Checking Off Boxes

Caroline and Zachary had arrived back in his suite, finding the monitors on, and showing everyone but Melinda playing hot potato with a dildo. Another monitor showed Melinda currently writhing in pleasure in her sleeping pod. Caroline was confused by the four women passing around the dildo, and scowled when she realized where Melinda was.

Zachary rushed over to the console and turned off the monitors. He said, “I wish these wouldn’t just randomly turn on for no reason. There doesn’t seem to be a way to even limit what causes it either.”

Caroline leaned against the back of the couch, scowling angrily at Zachary’s back, waiting for him to turn around. When he did turn around, he saw her expression and asked, “What’s the matter now?”

“Care to explain why Melinda is writhing around in our sleeping pod? She shouldn’t be able to be in that right now, so I’m guessing you were somehow able to open it.”

“So?”

Caroline asked angrily, “What did you do to her?”

“I took your daughter’s suggestion.”

Caroline sarcastically replied, “For some reason, I don’t believe you. There is no way Piper would have suggested you do whatever that was to Melinda.”

Zachary was really tired of the whiplash from Caroline and proceeded to the kitchen and looked at options for dinner. He did reply while examining his options. “Piper did actually recommend that I punish Melinda.”

“Bullshit,” Caroline said.

Zachary shrugged. “Don’t believe me if you want, but it doesn’t change the fact that she did. I determined Piper was likely right. I wouldn’t be able to simply move past what she put me through. So I gave her a taste of what I went through, though I was kind about it.”

“KIND!? How is making her suffer in pain kind?”

Zachary looked unamused at Caroline. Without responding, he went back over to the monitor console and turned on Melinda’s feed, then he found the volume control and turned it up.

Immediately, in surround sound, came moans of pleasure from Melinda. “Oh, God! Yes, fuck fuck fuck! OHHHHH!” Melinda was breathing heavily, but it was quite obvious that she wasn’t in pain at all. Zachary then turned off the monitor.

Zachary turned towards Caroline, “I’m having her experience what I went through every day, but instead of pain, it’s pleasure instead. I expect it is overwhelming for her, because the pain was certainly overwhelming for me. And before you go biting my head off further, I want to make two things very clear. First, Melinda said she’d accept nearly any punishment I wanted to dole out to her.”

“That doesn’t give—”

Zachary calmly said, “Be quiet,” cutting off her interruption, and Caroline found herself unable to speak. “Second, I gave Melinda the chance not to go through this. I even made sure to give the command in such a way that she could opt out after it was given. She chose this. Probably for a lot of different reasons, but she had several opportunities to back out.”

Caroline’s glare had intensified as she fumed at having her voice taken away from her.

Zachary said, “Now, you may speak again, but not while I’m already talking.”

Caroline clenched a fist and was close to shouting at him for what he had just done, but she took a deep breath. She attempted to keep her voice even, but there was clear anger seeping into her quiet voice. “How dare you. You have no right to take away my voice. You have no right to punish any of us either.”

Zachary shrugged, “Maybe I don’t, but as I’ve already said, you have no right to my body, nor do I have an obligation to help or protect any of you. What I’ve really wanted to do to Melinda is punch her square in the face. I’ve wanted to cause her even a fraction of the pain I’ve endured over the years. I’m not doing that, though. I’m not because I don’t think I’d like who I’d end up becoming if I did. None of us are happy with this situation. Deal with it. I’m already tired of hearing about how I’m horrible for wanting even a small amount of payback for significant suffering inflicted upon me.”

“Good people can forgive.” Caroline retorted.

“I never said I was a good person. I’m just a person. Besides, I’m not holding what you did against you. I’m fairly certain I’ll be able to move on from the things Piper did as well. Honestly, your hostility now is far more aggravating than finding out you abused your power over me when I was your advisee. Not to mention it seems rather hypocritical of you to accuse me of abusing my power when you did just that yourself.”

Caroline bit back her retort because he had a point about her being hypocritical. Not a large point, but simply because her abuse of power was on a smaller scale didn’t make it not an abuse of power. She thought about things, and at least from what she had learned, he had actually limited his actions based upon what each of them had done to him. Not to mention Melinda clearly feels guilty and wants to be punished. Is this really something I’m going to fight him on? Can I even fight him on this?

Caroline rubbed her face in frustration, and she really wanted to let out a scream of frustration but kept it bottled up. Caroline said, “I’m not okay with your behavior. Particularly towards Heather and Melinda.” Caroline let out a sigh of defeat. “I’m also aware there isn’t anything I can do about it either. As for my recent hostility, I think I’ve been justified in being upset at your actions and this situation. I’ll apologize for taking my frustrations about this situation on you, because at least somewhat I have, but I won’t apologize for calling you out on your inappropriate behavior.” Caroline paused for a moment and looked away from Zachary. “So… I’m sorry, I shouldn’t be taking the fact we’ve all been kidnapped and forced into this out on you.”

