Saga of Littown

Author's Note: While this story and its various chapters are primarily incest themed, it will often contain things such as excessive cum, anal play/pegging, and whatever else amuses me at the time. Reader discretion is advised.

****

Emily awoke to a day that seemed like any other day. She yawned and stretched, and debated going right back to sleep. Then she remembered what day it was. Her eyes opened wide and a big smile spread across her face. It was her little brother's eighteenth birthday.

She leapt out of bed with newfound enthusiasm and examined her lithe, naked body in her full-length mirror, as is traditional for female characters who have just been introduced. Having reassured herself that she was just as sexy as ever, she headed for her brother's room. She padded down the hallway as silently as a ninja. Her mother was probably up already, but her older sister Lilith would almost certainly still be asleep. It would never do to wake her up prematurely.

Emily cracked the door to her brother's room and peered in. Jaime was still snoring away. Good. She tiptoed closer, then paused as she realized she probably shouldn't wake him up while still completely naked. It might freak him out; after all he was a newly-minted eighteen year old, as inexperienced and naive as any other Littown teenager. She grabbed one of Jaime's shirts and put it on. It came down just far enough to cover her pussy and butt. Good enough.

"Wakey wakey!"

Emily pounced on her brother like a cat. Her face was mere inches away as his eyes opened and he yelped in surprise.

"Jesus, Em. You scared me."

"It's your biiirthdaaay," she replied in a singsongy voice.

"Yeah, I know."

"So you gottaaa get uuup."

Jaime groaned. "Shouldn't I get to sleep in if it's my birthday?"

"Nope. Gotta get up. Much to do. You don't want to be late for your first day of Over Eighteen School."

Jaime groaned even louder. He'd forgotten about switching schools today. But he was eighteen now, and as was traditional in Littown, once you were that age you had to move to a new school where everyone else was sexually legal as well. It made things simpler.

"C'mon, Jai," Emily said impatiently. "It'll be fun. We'll be back in the same school again."

She started shaking him to try and rouse him quicker. Her movement caused her to accidentally sit on his morning erection. They both felt the contact, but reacted very differently. Emily smiled to herself, and Jaime just tried to pretend nothing had happened.

"Ok, I'm up," he said, hoping that would be enough to get his sister off his back, so to speak.

Emily stood up, then waited for him to follow. She raised an eyebrow when he didn't get out of bed right away.

"Um, some privacy please?" he said.

"Why?"

"'Cause I'm not dressed."

"Ooh, you sleep naked too?"

"Out, Em." He pointed toward the door. "And stop wearing my clothes."

"Fine," Emily said. "But if you're not out soon, I'm coming back for you. And here's your shirt back."

She pulled Jaime's shirt up and over her head as she walked away, casually tossing it back in her brother's direction. He stared disbelievingly at the brief flash of his sister's naked backside before she was gone. He couldn't imagine what had gotten into her this morning.

Whatever the case, it certainly didn't help get his erection down. Jaime was fully cognisant of how super fucking hot his sister was, he just did his best not to think about it. Sometimes, like this morning, she made it impossible. He sighed and grabbed his cock. He'd have to rub one out quickly before she came back looking for him.

Very much unbeknownst to Jaime, Emily hadn't gone very far. She'd deliberately left his door cracked open as she left, and was now peering intently through the gap. She was still naked and could theoretically be caught by her mother or sister at any moment, but the risk was worth it. Her sexy--now fully legal--little brother was jerking off furiously, and she was fairly certain he was thinking about her while doing so. She was getting such naughty tingles from the whole situation.

Emily slipped a hand down to her pussy and fingered herself as she spied on her brother. He looked so enticing that she wanted to run back in and jump him, but of course that would just freak him out. Also it would be incest and bad and illegal and blah blah whatever.

Jaime came fairly quickly. Thoughts of his naked sister spurred him along nicely, as well as his natural teenage horniness. He shot a huge load into the shirt Emily had discarded before wiping himself off and throwing the shirt in his laundry basket. He knew he needed to get dressed and out of his room quickly before his sister returned.

Emily took a second to picture her brother dumping that same load of cum on the shirt while she was still wearing it. Her pussy gushed at the thought, but she didn't have time to stand there and continue playing with herself. If she didn't move she'd be caught for sure. She happily flounced back to her room and finally put some clothes on.

