Saga of Littown Ch. 07

"Would you like to be... punished, Emily?" Ms. January asked in the kind of voice that could make children cry from miles away. "Is that what you're telling me? If so, I have a contract for you to sign."

It began to dawn on Emily that she might be getting herself in over her head, and not even in a good way. "Um... on second thought, maybe I'll pass."

"That's what I thought." Ms. January resumed walking. "Come along, little one," she said with a tug on Jaime's leash.

Emily shrugged helplessly at her brother as he was led away. It was starting to seem like he might have been right to fear their principal this whole time. She needed to rescue him, and for that she needed backup. She reached into her butt and fished around for her phone. It was just as well she didn't use her pockets for carrying her things, since she didn't have her pants and god only knew where they were at this point.

Helpless, and without even his sister's moral support, Jaime was dragged into Ms. January's office. It was different than he remembered, though also very much the same. In a way that his brain couldn't quite process, it felt like two separate rooms had been juxtaposed onto each other. It was both a brightly lit, professional office, and a torch-lit, shadowy dungeon all at the same time.

"Is this the part where you torture me?" Jaime asked.

"Torture you?" Ms. January asked blankly. "Why in the world would I do that?"

"Because... I don't know, really. I'm just hoping you're not going to eat me, mainly."

"Oh please. Humans don't even taste that good. Mostly you're too fatty. And the processed sugars you all eat? Don't even get me started."

Ms. January held Jaime against the wall with one hand, and cuffed his wrists and ankles securely in place with the other. The manacles she used only appeared once she needed them. It was quite a neat trick, if one were in a mood to appreciate it.

"So... you're not going to eat me, or torture me," Jaime said slowly. "But you are, in fact, going to chain me naked to your wall."

"Correct. I might nibble at your soul a bit too, if I get hungry."

"What? But you said no eating!"

Ms. January, much to Jaime's amazement and discomfort, burst out laughing. "Ha! Like souls are a real thing. You humans crack me up."

She sat down at her desk, arranged some papers neatly, and began to comb through them. She made little notes, and occasionally jotted down a signature where applicable.

Once he got over his initial panic, Jaime began to feel like he wasn't being taken seriously. He was being held prisoner quite effectively, but it felt very wrong to him that his dominatrix-monster of a captor should ignore him in favour of paperwork. That just wasn't polite.

"If you're not going to physically or mentally abuse me in any way, could I please be let down?" Jaime asked. "It's just... this seems a bit boring, and also hard on the limbs."

"I need you to stay where you are for now," said Ms. January without looking up. "You'll be fine. You shouldn't be there long enough for any permanent harm to come to you."

Jaime continued to protest, but Ms. January drowned it out in her head. The boy might be super wicked hot, but his pleas were no less irritating than those of anyone else she'd chained up over the years. He was rather quick to assume there'd be a sexual torture of some kind, however, which suggested some very interesting things about his home life.

After a while, just to shut Jaime up, Ms. January stood and placed her hand on her student's temple. Her eyes fogged pure black for a second, then cleared again.

"There," she murmured. "You want sexy punishment, you'll get it."

Ms. January sat back down and fell back into her paperwork. Behind her, Jaime had gone unnaturally stiff and silent.

****

To Jaime's eyes, the room had changed significantly in but the blink of an eye. Instead of an office/dungeon, he had appeared inside a fancy bedroom of some kind. There was a huge, princessy bed taking up a large amount of floor space. Actual guttering torches lined the walls rather than any kind of electric lighting.

Perhaps most disturbing, Ms. January was no longer in her proper-but-tight-fitting suit. She now wore an elegant-and even tighter-evening dress. She was sipping a glass of what he hoped was red wine.

"This is all in your head," said the apparition of Ms. January before Jaime could formulate any questions. "The real me is a busy lady, and you were being a pest."

"Ah," said Jaime. "I guess that explains some things. Um... Ms. January's Ghost? Can I-"

"Please. Call me Lisa. I've a feeling we're going to be getting very... intimate."

The smile Lisa gave Jaime did nothing to reassure him. He tried telling himself that if it was his head, he should be in control. It was basically impossible to convince himself, however. The spectre of his principal was far too reminiscent of her real-world counterpart.

"Like, how intimate?"

"I'm glad you asked."

Lisa drained the last of her 'wine.' She stepped toward Jaime, manoeuvring skillfully into the best light. She brought a hand to her chest and slowly trailed it down her body. Her dress disappeared from top to bottom in time with her hand's movement.

