Saga of Littown Ch. 03

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.

****

Jaime woke up to the bizarre sensation of someone licking his butthole. He was lying on his back and his legs had been pushed up toward his chest to make room. He looked down to find his sister Emily with her head partly hidden behind his hard cock. She was busily tonguing away at him.

"What are you doing?" he asked.

Emily stopped licking and looked up. "Morning," she said cheerfully.

"Good morning to you too. But seriously, what?"

Emily tilted her head. "You don't like it?"

Jaime shrugged. "I dunno. It's weird, but... kinda nice? It's like... well, it's not like anything, really."

His sister seemed to parse his feedback, then gave a curt nod and started licking again. His butthole had never been more covered in saliva in his life.

"Em?"

"Oh fine. I'm getting you prepped."

"Prepped for what, dare I ask?"

Emily smiled and finally let go of his legs. He let them drop back down to the bed. She pulled out the nondescript bag Lilith had given him for his birthday. His eyes widened as he remembered what the bag contained.

"I found this just lying around," Emily said, pulling a brand new butt plug from the bag. "I thought that now might be a good time to try it out."

"It's not even mine," Jaime said quickly.

"Of course it is. It was in your room." Emily frowned. "Are you embarrassed about having it? You don't need to be, you know."

"Lil gave it to me. I didn't even want it."

"Oooh, it was a present from Lil. That actually explains a lot."

"Right, so we don't have to try it out."

"Au contraire. If there's one thing Lilith's an expert on, it's weird sex stuff. She wouldn't have given you this if you weren't going to like it." Emily pulled the bottle of lube out of the bag and tore the plastic wrapper off the top. "This might be easier if you roll over."

"Em...."

Jaime wanted to protest, but Emily wouldn't have any of it. She was far too intrigued to let the idea drop. She whipped out her sad puppy eyes and pouty bottom lip. Jaime never stood a chance.

"Fine," he said.

He rolled onto his stomach and, at his sister's urging, pulled his knees under him to stick his ass upward. She poured some lube in his ass crack, then massaged it in with her fingers. Again the feelings that Jaime experienced were new and unfamiliar, but not unpleasant.

"How's that?" Emily asked.

"It's... ok," Jaime admitted grudgingly.

"And how about this?"

Emily poked a finger gently into his butthole. She only had small fingers, so it wasn't much of an intruder at all. It didn't hurt the way Jaime had feared it might. It felt kind of interesting, actually. In some ways the sensation was more anticipatory than physical.

"That's fine," he said.

Emily nodded to herself and carefully added a second finger. She stuck them in deep and wiggled them around. Now Jaime could really feel something happening. He was mildly distressed to find that he actually kind of liked it. It was a new and decidedly sexual touch on a previously unexplored part of his body. Mostly it made him very confused.

"Right, time for mr. plug," Emily declared.

Jaime felt a disturbing sense of longing when her fingers withdrew. He was just starting to get used to the idea of being anally penetrated by his sister.

"Wait. Em, this doesn't make me gay, does it?"

He couldn't see the look of sheer incredulity she gave him.

"Well," she said in the tone of voice one might use with a particularly slow child, "I'm a girl, and we've spent the past two days with your penis inside me at every conceivable opportunity. In fact, you can't seem to stay soft when I'm around. And you seem to react to other girls being sexy too. But no, you're right. Maybe having a girl play with your butt makes you a guy who enjoys sex with other guys."

"It sounds completely fucking retarded when you put it that way," Jaime said sheepishly.

"'Cause it is."

Emily licked the brand new butt plug for luck. She pressed it against her brother's asshole, then shoved it in without giving him any more chances to protest.

Jaime experienced a brief flash of pain as the widest part of the toy entered him, but it was over before it registered. He was left with the sense that... something was there, where it shouldn't be. It didn't hurt, and didn't feel gross, but also didn't feel like any particularly sexual.

"That's it?" he asked.

"That's it. Do you like it?"

"I don't not like it. But it's not really doing anything for me."

"Hmm...."

Emily quite enjoyed playing with her brother's butt. He looked so sexy and vulnerable with his face against the mattress and his ass sticking up at her. She wanted him to enjoy it too, but so far the results had been mediocre. She reached out and touched the base of the plug, wiggling it experimentally.

