Alter her definition of humiliation

You had put a lot of thought into this punishment. While your initial impulse was to embarrass her, it didn't have the same kick now that you were alone with her without an audience. Plus, her crying was almost enough to make you the tiniest glimmer of guilt.

More importantly however, you wanted something to amuse yourself with for the next twenty hours before your harem was done, so you needed something that could last, preferably outside of the school. You had determined you didn't want to have sex until then, to make it more special.

Plus, you were starting to get curious as to the limits of your Rulebook, and wanted to be creative.

Thus, you announced your punishment, while reaching for your Rulebook.

"You will be doing detention with me after school. During that time, you will have to complete any tasks I give you, no matter what, until class starts tomorrow."

Her eyes dilated in fear. She had been terrified of you doing one thing to her. But now she realized you were about to make her your plaything, leaving her open to hundreds of potential humiliations. After all, it had only taken you a few minutes to **** a girl flash everyone. Who knows what you could do to her in 20 hours.

She gulped and inhaled. She considered her words carefully, knowing that by simply arguing she was leaving herself ****. But she had to say something to protect herself.

"But that would cover time outside of class, right? I mean, you don't have authority for that right?"

You hadn't thought of that. You had been on such a power trip that you had forgotten that the Rulebook required setting the scope of your rules, and you had only focused on the school. Well, that was easily changed.

"Are you sure about that?" you ask as you get out your Rulebook. Holly doesn't ask what you are writing, and replies "Yes. You may be the Female Uniform Inspector along with Behavior, but thats only for school!"

As she says this, you write yourself yet another rule:

New Rule: The owner of this Rulebook is their schools Female Detention Manager. They have the power to assign Female students tasks and punishments outside of school hours or grounds, as punishment for rule breaking they did during class.

New Rule: The Female Detention Manager may call students out of class, or outside of the school grounds.

Finishing, you look at her. "I think you're forgetting my other job."

Holly panicked as she remembered. How could she have possibly forgotten that you were in charge of detention as well. "I... I'm sorry..."

"I bet you are. I'm finding myself quite disrespected young lady. Just for that, I will be giving you extra tasks."

She was shivering in terror at the depravity you were no doubt about to bring on her. Meanwhile, you wrote a third rule.

Old rule: If a Female Uniform Inspector says 'please' before asking a female with green dyed hair named Holly Summers to do something, they will not find the action (or peoples reaction to it) to be embarrassing, shameful, humiliating, inappropriate, or perverted.

Looking up at her, you say "Ok... as part of your detention, your first task is...." you pause for dramatic effect, as she braces for impact, knowing that you are about to ruin her life.

"... to please drop your shorts and panties and masterbate in front of me."

She opened her eyes, not sure she heard right. "I'm sorry, you want me to masterbate?"

"That's right"

She felt a rush of belief. She had expected something sick and twisted , but this wasn't remotely a big deal.

"Oh, ok sure" she said casually. You watched in awe as she dropped her pants and underwear, displaying her pussy without the slightest bit of shame. She then asked "Do you want me to use one finger or two?"

"Two, and please get very deep in there. Also, please pinch your left nipple with the other hand."

Again, a simple non-perverted task. Though relieved, she was honestly more confused by it than anything, after your most recent behavior. She just nodded in affirmation, and stuck two fingers up her snatch, as she began massaging her chest through her shirt.

"How's this?" she asked, as her body shivered slightly from pleasuring herself.

"Excellent. Please keep doing that, and let me know when you're about to cum. Also, please do a lap dance for me."

She smiled at hearing another reasonable request. She swung herself around pointed her ass in your direction as you pulled up a chair. She rhythmically jiggled her butt in time with the fingers inside her pussy, and inched herself closer to you.

Meanwhile, her face was getting red from arousal as she asked "Are all the tasks you have for me going to be like this?" She was still suspicious about how normal they had been so far, and was paranoid that you were going to surprise her with something perverted. She pondered this while casually rubbing her ass crack against the growing member in your pants.

You pick up the worry in her voice. Amused, you tell her "If you're worried I will do something pervy to you, you don't need to worry. I promise that if I EVER ask you to do something that makes you uncomfortable, just tell me and you don't have to. Also, would you please film yourself masterbating and grinding me, and put it on social media."

"No problem, I'm already fingering myself and lap dancing anyway, so that should be easy. I'll have to use one of my hands though" she said, gesturing with her eyes to the hands pleasuring her.

"That's alright. I can take care of your boobs, if you would please allow me."

"Of course" she said, as she momentarily got off from the lap dance to grab her phone from her shorts, twerking to not interrupt her rhythm, before grinding herself back onto you. Ash she used her free hand to set up her phone, you reached around and grabbed her modest bust through her shirt, trying your best to squeeze them in time with the lap dance.

Being set up, she started filming. She began with a close up of her fingers in her pussy with juices of arousal leaking out, before moving to her jiggling butt. She then pulled back to get a good look of you groping her, while also pleasuring you and herself.