Zachary replied, “Thank you. I appreciate that.”

There was an awkward silence that lingered for a long time. Zachary’s stomach broke it as it gurgled, causing him to ask, “What would you like to do for dinner? We could use the interface in the kitchen to order something, but that is just going to result in Heather cooking it and bringing it to us. The alternative is to make something ourselves.”

Caroline moved to the kitchen. “Out of the way. I had planned on making dinner tonight. Should be ready in about thirty minutes. Assuming all the ingredients are available.”

Zachary said, “They should be; just think about what you want when opening the door to the fridge, pantry, or cupboard, and it should be there.”

Caroline went to work. She started boiling some water, and then proceeded to dice onions, garlic, tomatoes, and green peppers.

Zachary stepped out of the kitchen to let both of them have some space to cool off. The room quickly had a fragrant smell from Caroline’s cooking, and Zachary’s stomach was practically begging for food by the time it was ready.

Zachary was surprised when Caroline brought out two pasta bowls filled with spaghetti and meatballs. She went back and grabbed a block of fresh parmesan and a cheese grater. “Parmesan?” Caroline asked.

Zachary nodded, “Please.” Caroline started to top his pasta and waited for his signal that it was enough cheese, and then she did the same to her own.

Zachary asked, “Is this homemade pasta sauce? It doesn’t look like it was from a jar.”

“It is. It only takes a little bit more effort to do, plus I was planning on trying to impress you this evening.” Caroline seemed a little sullen as she said that.

“I noticed the past tense there. Meaning you’ve decided you aren’t going to try to do that anymore?”

“At this point, I don’t think it would really make a difference. We clearly aren’t compatible. I’ve also already made it clear, I’ll do whatever you want to protect my daughter… not that you seem willing to take advantage of that offer.” Caroline stabbed a meatball, annoyed.

Zachary finished his first bite of food. “Damn, this is really good. As for not being compatible, I suppose... I don’t think we’d be a good match under typical circumstances for sure, but that’s mostly because of the age gap.”

Caroline looked at Zachary skeptically. “Are you really saying that if not for the age gap, you think we would work? We were arguing with each other for about half of the day.”

He nodded. “True, but have you noticed after those arguments we’ve both been able to continue to interact with the other fairly easily? There’s also the fact that most, if not all, of our disagreements were about things that likely wouldn’t have normally been a problem.”

“I definitely would have taken issue with how you’ve been acting.”

“Yeah, but again you’re forgetting something. My actions are limited by the ability for me to simply leave this situation, too. All the problems you have with me about Heather vanish if I weren’t literally stuck with her. Melinda too. That’s because I would just not interact with them in any form. Which I doubt you would object to that response. Really, think about it. If you ignore the things that are happening because this situation prevents an alternative, what are the reasons against us having a functional relationship with one another?”

Caroline thought about Zachary’s question for a while as they ate. He has been surprisingly reasonable and understanding about some things. For the most part, he hasn’t really been prone to rash reactions, and the few I’m aware of are either understandable or were something that wouldn’t normally be encountered… He did invite Piper up to his room on the first night even though he was angry with her, just to keep her out of that hellish room. When Piper was in trouble, he also came without hesitation and treated the situation seriously, even staying so I wouldn’t have to leave.”

Caroline started to frown as she realized that there were a lot of things she did like about him, and she did appreciate quite a bit of what he had done. God… I think he’s right. I mean, I even called him attractive earlier. It had been several minutes since either of them had spoken, as Zachary could tell Caroline was thinking over his question and was content to let her. Caroline said, “You might have a slight point. I guess the age difference would be the biggest obstacle between us under normal circumstances. That and…” Caroline wasn’t actually sure if she wanted to broach that topic.

“And what?” Zachary asked.

“Well, I’m still in love with my late husband.” Caroline figured it would be best to get it out there now.

Zachary thought about that. “That would make things more difficult, but I don’t think that would be a deal-breaker inherently. At least from my end. I guess it would depend on whether you were capable of opening yourself up again or not.”

“I don’t think I’ll ever stop loving him,” Caroline replied.

“That doesn’t mean you couldn't find love again.”

Caroline shrugged, “Maybe. I know Piper has wanted me to try dating again. I’ve never really wanted to. Now I guess it’s a moot point as I’m yours.”

Zachary replied, “Caroline, I’m not going to impose anything on any of you. If, when this is over, and we get to go home, you want to find someone else, I won’t stop you. I’ve got a feeling that Delilah will see to it that won’t really be an option for most of you, but I can’t do anything about that.”

Caroline nodded, “Yeah, I somehow doubt that the demoness will allow that, considering she literally called us your property, and that our sole purpose in life now is to please you.”