"Ooh," said Jaime before Emily could ask how it felt.

"You like that?"

"Yeah, that's nice. Weird, but nice."

So Emily wiggled the toy, and pulled it slightly out, and generally just played with it. Jaime moaned and squirmed beneath her. She had him now.

"We'll make a butt slut out of you yet," Emily said.

"Hey! Don't make me sound like a weirdo."

"Perish the thought."

Emily wrapped one hand around her brother's hard cock while continuing to finger his toy with the other. It might have been an illusion, but she could have sworn she felt his cock react to the movements of the plug in his ass.

Jaime was going crazy and getting very close to orgasm. Sensing his impending release, Emily flipped him over and threw her mouth over his cock. She bobbed her head up and down a few times until he came. She greedily swallowed her delicious, incesty breakfast. She'd worked hard for it this morning and she deserved every drop.

Emily sat back on her heels with a catlike look of self-satisfaction. Her tummy distended outward just as the day before.

"You look a little bit pregnant," Jaime observed.

She wrapped her hands around her belly and smiled. "My yummy cummy tummy baby." She giggled happily.

"Lovely. Can you take the plug out now?"

"I could. Orrr you could leave it in for the day. It--"

"No."

"But--"

"No."

"Fine."

Emily pulled the toy out of her brother's butthole with a 'splop.' She carefully set in upright on his dresser.

"You'll need to wash that," she said.

"Yeah, yeah. What are you still grinning about?"

"You're my buuutt sluuutt now."

"Shut up."

Jaime raked his fingers along his sister's unprotected side. She shrieked and tried to fend him off.

"No fair, no fair! My tummy's all full. You can't tickle me right now."

That didn't stop him. He went for her again and again until she had to leap out of bed. He faked a lunge at her and she fled the room. Just as well, they had to get ready for school soon, and if they ended up fucking that just wasn't going to happen.

****

Jaime made it to English class without incident, but that was the part of the morning he was worried about. He felt like Ms. Penny was staring at him constantly. Every time she came near his desk she seemed to find an excuse to bend over and 'accidentally' show off cleavage you could lose a whole snowboarding team in.

Even worse was the end of class when he had to hand in his special assignment. He was scared she'd be offended by the naughty filth Emily had helped him write. On the other hand, he was downright terrified that she'd like it.

"Do you have something for me?" Ms. Penny asked.

Jaime handed over the tale of debauchery. "I hope it's ok," he said.

"I'm sure it will be."

"I better get going then."

Jaime inched toward the doorway. He had half a mind just to bolt and get out of there as quickly as possible.

"Please, stay. Let me just glance over your story."

Ms. Penny started reading. Jaime shifted awkwardly from one foot to the other. He really didn't want to be there when she got to the worst and most implausible bits. His sister had perhaps too much of an imagination.

He was only mildly surprised when Ms. Penny started absently unbuttoning her blouse. Her massive tits spilled out more with every flick of her fingers. Jaime wasn't sure if it was just a habit for her, or if she'd gotten so into the story that she'd forgotten he was still in the room.

After her shirt was fully opened, she undid her bra and let it fall to the floor. Her breasts bounced free, causing a minor tremor in the tectonic plate beneath the school. Jaime couldn't help staring. They were too big to actually be properly sexy, but they were a fascinating display all the same.

"Cum on my tits," said Ms. Penny.

"What?"

"Cum on them. I can see it in your writing. You desire them beyond any healthy degree, and you need to release that desire somehow. Cum all over your teacher's gargantuan breasts!"

Her eyes continued to scan the story, while her hand was shoved down the front of her skirt. Jaime heard the schlicking sound of furious female fingering. He wondered if it would even help if he explained that the fantasy wasn't his. Probably not. He was just a puppet in his teacher's weird universe at this point.

Since Jaime had yet to move, Ms. Penny took some initiative. She dropped to her knees in front of him and tore open his pants. His hard cock proved to her that she was right, that he needed her in an inappropriately sexual way. It didn't occur to her that he was basically just always horny.

Ms. Penny wrapped her breasts around Jaime's cock. It was a bit like using three or four packages of rolls for a single hotdog. Jaime was worried if he fell into her cleavage, he'd never find his way out. He grabbed a desk behind him and held on, fighting against the gravity pull of the twin moons encompassing his dick.

