Big purchase

Leo hadn't come to me right away. He spent his time in the library. Like the entire day. I realized he was trying to improve his grades. But here in this magical world full of magical creatures and monsters, his grade wasn't just determined by his knowledge.

It's why combat was a required subject. Eventually he'd have to start working out if he wanted to truly get the top spot. And not just working out his body, he'd have to flex his magic as well to improve it.

Well, seemed there wasn't going to be anything interesting from him for the moment.

Luckily however this Saturday had Cassandra out swimming early. Well, not swimming actually. The teacher had them all lined up naked. I had to approve of her truly, her breasts sure were nice and large compared to her peers.

Of course she was nervous being naked but not as much as she should be since she ended up sucking on the teacher's cock for a few hours yesterday after Leo **** her. He had them lined up for a reason though, he was giving out new swimsuits. Similar to their old one piece swim suits but were now thinner. By that I mean the part that covered their crotch was skinnier and the cleavage cut lower. For Cass that meant no matter what she did the outer ring of her nipples were visible.

She complained saying hers was too small as she struggled to hide herself from him. But he was forcing her to wear it saying. "If you want to be good at swimming you'll have to either lose those juggs or learn to deal with it. I'll be keeping an eye on you, if you fail to keep up I'll have you perform some extra lessons." Of course I knew no matter what she did he'd be bringing her in for extra lessons.

I looked at the task list seeing that there was a new task for a swimsuit picture of Cass. I smirked reading it. 'I heard the swimming club got new uniforms, get me a photo of Cassandra in her new swim suit' I sent it to Leo's list before giving him the desire to look at the list.

He wasn't planning on doing any tasks today but seeing the new one that he previously easily completed there he made plans to complete it.

So Cassandra spent her time swimming. Not for long though because she was called out. She was just talking to him when Leo arrived. Taking that moment to adjust her swimsuit so it wouldn't be digging into her crotch so tightly.

Leo's wide eyed gaze at her ill fitting swimsuit reminded him of the situation. Though it was also starting to arouse him from the looks of it. He seemed to have forgotten about taking the picture but remembers as she was being led into the changing room.

The picture he took showed her ass being squeezed by the teacher as he lead her away. Leo looked like he was going run into the changing room after them to watch. Instead he waited and tried to sneak in.

Well he got lucky on his first attempt, it was blind luck that his timing to enter the changing room was missed by all the girls swimming.

He was just in time see a naked Cass laying back with her arms over her head again. Unlike before though where he massaged her body first before moving on to her breasts and eventually her slit. He started with them first. One hand pinched an erect nipple as the other dug into her virgin slit.

Leo was taking photos like mad. Well, he might actually have a use for those pictures after the suggestive photo that indicated she was going to be spending time with the teacher in the changing room. Sure enough as I was watching them there was now a new task listed.

I smirked reading it. "Holy shit! She's totally going to be getting some. Will pay big money if anyone can get me a photo of what they're doing in there." The changing room was notoriously difficult to get into, so there was big money up for anything that had to do with going in there.

Well, I sent the new task to his list. Even making it vibrate subtly that caused him to look at it.

I was curious weather his greed for money would win out over his desire to protect her. Or if he was just enjoyed having his crush be the subject of someone else's sexual desire.

But his face was conflicted staring at the photo of her naked body being fondled. He definitely didn't want to I could tell. But then he was brought out of his contemplation by a moan.

He looked back at them to see her legs now spread open and up as the finger were spreading her open. He snapped another photo before deciding to leave. He had chosen not to send the photos, but he would soon enough especially as he was heading for her open locker. Grabbing her uniform, underwear an all and shoved it into the list where they appeared in front of me.

Leaving the locker room was much easier than entering it as he wasn't heading towards it and he wasn't walking away clutching panties or anything of the like so he was barely spared a glance as he left.

I was honestly not expecting him to complete this task on the first loop. He definitely wont be able to complete the next one on this loop though. 'Sneak into Cassandra's room and replace a uniform with the modified one.' Reward was Unlimited sex with Sam. Another reward he would be tempted by. Well he might not be able to sneak into her room this loop but I can practice modifying the uniform in the meantime.

Leo was headed straight for me. I made sure to lay out the uniform across my desk as I held up the panties inspecting them as he walked in.

Seeing him I spoke casually. "You know, for a virgin she's got quite a sexy taste for underwear don't you agree?"

He just glared at me. "Oh come on, its not like she's your girlfriend. And its just her panties, not like I'm waving around photos of her naked body." I dropped the panties down and changed the subject. "Well, what can I get for you then? I assume you're here to buy something."

He flushed red before speaking. "You said I can get blowjobs from Sam now right?"

I nodded before speaking in a tone that said I was sure she wouldn't. "Well, I already gave her permission to, whether she actually will is another thing entirely. You'll have to convince her yourself."

