Lillian's First Step

Cassandra felt her head spinning, the world was so very new, and though she knew about it in a sense, it only went so far as to drive in the fact that she didn't really know about it really. She had the knowledge, the cold and distant information which she could access whenever she needed to, but it was like being able to open up a guidebook and flick to the correct page. Just because the book said something didn't mean you really understood it, and it didn't cover everything.

For example, nudity.

According to the information she had been given, humans typically didn't like to be naked except with people they trusted. Especially female humans such as herself. But as Lillian had pointed out, Cassandra was naked now, and it was inspiring certain feelings in her. Her skin tingled, little waves of pins and needles travelling up and down her spine. She felt moved to cover herself, though she didn't quite know why the idea of Lillian seeing her breasts or her vagina were so worrying to her. The thought of it made her breath quicken, and the blood rush to her face.

Lillian noticed this and laughed, the sound was unpleasant.

"You really did give me everything I want! Cassandra, you're so embarrassed by this, but you don't even know what being embarrassed is, do you?"

"I don't... I don't understand..." Cassandra said,

"Oh this is precious." Lillian smirked, "I didn't think I'd get to have such fun right away! Let's start with the basics, do you know that hot, dark feeling that you're experiencing now? The one in the pit of your stomach, which flares every time I look at you? It's embarrassment. You're ashamed because I am seeing your naked body, even though you don't want me to. You see? It's tied to your self worth, and your own desires."

Lillian turned away, seeming to think as she moved back and forth. There was excitement to her motions. Cassandra wanted more than anything else to find some cover for her body, but she knew that Lillian wouldn't want her to. That was part of the rule which had created her. She was loyal, not just obedient. That meant she tried to anticipate Lillian's desires, even if she didn't like them. So no matter how hot her body got, or how the strange feeling of humiliation swept through her, she didn't cover herself, standing as she had been placed.

After what seemed like an eternity, Lillian stopped pacing.

"If you're going to be my ****, you're going to have to know your own body pretty well. That way, you can apply that knowledge to other women as well. Stand still for a moment."

Cassandra's body obeyed without her consent, her muscles stiffened without leaving time for her to consent to it or not. Lillian approached, Cassandra saw the lust in her eyes, and it was scary. It wasn't just lust for her body, Cassandra realised, but lust for the power over her that she had. Lillian was getting off on being able to **** her to do anything she wanted.

"Let's start with the two most important areas." Lillian said, "The first and most obvious is the tits. I notice that yours are bigger than mine. Is that another change based on my subconscious desires?"

"I...um...it was randomised, mistress..."

"I see. And I could make them bigger or smaller if I wanted?"

"W-with a rule, yes..."

"Good," she smiled sweetly, "I'll be sure to remember that for later. For now, I am going to show you what they are for. For some women, the breasts are used to feed babies, but that's not your role, my dear. Your breasts have only one purpose. And that is to further your humiliation."

Cassandra gasped as Lillian's hand swiped out, moving faster than thought. It was followed by a small explosion of pain as the palm struck her right breast, the feeling swept through her and made her gape, Lillian chuckled at the look on her face.

"They're sensitive, right? Both to pain and pleasure. Don't worry, you'll get a chance to feel both before too long."

Lillian slapped her chest again, a short, sharp impact which sent a wave of pain sweeping through her. Cassandra wished dearly she could move or shield herself, but her body was locked in position. Lillian seemed to enjoy watching her breasts react to the impacts, seeming them move and shake.

"Maybe the bigger breasts did come from me after all." She said brightly, "This is kinda fun. Watching them move with one eye, and seeing your face with the other. How do you like being human so far, Cassandra?"

"I...it hurts, mistress..."

"Then, we'll start on pleasure."

Lillian's hands moved to her breasts more gently now, her fingers spreading out to massage the skin. The pleasure Lillian had promised started low, a sort of gentle stimulation that got stronger and stronger as the other woman teased her chest. Lillian paid particular attention to her nipples, and her areola, circling them and grinding them, stroking them and squeezing them. Before too long, Cassandra felt her legs start to shake, it was becoming harder and harder to control her breathing.

Lillian giggled, the sound seemed rather strange coming from her mistress, far too innocent.

"Are you enjoying this?" Lillian asked, "Technically speaking, you've never done any of this before, have you? I'm your first... How wonderful for the two of us, let's try to make it memorable..."

Next, Lillian slowly dropped to her knees, Cassandra could feel the other woman's hot breath between her legs, tickling the hair on her womanhood. She threw her head back, her body felt hot and strange. Her fingers and toes were tingling, and a strange heat had overcome her inside. She couldn't seem to catch her breath. The part of her which was the textbook told her that she was sexually aroused, but this knowledge was like ice in a furnace when set against the reality of her situation. She felt humiliated as Lillian's fingers started to stroke her mound, gently tracing the shape of her vulva. It was much more intense than when she had stroked her breasts, and Cassandra felt her whole body start to react, the heat between her legs got more and more, and she started to feel a dampness leaking out from between her lower lips.

"I see you still have your pubes." Lillian said, running her fingers through Cassandra's pubic hair. "We'll need to fix that later. For now, though, we're going to focus on this."

Cassandra jumped when she felt Lillian's finger poke at her opening, her lower lips were **** aside, just a bit, and she felt the tip of Lillian's finger. Her body begged her to move forward or to move away, the rising tide of arousal and humiliation combined to make her want to do something, anything! But she couldn't, her own power held her fast.

"You know what this is, right?"

"Y-yes, mistress. This is my vagina..."

