Hell of a Hello

While selecting an option, Alex suddenly received another text notification reminding him of the others he hadn't read yet. Realizing he shouldn't delay his response for no reason he quickly picked the first option and swapped to his texting app. This, however, is not the only punishment Alex received as he had clicked through the earlier popup too quickly to read the whole message. If he had read it he would have seen:

An additional punishment will now be upgraded to encourage immediate contact. Until contact Punishment: Flaunting Fashionista (ii) will be upgraded to Flaunting Fashionista (iii).

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; sustained wearing results in user feeling feverishly hot and stuffy. Additionally, user will derive significant enjoyment from showing off outfits to others, happy to model on a makeshift runway at any time.

Going through his messages in order the first Alex opened was from Vanessa.

Vanessa: Hey there, just checking in. I wanted to make sure you were still wearing your gift.

Looking past his large chest Alex confirmed that he was still wearing the prosthetic Vanessa had gifted him. Although it did feel a bit sticky and gross on the inside. Probably just a side effect of the glue, he'd need to wash it and take a shower before he went out today.

Alex: Yep, it's still on. Just like I promised!

Vanessa: Well I'm glad you like it so much. I don't need anything from you today but I might have something tomorrow, I'll let you know.

Alex certainly did like it. Wearing his gift made pants fit so much better it was like a dream. Before checking the rest of his texts Alex decided that it was time for that shower. Moving to the bathroom Alex used the solvent Vanessa had given him, which he had kept in the purse, and removed his prosthetic vagina before hopping into the shower. Using his own toiletries for the first time in days felt surreal. He actually kind of missed the smell of the flowery body wash he had gotten used to but he finished cleaning himself all the same.

Upon leaving the shower Alex suddenly realized just how much hair he had. It's length was down to about his mid-back. Had it really been so long since he had gotten a haircut? For a moment Alex considered going to get a haircut today but for some reason the mental image of him having a buzzcut upset him deeply. He quickly abandoned that idea as he wrapped his hair in a towel and began drying off. Once he was sufficiently dried off Alex washed his prosthetic in the sink, dried it and glued it back onto his groin.

With his body cleaned and his beloved prosthetic reattached, Alex went to his room to get dressed. But as Alex stared at his closet he didn't feel drawn to anything. He even tried some shirts and pants on but not only were they boring but they also itched like crazy. He honestly couldn't even imagine being outside in any of these outfits, why had he ever bought these clothes in the first place?

Eventually Alex decided that maybe he could try borrowing something from Ethan since his own clothing was so disappointing. Returning to Ethan's room Alex's eyes were drawn to something in the corner of the room. It was an open box of clothing left behind by Ethan's ex. On the top of the pile was a pair of micro jean shorts that Alex needed to wear. They were going to be so sexy on him he could tell, he just needed the right top to go with it. After a little digging, he found a black mesh crop top to go with the shorts. Sure it had an built-in bra but that barely mattered with how sexy it was. Grabbing a black lace thong, Alex got dressed in the ensemble. Not only was he looking hot, he was also blatantly flaunting his hourglass figure which was a nice bonus in his mind.

Finally happy with his state of dress, Alex reopened his phone to look at the remaining texts. First up was Katy.

Katy: Heeeeeey. I'm going to guess that last night went well since you didn't come back. I've been thinking that we haven't hung out in a bit so we should have a trip to the mall! I'll even buy you some stuff to sweeten the deal.

Alex: You had me at "buy". I'm in, can you come pick me up? Here's the address.

Katy: I knew you'd say yes. I'm nearby so I'll be there in a few minutes, see you in a bit!

Pleased with the idea that Katy would be spending money on him, Alex now opened his final message which was from Gavyn.

Gavyn: Did you want to do some more studying tonight? We're running out of time until the exam.

Alex: Sure let's do it. I'm ready for another intense session.

Gavyn: Great! I'm free anytime after 5 so just let me know and I can meet you at the library.

While texting Gavyn Alex had walked outside, having borrowed a pair of heeled sandals from Ethan's ex. Looking up he saw Katy pulling up to the apartment complex so he rushed over to her. Upon reaching her he gave her a full kiss on the lips which garnered a blush from both of them. Alex wondered when the hell he had gotten so bold while she complimented his outfit as they drove off to the mall.