He got a confident smirk that said he knew otherwise. "Well, I'll figure out that part... Am I able to upgrade this yet?" He held up his grey stone tablet.

I shook my head "Nope. Close but not quite." That conflicted expression of his returned, definitely debating weather to give up the photo of Cassandra being fingered.

After a moment of him still conflicted I spoke up. "What's bothering you then?"

He sighed before explaining. "Well, I did get... pictures of Cass being... Fingered that someone asked for."

I spoke in a happy voice then hoping to convince him. "What are you waiting for then?"

Angrily he shot back. "I can't just sell a picture of her like that!"

I sighed dramatically. "Listen kid, let me tell you something important: 1. She's not your girlfriend at the moment. 2. No matter what you do at the end of the year you'll be looping back to the start anyways because you're not her boyfriend. So make use of this bonus you got and sell the photo, even if she ended up finding out about what you did she'll forget it when you end up going back in time anyways."

That seemed to have made him realize he was being stupid about it. He seemed to forget that no matter what he did he'd end up going back into the past anyways. "All you have to do at the end is make sure you get everything right and nothing you did to get there would effect the outcome. So feel free to throw her under the bus a few times if it will get you closer to that end you're looking for."

He blinked a bit as it seemed the point finally drove home. "Ah, I guess you're right. I didn't really look at it that way. But what's a bus? Some type of monster?"

Ah shit I forgot, vehicles aren't a thing. Why make horseless carriages when the important people can just fly wherever they want. "Yeah, sure kid. A huge monster with a poisonous breath..." I tried my best not to laugh at my attempts to pass it off. He seemed to accept it though, and when he was about to cash in a photo he paused before deciding on the other picture where she had spread her legs and his fingers had slipped into her to spread her wet slit open.

He would have gotten the same price for the more modest one with her legs closed tight but actively chose to send the one that made her look like more of a slut. Maybe I misunderstood him, now that he was more aware of the lack of consequences he might actually enjoy watching her play around.

I clapped my hands together. "Well, that certainly got you enough money to buy one of the upgrades. Which one do you-"

"I want the third option. The image to see what she is doing at this moment." He thrusted the bag of cash towards me and I activated that part of the slate. He got to see just what he was missing having dipped out early.

Cassandra was still laying on her back. But instead her being fingered the teacher's massive balls were on her face as his cock was down her throat. She had taken over the act of playing with her pussy. Using both hands to spread herself open as she ran her fingers over her slick folds.

His eyes were wide as realized just how far she was letting him go. I spoke then. "It will also show you any enchanted magical items she has on her or any spells that get cast onto her. You can also toggle the option to view her clothes or not, but of course she obviously isn't wearing any so its just her right now."

He nodded indicating he heard me but refused to tear his eyes away from the tablet. Lucky him too, she was getting a stomach full of cum at that exact moment. The cum glowed a pale red light on her body, this was because he magical enchants his cum to be addictive.

She sat up trying gasp for air but ended coughing as the thick cum was **** out of the way for air. "Why's it glowing?" I reminded him of what I just said. "It also detects enchantments and spells. So that cum must be magically enhanced"

Then to his astonishment she took her breast in hand lifting it up to lick the cum that fell onto them. I decided to inform him of just what he was doing to her. "He makes him cum addictive with magic, she's already incapable of resisting him. Usually it takes much longer for him to get a girl to swallow his cum easily like that, but someone fed her a powerful aphrodisiac yesterday and she was **** to drink the cure for a few hours straight."

It was common knowledge that the cure was cum so I didn't have to explicitly say it. But he seemed to realize he did this to her. His face went back and forth from conflicted to aroused. He liked her but also desired to sexually manipulate her. I think he'd have an easier time of it if he was the one doing the actual manipulating.

He quickly spent the last of his money buying a single potion. I liked to call it the 'speed reading' potion but it just made it easier to understand and retain the information in the books. Then he left mumbling his thanks.

That was a more eventful morning than I thought it was going to be. Well, with Leo taking his studies more seriously now he might actually progress faster than I thought. Then he can freely go about playing with Cassandra and he wouldn't have to suffer through her spending time with people he didn't want her to.

But now I was frustrated from watching Cass and Sam had turned down his request for a blowjob, instead she was using her feet on him as she berated him for being a pathetic guy who like watching Cass be played with by other men.

That's when I remembered I still had a failing girl in my class. I almost felt bad for the poor girl she wasn't ready but I needed an outlet. I picked up my list of failing people in class when I noticed that the list had grown...

I recognized the names... they were all the ones who were trying to get me to fuck them. They had found out that if they got bad grades in my class they'd get to spent time doing sexy things with me. They were purposefully doing badly. I did spot the name of one I really wanted to talk to. It was the one I told to spread the word about getting a boyfriend just before I looped back. I wanted to know what was up with her and how she remembered what I had told her.