Mommy Daycare Ch. 04

Jaina shivered as she contemplated exactly what she was getting herself into. She didn't even know for sure if she could take her brother in her ass. But there was no question in her mind one or more of them moms would manage it sooner or later. Wouldn't she feel silly if she didn't get to be first just because she was worried about the physics and logistics of it.

Jaina licked Olivia with renewed determination. She almost didn't even realize how wound up Olivia was getting until she had to grab her more firmly to stop her wiggling around so much. Olivia was getting all moany and squirmy, but settled down a bit when Jaina rubbed her pussy, and calmed even further when she had a nice cum.

"There, not so bad, is it?" Jaina said soothingly as she slid Olivia's plug in afterward.

Olivia rolled onto her side and reached back to finger her butt plug. "It's weird," she said.

"Weird but good," Alanna said, having been lazily watching and playing with herself. "Does funny things to my pussy."

"And my butt's so full now," Olivia said.

Jaina repressed a noise in her throat as she thought about how full she wanted her own ass. Now that it was in her head, and after licking so many mommy-asses all in a row, not to mention plugging them, she had her sights firmly set on her brother.

She needed to do it. And she needed to do it quickly before she got less horny, or someone made her cum, or just lost her nerve.

In front of everyone though? That didn't seem smart. But it would make a hell of a claim.

And it wasn't like they could just disappear for a while. There were too many moms here for Riley to take care of them all. Riley was only part-time, after all, even if she'd been relaxing since she got there that morning, and should have lots of energy.

Jaina grinned as she looked over at Riley and saw that she too was lazily playing with herself, having had a lovely choice of looking between Jaina and Kaden for some sexy stimulation.

Jaina padded over and sat herself down on the end of Riley's lounger. "How's it going?"

"Pretty good. Lovely morning."

"It is, really."

"You're not gonna try and plug me too, are you?"

Jaina tilted her head. "I wasn't. But... I could. Would you like-"

"No thanks."

"Are you sure? I'd lick you really good first."

"I'm sure you would."

Jaina grinned. "You're all hor-ny aren't you? Jealous I didn't plug you first?"

"Hardly." Riley shrugged. "But I guess if everyone's doing it..."

"Ha, alright. Which colour you want?"

"You have to do it too."

"Sure thing. But later, ok?"

"Later?" Riley frowned. "That's not like you."

"Ah! What, like I just can't help doing every sexy thing that comes my way?"

"I mean... you fuck your brother. And mom. And everyone else here."

"So do you! Kinda."

"Kinda. Right. And I know you'd love to plug me, 'cause that's just your kind of thing."

"Maybe."

"So what else is so important that you won't do it now?"

Jaina looked around, then scooted in closer. Riley moved her legs to the side and stopped masturbating as Jaina leaned in.

"I think I'm gonna see if Kay'll fuck my butt," Jaina whispered.

Riley's eyes went wide, but only for a second. "Oh wow, really?"

"Yeah. All these butts this morning... I mean, I gotta do it."

"Before someone else does, you mean?"

"Oh you think you know me so well, huh?"

"I do think that, yes."

"Well... maybe." Jaina shifted nervously. "You think I can do it?"

"Get him to fuck you? Are you kidding?"

"No. I meant more, like, can I take him in my butt."

"I assume so."

"I don't really do much butt stuff, you know."

"Sure. But if anyone can get fucked in the ass by their brother and love every single second of it, it's you."

"... is that a compliment or an insult?"

"Some of both, I think."

"Oh."

Riley patted Jaina's leg. "No for real though, you'll be fine. You know you will. I'll be here just in case."

"It's not too slutty of me, is it? Everyone might watch and stuff."

"Dude, obviously they will. Just go inside if you want privacy."

"We can't leave the moms all by themselves."

"They're grown women. They can handle themselves alone for a bit."

"I don't know..."

"Jay, babe, you can just say you want everyone to see Kay fucking your ass."

"That's not it!"

"Yeah it is. I'm not fighting about it with you. But yeah, it totally is."

"What kind of supportive friend are you anyway?"

"The kind who supports you being your brother-slutty self and fucking your brother every which way, including in front of other people, and including in front of your guys' mom."

"Well... good, then."

"Good."

"Great." Jaina stood. "I'm gonna go fuck my brother then."

"In your butt."

"Yes. In my butt."

Jaina felt Riley's eyes on her as she marched over to Kaden. That was fair enough, really. She'd be watching too, situations reversed.

Kaden had long since finished up in Luna's pussy, presumably dumping a nice big load in her.

Luna and Mary were currently both toying with him, nuzzling and licking his cock. Either they were cleaning him up, or getting him all revved up to go again. Probably some of the former transitioning into much of the latter.

Jaina didn't care. Ordinarily she'd let the moms have him, but now wasn't the time to be polite and wait for her turn. She just stalked up, grabbed Kaden's hand, and started pulling him away.

The moms grumbled a bit about having their boy yanked away like that, but it didn't take long for Mary to start trying to lick cum out of Luna's pussy. Jaina was pretty sure they'd be fine.

"What's up?" Kaden asked, clearly amused at Jaina's suddenly possessive behaviour.

"I need you for a bit."

"What for?"

Jaina stopped by a free lounger and turned to Kaden. "To fuck my butt."

"Your... butt?"

"Yeah."

A slow, sly smile spread on Kaden's lips. "Interesting. I'm down."

"I thought you might be."

"Where we sneaking off to?"

"Nowhere. Can't leave the moms unattended."

Kaden looked disappointed. "Oh. So later then?"

"No. Now. I've been playing with butts, and I'm all horny now."

"Me too. But... are you sure?"

"Yes. If I wait one of them might get you first."