As they entered the mall Katy grabbed Alex's hand and began dragging him along to a salon. "So I was thinking we could start with a salon trip. We can get some mani pedi's to start and after that we'll get tans. I really think you'd look hot with a nice tan so I've been waiting to take you out to one of these places for days. After the salon we can go to a piercing studio like I promised the other day and then after that I have a surprise. We can also go jewelry shopping after everything else since you wanted your own stuff, how does that sound?"

Alex was a little overwhelmed by Katy's day plan and he wasn't exactly happy about how feminine it sounded but it honestly wasn't all bad. Katy said she'd be paying after all so that in and of itself made him happy and she was right about him wanting more accessories. Plus she said that a tan would make him hot and Katy was a certified babe so he trusted her advice. "Yeah that sounds great, let's get going."

At the salon Katy walked up to the receptionist, "We'd like some french tip mani pedi's and a tanning bed session for my friend, on me." She turned and winked at Alex as she mentioned the fact that she was paying.

The mani pedi was fairly uneventful although it was certainly relaxing. The nail artist did ask Alex about his "love life" which threw him for a bit of a loop. He told the lady that he didn't have any commitments at the moment, too embarrassed to admit that was a virgin and he had never had a long term girlfriend before. After saying this Katy whispered something to the nail artist which caused the pair to start a giggling fit.

"So that's what you meant by no commitments. No need to be so modest about it hun, I'd be bragging if I were you."

Alex didn't understand what she meant by that at all. He was about to ask Katy what she had whispered when the nail artist announced their nails done. Alex's hands now sported half inch, rounded, french tip nails. Their presence made his hands seem longer and slimmer, more elegant even, and Alex was beginning to second guess the salon trip. Until he saw Katy pull out her credit card to pay. The sight of her doing so was enough to make his heart swell with happiness.

"What are you standing around daydreaming for?" Katy's voice snatched Alex's attention, "Go get your tan on! We're on a schedule here!"

Alex was practically chased into an adjacent room where a worker was waiting for him, "Ah, you're here. The machine is ready for you, just strip down to whatever you are comfortable with and lay down inside the booth. There's a button to close it from the inside and you don't have to worry about being in there for too long because it will open automatically when the time is up."

With her explanation done the worker left the room for Alex to undress. He considered going fully nude to get the full tan but he realized that his prosthetic would definitely look mismatched if he tried that so instead he opted to strip to his underwear. It's a good thing that he had worn a pair that rode up his butt, that way he'd get more of that sexy tan.

After the tanning bed had finished it's magic Alex climbed out with a brand new alluring glow to him. He was honestly surprised at how much of a difference just one session had made for him as he redressed to show Katy. Katy, of course, absolutely loved it and gushed about how good Alex looked. Katy's stream of compliments was interrupted by a text on Alex's phone.

Ethan: Hey I just got back from my classes, sorry I wasn't around when you woke up. You left your clothes here, guess we'll have to have you come get them some time huh? You didn't leave naked did you? What are you wearing now?

"OMG you have to send him a pic!" Katy was reading Ethan's message along with him. Without missing a beat she started guiding Alex into a pose so he could snap a selfie. His shoulders were back with his boobies pushed out, his lips were pursed, and he held his newly manicured fingers in a peace sign. The picture was then taken and sent out.

Alex: I borrowed some clothes, hope you don't mind. I think they look pretty good on me, don't you?

Ethan: Hell yeah, you look fantastic. I've been feeling a little hot today so I'm not wearing too much myself.

Ethan sent a selfie of himself in the mirror shirtless.

Alex: It must be hard for you to look bad when you have a body like that. Anyways I gotta go, my friend is dragging me to a piercing studio.

Ethan: Make sure to send more pics

Alex and Katy then went on to go to a nearby piercing studio. This time Alex wasn't nearly as hesitant, while borrowing Katy's jewelry had worked so far he was itching to get his own and he definitely need the earrings for extra accessorizing. It was a quick process and by the time it was done Alex was sporting a pair of large hoop earrings and even a nose stud that Katy had convinced him to get, on her dollar of course.

After taking some photos and sending them to Ethan, which was met with approval, Alex was ready to walk out when he was stopped by Katy, "It's time for that surprise... this place doubles as a tattoo parlor and you're gonna get one! You can pick whatever you want but I'm sure you want me to pick since I'm the one paying."

While Katy was being sarcastic that didn't stop Alex from believing her, "Oh for sure! Pick what you think would look best."

"Seriously?" Katy gave Alex a tight hug which made their tits press together, "You won't regret it! I'll make sure to pick a good one!"

