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Chapter 23
by
ShimoDragon
Which Punishment?
Tantalizing Touch
While she was considering her options Cindi couldn't help but notice that her legs were feeling a little itchy. It had been a few days since she had last shaved so they probably needed a touchup. Now that her mind was on smooth skin, she decided to select Tantalizing Touch. It would be so convenient to never have to shave or moisturize ever again, too bad the punishments didn't affect her in real life.
Cindi's train of thought was interrupted by two back to back notifications on her phone. Looking at the first she saw that it was a text from Ethan.
Ethan: Hey, you're close with Cindi right? Could you give me her number? I forgot to ask when I last saw her and I need to talk with her about something.
Cindi: This is Cindi, what did you need?
Ethan: Oh, what a coincidence! I wanted to ask if you were okay with having our date be tonight? I can come pick you up for dinner around 7 if that works for you. You live at the Theta Theta Theta sorority, right?
Cindi: Yep, that's right. 7 works perfectly, I'll be ready for you!
Ethan: That's great to hear! I can't wait to see what you'll be wearing ;)
Cindi couldn't wait for 7 to arrive, she was so excited for the free meal to come. The thought of being able to eat delicious food and not having to pay for it made her giddy. She would, of course, need to be careful. She didn't want to put on any weight around her waist, otherwise she might ruin her hourglass figure.
Moving on to the second notification Cindi saw that it was a text from her boss Dan.
Dan: Hey, I know I said that you can show up whenever you'd like but do you think you could come for a shift today? It doesn't need to be a very long one, you'd be off by 5. One the other girls got sick and we have a very important customer coming in today. He's a huge investor in the company so it's important that we keep him happy. I need you to fill in for his favorite waitress, do you think you can handle that?
Cindi: I'll head over right now. You can count on me!
Dan: Thank you so much, you're so reliable! I'll help you get settled once you're here. Oh, and don't bother bringing your uniform you'll need a new one for the back anyways.
A shift at work was perfect! Now she'd be able to keep herself busy until dinner with Ethan. No more agonizing over the wait, not to mention that she was steadily improving Dan's opinion of her. Without wasting anymore time, Cindi began her relatively short walk to work which was fortunately closer to the campus than it was to the sorority.
Alex walked into Barista 'n Bikini's with a slight haze over his mind. He was pretty sure that he had come in to work a shift, but at the same time something about working here seemed off to him as though it shouldn't make sense. Before he could think about it more he was pulled aside into the employee changeroom by Dan.
"Thank you so much for coming! I would've been screwed without you! You're so helpful, you know that?" Dan thanked Alex profusely as he fiddled with a locker, "Hell, if you do well out there I'd be happy to give you a bonus. That's just how important this is."
"No problem Dan!" Alex replied enthusiastically, all of his hesitation suddenly gone, "Always happy to help out!"
"Great attitude! Keep that up when you're serving Mr. Baldwin, he's the important customer," Dan finally opened the locker and pulled out some orange fabric, "Here's your new uniform and I left your employee ID in your locker, the code is 44-69-10. Now get changed and get out there!"
Alex took the clothing and was shocked to discover it was a G-string bikini. "I don't think I can wear this..."
"Oh you can wear it, don't worry. They're tiny sure, but it's still just a bikini," Dan reassured Alex, mistaking his hesitation for that of legal worries, "Besides, it's a private business. You can't get in trouble here."
"Oh good, I'll get changed then," Alex replied as Dan left the room. As long as he could wear it there was no real problem. Besides it was pretty sexy and would show off his hourglass figure so all things considered wearing it wouldn't be so bad. He pulled the bottoms over his prosthetic vagina and let them settle comfortably in his ample cheeks. He shuddered as the fabric slid over his silky smooth legs, but he quickly moved on to hooking the top around his melons.
Satisfied with how the bikini clung to his body, Alex stepped out of the changeroom where Dan was waiting for him. "You look great. Now head over to table 4 in the back lounge and take Mr. Baldwin's order; and no matter what do not make him mad, understand?"
"Yes sir!" Alex stood up straight, causing his chest to jut out. Since he had arrived he had gone from hesitation, to complacence, to pride. He didn't care that he was wearing a bikini, he looked great in it. "I'll make sure to give him my best customer service!"
Walking out into the lounge Alex took notice of the vastly different atmosphere from the main restaurant. While the front was well lit and somewhat child friendly, despite the scantily clad waitresses, this was dim and sensual with slow jazz playing in the back ground. The girls walking around serving drinks in bikinis certainly caught Alex's eye but he tried not to let himself get distracted. Unknown to him, however, pretty much everyone in the entire lounge considered him to be the hottest of all the bikini babes.