The two had finished their meal by this point. Zachary stood up and took the dishes back to the kitchen, rinsed them, and left them in the sink. When he came back, he began, “Look, I know things have been weird at times today, so if you’d like to wait until the morning, that’s fine, but you did say you’d like to earn some points…” Zachary trailed off, not really sure how to ask this of her.

Caroline nodded and stood. She took him by the hand wordlessly and led him towards the bed, and then when he was at the foot of the bed she shoved him onto it forcefully and climbed on top of him. She took his hands in hers and slid their hands above both of their heads as she leaned down and kissed him fiercely. Her hair dangled, framing her face, as she pressed her breasts against his chest. She let go of his hands and slid her own up under his shirt and began pulling it off. She let him pull up her sweater right afterwards. As soon as her sweater was off, he stared up at her slack-jawed, as that had been the only layer she had been wearing all day.

+2 VP Show Breasts, Look at those bazongas!

Caroline’s breasts were now massive, and looking at them closely, he thought surprisingly perky. Caroline just stared down at him and shook her head, muttering, “Men…” She grabbed his wrist and pulled it up, placing a hand on one of her breasts. “Don’t just stare; I figure this is what you want.”

Zachary did fondle her breast for a moment, but after a short moment he pulled himself into a sitting position with Caroline straddling his lap. Caroline wrapped her arms around his shoulders to keep herself from toppling backwards. He said, “You aren’t wrong that I’d love to play with your breasts, but what do you want? What are you comfortable with?”

+2 VP Breasts Touched, If only they were milkable

Caroline didn’t immediately reply and refused to maintain eye contact with him. “I’m not really comfortable with anything we’ve done physically. Maybe when I sat on your lap in the elevator, but that’s about it. As for what I want, I’d like to get to about fifteen points if at all possible. Could… could you maybe suggest some options to help with that?”

“I can, but unless you get me off, I’m not sure you’ll be able to get that many.”

Caroline closed her eyes, and her lips formed a tight line for a moment. “I… I suppose I can do that, but how about you tell me everything else you’ve noticed that has earned points first?”

Zachary nodded, “Lose the skirt, and any panties if you’re wearing them.”

Caroline nodded. She stood and then slipped both off her skirt and panties. Zachary eyed her up and down appreciatively, causing her to blush. She lay down on the bed next to him, crossing her legs. She eyed his naked torso appreciatively in return. She looked away when she noticed that he saw she was staring.

+2 VP Show Pussy, To bad he can’t pop a bun in this right now.
+1 VP Nude, A shy cougar? What the fuck is this bullshit!

She asked, “Okay, so what else?”

Zachary said, “Well, the only other things so far I’m certain of are different ways to get me off, and giving you a spanking, but I’m not sure if a simple swat on the butt is enough or not. Every time I’ve spanked someone has had a bit of… I guess dominance or punishment about it?” Zachary didn’t sound very sure.

“How did Heather get so many points? Because you seemed rather opposed to the idea of ever sleeping with her again.”

Zachary said, “I am still rather opposed, but we’ll see… As for how she earned points, I’m not sure exactly what the cause was except for when she put on the chastity belt herself. I have some guesses as to things that would earn points though.”

“Enlighten me,” Caroline replied.

“Well, anything that causes one of us to climax is likely to earn points if it is in a unique category. I also think anything where I’m exercising control or power over you, or you’re submitting to me.”

“Like what?”

Zachary said, “I’m not sure, but maybe something like kneeling at my feet, and calling me your Master. Though there seems to be more than a technical act to some of them, so it might not work if you’re just doing certain things for points.”

“Huh? What do you mean more than a technical act?”

Zachary couldn’t help but stare at Caroline’s magnificent breasts as he replied, “Well, you know how when you brought Piper to me two days ago she was naked?”

Caroline frowned at the memory. “Yes, why?”

“Well, I saw her naked at that time; I even carried her while she was naked, yet she didn’t earn any points for me seeing her nude at that time. Whereas you earned the points as soon as your sweater or panties hit the floor.”

“So context matters.”

“Yeah.”

“Great, there goes the plan to beg my Master to screw my brains out. Oh well.”

“I’m willing to bet the screwing you would earn points, but unless you were sincere, I doubt the begging or calling me Master would get you anything. Also, we aren’t having sex tonight.”

“I thought you said I’d need to get you off?” Caroline asked.

“You do know there are ways to do that besides traditional sex, right?”

“Oh… you meant… I’ve never given a blowjob or handjob before.”

Zachary said, “Well, how about a boobjob? You’ve certainly got the equipment for it. Plus you’d get the first-time bonus. Pretty sure it’s double points.”

Caroline frowned at him. “I’m supposed to what? Squish your penis between my breasts?”

