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Chapter 22 by ShimoDragon ShimoDragon

What's next?

Receiving Gifts

Receiving Gifts? Alex could hardly see how that could be a punishment as he happily selected the option. The moment he tapped his thumb against the screen several pop-ups appeared for him to read. Still feeling mentally drained, however, Alex decided not to bother and quickly closed them all before also closing the app. Had he chosen to read the pop-ups, Alex would've seen that quite a lot had changed.

Selecting random punishment upgrade... B is for Boobies (II) has been upgraded to C is for Cleavage (III).

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

Synergy created: It's a (growing) piece of cake + Waisting Away + C is for Cleavage (III) (or higher) = Hourglass Symmetry. Pears: Exhibiting The Finest of Fruits will now be replaced by this new synergy.

Hourglass Symmetry - User will proudly refer to their body shape as an hourglass, both in conversation and internally; furthermore, user takes **** pride in their body shape, and will constantly attempt to maintain, flaunt and/or advertise their shape, whether via social media, conversation, clothing, or misc. Synergy will be replaced if user transitions to another body type via other transformations.

Forcefully unlocking random synergy... Beauty Fanatic and it's necessary punishments will now be applied.

Beauty Guru + Hair, Hair, Everywhere + Master of Accessorizing = Beauty Fanatic

Hair, Hair, Everywhere - User begins to feel 'naked' with short hair, and will attempt to grow or put in extensions if deemed too short.

Master of Accessorizing - User must wear three accessories at any time, with failure to have 3 equipped making the user feel akin to naked. Includes any commonly accepted fashion accessory.

Beauty Fanatic - User's appearance is always flawless while being viewed, with perfectly applied makeup and perfectly styled hair. Additionally hair will begin to rapidly grow to a minimum of 20 inches in length before returning to a normal growth rate. Falling to properly accessorize in a social setting will cause the user to feel exposed and cloud their mind significantly.

As always, Alex was completely oblivious as his chest grew a size and the neckline of his sweater magically descended in order to show off his cleavage. What he did notice was how he was beginning to feel exposed. I wish Katy had given me a necklace or something with this outfit... Alex thought to himself, The scarf and purse were nice but I still feel a bit naked.

As Alex considered his disappointing lack of jewelry he received a notification on his phone from Katy. What perfect timing!

Katy: Heyyyyyyyy, are you done that study date yet?

Alex: Yep, just finished. Do you need something?

Katy: I don't need anything but Vanessa has been looking for you. Apparently she has a gift for you.

Alex's eyes lit up at the message on his phone. He'd never turn down a chance for a gift!

Alex: Oooooh how exciting! I'll head over now. Speaking of gifts, do you think you could let me borrow some of your jewelry? At least until I get my own.

Katy: Of course roomie! What's mine is yours, and don't worry, by the time I'm done you'll have a boatload of accessories that'll make you shine like the stars!

Alex: Thanks Katy, you're the best! ttyl


Back at the sorority, Alex was heading to Vanessa's room. He had made a quick stop with Katy to borrow a simple heart necklace and a bangle. Katy tried to get him to put on some earrings only to remember that his ears were still not pierced. After promising to get them done when they went shopping for jewelry, Alex left for Vanessa's room.

It was fairly late in the evening and Alex was really horny, not at all helped by the fact that Katy had only been in her underwear. He desperately wanted to go jerk off but Vanessa was waiting with a gift so that would have to wait. Finally arriving at Vanessa's room he knocked on her door.

Barely a second passed before the door swung open and Vanessa was inviting him inside. She must've been waiting eagerly. She subtly locked the door behind him as she lead Alex to take a seat on the bed.

"Congrats on Pledge Princess, by the way," Vanessa unceremoniously threw a large pink dildo towards Alex, "Here's your gift." She had wanted to get Alex something simple like makeup but she didn't know what brands she used so she figured that a dildo would be a safe bet considering how big a slut she was. Either way, the gift itself didn't matter. What mattered is that she had gotten Alex alone.

Alex picked up the dildo with a conflicted expression. He was really happy about the gift and he was obviously going to keep it but he couldn't see himself using it at all.

Vanessa noticed Alex's expression and began to worry that she had made the wrong move, "You like it, don't you?"

Immediately, Alex's expression shifted to pure joy, "Of course I do! Thank you so much!" He was so excited to finally have his own dildo. What an amazing gift!