Sashaying over to table 4 Alex laid his eyes on the infamous Mr. Baldwin. He wasn't exactly ugly but his thinning hair and oily skin did him no favors. He appeared to be in his mid 40s and judging by his flashy watch and stylish suit he was probably quite wealthy. He was also notably large, though Alex couldn't tell through the suit if he was buff or fat.
As Baldwin saw Alex approach his annoyed scowl changed to a hungry grin, "Well it's about time. I've been sitting here for 20 minutes. I still can't believe that Mary went and got sick but I must say, you are quite the replacement. Well worth the wait, without a doubt." Baldwin licked his lips as he looked Alex up and down, taking in his every curve.
"I'm so sorry you had to wait for so long Mr. Baldwin, I can take your order now if you know what you want." Alex brushed his hair behind his ear as he spoke. It was quite a bit longer than he remembered it being, last he checked his hair was just above shoulder length but now it was well past his shoulders.
"Please call me Jim. I'd love to order, why don't you take a seat so I can show you exactly what I want," Baldwin held the drink menu in front of him in one hand and gestured to his lap with the other.
Alex barely even hesitated before he planted his huge ass on Baldwin's lap. Dan had asked him not to make Baldwin mad and he wanted to be helpful. On top of that, he was sure that Baldwin would give a huge tip if he left happy. With the two of them being far closer than Alex would ever normally want or allow he turned to look Baldwin in the eyes, "Now why don't you show me what you want?"
Baldwin smirked, he loved it when the girls were obedient. "I can see one thing I'd love to get my hands on..." He rested his spare hand on Alex's hip and began caressing his waist. It was the best feeling skin he'd ever laid his hands on, far better than his wife's that was certain.
Alex's mind fired off the second Baldwin touched him while his member began to stir and strain inside its silicon disguise. He struggled to stifle a moan as the hands danced up and down his waist. The electrically arousing touch of the older man caused Alex's mind to cloud up and he started to forget where he was. The only sense he was registering was touch and while the caressing of his hips certainly had his attention he also couldn't help but notice a prodding at his backside. It was like he was sitting on some thick rod and it was kind of irritating. He started wiggling his ass around and around until the thing he was sitting on had a more comfortable position nestled right between the cheeks of his plump cake. It was then that he realized that the sensations on his waist had stopped and he began to refocus.
Baldwin was in heaven. First this girl had sat on his lap like he asked, then she let him feel her up, and now she was grinding her ass on his cock. Mary was great but the most she had let him do was pinch her ass every now and then. After recomposing himself he pointed to the menu in his hand, "I-I'd like a bottle of pinot noir this afternoon. Try to make it snappy, alright? I don't want you out of my sight for longer than necessary."
"O-of course Jim," Alex shook his head to clear the fog as he stood up. "I'll be right back with your wine."
Baldwin watched Alex's ass sway as he walked off and he made up his mind. He had a new favorite at this branch of Barista 'n Bikini's.
The remainder of Alex's shift was more of the same. Baldwin would stare down his cleavage as he poured wine or slap his ass as he walked past but Alex was feeling just so helpful that he wouldn't argue. By the end of Baldwin's stay he personally walked Alex right up to Dan, with his hand on his ass the whole while.
"Dan! There you are! I wanted to personally thank you for setting me up with this beauty today." Baldwin referred to Alex as if they had been on a date, "You have to make sure you give... Sorry what was her name?"
"She's Gloria," Dan answered with enthusiasm, "She's easily the best girl we've had in months."
"I couldn't agree more. Make sure to give her a raise of some kind, she deserves it. I'd also like to request that Gloria be my waitress for any of my future visits as well." Baldwin leered at Gloria as she smiled at him.
"Consider it done!" Smiled Dan, "I'm glad you enjoyed your stay!"
After Baldwin had left Dan handed Gloria a hundred dollar bill, "Consider that a bonus for the stellar service you gave today, you've earned it."
Gloria jumped for joy, nearly causing her titties to fly out of her bikini. With this and Baldwin's tip her bonus earning were over 200 dollars today! She leapt forward to hug Dan, "Thank you so much Dan! But did you really expect anything less than stellar service? You should know that I'd do anything for a big tip. Anyways, I have a dinner at 7 so I need to run. See you later!"
Had Gloria not ran into the changeroom Dan would've stopped her there and offered her the big tip she was looking for. Honestly he was tempted to go into the changeroom and offer it regardless but he was still a professional. He couldn't just walk in on one of his half naked employees. Next time she came in he'd make his move but for now he would have to wait.
Gloria walked into her room to see Katy doing her makeup at the vanity, she must've had plans for the evening as well. Stepping over to the closet she searched through her clothing for something to wear but nothing felt right. She was just planning to hangout with her close friend Ethan so she had intended to dress casually but nothing she looked at felt nearly sexy enough for a night out. She was struggling to try and balance these opposing styles when Katy got up from the vanity.