The world's most absurd tit-fuck just wasn't going to get Jaime off. His teacher was enjoying herself, and it definitely felt good. Breasts were breasts, and they were lovely and soft and warm around his cock. They just weren't anything to compare to his sister and her perfect little pussy.

Jaime closed his eyes and thought about Emily. He thought about her tight, wet holes and how Ms. Penny's tits just didn't even come close. He thought about his sister's lithe naked body, her smile that could melt him, and her mischievous blue eyes. He thought about how happy he'd be if he could spend every waking and sleeping moment buried deep inside his sister's pussy.

Then he was cumming. Thinking about Emily had done the trick. Ms. Penny squealed in unconcealed delight as her breasts were unceremoniously covered in her student's semen. Despite the quantity of cum, there still wasn't enough to actually give her a proper coating. It was like a half-assed paint job on a wall, with patchy bits and uneven layers. It was, also, more cum than Ms. Penny had ever seen in one load, which only reinforced her delusion of forbidden attraction.

"Do you feel better now?" Ms. Penny asked.

"I feel... like I just came," Jaime answered honestly.

He put his cock away, and just in time too. The door burst open in a rumble of mostly figurative thunder and lightning. Principal January stood in the doorway with eyes aflame.

"What is going on here?" she demanded.

Jaime ducked behind a desk. It wouldn't really protect him, but it felt better than nothing. Ms. Penny was a little more assertive than him.

"My stupid bra broke on me," she said. "My breasts are so big it's hard to find anything that lasts. They must have torn my shirt open when my bra let go."

Ms. January narrowed her eyes. She didn't believe the excuse, but the English teacher's breasts were quite ridiculous. It could happen.

"Then what's all over your crazy-huge tits?"

"Moisturizer," Ms. Penny replied smoothly. "Can't let these babies dry out."

She rubbed Jaime's cum into her tit-flesh. It took a quite a long time. Some cum had hit her chin, so she rubbed it into her neck and face as well.

Ms. January was annoyed that she couldn't get anyone in trouble. She knew that sexy naughtiness had happened, but she didn't have sufficient proof. She flashed an evil, humourless grin at Jaime and Ms. Penny before stalking off.

"That was close," Jaime said.

"Oh, don't worry about Principal January," Ms. Penny said. "She's just very diligent about looking after her school. She's really quite a sweet lady."

Jaime was baffled. "Did you not see her razor sharp teeth? And her eyes have actual fire in them when she looks at me. Actual, literal fire."

"You've got quite an imagination." Ms. Penny picked up the story he'd written. "And if you ever want to put that imagination to use again...."

Jaime took off before she finished her sentence. He ran like the wind, hoping like hell he wouldn't run into the principal. There were too many layers of crazy going on in the school. He just wasn't ready for this shit.

****

At lunch time, Jaime found his sister at her usual table. Her, Lindsay, Cindy, Mindy, Windy, and Zindy were all sitting together and chatting away. He didn't even mind there being such a group of them this time. The safety of numbers was appealing.

Lindsay made eyes at Jaime as soon as he sat down. "Heyyy, Jai."

"Uh, hey Lindsay."

"Need any 'help' today?"

Jaime blushed. He had no idea whether the other girls had been informed of the blowjob he'd received from her yesterday.

"We're a very helpful group," Mindy chimed in from across the table. She winked suggestively at Jaime.

The other girls started to add their own subtle invitations and innuendo. Possibly some of it was just teasing, but Jaime assumed there were some real offers being made.

"Alright, alright," Emily said, taking charge of the table. "You guys need to stop flirting with my brother right in front of me."

"I knew we were making you jealous," Mindy teased.

"Am not," Emily said, but her face reddened as she protested.

"Yeah, come on guys," Zindy said. "Em probably just doesn't want to think about her hot brother doing super sexy stuff with any of us."

"Oh, right," said Cindy. "Because thinking about her brother sexually would be kind of incestuous. Incest is bad, as everyone knows, and is icky and gross and stuff also."

Despite the fact that every girl at the table regularly had sex with their brother, none of them dared make that fact public. It put them in a weird spot sometimes where they had to pretend not to enjoy the idea of sisters and brothers fucking.

"Yes, bad and icky," Emily agreed. "And not at all super hot and amazing and the best thing ever."