Jaime, much to his confusion, made it downstairs to the breakfast table before Emily. Further confusing him was his mother's appearance as she delivered his food.

"Happy birthday, son!" Christine said as set his plate down in front of him. "Pancakes, bacon, and eggs. Your favourite." She kissed his forehead lovingly. "Hang on a sec and I'll grab you some orange juice. Big day today, after all."

"Mom, what... I mean, thank you," Jaime said, remembering his manners. "But what are you wearing?"

He could see what his mother was wearing, of course, but he couldn't believe it. She was clad in her usual full-length cooking apron, a pair of panties, and nothing much else. First his sister's antics, now this?

"I know, dear. I wanted to make sure I had breakfast ready for you today, and I didn't have time to dress properly." Christine grinned at the bright red colour her son's face had gone. "I know it's weird seeing your mother this way, but you have to admit I don't look half bad for my age." She did a quick twirl to show off her sweet milf figure.

"You are super hot, Mom," Jaime admitted. In fact, as far as he was concerned, she had a luscious ass any porn star would be jealous of. But she was his mother, dammit. "You usually, like, cover up more though," he hinted desperately.

"Don't worry, I'm going to go get dressed in a minute. Just had to make sure my baby was taken care of on his most important birthday."

Christine gave Jaime another peck on the forehead. She turned to go get his juice just as Emily finally showed up. She'd taken the time to select a tight, sexy outfit and put her hair up in pigtails. She whistled when she caught sight of her half-naked mother.

"Damn, Mom. That's a hell of an outfit."

"Oh stop. Just running short on time this morning is all. Besides, everyone in the house is eighteen or older now so it's not a big deal."

"That's true," said Emily, grinning at her brother who was studiously ignoring both of them. "Things might just get a little looser around here now."

"Behave yourself," Christine admonished. She gave her daughter a kiss too, then absconded to her room.

Jaime had another full erection by that point. He was hoping it would go down on its own before he had to leave the table. Stupid female family members being all inconsiderately sexy.

"Mom's still pretty smokin', huh?" Emily said. "I mean she's getting pretty ancient, like thirty or something almost, but just look at her."

"She's our mother," Jaime said, still blushing. "We shouldn't be looking at her like that."

"Sure, yeah. Fair enough. But seriously, if she wasn't your mom, you'd do her, right? Like, you wouldn't even have to think about it."

Jaime grudgingly nodded. "Yeah, I would. Same with you, if you weren't my sister."

"Aww, that's so sweet."

****

All too soon it was time to head off for school. Jaime was still nervous about starting at a new school, but having his sister at his side did help. She was rocking the sexy schoolgirl look this morning, which contributed to taking his mind off his anxiety.

"Hey guys, wait up!"

Jaime and Emily were only at the end of their driveway when they heard someone call them. They turned to see the neighbour girl jogging toward them. Alyssa had lived next door to them since forever, and was practically the same age as Emily. Jaime had been nursing a mild crush on her for a while, but she was a little too much like a sister to him to ever do anything about it. He perked up further when he realized she'd be going to school with him now too.

"Happy birthday, neighbour boy," Alyssa greeted him. She stepped in and gave him a big, familiar hug.

"Thanks," he said.

"Yup, big day for my li'l bro," Emily chimed in. "Finally going to big kid school."

"I was pretty sure that was today," Alyssa said. "This is gonna be so awesome."

Alyssa linked her arm with Jaime's. As though psychically linked, Emily did the same on the other side. The two girls marched him down the sidewalk, still chatting away about how great things were going to be. They arrived at their bus stop only moments before the bus did.

Emily dragged her brother to the very back of the bus, and Alyssa followed along right behind them. The girls sandwiched him between them in a seat that really wasn't big enough for the three of them. Jaime had to put his arms around their shoulders to try and make room. He certainly didn't mind being snuggled up so tightly with Alyssa, although he was a little leery of the same with Emily. Especially when she'd been so weird already that morning.

It didn't take Jaime long to notice that he had a pretty good view down the girls' shirts. Once he'd realized that, he couldn't seem to stop looking. Even when he tried to be polite and turn his head away, he'd just find himself looking at the other set of cleavage whether he wanted to or not. Emily and Alyssa, by silent girls' agreement, pretended not to notice his staring at first. They waited until he had a noticeable tent in his pants before saying anything.