“That is the general idea, yeah. Do you really not know about this kind of thing?”

Caroline replied, “Remember how I said my libido has been non-existent for years? There’s a reason I have only one child. I just was never very into sex. I never denied my husband sex when he wanted it, but we didn’t have a lot of it.”

Zachary looked at her, blinking slowly. “Wow… that sucks.”

“I’m quite happy with how my relationship and my life went. The only major exceptions were my husband dying young and being brought here.”

“Sure… still sucks that sex wasn’t that great for you.”

“Don’t insult him.”

Zachary held up his hands defensively, “Whoa there, I was not implying your late husband was inadequate. For some, sex just isn’t all that great, and that sucks because sex feels awesome.”

“If you say so…”

Zachary reached out and started to gently massage Caroline’s breasts, focusing on her nipples. She let out a surprised gasp of pleasure as he continued. He said, “You very much seem to enjoy this.”

Caroline bit her lower lip. “I certainly don’t mind it. It definitely feels better than it ever did before as of two days ago. Honestly, they’ve been rather distracting all day, rubbing against my sweater.”

Caroline let him continue to play with her breasts for a while, and several times she nearly reached out to undo his pants button, but she kept hesitating and not doing it at the last moment. Finally she managed to work herself up enough and undid his pants. He stopped playing with her breast long enough to help her remove his pants and underwear.

Caroline asked, “So what’s the best positioning to do this? I’m going to need your guidance here.”

“Umm…” Zachary hesitantly began, “I think either I lie on my back or sit on the edge of the bed.”

“Lie on your back because I’m not kneeling on the hard floor.”

Zachary obliged her. Caroline tried several positions to allow her to squish her breasts together around his dick but found most of them rather problematic. She eventually found one and was surprised at how easily it fit in her cleavage, almost as if this was one of the natural uses for breasts. At least breasts of her size. Zachary let out low moans of pleasure as she worked on getting him off. Several times he started to reach out to place a hand on the back of her head, but each time he stopped himself, letting her continue.

All of a sudden, Zachary let out a louder moan and thrust his hips upward, and his load shot up and started to cover Caroline’s breasts. Caroline pulled back and frowned. “A little warning would have been nice.” She complained.

+3 VP Paizuri (First x2) Well, at she milked her bull, that’s something I guess...

He raggedly breathed out, “Sorry. I didn’t think I was so close.” He took a minute to recover, which Caroline used to go grab a towel to wipe off his cum. When she returned to the bed, he asked, “Would you like me to return the favor?”

“What?” Caroline asked.

Zachary decided to simply be more direct, since Caroline clearly wasn’t that versed in sex terms. “Would you like me to get you off? It’s normally considered impolite not to at least offer after your partner gets you off.”

“I’m fine. Are you satisfied?” Caroline asked, sounding at least somewhat hopeful that he was.

“Yeah, that was fantastic. Different but fantastic.” Zachary looked at the scoreboard and saw Caroline had reached her goal of fifteen points. “Well, I guess you’ve got your points.” He said it in a slightly disappointed tone that it had been so transactional, but he knew he couldn’t expect any of them to be enthusiastic about a guy they were being forced to be with.”

“Sorry,” Caroline said, which caught Zachary by surprise. “It can’t feel great knowing I did that because I needed the points, but I also need to manage my gain carefully. Actually, speaking of that, you might want to be careful with Lynn.”

Zachary frowned at her, warning him about Lynn again.

Caroline quickly clarified, “I don’t mean that she’s planning something. I meant you should be careful with her to protect her.” That caught his attention, so she continued, “You shouldn’t let her gain too many points too quickly.”

“Why not?” Zachary asked, as he was unsure why that would be a bad thing.

“I’m guessing you’re going to have sex with her tomorrow night. Which is fine; that’s your business, but what happens if she gets to fifty points by the end of this round? Next round she’ll need to net another twelve... or maybe thirteen, depending on how Delilah rounds. The thing is, we all expect it would be possible to lose points from the challenges. So she doesn’t need twelve to be safe; she needs more like twenty-five or thirty. Then if she doesn’t lose any VP from a low placement in the challenge, she’d be at maybe eighty.”

“What’s your point?”

“We haven’t been told how long this competition will last or if getting over 100 VP is enough to prevent the issues with weekly VP gains. Do you think you’ll be able to manage getting her say forty points a round for several rounds when various options will become worth fewer and fewer points?”

“Well, shit,” Zachary said, realizing she was quite right.

“So be careful and pace yourself.”

“Thanks. Do you want to turn in for the evening?”

Caroline nodded, “Yes, but I want to shower first.”

Caroline left to shower, and Zachary went and picked up their clothes off the floor. He put on some sleepwear and fixed the covers before getting into bed, waiting for Caroline to join him. However, he ended up falling asleep before Caroline left the bathroom.