Despite her anxiousness, Jaime couldn't help but stare at Lisa's glorious tits as they were exposed. They were pure, unholy perfection; built to make men explode in their pants. The lines of Lisa's tummy and hips were equally sinful.

The last of the dress vanished in an instant, all at once. It was a little jarring after the slow tease the top half had been, but not as much as what was revealed. Between the legs of the single most feminine figure imaginable hung the largest cock Jaime had ever seen. It reached down nearly to the floor, and must have only just barely been covered by the dress.

"Holy fuck!" Jaime said with wide eyes.

"Nothing holy about it, I'm afraid."

Lisa sashayed closer. Her heels clicked loudly on the floor with every step. She was fully naked except for her stilettos, necklace, and earrings. Her massive penis swayed hypnotically in time with her movements.

"What can you possibly hope to do with that? It's too big."

Lisa smiled wickedly and put her hands on Jaime's shoulders. She pushed him to his knees in front of her. Her cock was just starting to twitch to life; quite a long process given her size.

"We'll make it fit," she assured him. "But first you'll need to get me hard."

"I don't think-"

"Start licking, little one. Or it's only going to get worse for you."

Fully cognisant of his own helplessness, Jaime leaned forward and gave Lisa's cock a big lick. He did it again and again, though only hitting a small fraction of its total surface area. He could easily run out of saliva if she tried to make him lick the whole thing. Still, it seemed to work. The giant penis before him became progressively harder as he licked, kissed, and sucked on it.

"Mmm, good boy," said Lisa. She stroked Jamie's hair affectionately. "That feels niiiccce."

Before long, her cock was fully hard and jutting out horizontally from her lithe body. Jaime stilled worked away at it in the hope that she wouldn't try inserting it into him. His hopes were entirely in vain.

"My cock's going inside you, you know," Lisa said.

Jaime shook his head desperately. "It won't fit. It'll break my jaw."

"You're right, it would be bad to try and shove it in your mouth. Luckily, you've got a hole that stretches much more nicely."

Lisa picked Jaime up and threw him effortlessly onto the bed. He bounced on the crimson sheets, then tried to sit up.

"We could just cuddle," he said. "That would be fun, wouldn't it?"

"Nope." Lisa twirled her finger in a circle. "Hands and knees, thank you."

Jaime sighed in resignation and adopted the requisite position. His cute little butt stuck out at Lisa and her massive, unwieldy erection.

"That's more like it," she said.

Jaime flinched as Lisa landed on the bed behind him. Her fingers pulled his butt cheeks apart. He braced himself for whatever was about to happen, but the only thing he felt was a soft, wet tongue caressing his butthole. He relaxed slightly since this was something he had experience with and could handle.

Lisa licked all over Jaime's ass, up and down his crack, and with a particular focus on the crinkled hole right in the middle. She pressed the point of her tongue against his butthole, and with enough pressure it slipped right in.

The slender, flexible tongue explored Jaime's anal cavity to a much greater depth than he believed possible. It filled up his ass, and somehow kept going deeper inside him. It wormed its way through his insides; at times tickling, at others turning him on like crazy. It was by far the most thorough penetration of his life, culminating in the tongue coming up his throat and out from between his lips. He was fully impaled on a phenomenally long and dextrous tongue, and he was rather enjoying it.

For a while, Lisa simply tongue-fucked Jaime. Her tongue pushed, retreated, and flexed inside of him. She did things to him that weren't physically possible, or indeed morally acceptable. But she knew what she was doing, and her young victim writhed in pleasure at her exquisite internal caresses.

When Lisa finally retracted her tongue, Jaime was left with a feeling of emptiness and longing. At last he understood something of what Emily felt after one of their hours-long fuck sessions. He desperately needed more, and he wiggled his butt in the hopes of getting it.

"You aren't done, are you?" he asked.

"Oh no," Lisa replied hungrily. "I've only just gotten warmed up."

Somehow Jaime had forgotten the massive beast between Lisa's legs. Such was the power of her mighty tongue, it seemed. He flinched in surprise as the huge head of her cock pressed against his well-loosened and lubricated asshole.

"No! Wait!"

"Hush, little one. Don't tense up, or this is going to be somewhat unpleasant for you."