"Well well, someone's excited," Alyssa said.

Jaime glanced down at himself and immediately flushed in embarrassment. He tried to pull his hands down to cover himself, but his arms were stuck in an awkward position. The three teens were simply crammed in too closely for him to manoeuvre.

"Oh he's been very excitable this morning," Emily said, happy to join in teasing her brother.

"Really?" Alyssa said. "How interesting."

As though it was the most natural thing in the world, she put her hand right on top of the bulge in Jaime's pants. She toyed with his erection, pressing and squeezing it, without seeming to give it any consideration at all. Jaime wasn't sure what to do about that except that he very much didn't want to draw attention to them. He sat frozen and silent, enjoying the sensation of a pretty girl playing with his penis.

Shortly after, Emily's hand joined Alyssa's. Jaime was too horny to care much at that point. And even if he were to stop it, he reasoned, how would he even do it without causing a scene? So he sat obligingly still while both his sister and childhood friend molested him all the way to school. He was an absolute horny mess by the time they arrived.

"What am I supposed to do now?" Jaime asked.

"Get off the bus. Duh," Emily said.

"Yeah, but I mean...." Jaime gestured at his crotch.

"Don't worry. We got your back," Alyssa said. "So to speak."

The girls flanked Jaime as they entered the school. They walked slightly in front of him, which in theory screened him from prying eyes. He still noticed an awful lot of speculative looks, especially from girls. Every now and then he recognized someone, usually from his old school. It was even more embarrassing to think that one of them might realize what was going on. He looked down to try and avoid eye contact with anyone, but that just meant that he was staring at Emily and Alyssa's butts.

"So you have to go see the principal first," Emily told him. "She basically has to deal with each new student individually. Give you your schedule and everything."

"Should I be worried?" Jaime asked.

"Nah," said Alyssa. "She's tough, but she takes it easy on newbies. And she's got a soft spot for cute boys anyway."

"What?"

"She's kidding," Emily said. "Mostly."

Jaime wasn't sure what to make of that. He was dropped off unceremoniously at the principal's office and abandoned by his escorts. It seemed he was expected, and the secretary waved him right in.

The woman sitting behind the desk in the principal's office conformed almost exactly to Jaime's expectations. Her dark hair was pulled back severely, her suit was tight and business-like, and the glasses she wore only intensified the piercing effect of her eyes when she looked up at him.

"Jaime Nallister, I assume?" were her first words to him.

Jaime swallowed back his nervousness. "Uh, yes." He paused, then added, "Ma'am?"

Much to his relief, she actually gave him a faint smile in return. "My name is Principal Lisa January. You may call me Ms. January." Her lips twitched into another faint smirk. "Or Ma'am if you so prefer."

"Yes... Ms. January."

Principal January finally gestured to the chair across from her and Jaime gratefully sat down. He was feeling a little weak under her constant hawk-like observation.

"I understand switching schools so abruptly can be tricky for my students. I'm sure you understand the rationale behind keeping students older than eighteen separate from those who aren't."

Jaime nodded. "It, uh, makes it easier for authors and sexy shenanigans and whatnot," he said, reciting what he took as common knowledge.

"Just so. That being said, this is a place of learning, and sexy shenanigans are strictly prohibited. Is that clear?"

Jaime hesitated. He was out of his depth. "But then why--"

Ms. January stood up out of her chair. She leaned in toward her newest pupil, and her body seeming to grow in size. Her teeth shone with an impossible sharpness, while her eyes burned with actual, literal fire.

"I said: Is. That. Clear."

Jaime, shocked by the sudden force behind Ms. January's words, meekly nodded. "Yes, Ma'am."

"Good," she said, resuming her former state of total composure. "Other than that, I think you'll find your experience here to be pretty much what you'd expect. You'll reacquaint yourself with friends who made it here before you, do your schoolwork, and before you know it you'll be graduated. If you have any other questions you may ask them now, or at any time in the future. I am here first and foremost for the benefit of my students."

"Thank you?" Jaime hazarded. He blinked repeatedly, deliberately, but his principal looked perfectly ordinary now, and he couldn't figure out what possible trick of the light had made her seem monstrous to him mere seconds ago.