"What's up? You're really struggling here, aren't you Cindi? Do you want help picking something out? What's the occasion?" The ever nosey woman barraged Cindi with questions.
"Help would be really nice, thanks," Cindi turned to address her roommate, "I'm having dinner with this guy Ethan and I can't decide on what to wear."
"I didn't know you were dating people besides Will! You are such a little slut!" Katy playfully slapped Cindi's arm in mock shock. "Not that I'm much different. I guess neither of us can get enough when cock is involved, huh? Don't worry, I won't tell Will and I'll help you choose the perfect outfit!"
"Thanks a bunch bestie," Cindi replied as her thoughts began to drift. Before she was only thinking about the meal but now she was far more interested in what Ethan would do to her afterwards. She only hoped he turned out to be a good size, it would be really disappointing if he was small.
"Here we are!" Katy snapped Cindi out of her fantasizing, "This will be perfect since you're trying to impress him." She held out a pale pink mini strapless dress with a boob window so long it would easily show off her midriff.
"You always know exactly what I need Katy! I'm going to get changed right now!" Cindi quickly ran to get dressed along with a black thong, no bra, and matching strappy stilettos. As the dress nestled over her hips, ending just low enough to barely hide her lingerie, she couldn't help but smile. Looking like this she'd be able to get Ethan wrapped around her finger, which would hopefully end with her wrapped around his shaft.
The more she thought about Ethan the hornier Cindi got, until she decided she'd spent some alone time in the bathroom as she waited for her date to arrive.
Cindi shifted in her seat as she and Ethan waited for their food to arrive. They had only been waiting for about 5 minutes in the ornate, fancy restaurant, but it felt like an eternity. Before leaving, Cindi had jilled herself off as quickly and vigorously as she possible could have but she wasn't able to cum. The whole ordeal had only made her more horny and now she could barely focus on anything but Ethan.
Her full attention had been placed on seducing and impressing Ethan. She had rubbed his thigh on the drive, she had made sure to give him a clear view of her cleavage as the were seated, and she made sure to press her boobs together as she hung onto his every word and laughed at each of his jokes. She absolutely needed Ethan to be enamored with her so that she could get to that precious snake in his pants.
From Ethan's point of view Cindi's plan was an undeniable success. He was ridiculously turned on by her sexy outfit and the way she displayed her body for him. He didn't like to use the term freely, but he was starting to think he might be in love with Cindi. Sure she was doing the standard laughing at his jokes and pandering to his ego, he'd been in enough dates to see what she was doing, but at the same time he could feel a sort of chemistry he couldn't deny. Like she could easily be his best friend if he didn't want to rail her so bad. It honestly made a lot of sense that she got along well with Alex.
As Ethan thought about how perfect Cindi was, he decided to lay his hand on top of hers. Even the merest of touch made Cindi need to stifle a moan. Clearly they were both ready to move on to "dessert" even though no food had been served. As if on command, waiter returned with a plate of caprese salad.
"Excuse me sir, we didn't order this," Ethan addressed the waiter.
"It's on the house, specifically for the lady." The waiter turned to Cindi, "I hope a princess such as yourself enjoys it. I can give you plenty more if you'd like..."
Cindi began to imagine what the waiter's package may be like when her thought's were interrupted by Ethan "Hey buddy, back off. She's my date and she's clearly not interested in you."
"Yeah, thanks for the salad but you aren't my type," Cindi waved off the waiter, suddenly disinterested in him entirely.
"Come on baby, I promise I can show you a good time. I'm on the job but if we hop into one of the bathrooms I'm sure we could have some fun."
"Alright, you know what? This treatment is unacceptable, we're leaving." Ethan stood and helped Cindi up out of her chair before leaning in to whisper in her ear, "Besides, I'm craving you far more than any food." She practically melted at his breathe while the pair walked out with the **** waiter following them to the door. To his dismay, his pleas were left unheard as the couple drove away.
The door to Alex and Ethan's apartment wasn't even fully open before Cindi started ravenously making out with her date. Ethan was feeling pretty damn aroused but compared to the wild beast that was Cindi he was like a timid kitten. Her tongue explored every inch of his mouth as she attempted to undress him and drag him to his bedroom at the same time, casually kicking off her heels along the way. Following her lead, Ethan returned the kiss with equal passion and caressed her body while trying to unzip her dress.
By the time they had moved from the entryway to the bedroom both were topless, Ethan's shirt was discarded on the hallway floor and the top half of Cindi's dress had been pulled down to her waist. They each took a brief pause from exploring each other's bodies in order to fully strip. Ethan was still in the middle of stepping out of his boxer briefs when Cindi began making out with him again. Her erect nipples and perky breasts rubbing against his own chest. He couldn't stand it any longer, he needed to be inside of her.