"But-"

Jaime couldn't speak. The pressure on his butthole increased quickly until the head of Lisa's dick popped inside him. It was enormous, and stretched him out like nothing else ever had. Even her tongue was nothing compared to this new invader.

"Feels good, doesn't it?" Lisa cooed softly. "Getting all filled up with cock... I'm actually kind of envious of you right now."

"We could... switch... if you... want," Jaime panted.

"Ha! No thanks. I'm envious, but my dick still needs some love. Your sweet little ass is getting a good pounding, and that's all there is to it."

Lisa shoved her cock in farther, but not much. It was a very tight fit, after all. She thrust her hips with powerful strokes, burying her huge shaft inside Jaime an inch at a time. It was slow going, but steady progress was made.

Jaime moaned with every ass-rending thrust. He was being stuffed and stretched, and his internal organs were being battered aside to make room for Lisa's cock. Somehow, though, it didn't hurt the way it should have. Mostly it gave him an increasing sense of pleasurable fullness. The slight discomfort of having his ass totally destroyed only added to the effect.

Lisa fucked her way deep inside Jaime for what seemed like hours. There was so much cock to be shoved in, and it only became more difficult the deeper she got. At last her hips pressed against Jaime's butt cheeks. Her massive shaft was fully entrenched.

"There we go," Lisa said. "All in. That wasn't so bad, was it?"

"I... can't really... breathe properly."

"Ah, yes. I'm probably squishing your lungs a bit."

Jaime felt his tummy with one hand. There was a sizable bulge from the cock inside him. He ran his hand upward, following the shaft until it disappeared beneath his rib cage.

"This... can't be... healthy."

"Enh, probably not. It's all imaginary though, so it's fine."

"Doesn't feel... imagin... ary."

"Well it wouldn't, would it?"

With a firm grip on Jaime's hips, Lisa pulled back then rammed herself forward. Now that she had full access, she needed to give him a proper butt-fucking. She built up to longer and harder strokes, and soon Jaime was reduced to a drooling, sex-overloaded mess. Lisa smiled to herself; now things were really getting fun.

****

Back in the real world, Principal January was still calmly sitting at her desk. Despite her intense focus on the papers in front of her, she didn't so much as flinch when her office door was kicked in. The poor door slammed off the back wall, and a hail of splinters filled the air.

"What the fuck did you do to my brother?!"

Ms. January looked up impassively. Lilith stood in front of her, about ready to tear someone's head off. A still bottomless Emily peeked out from behind the safety of her big sister.

"He should be here," Emily said. "It's where she brought him."

"Your brother's fine," Ms. January assured the sisters. "There was no need for damaging my office."

"The hell there wasn't," Lilith said. "You know better than to mess with my siblings."

"Indeed," said Ms. January. "But I'm afraid they've been very naughty. Breaking school rules with no regard for the consequences."

"I don't give a shit. Where's Jaime?"

Ms. January waved a hand, and again her office melded with a vague semblance of a medieval dungeon. Jaime came into view as though he'd been there the whole time, but somehow the girls had been unable to see him. He was still chained in place, and his eyes were rolled back in a sex-trance. Emily tried to run to him, but Lilith grabbed her arm and held her back.

"Let him go," Lilith said.

"I'm afraid he's broken some very sexual rules," said Ms. January. "And he must suffer the requisite fallout of his decisions."

Lilith sighed. "Alright, Em. What did you and your brother do?"

Emily cleared her throat nervously. "Well... we mighta, like, fucked one of our teachers in front of a whole class."

"Aaannnd?"

"And started an orgy slash gangbang slash bukkake. It was an accident though, I swear."

"Yeah, I bet." Lilith turned back to Ms. January. "Alright, Lisa. We doing this?"

"Careful, Lil," Emily whispered. "She's, like, an actual monster-lady. She could eat us or something."

"Nah, Em. She's a demon. And she doesn't much eat people. Especially me."

"Your sister's correct, Emily," said Ms. January. "I have remained entirely within the rules. There's no need for calling anyone a monster."

"You've got my brother all chained up and unconscious," Emily said. "That's not very rule-abiding." She paused, suddenly realizing she had no idea what the rules actually were. It had never been important to her before. "Is it?"

"Em, hush now," said Lilith. "What the fuck do you want, Lisa?"

"As I said-"

"I know, I know. Rules. But I know you don't much give a fuck about them unless they serve your purpose. So I repeat, what the fuck do you want?"