Vanessa was considerably confused but she decided to brush past the strange interaction to get to the reason she lured Alex into her room alone. It was time to confront her about her identity!

"So... do you remember at the pledge contest when you told me your name was Alex?"

Alex looked up from his new toy and gave a quick nod, "Yeah, that's when we met."

"I just wanted to double check because according to everyone else in Theta Theta Theta your name is Cindi."

"Yep that's right, I'm Cindi." Cindi nodded her head again, clueless to the fact that she was contradicting herself.

"So did you lie to me? You told me your name is Alex! What's the deal?" Vanessa was beginning to become impatient.

"Well yeah that's my name, I'm Alex." Alex was really confused as to where the conversation was going.

"Are you fucking with me?! Everyone says you're Cindi, so why do you go by two different names?"

"I don't go by two names, it's just Cindi." Cindi was starting to feel guilty. She was obviously upsetting Vanessa but she had no idea why.

Before Vanessa could continue her fruitless interrogation something completely unexpected occurred. Her confusion and frustrations towards Alex/Cindi was suddenly replaced by an inexplicable and powerful lust. She needed to take her right then and there and she could not for the life of her explain why. Unknown to Vanessa, she had become the target of Prince(ss) Charming was now afflicted by an uncontrollable need to bed Cindi.

She lunged forward without any hesitation as her lips locked with Cindi's. Cindi was taken aback by the sudden intimacy but she wouldn't dare stop Vanessa. She was incredibly hot and Cindi was incredibly horny. They continued to makeout passionately with hot breath and teasing tongues until Vanessa couldn't stand it any more and pushed Cindi down onto the bed so that she could have the space to undress. Cindi took the hint and began to peel off her skin tight sweater leading to the both of them in only their lingerie. Cindi in red and Vanessa in black.

As Vanessa stood before her object of desire, drinking in the tantalizing figure encased in skimpy red fabric, what was left of her rational thinking attempted to make sense of the scenario. Sure she had always been a little bi-curious but she had never actually done anything with another girl before. Yet for some reason she wanted the girl in front of her far more than she had ever desired any man in her life. She couldn't explain where these feelings had come from but they were very real and she couldn't hold them back any longer.

Vanessa practically leapt upon Cindi as the pair began caressing each others bodies, lips locked once again. While Cindi kneaded Vanessa's ass, Vanessa was unclipping Cindi's bra. Once the cups had fallen and Cindi boobs were free Vanessa broke off the kiss in order to start suckling Cindi's nipples. Within seconds Cindi's moans evolved from short and breathy to loud and needy. She had never felt anything quite like this before and she was loving every moment of it. Cindi then awkwardly raised her legs and grabbed Vanessa's thong with her feet to pull it down. The second the fabric was low enough Cindi began fingering Vanessa in return.

Sensing that she needed to pick up the pace, Vanessa used her free and to lower Cindi's panties while the other worked on massaging the tit that wasn't being sucked. With both of their bottom halves bare Vanessa decided it was time to return the favor and began to finger-

"You're a guy?!" Vanessa looked down to the dick in her hand. I was on the smaller side but it was indeed a dick and not a vagina.

"I'm not just a guy. Tonight I'm a man!" Alex was too busy riding his sexual high to notice any surprise in Vanessa's voice.

As confused as Vanessa was, her need to fuck to completion was too powerful to ignore. She began to jerk Alex off with her right hand while her left picked up the dildo she had gifted him and slipped it between his bountiful cheeks to massage his prostate. She pumped him from both ends while he went to town on her coochie. As strange as this was she had to admit that Alex was surprisingly good in bed. His fingers were getting her off far faster than she would've expected and so she decided to pull out all the stops to make sure they finished at the same time.

Lowering her mouth back onto Alex's perky nipples Vanessa began to stimulate him on three different fronts, his tits, his ass, and his cock. It wasn't long before Alex could feel his climax coming and he made sure to let it be known.

"I'm going to cum!" He have groaned, half shouted.

Having a moment of clarity Vanessa realized that she did not want to receive a facial so she aimed Alex's dick away from her face as he unloaded. Ironically the angle was just right to coat Alex's titties in his own semen. Right as Alex completed, the door to Vanessa's room opened before slamming shut again.