As he lined up his cock to penetrate Cindi's vagina she pushed him away lightly, "Sorry babe, the front door is closed." She seductively climbed onto the bed, extremely conscious of how her movements were affecting Ethan, where she presented her fat ass to him, "It might be a bit of a tight fit for a big guy like you but I'm sure we can make the back door work just fine." She made sure to wiggle her hips for emphasis; she had been ready for his big guy since before dinner and now it was time to claim her prize. Ethan didn't need any more guidance as he mounted Cindi and started plowing her like there was no tomorrow. The time for foreplay was long over and they both knew it.
Cindi was in heaven. This was hardly the first time she had been railed from behind but something about it felt different. Her raw lust was far greater than it had ever been before, the other times she had taken dick she had only wanted it but this time she practically needed it. Every pump of Ethan's meaty shaft into her tight ass was both a shot of ecstasy and endorphins. She could feel her "clitty" strain for freedom as she came for the first time, but she was still far from done. She needed more from Ethan, she wouldn't stop until Ethan's balls had been drained into her.
Cindi began to move her hips in time with Ethan to try and get him deeper inside of but that wasn't enough. She puckered her anus and twisted her hips to do anything to make the pleasure mount faster but nothing was good enough. Ethan, however, did take the hint thanks to Cindi's ever needy moans and sped up his pace until Cindi couldn't stand it any longer and collapsed on the bed. Worrying he may have gone to far Ethan began to slow his pace again before Cindi screamed at him.
"Don't you dare stop! Keep fucking me until you have nothing left to give!"
And so he did. Ethan's stamina was impressive as he continually plowed Cindi even as she struggled to support her own weight. She had came at least 3 more times before Ethan emptied out the last of his seed into her and collapsed into her. For a moment there was no talking, just heavy breathing and a pleasurable haze. Cindi couldn't even feel her legs, she had been fucked that powerfully.
With his deflating cock still nestled in Cindi's backside, Ethan wrapped his arms around her and began playing with her boobs. "Well that was pretty great, huh? Sorry we never got to have that dinner I promised you."
"You and I both know that the dinner wasn't as important as this," Cindi giggled, "And you're right, that was great. I feel like I need to do something for you in return for showing me such a good time..."
"All you need to do for me is put your number in my phone so we can do something like this again in the future," Ethan whispered in her ear as he handed her his phone.
Cindi said nothing in return, she was too busy trying to hold back her resurfacing arousal. The way he was tweaking her nipples and blowing in her ear was driving her crazy even though they had just finished. If she had the strength to move she would've even offered another round. Instead she started putting her number into his phone like Ethan asked her. She was surprised to find her number under the name Alex but figured it must've just been a mistake. After changing the contact name to say Cindi Summers, she turned off the phone and snuggled in with Ethan where they spooned for the rest of the night.
Alex's eyes fluttered open gently as he woke naturally for what felt like the first time in weeks. As was becoming the norm, he didn't remember much about the night from before and anything he did remember he couldn't focus on before his attention was caught by something else. That something being the fact that he was in Ethan's room for some reason. Had he come home drunk again and accidently slept in the wrong bed? Alex thought for a moment about how he didn't used to be such a party animal but now a days he was blackout every other night. That thought quickly left his head, however, when he wondered where his phone was.
Getting out of bed Alex realized he was naked but brushed that fact off as he went out into the hall. There he spotted a tiny pink purse on the ground with his phone poking out of it. Grabbing the device he noticed that he had multiple missed texts, but those didn't matter. Right now Alex just needed his fix of Gem Ladies.
Lying back down in Ethan's bed, Alex saw that it was almost noon. He must've been really exhausted to have slept in that late, but again that was not his current focus. Opening up his favorite app Alex was met with a message:
USER has failed to contact Gem Ladies customer service staff within 24 hours since being placed on SUSPICIOUS list. Please contact us to verify you are an actual human. An additional punishment will now be upgraded to encourage-
Alex didn't bother reading the rest of the message before he closed the text box. Playing the game as soon as possible was far more important that dealing with some kind of help desk. Unfortunately, Alex's futile attempts to win at his beloved game were fruitless as usual. He gazed at the three new punishments that were displayed for him to choose from.
Punishments:
Hell of a Hello - User's lips become plump and pillowy and will now be **** to greet others with a kiss. Strangers will typically only receive a peck on the cheek but friends will get a full kiss on the lips. In other words, the closer the relationship, the more intimate the kiss.
Requited Love - User finds themselves sexually attracted to anyone who finds them sexually attractive.
Sound the part - User speaks with a husky, erotic, bedroom tone when talking to someone.
What punishment does Alex choose?
Custom Girls
Involuntary sluts
An App that can women to follow rules of behavior against their will.
Updated on Jun 14, 2026
by duduvar
Created on Aug 21, 2020
by duduvar
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