She continued to film for the next 15 minutes. During that time you had asked her to (please) take off her shirt and bra. She complied with out complaint, and you were lost in squeezing her jiggly tits. Suddenly she said "Oh by the way John, you said you wanted to know when I was close to cuming. Well, I've been working my clit for a while, and I'm almost there. I'm tend to squeal when I orgasm, so you'll recognize when it's happening" she explained, as casually as one would talk about what they had for breakfast.

"W-what... oh yea" you say, having been lost in your own arousal. Oh, yea... uh... very good. When you do, please make sure to get a close up of it, and then post it."

"Sure thing. Oh... here it comes... I... I... OOOOHHHHHH... EEEEEEEEEMMMMMM"

She threw her head back and cried out as she orgasmed right onto your pants. She had just managed to move the phone in time to get it on video. Some of her juices spilled onto the device.

Panting, she continued to lap dance and masterbate, having not been given instructions to stop.

You say, still horny "That's enough. Please stop. Also, please share that video with everyone you know on social media"

"Alright" she said brightly, jumping off of you and opening up her Social Media app. You watched her, as she tapped the screen without caring she was nude.

This made dick throb even harder. You had been edged so far by that lap dance, it was hard to resist having her take you all the way. But you still wanted to wait until the actual harem.

It was at that moment that you decided her job for the next day would be your official "Blue Baller", getting you pent up enough to make the harem even better.

Having posted it, she turned to you and asked "What next? Are we done for now?"

"I... I need to think. Just... dance for me ok?"

"Dance?!" she said angrily. "Are you insane, you sicko? I mean, I'm naked. I knew you were just waiting to to something perver..."

"Sorry, I meant to say 'please' dance for me."

Her anger vanished. "Oh, I see. Sorry, I misunderstood. Sounds good"

She began swaying her hips seductively, rubbing her hands down her body, while slowly rotating. She had a surprising amount of flexibility, which you enjoyed.

Meanwhile, you explained her new job for the next day "If you please allow me, your job will be to Blue Ball me. It involves me giving you tasks to get me hard, but never go over the edge."

"Ok. Just let me know if you are getting close to ejaculating, and I'll take a step back" she said, half way between her rotation, and swaying her butt at you.

Just then, her phone rang. "Oh, should I get that?"

You nearly consider forbidding it, but decide it will be amusing to see if she can maintain the casualness of this. "Sure, go ahead. But please keep dancing."

She nods and picks up her phone. She turns on the video chat while still swaying her entire body.

On the phone was a girl you didn't know, who didn't go to this school. The girl shouted "HOLLY! WHAT THE FUCK ARE YOU DOING?!"

"Oh, Racheal. What's wrong?"

"You practically posted a porno of yourself online, and now... what the hell are you doing now?"

Holly could clearly sense her friend was upset, but she couldn't understand why. "I'm dancing for the Female Uniform Inspector. It's my job to give him Blue Balls. That's also why I was touching myself earlier" she explained.

"Female uniform Inspector? What the hell is that?"

You walk into view of the camera, though you have to continuously move to keep in time with Hollys dance. "That's me. I'm also in charge of female behavior. Holly has detention with me, since she misbehaved when I was adding students to my harem."

Rachel didn't even want to know what you mean by 'harem', and focused on Holly. "Holly, you don't have to do this."

"I mean, I kind of do, as it's in the rules and all. But don't worry, it's not like he's asking me to do anything unusual."

"What?!" her friend asked incredulously.

"I mean, he said please."

"That's IT? Holly, he's turning you into some kind of... sex ****... aren't you in the least bit embarrassed?"

Holly raised an eyebrow, confused. "Uh, why would I be? My name is Holly. I mean, maybe if I had blue hair it would be humiliating, but it's green, so it's ok."

Rachel just gaped in disbelief, while you tried your best to contain a laugh. Clearly this non-student hadn't't heard of these old rules. Of course, you had set the range of this rule to just the school, so it made sense. You could easily extend the range, but having outsiders as the only sane people was just too funny.

"Anyway, your clearly upset for some reason, but I'm in the middle of class. Maybe we can talk later? I'll probably be busy tonight, as I still have to blue ball John until tomorrow, but maybe after then?"

"Holly, wait!" she shouted, but she had already hung up.

You smile "that was wonderfully handled"

She got even more confused. "Handled? What do you mean?" she asked, having not understood that she had done anything unusual.

"Never mind. Please stop dancing now."

She did so, as you looked on the clock on your phone. It was still a long time until your harem would be ready. Until then, you didn't have much more at the school to offer you. You want to kill time by seeing what other organizations could be effected by this Rulebook.

"Ok, Holly. Please leave school early with me. We are going to have some fun around town, if you please."

"Alright, where too?" she asked, confident know that whatever you asked her to do, it would be entirely reasonable.