"Goddamn it Vanessa!" A girl, presumably Vanessa's roommate, yelled through the door, "I told you to warn me before you bring someone back to the room! You've got 5 minutes to get them out of there!"

The unexpected interruption must've ruined the mood for Vanessa because she was suddenly disinterested in finishing herself. She looked over at Alex's laying in the after glow trying to work out what was going on. As she tried to put the pieces together she remembered his reaction to the dildo she had gotten him and an idea hit her.

"Hey, I know this is a weird time to ask..." Vanessa started awkwardly, " But you remember how you owe me 20 bucks, right? Think you could pay me back now?"

"Sure, of course." Alex stood up, still fully nude, and sashayed over to the purse he had brought to pull out a crisp 20 dollar bill and hand it to Vanessa.

Vanessa couldn't believe what she was seeing but she still needed to test her theory, "Random question, what's your opinion on guys? Like sexually?"

Alex chuckled a bit, "Don't get me wrong, I'm not homophobic or anything but I don't swing that way. I'd much prefer a knockout like yourself."

Vanessa ignored the flirting as she moved on, "But you're a huge slut for cocks. You love sexy guys, don't you?"

"More than anything!" Alex responded eagerly, "Nothing better than a ripped guy with a big cock, am I right?"

That settled it. Vanessa had no idea why but Alex seemed to believe anything told to him! While she had no clue how he got such a feminine body it made perfect sense that people would assume he was a girl and then he would also believe it! This was huge.

Vanessa rushed Alex in redressing, taking notice of the way his panties made it look like he had a cameltoe despite his lack of a vagina. Yet another mysterious property of the inexplicable girly boy she had come across. As soon as Alex was out the door Vanessa got to work on planning. Having an obedient, gullible slut at her disposal would be very valuable...


The next morning Alex was groggily woken early to the feeling of Katy shacking him awake, "Hey I heard about what happened with you and Vanessa last night. Didn't realize you went both ways, I'll have to remember that..." Alex was still half asleep so he didn't really process what she was saying. "Anyways, she's asking for you again. Apparently she has another gift for you. You've got a real sugar momma on your hands, huh?"

Alex instantly perked up at the mention of a gift. He was barely even paying attention as he rushed to get dressed, throwing on a cute thigh-length skirt and a pink low-cut top. He rushed over to Vanessa's room as quick as his legs would take him and upon arriving he was immediately rushed inside by an eager Vanessa.

"I've got something really special for you this time Alex!" She had spent a ludicrous amount of money on same day shipping for the already expensive item but it would be well worth the investment.

Vanessa could barely contain her excitement as she handed Alex the box holding his gift. He eagerly opened it only for his expression to change to one of confusion as he laid his eyes on what lay with in. He picked up the silicon mass and looked to Vanessa, "Did you get me a fleshlight? I'm seriously asking, I don't know what this is."

"No silly, it's a prosthetic vagina!" an impish smile crossed Vanessa's face, "I know you've always wanted one! So go ahead, put it on. If fact, you should start wearing it every day. Could you do that for me?"

Vanessa didn't realize that Tell Me About Myself would not have a constant effect on Alex and therefore wouldn't influence him into wearing the faux vagina everyday, however Passionate Debts caused Alex to view himself as indebted to Vanessa so he figured that wearing a prosthetic everyday would be a perfect way to repay that debt.

"You are so right Vanessa! Could you help me put it on?" Alex asked as he began to remove his skirt and panties.

"Of course, what are friends for?" Vanessa was incredibly pleased with how well things were going as she helped apply the adhesive for the vagina and get it into place before hiding the edges with some make up. It looked perfect, she couldn’t see even a hint of a male bump! There was absolutely no way to tell that Alex was a guy now! The last thing she needed was someone else finding out Alex's secret and trying to use him for themselves. The expensive prosthetic was so realistic it was basically impossible to tell it was fake unless someone tried to stick their dick in Alex. Considering that he and Will had apparently had sex already and he still hadn't been caught, Vanessa wasn't worried that something like that might happen.

"You feel soooo sexy in that, don't you?" Vanessa began to lead him into the next part of her plan.

"Oh definitely. I'm so hot right now!" Alex couldn't help but admire his pristine pussy and hourglass figure in Vanessa's mirror. He'd never really thought about it but his curves really did look great!

"You know what would make you feel even sexier? Showing it off to someone, and I know just the guy for it. Trust me, you'll love him. Besides, you owe me one so you should help me out with this."