After looking through the options for a bit Katy pointed to one and asked, "How about this?"

She was pointing at a lower back tattoo of roses and thorns with the words "Naughty Girl" written in cursive in the center. While Alex typically would've called her crazy for even suggesting this tattoo he was literally unable to regret her choice, plus he was already complacent thanks to her buying it for him. Instead all he said was, "If you picked it then it's perfect."

One long and fairly painful hour later Alex walked out of the tattoo parlor sporting a fresh tramp stamp, fully shown off by his crop top, and he couldn't have been happier about it.

A couple hours had passed and the pair were getting ready to wrap up the shopping trip. Alex now had a full collection of fancy and feminine jewelry for any occasion. As they were heading to the exit Katy stopped to go to the washroom while Alex waited outside. It was then that he spotted a familiar face, and while he couldn't quite place where he knew it from he did know that he owed it a favor.

Kyle was chatting with his friend Peter when suddenly he was turned around and given a quick peck on the lips. Looking at the girl who had kissed him she seemed almost as surprised about it as he was. Kyle's surprise, however, was quickly replaced by shock as he recognized the girl in front of him. It was the customer that he had plowed back at The Brooding Dragon a few days back!

"Hey there, it's been a while," the girl awkwardly tried to draw attention away from the kiss she had just given him, "I just wanted to thank you for last time, I feel like I need to do something in return. Is there anything you need?"

Kyle had seen this kind of girl before. He'd get close to them to milk them of their cash and suddenly they think he's their boyfriend. Admittedly this was partially his fault since he had fucked her raw in the private room but he had no clue what had even come over him that night.

"Hey, look. You really don't need to pay me back. It'd probably be better if you just forgot about it," Kyle tried to let her down easy.

"I can't just forget about it! I NEED to pay you back somehow," she grabbed onto his arm. Great, she was getting clingy now.

Kyle looked around trying to think of something absurd to ask from her in order to shock her back to reality when it hit him, "Fine then, if you want to pay me back so badly you can do it by taking my friends virginity." He pointed his thumb at Peter who looked back at him with a mixture of shock, anger, and embarrassment.

"Deal!" She took Peter's hand and started dragging him to the men's room before either of them even had a chance to object.

Inside, Alex pushed Peter into one of the stalls with him before locking it. Under normal circumstances Alex would never even consider doing something so gay but he was just repaying a debt so it didn't actually count as sex. In other words, his masculine pride was completely safe. He swiftly unbuckled Peter's pants in order to free his dick while the confused, yet excited man pulled out his phone. Once Peter's cock was out Alex noticed that while it was twitching to life it wasn't nearly erect enough yet. He spat into his palm and started to work his hand up and down Peter's shaft while gently fondling his balls with his spare hand in order to get him hard as fast as possible.

Peter moaned as Alex's touch got him to full mast but things had only just begun. Alex wiggled out of his micro shorts and moved his thong to the side as he lowered himself onto the seated man's rod. It took a good deal of Alex's leg and core strength to keep himself stabled as he penetrated himself on Peter's shaft. It was an awkward job in the cramped bathroom stall but Alex dutifully raised and lowered his hips on the erect cock.

While he was doing this solely to take his partners virginity he couldn't help but be stimulated by the mass impaled in his backside. Alex felt himself stiffen as he continued to take the other man's phallus. For fear that he might get aroused, thus making the action gay, Alex sped up his pace. The rhythmic pumping drew more and more moans out of both parties until Peter finally unleased his load and came in Alex's ass.

Alex was quite pleased with himself, not only had he completed a job well done but he had also came himself. His self satisfaction was interrupted by Peter's voice behind him, "C-can I send this to some of my friends?" Alex turned to see that Peter had been filming or taking pictures the whole time.

"Sure thing, stud. You've deserved it." Alex easily caved to the request thanks to Passionate Debts.

"A-awesome," Peter was near speechless from the experience as he sent a video into a group chat showing him being rode by some buxom babe with a tramp stamp.

Only slowed by a quick cleaning of any splattered cum, Alex left the men's room where he was immediately met with Katy, "You seem to be having a good time, huh?"

Slightly embarrassed that Katy knew about his debt payment, Alex blushed and turned away, "How did you know...?"

"Honey, I could hear the two of you from the women's room. You weren't exactly being subtle." Katy pestered Alex as they began walking out of the mall.

"So other people heard too?" Alex's blush deepened, his only solace being that it didn't count as real sex.