Ms. January calmly folded her hands on the desk in front of her. By most appearances, she might have seemed like a perfectly ordinary principal dealing with a troublesome student. The giveaway was her eyes. They flashed with unearthly self-satisfaction.

"I was very disappointed when you banned me from your club, Lilith," said Ms. January. "It's ever so difficult finding a place to hang out and unwind the way I need to after a stressful day dealing with hooligans and sexual deviants."

"You were branding my boys, Lisa. Like, with some kind of fucked up demonic fire. We couldn't even tattoo over them to cover them up."

"They wouldn't be very good brands if they could be hidden, now would they?"

Lilith sighed and pinched the bridge of her nose. "If I let you back in, will you behave yourself?"

"I will certainly do my best to-"

"Yes or no."

"Very well. Yes, then."

"Fine. I'll talk to my people, and you'll be on probation for a while, but-"

"Absolutely not! Probation is out of the question."

Lilith's eyes flashed with the same intensity as Ms. January's. "That's the deal. If you can't behave yourself, you'll be back out on your ass. Don't test me, Lisa."

Emily huddled behind a chair as the two women faced off. An eternity seemed to pass as they stared one another down. If Emily didn't know any better, she'd swear they were communicating with some kind of familial telepathy or something, the way she sometimes did with Jaime. She was kind of regretting not taking the time to fetch her pants. It felt a bit silly to be in war zone with her nether regions on full display.

"Fine," said Ms. January at last.

"Fine," echoed Lilith.

The two nodded, and the moment passed. Ms. January stood up and turned to a still-captive Jaime.

"I'll just get your brother free," she said. "Then perhaps I'll see you at your club later."

"I suppose so," said Lilith. "I'll have to keep an eye on you, after all."

Unfortunately, just as Ms. January approached Jaime to let him go, he arrived at a critical juncture in his dream-fuck. He'd been pounded for so long, by such a large, magnificent cock that he actually started cumming in the physical world at the same time as in his mental one.

"Eek!"

Ms. January was thrown back against the far wall by a hurricane of semen. Even she couldn't resist the sheer natural force of such a quantity of cum being shot out. She was soon completely drenched and quite gooey.

"Aw, shit," Lilith muttered. "That was some bad timing."

"What's going on?" Emily asked. "Usually Jai doesn't just cum for no reason."

"I assume he's being mind-fucked. You know, in a somewhat more literal sense than usual."

"Oh. I see." Emily stared at the unceasing flow spewing from her brother's cock. "Well, I should probably do something then. Principal January needs to un-mind-fuck him or he may never stop cumming."

Lilith nodded. "Godspeed, little sister."

Emily pulled out her butt plug. She judged the distance, then got a running start and launched herself ass-first through the air. The only force in the universe that could contain the sheer quantity of cum Jaime was producing was his sister's butt. Much depended on her skill at taking it up the ass from her brother.

Emily's aim was true, and her butthole landed precisely on the head of Jaime's cock. Being his butt-slut had paid off, and she took his whole shaft up her bottom before her feet even touched the floor again. She moaned happily at both being anally filled up with brother-cock, and internally torrented with a natural disaster's worth of cum.

A very shaky Ms. January regained her footing once the deluge had ceased. She'd lost her clothes in the initial blast and was naked except for her heels. Cum covered every inch of her skin, and even some of her interior. She had to fake a sneeze to clear out her nostrils.

"Your brother's really something," said Ms. January. "This is... impressive."

"Mmm," Emily agreed dreamily. "Isn't it though."

"Don't get any ideas, Lisa," Lilith said, folding her arms. "I expect you to leave my siblings alone."

"Of course, of course." Ms. January waved her hands dismissively. "But that doesn't mean I can't appreciate a sexual prodigy of such high quality."

"More like quantity," Emily giggled. Her tummy was rapidly inflating to the size of a beach ball, and still the cum wasn't slowing down.

Ms. January stepped carefully on the slick floor. She reached out and lightly touched each of Jaime's manacles, which then fell away and let him free.

"Don't forget to un-mind-fuck him," Lilith said.

"You think I'd forget something like that?" Ms. January asked, acting hurt at the very suggestion.

"If you thought it'd be funny, sure."

"Wait! Not yet," said Emily. "He's still cumming in me."

"Fuck's sake, Em," said Lilith. "You let Lisa fix our brother this instant. I am not explaining to Mom why you burst like a water-balloon because you wouldn't let Jaime stop cumming up your butt."