knees and began to crawl seductively to the pink phallic planted centerstage. Upon reaching it he eagerly gave long licks up and down the shaft before kissing the tip and letting his lips envelope the length of it in a slow yet steadily hastening up and down motion. This isn't nearly slutty enough yet, Alex thought to himself. He picked up the dildo and hiked up his skirt to tease the tip of the sex toy against his pantied groin. The crowd went wild seeing Alex press the dildo against the lips of his obvious cameltoe. Deciding that that was enough teasing Alex returned to the task at hand. He placed the dildo between his boobies and pressed them together giving a boobjob while his mouth bobbed up and down over the tip, all the while grinding his hips in a humping motion with panties still in plain view. The cheering from the crowd was deafening as Alex continued his display of feminine sexuality for another full minute. Once he finished Alex licked his lips happily, that was definitely enough to pay Katy back. Satisfied, he placed the dildo back where he found it and sauntered off stage.

"Wow. Just wow." Katy was waiting for him clearly impressed, "You worked that cock like a pro! I can see why Will likes you so much."

The two extra girls gave a performance that was subpar, as expected and while Vanessa certainly gave a stimulating performance she was nowhere close to the proficiency that Alex had displayed.

"Quite the performance ladies, well done!" The announcer was back on stage once again, "For the final challenge I'll need the contestants to head inside to change for the wet t-shirt contest! For this round the judging panel will be entirely made up of Alpha Alpha Alpha brothers so be ready to look sexy for them!"

Alex and the three girls were ushered inside by Katy where they were each stripped down to their underwear and given a long white t-shirt to wear. It was at this point that Alex noticed that Vanessa was very well endowed, having at least a pair of D cups. He felt himself stiffen a bit at the sight of her in her underwear and hoped that no one would notice his hard-on. Vanessa, on the other hand, couldn't help but notice how the t-shirt Alex wore hugged her every curve. From the huge ass to the thin waist to the perky breasts, Alex really seemed to rock anything she wore.

Back outside the four contestants lined up on stage face the three fraternity judges, including Will. "Alright boys you know what to do..." The three of them revealed large pumping water guns, "Give 'em a nice facial!"

The boys pumped up their water guns as if they were jerking themselves off and then sprayed down the hapless girls (plus Alex). The shock of the cold water caused Alex to shy away from the blasts along with the two extras but Vanessa stood proud and took every last drop. After the barrage had ended the lingerie of each contestant was on full display through the soaking wet t-shirts they wore. The wet fabric clung to Vanessa's impressive bust as she willingly showed off everything she had, making her a clear favorite. Alex's lack of a bra garnered quite a bit of attention as well, allowing his nipples to be clearly seen through the transparent shirt. It would've been quite close had it not been for Alex's constant fidgeting and shying away. He felt so exposed and the shirt was itchy. It was embarrassing to be seen in clothing that was so plain, he definitely needed something cuter.

After some deliberating and a quick change back into their original outfits the contestants lined up to hear the results. The announcer walked on stage holding a comically large cheque labelled "new wardrobe" and a tiara. "Okay girls, I know you've been waiting all morning to hear the results so I won't keep you waiting any longer. The winner is... Cindi! Congratulations on being crowned Pledge Princess!" The announcer placed the tiara on Alex's head and handed him the giant cheque as the crowd clapped and cheered.

Before Alex could say anything Katy ran up on stage and gave him a big hug, "You did it, you won! You're officially a sorority sister, Cindi!"

"I know I can't believe it!" Cindi replied with an equal amount of enthusiasm

"Nice job babe, you were super hot out there," Will came up from behind Cindi and pulled her into a deep kiss. Their tongues explored each others mouths as Will kneaded Cindi's tits with his free hand. She weakly attempted to stop his hands but she was far to focused on the sensations of their mouths to really care.

"Now, now, you darn lovebirds. I hate to break this up but now's not the time," Katy jokingly scolded the pair, "Cindi and I have to spend the afternoon on a shopping trip, afterwards the two of you can have as much fun as you want."

"Alright, have your way." Will released Cindi's boobies as he relented, "Just make sure that that new wardrobe has something for the bedroom."

"Trust me, that is a guarantee." Katy giggled with Cindi as the pair walked away to her car.

Vanessa watched this interaction unfold with great confusion. That girl had called herself Alex but now apparently her name was Cindi. Had she been lied to? That wouldn't make any sense. For what reason would she lie about her name. Something strange was going on and Vanessa felt a gnawing desire to find out what...

Buckled into the passenger seat of Katy's car, Cindi decided that the drive to the mall would be the perfect time for another match of Gem Ladies. She pulled out her phone and began swiping away in the ever addicting game. The level she played was standard in every way, standard in the lack of surprise gimmicks and standard in her unsurprising loss. Once again faced with the familiar defeat screen she read through the provided punishment options.

Punishments:

C is for Cleavage (iii) - User grows to C-cup size, must show cleavage, +previous changes

The Snowball Effect - User will slowly get hornier throughout the day. User will not be able to get themselves off and will instead need help from someone else.

Appeaser to a Fault (ii) - User is addicted to conversation/self-promotion and feels mental anguish if a conversation ends in a negative manner and/or mental fog if unable at make a connection with someone. Unable to prevent themselves from conversing, and to end a conversation can lead to something close to physical pain.