"You may pick up your schedule with my secretary."

That was dismissal enough for Jaime and he practically leapt out of his seat. Ms. January's eyes remained locked on him as he scurried out the door.

"He is a cute one though," she whispered to herself.

****

Jaime, having been given helpful directions by the secretary, made it to his first classroom without incident. The class itself was little more than a blur to him, and he couldn't have said afterward what he had supposedly been taught.

Emily was waiting for her brother when he stumbled out of the room after the bell. She was accompanied now by Lindsay, one of her long time best friends.

"Hey, Jai," Lindsay bubbled cheerfully. "Happy birthday."

"Thanks, Lin," he said. "What are you guys doing here?"

"Gonna take you to your next class," Emily said. She grabbed his shoulder to turn him in the right direction. "Guess what? We're gonna be in this one with you!"

Jaime felt some relief at being back with familiar faces as he was once again marched along to his destination. He was still feeling a little shaky from the principal's 'welcome.'

"You feeling ok, dude?" Lindsay asked.

"Um, kinda. Mostly," Jaime said. "I had to see the principal earlier and--"

"Oh, yeah. I hear ya. Don't worry, you'll get used to it."

"I feel like she coulda broken me in two, and not even broken a sweat doing it."

Emily thought back to her experiences with Ms. January. "Yeah," she said dreamily. "Can you imagine her tying you up and disciplining you though? You wouldn't be able to walk straight for a month."

Jaime gaped at his sister. "What?!"

Lindsay giggled. "Your sister has a bit of a thing for our dominatrix of a principal. Didn't she tell you."

Emily was finally the one to blush. "I do not. It's just... if you had to be spanked vigorously by a hot, domineering, older woman, you'd pick her, right? I'm not the only one who'd say so."

"I think the point is you're the only one who ever imagines such a scenario," Lindsay said, playfully nudging her crimson-faced friend. "And your protestations just aren't as convincing as you seem to think."

Emily and Jaime both went quiet for a moment. They each pictured a similar version of a scene involving Emily at Ms. January's mercy. Jaime shook his head clear once he realized what he was doing. Emily let hers go only wistfully, and with a regretful sigh.

"She likes the boys too much for that anyway," Emily said under her breath.

"What was that?" Jaime asked.

Lindsay just smiled.

The class the three of them shared was English, taught by Ms. Penny. She was a much friendlier looking authority figure than the principal. She had lighter hair, softer eyes, and a smile that seemed permanently affixed to her lips. She was also had the absolute biggest pair of tits on her that Jaime had ever seen.

Jaime sat at a desk next to Emily, with Lindsay on the far side of his sister. It wasn't long into the class before Emily passed him a slip of paper.

"She's got a nice rack, huh?" she had written.

Jaime glanced at his sister, who was smirking back at him. So she'd caught him staring at Ms. Penny's ridiculously massive chest region. He hadn't realized he'd been quite so obvious about it, but how could he not? Their teacher was so top heavy she looked like she'd tip over if you gave her a tap on the back.

"It's alright," he wrote back.

Emily rolled her eyes at his response. "Just alright?"

"What do you care?"

Emily didn't really care, except that she was bored and wanted to pick on her little brother now that she had the chance. He wasn't taking the bait the way she would have liked.

Jaime was able to pay attention and even take some notes for a few minutes while his sister deliberated. He was kind of nervous about passing the note back and forth, and was glad of a break from it. Emily might have become used to how things worked in this school, but he hadn't yet. He was still new and unsure of how teachers ran their classrooms, or what kind of workload was to be expected.

Eventually Emily passed the note back. "I just wanted to know if you wanted to...." What followed was a filthy description of an utterly depraved sexual act, the focus of which being their teacher's awesome tits. Jaime went bright red as he read it, and much to his chagrin his cock reacted as well. It was straight up pornographic.

Emily made a show of not looking while Jaime read her newest question, but in fact she didn't even blink as she watched him from the corner of her eye. It was all she could do not to laugh. Maybe she'd gone a little overboard, but she'd definitely gotten a reaction out of him this time whether he responded or not.

Unseen by either sibling, Ms. Penny was suddenly next to Jaime. She snatched the note from his hand and kept moving like it was an everyday occurrence for her.

"I'll speak to you after class, Jaime," she said without even looking at him.