"Vagina..." Lillian made a face, "That's such a cold word. Let's try something else, shall we? Hmm, ''womanhood'' is too dignified for a slut like you. ''Pussy'' isn't degrading enough. I know! From now on, you're only allowed to refer to this as your cunt, got it? No matter who you are talking to, or how official it might be. That's a rule."

Cassandra nodded, trying not to moan as Lillian continued to stroke her womanhood, her mistress' fingers felt long as they curled about her mound, stroking and teasing it with a casual cruelty. Building her pleasure without any intent to actually follow through.

"Additionally..." Lillian said, as though still thinking about rules, "As a new rule, from now on, whenever you are inside any building, you have to be naked unless someone tells you differently. Someone with authority, I mean. People might consider this strange, but it won't be considered illegal or problematic. Naturally, I am always considered to have authority, and can override anything else."

"Y-yes, Mistress..." Cassandra moaned, Lillian's fingers were gently forcing their way inside of her now, moving back and **** to tease her pussy. Cassandra was breathing heavily, her lower half was feeling hotter and hotter, Lillian's probing digits were slowly driving her to the edge.

"To the rest of the world, the two of us will be considered cousins, but no one will think it's weird that you're totally under my control. In fact, it will seem normal to them. Likewise, if I do anything sexual to you, even in public, no one will think that I am in any way strange or out of the ordinary for doing so. You however, are not protected, and people can still react to you with shock, outrage or lust. Though, your naked state is not illegal, many people will still have problems with it..."

Lillian drew her finger out of Cassandra's pussy, raising it up so that they could both see how wet it was.

"Looks like you're looking forward to your new life," Lillian chuckled, "Just to reward you for being so willing, if anyone has a problem with you being naked, you're to offer to let them punish you in any way they see fit." Lillian's gaze hardened for a second, "But you will never be put in any real danger beyond humiliation or degradation. After all, the whole point is for you to serve me."

"Good girl!"

Cassandra moaned. Lillian was rubbing her vulva with her palm, moving fast enough that the stimulation was almost overwhelming! She felt Lillian's hand moving back and forth, the friction made her skin tingle, tearing the sound from her throat.

"If you serve me well, you'll get much more than this. But if you serve me badly, I'm afraid what you'll get is mostly pain. Like this."

Cassandra's eyes snapped open suddenly, Lillian's fingers flicked out, striking her engorged clitoris with a flick. Cassandra gasped, the pain thundering through her body. It didn't feel good at all, and she felt tears welling up in the corners of her eyes.

"Do you understand your position?" Lillian demanded, her face hard and her eyes steely.

"I...I understand, mistress..." Cassandra said, "C-can I move please?"

"You mean you've been holding yourself there?"

"You wouldn't have wanted me to move..."

"Excellent!" Lillian said, "So you're bound by my intention, not just my orders! That's great! But no, not yet. I'm not through making new rules yet. In fact, now that you mention it, I think this position is a bit too dignified for you. Yes, indeed. Cassandra, I want you to get on the ground and spread your legs, then finger your hairy little cunt. But you're not allowed to cum."

Cassandra wanted to rage against the unfair rule, her heart pounded, and she tried to resist, but her body simply did what it was told, she felt her legs curl, lowering her to her knees, and then she fell onto her ass, her legs spreading as far as they could, so she felt as exposed as possibly. Her pussy was already throbbing with want, desire sparked through her, but she had never fingered herself, and it was clear from the way she talked that Lillian didn't just mean a gentle penetration as she had done herself. That was why a moment later, Cassandra felt her finger started to move in and out of her pussy, the speed and power increasing as she got a feel for it. The rhythm made her clench her teeth, fire and heat washed through her as she went, her nerves started to scream, desire rising and rising. Before long, she was doing it with two fingers, and then three, her legs were tense, her face was red. She felt absolute humiliation as Lillian towered above her watching with a smug smirk.

"Let's see now, that's enough rules about you. Let's try something else. Old rule, the college which I go to is now altered as follows. All of the students there except for myself are now prisoners, who have been sent there due to crimes that they committed. Whole technically an educational institute, the campus really focuses on degrading and humiliating them, recording it for a website which they use to raise funds. In fact, certain favoured students are **** to livestream their suffering, and even interact with their chats."

"Hah....y-yes mistress..." Cassandra bit her lower lip, her hand was pumping back and forth now, the speed was as fast as she could go, the stimulation hit her like a brick, making her nerves tingle and her voice moan. It was hard to focus, to hear what was being said, but she knew that she would be punished if she didn't catch it all. Added to this, there was a terrible weight forming in the back of her mind as the pleasure from her masturbation continued to build and build. She'd never done it before, but she should have cum by now. Except that Lillian had disallowed it, and all Cassandra could do was wretchedly hope against hope that she would be allowed to climax soon.

"I, of course, will not be a prisoner. Instead, I shall be one of the staff of the college-prison, the high corrections officer. I do like the sound of that. My role shall be to assign punishments, with nigh unlimited authority."

Cassandra grunted, her breath catching in her lungs, her chest was heaving now, the pleasure crashing against the mental blocks which held it in check. She could hear it roaring in her ears, a tingling promise that raced down her spine. She wanted to cum more than almost anything else, she was surprised and scared by how strong the urge was.

"And as for you, my dear, you will be one of the students. Quite naturally, no matter how far apart we are, you will always be able to hear my words, so that I can make rules as needed."

Cassandra realised she could wait no longer, before she could stop herself, she blurted out.

"Mistress Lillian, c-can I please cum? Or at least stop fingering myself? Please!"

"No to both," Lillian said, "The day is still young after all, and we have a lot more to do together."