Katy continued to playfully tease Alex about his fairly public hookup all the way home as the pair drove back to the sorority.

Back at the sorority it was getting late as Alex sent a text to Gavyn to tell him that he was ready to study. He was about to leave when Katy stopped him with a question, "Where are you going now?"

"Oh I was going to go study with this guy in my class," Alex replied, "We have an exam soon."

For a moment all Katy could do was laugh, "HAHAHAHA! Very funny, but we both know that a girl like you doesn't care about studying. You must really want to fuck him if you're willing to pretend to study. How good looking is he? Or do you just have a thing for nerds?"

"Yeah you caught me," Alexa sighed in defeat now that her true intentions were revealed, "I don't know what it is but something about him just really makes me want to get into his pants."

"That sounds more like my favorite roommate," Katy smiled at Alexa, "Now go get him, sexy! But, uh, maybe take a shower first. You're not exactly fresh after your fling at the mall."

Realizing that she was definitely right, Alexa took a hop into the shower before taking off. After redressing Alexa was on her way and she noticed quickly that she was garnering quite a few stares from men and women alike. Her confidence was skyrocketing and she felt great with all the eyes on her and her outfit. If she was this attractive to complete strangers she should have no problem seducing Gavyn.

Walking into the library Alexa saw Gavyn arrive at the same time from a different entrance. She ran right up to him and grabbed him by the arm, making sure to press her milkers into him, "Hey Gavyn, I was thinking we should take a table in the corner this time. Something more secluded, you know?"

"Uh, s-sure! Sounds great." Gavyn was in no position to decline with Alexa clinging onto him.

The pair moved to a quiet corner of the library where they sat down and Gavyn took out his textbook and notes. For the next 5 or so minutes Alexa did everything she could to try and send Gavyn some hints and signals that she was here for a much more intimate reason than last time. She pressed her cleavage together, gave him longing looks, caressed his thigh, and even suggested they "finish studying early" tonight but Gavyn was either too shy or too dense to catch on. Most likely to was a mixture of both.

Eventually Alexa realized that she was going to have to take the initiative if she wanted anything to happen. In the middle of Gavyn's droning lecture about numbers, or whatever, Alexa accidentally dropped her pencil under the table which had been entirely unused up to this point.

"Whoopsie, let me just grab that," Alexa abruptly interrupted Gavyn as she ducked under the table. Once down there she didn't even bother picking up the pencil as she turned to face Gavyn's groin, "Hey, have I mentioned how grateful I am that you've been willing to put in all of this effort? Even if I have, it's not for the reason you think. I don't give a damn about this class, I'm just happy that you like me enough that you'd be willing to tutor this girl that hasn't been to a lecture in over a week. So since you've shown me how much you like me, I think it's time I show you how much I like you in return."

Alexa reached forward and began unbuckling Gavyn's pants. He flinched, initially surprised by the sudden touch from beneath the table, but it was only moments before he relaxed entirely. He honestly thought he must be dreaming but on the off chance that this was real then wanted more than anything to just let it happen. Meanwhile, Alexa had finished pulling down both Gavyn's pants and boxers to his ankles. His cock was already rock hard and dribbling out a little precum. It seemed as though Gavyn had noticed some of her earlier flirting after all if he was already this riled up.

Not willing to wait another second, Alexa started vigorously sucking Gavyn off. She took his sausage into her mouth like she had been starved for days, and in terms of blowjobs she basically was. With all the anal she had taken recently Alexa had almost forgotten the simple pleasures of taking a dick in her mouth and absolutely draining a guy. She absolutely loved everything about it, the thick presence in her mouth, the full control of someone else's orgasm, it was amazing.

This was all Alexa could think about as she wrung out Gavyn's shaft. All things considered it wasn't a very long time, especially with the way Alexa teased his nuts which brought Gavyn to his climax much quicker. Eventually Gavyn exploded into her mouth and Alexa made sure to gobble down every last drop like the little slut she was. After a brief pause to wipe the cum off the edges of her mouth Alexa finally crawled back out from under the table.

"Well that was fun," Alexa pushed her flowing back length hair behind her ear, "Next time lets go somewhere a little more private than the library though. We didn't get to cover nearly as much as I wanted to."

It was all Gavyn could muster to nod in response as he sat there in pure bliss. Realizing that he was fully out for the count, Alexa took that as her cue to head home for the night. So she sauntered off with her tiny shorts leaving little to Gavyn's imagination, making him even more excited for their next study session.