She secretly grabbed Jaime's hand under the table even as she spoke. He was glad of her reassuring touch; not because he thought she meant anything she said, but because he hadn't had any physical contact with her in at least an hour.

There was a lull around the table as everyone daydreamed about their respective sibling fuckbuddy. Every now and then one of the girls would mumble "ick" or "totally not sexy at all" just to keep up appearances. One by one they made excuses to disappear and find a secret place to masturbate.

****

Jaime almost made it to the end of the day and was counting down the minutes until he could leave. Unfortunately, his path nearly crossed with Principal January for the second time that day. She was gliding through the halls, hands clasped behind her back. She gave every appearance of being on a gentle patrol of her school. Jaime might have believe the facade if he hadn't been so certain that her feet weren't actually touching the floor.

He needed somewhere to hide. In his panic, the only place he could think of was the girl's locker room he'd taken refuge in once before. This time when he entered, it was already occupied. He was relieved to see that it was the same volleyball team that he'd met before. Trying to explain himself to a whole new group of half-to-fully naked girls would have been daunting.

Some of the nearer girls smiled as he entered. He'd been established as Not A Perv, so it was alright if he wanted to stop by and perv on them a little. The girl nearest to him bent over and pulled down her panties, apparently unconcerned that he could see every detail of her pussy and butthole.

"Jaime!"

Katelyn, the captain, had spotted him. She was part way through stripping down, and only had on her shirt and socks. Jaime tried valiantly not to stare at her bare pussy.

"Hey, Kate," he said.

"Those girls giving you trouble again?"

Technically he was having trouble with some girls, but not the purple-haired ones Katelyn was referring to. Even more technically, his current troubles were more to do with women, and woman shaped monsters, rather than girls per se.

"Kind of," he said, splitting the difference.

"Well we're just finishing up here. You're welcome to hang out for now."

"Thanks. I appreciate it."

He also appreciated a girl who had just come out of the shower. She had dried herself off, then started doing some stretches. She was both very nude, and very limber.

Katelyn drew Jaime's attention back to her when she resumed removing her clothes. She shed her top and sports bra, then dealt with her adorable little socks. She was amazingly hot without any clothes on. Her dedication to her sport had given her a toned body, and a butt worth committing multiple acts of genocide and some light treason for.

"Do you want to shower with us?" Katelyn asked. "You know, as long as you're here."

"Oh, I don't know...."

Jaime suddenly found himself the centre of attention. Eavesdropping girls had encircled him, and he was being surrounded by naked boobies.

"C'mon, it'll be fun," Katelyn said. "It really helps build our team spirit."

"Yeah," agreed a girl beside Jaime, "especially when we lick each other's--"

"Shush," said another girl. "No one outside the team is supposed to know about our wicked sexy team-building sexy time fun times."

"Oh right. Sorry. Forget I said anything."

Katelyn rolled her eyes. It was like herding cats some days. "Anyway, secret lesbianism aside, it's still a good time. What do you say? Team shower?"

There was a circle of naked girls around Jaime, all giving him pleading puppy dog eyes. None of them were individually as convincing as his sister, but there were a lot more of them.

"Sure," he said. "Team shower."

The girls cheered, then moved as one to help him disrobe. He was naked and being dragged to the shower area before he even really understood what was happening. Once under the hot water, he found that the girls were still clustered around him far more than was efficient. Many of the girls weren't even under any water, and there were plenty of shower heads that weren't being used.

"So can we do secret team sexy time fun time sex stuff with him now?" a girl asked.

"He's not a team member," Katelyn reminded them. "And you're all going to be late getting out of here if you don't get showered off. Spread out already."

Katelyn tried to shoo her girls away from the cute naked boy in their midst. She might as well have tried to get the wind to change direction by blowing on it. Even girls who'd already gone through the shower were wandering back in and joining the crowd. Jaime was the lone male island in a sea of horny, naked, eighteen year old girls.

"Maybe he could just perv on us a little," came another suggestion.

"No, if he pervs on us we have to punish him. That's the rule."

"Well what if we perv on him? Is that ok?"

Katelyn didn't know what to do with that. There was no precedent set for a boy wandering into a girl's changing room and him being the one getting ogled. She was the captain though, and if she wanted to keep her authority she had to be decisive. In the game of girls' extracurricular activities, you win or you die.