Jeffery Mason was sitting in his office grading his student's papers when he heard a knock at his door. Probably another student with a question about the upcoming exam. He sighed and set down his pen before replying, "The door is unlocked, come in."

"This is Mr. Mason's office, right?" The door opened and in walked an incredibly attractive young woman. Her wavy shoulder length hair framed her perfectly made-up face delicately and her tight skirt and blouse showed off her hourglass figure quite nicely.

After taking a moment to drink in her appearance, Jeffery finally responded, "I'd prefer if you called me Professor Mason but I'll let that slide. More importantly, I don't believe you're in any of my classes. I'm sure I would've remembered a face like yours. Who are you and what do you need from me?"

"Well," the girl stepped forward, idlily twirling her hair with her finger, "My name is Cindi and I have this friend in one of your classes, her name is Vanessa." Jeffery remembered that name, another looker from his afternoon lecture. Academically she was fairly average, usually getting grades in the high C's to low B's.

"She's been really stressed out by her classes lately," Cindi continued, "so I wanted to come by and see if there was anything I could... do about it?"

Jeffery couldn't believe what he was hearing. Was this girl suggesting what he thought she was? He needed to stay professional until he was absolutely sure. "Well I'm not certain, that depends on what you're offering. In most cases I'd say no without question but I like you and I'm feeling generous."

In one swift, elegant motion Cindi pulled down her skirt and panties revealing her pussy to the professor. "Do I really need to spell it out for you? I'm offering myself." She stepped out of her dropped clothing, the click of her heels carrying her towards Jeffery's desk. He was completely entranced by the buxom beauty as he reached out to grab her wide supple ass.

"Not yet," Cindi lightly slapped away his hand, "You only get to look this time, but if Vanessa's paper gets an A then next time I'll be happy to do something for you, understand?" Cindi spoke as she pulled up her blouse exposing her bare breasts.

This was insane. Jeffery had always wished from the bottom of his heart that something like this would happen but he never actually expected it to! Yet here he was face to face with the naked body of a girl who looked even better than some porn stars. It was his deepest kink come to life!

"Yes, I- uh- I think we can make a deal then," It was taking most of his willpower not to touch the angelic beauty before him, "I'll raise Vanessa's grade and you can provide me with... services, in return."

"I knew you'd see it my way!" Cindi leaned forward and hugged Jeffery, giving him a face full of her naked tits. She then turned to redress in her clothes, "I better get going now, wouldn't want anyone to walk in on our deal, huh?"

Jeffery couldn't help but agree as he watched her ass shimmy back into her pink panties. He was really going to need to start locking his office door.


Outside the office Vanessa watched as Cindi exited and ran towards her. "You were so right!" Cindi bounced with glee, causing her boobies to jiggle uncontrollably, "That felt sooooo sexy, and he was pretty hot too!"

"So it worked then? He's gonna start giving me A's?" Vanessa raised her eyebrow, she wasn't sure how reliable Cindi would be with how ditzy she was.

"Yep! I said everything you told me too and he ate it all up. I even saw him scrambling to find you paper as I was leaving."

This was great! She knew Professor Mason was a huge perv. He'd always eye her up anytime she went to class. While she'd never whore herself out for a better grade whoring someone else out was perfectly acceptable in her books. Now she'd just have to see if any of her other professors would accept a similar deal. Alex was going to make Vanessa's college experience a breeze!

"Great work Cindi! I'll shoot you a text next time I need something. Stay sexy, girl!" Vanessa waved as she walked off.

Cindi felt so amazing that she was able to help out her friend and be sexy at the same time. She decided that such a job well done deserved a reward and she pulled out her phone for a game of Gem Ladies. Unfortunately, her good mood caused her to be a little overconfident as she made a fatal mistake right before the end of the level. Looking through the provided punishments she wondered what she should choose.

Punishments:

Alternative Payment Methods - User will offer sexual service instead of money for any transaction.

Flaunting Fashionista (III) - User becomes unable to resist wearing cute or sexy clothing. Plain or conservative clothing will cause the user to feel itchy and naked if worn. Additionally, user will derive significant enjoyment from showing off outfits to others.

Tantalizing Touch - User's skin becomes as supple and smooth as humanly possible and becomes significantly more sensitive and aroused by touch.

Which Punishment?

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