"I don't know what I'm gonna do," Alex lamented to Maddie as they ran side by side on the gym treadmills. It was the next morning and she had invited him to join her for an early workout. They had already completed the bulk of the routine and now they were finishing off with a cooldown run "I'm not at all ready for this exam. I don't remember a single thing I studied last night, it's like I'm not learning anything at all!"

"It sounds like you don't even want to be in that class, why are you taking it?" Maddie questioned.

"It's mandatory for my stupid major," Alex sighed, he noted that his stamina had gotten a lot better since he started working out with Maddie and at this point his breathing wasn't even affected by the jog, "but if this is what my future classes are going to be like I'm not sure I should stick with it..."

"Well why don't you try modeling or fashion, something like that," Maddie offered her advice, "You already enjoy modeling my stuff so why not work towards making it your job? If I were you I'd do it, you've got a killer body and since you're planning to switch majors anyways then it wouldn't hurt to give it a shot."

Alex considered her words for a moment. Everything she said was true, he had the perfect body for modeling and he liked doing it. He honestly couldn't see a reason to turn down her suggestion, "You might be right, I think I'll try modeling after all!"

As Alex made up his mind, Vanessa walked up to the pair, "Hey bestie! What's up?"

Earlier that day Vanessa had decided she'd shadow Alex to learn more about his relationships and make sure there wasn't anyone else suspicious of his condition. She had him wear a wire tap on his sports bra underneath his tube top and then forget about it so that she could listen in from a distance as she tailed him. After hearing Maddie suggest switching majors, however, she couldn't help but get involved. Having Alex switch to modeling sounded like a great idea to get him further entrenched in his new identity and further bury the old one.

"Hey Vanessa! We were just talking about how I'm going to switch to a modeling major." Alex replied, happy to see his bestie. He automatically tried to give her a kiss but wasn't able to reach her from the treadmill.

"That sounds like a great idea! You'll need to talk to some of the school staff but don't worry I can help you talk to them, I know you get shy sometimes so you can count on me to be right there with you," Vanessa barely managed to keep herself from showing a devilish smile as she manipulated Alex, "How about we go once you finish up here, I'm already done working out myself. I can tell you're dying to switch as soon as possible."

"You know me so well! Thank you so much Vanessa, what would I do without you?" Alex would've hugged her if he wasn't on a treadmill. Instead he just gave her a high five.

After finishing their run Alex and Maddie made their way to the changerooms. Typically Alex would change and shower at home but he was so excited to become a modeling major that he couldn't afford the detour. He was just about to waltz into the men's room when he was grabbed by Maddie.

"Hey, careful there! You almost walked into the wrong room accidentally." She told him as she dragged him into the women's room.

That was a close one, but it was a good thing that Alex had Maddie lead him to the real men's room. It was certainly surprising that there was so many women in various stats of undress in the men's room with them but this was the correct room so clearly they must have all been mistaken. Oh well, he wasn't going to complain of some ladies wanted to show off for the guys, although he seemed to be the only guy around at the moment.

As they changed Alex couldn't help but sneak peaks at Maddie's naked form, she was super toned with the only noticeable fat on her being her natural butt and breasts. His member strained against its silicon confinements as his arousal grew, yet there was no outside indication of this. Normally Maddie wouldn't have noticed Alex's peaking but she found herself sneaking peaks at Brit's own assets, feeling a little jealous of her great proportions, which lead her to catching the stare. This lead to Maddie wondering if Brit was bi, but she decided not to ask for now.

With Alex changed into a spaghetti strap top and a dangerously short skirt he was ready to meet up with Vanessa. He waved goodbye to Maddie as the two of them left to visit the student services office. Along the way Alex decided to pull out his phone to play a game of Gem Ladies. He was doing fairly well until his attention was drawn by Vanessa.

"What are you doing?"

"Oh it's just a mobile game I like. It's pretty fun," Alex replied, only to turn back and see that in his distraction he had made an accidental move that completely threw off his combo. He sighed as he tried to salvage the level but as expected he lost in just a few more turns. Realizing that they had already made it to the student services office, Alex hurriedly selected a punishment before locking his phone.

Punishments:

Magic Fingers - User's vagina becomes extra sensitive and wet to fingering specifically.

Familiar Tone - Others will hear the voice most appealing to them when hearing user speak.

What's a dollar? - User becomes terrible with money, will frequently spend beyond their means.