Kaden laughed softly. "You're getting to be a jealous little thing at times."

"Nuh uh! But I'm your sis-ter. You have to love me best. That's all."

"Jealous."

"Shush."

"I think you just want everyone to see, hm?"

"That's irrelevant."

"Is it?"

"Do you wanna fuck my ass or not?"

Kaden grinned wider, then put his hands on Jaina's hips, pressed right up to her, and kissed her. He was all warm and solid against her. His cock pulsed where it was trapped between them.

"You know I love you," Kaden whispered.

Jaina melted at the casual sincerity in his words. "I know."

****

Kaden was so fucking excited. His sister had a particular talent for getting him all worked up, but this was one of those things that was on a whole different level.

She wanted him in her ass.

Part of it, Kaden assumed, was some small jealousy, even if she denied it. A greater part would be straight up horniness. He understood that. As frequently as he came these days, he still found himself hopelessly, stupidly turned on at times. Probably that was part of Jaina's thing.

They stood there, all pressed together, kissing each other with greater urgency. Jaina guided his hands to her ass and left them there. He grabbed her butt, spread it, and teased her tight little butthole with his fingertips. Every touch made her pant and grind even harder on him.

"I want you in there," she whispered urgently.

"Unf. I know."

"No one else has ever been in my butt."

"Oh god. I've never done anal either."

"Mmhm. So it'd be a first time for both of us."

"True."

Jaina kissed Kaden tenderly. "I kinda really like that."

"Me too. Especially with you."

Kaden's cock throbbed and her rubbed it harder against his sister. She met his eyes while grinding right back.

"You're gonna have to be gentle."

"Ha. There's something I don't hear from you very often."

"I'm serious."

"I know. I'll be good."

"You better be."

Despite Jaina's attempt at confidence and self-assuredness, Kaden could sense the hesitancy and nervousness there too. He didn't want to suggest postponing, both because he was all excited now and because he didn't think that would really help.

Sure, not doing this right now in front of four mommies and a best friend might make it easier, but having too much time to worry about it might just be worse. Plus Jaina wouldn't get to anally claim him in front of everyone, which he was pretty sure was important to her.

Kaden kissed her. She thought it was just a regular kiss at first, but he held it a long, long time. He made sure she knew how much he cared, both in the moment and just generally. He kissed her until they ran out of breath and had to break off panting. Her eyes gleamed all the brighter as they stared at each other.

"You're the best brother," Jaina said quietly but definitively.

"Glad you think so."

Jaina held eye contact for a moment, then slowly and seductively turned around, bent over, and crawled onto the free lounger next to them. She held herself on her hands and knees for a moment, then lowered her chest, leaving her ass sticking up for him, presenting her virgin butthole for his brotherly approval.

"Fuuuccck," Kaden moaned.

Jaina grinned at him. "Better treat it good."

Kaden nodded. There was lube handy, which he'd need, but eating her out came first. Had to do this right.

Some idly curious glances were coming their way as he knelt behind Jaina and gave her bum some soft kisses and loving licks. A brother eating his sister's ass wasn't the same shocking occurrence here that it would be most places. Everyone was pretty much ok with stuff like that. Even Olivia had been spying and must have seen plenty of similar things, even if she was brand new to participating.

But there was an energy and tension now that was all its own. Kaden wasn't sure if everyone could feel it, or just him and Jaina. In his mind it was all too obvious, but he really didn't want to spend the time or energy to look around and determine how obvious it was to anyone else.

He did, however, notice without looking particularly hard that Riley was playing with herself and very clearly watching the sibs while doing so. Riley was a hard one to read at the best of times, so he wasn't totally sure it meant anything.

Jaina got extra squirmy under his anal attention. Way more than usual. She couldn't wait. Already getting impatient. He knew how she felt.

Goddamn. His sister's butt. All his. Just as soon as he wanted to go for it.

Who was he kidding. He wanted it now.

Kaden abandoned his licking while Jaina's tight little hole was only mildly shiny with spit. He grabbed lube, drizzled some on her, and worked it into her asshole. She gasped and whimpered a bit, indicating he was going too fast. Which he probably was. He was getting all wound up over this. But she pressed back against his fingers too, non-verbally begging for more.

"Tell me if it's too much," Kaden whispered.

Jaina shook her head. "Just do it."

"I don't want to hurt you."

"Kay, I need you in my butt."

Kaden's cock twitched. "Say that again."

Jaina grinned over her shoulder, still nervous, but horny and amused too. "Your sis-ter needs you in her little butthole."

"Unf."

"That what does it for you?"

"I mean, obviously it does."

"I don't know how much more obvious I can make it." Jaina wiggled her hips, emphasizing how her ass was stuck wantonly in the air for him, ready for whatever he wanted to do to her.

"It's not about being obvious. Just... I don't know. Hearing you say it out loud. It's different."

"You like that better than my little butt all waiting for you?"

"... both. Both is good."

"Mmhm."

"Jay?"

"Yeah?"

"I'm gonna fuck your butt."

"Ooh."

"In front of everyone."

"Hnngg."

"All the moms are gonna see. They're already watching."

"So dooo iiit already."

Kaden groaned. He poured a little more lube on Jaina's ass, finger-fucked her tight butthole harder, then ran his slick hand up and down his erection.

Jaina was waiting for him to fuck her. To take her ass. He wasn't convinced she was ready, but she certainly wasn't going to be patient.

She moaned softly as he pressed his cock to her butthole. For a moment she was just happy to have to rubbed up on her, threatening to penetrate, but she soon was whining for more.

"Well, here goes," Kaden mumbled to himself.

An initial sharp gasp was the only sound for a long moment as Kaden pushed harder and slowly forced Jaina's bum open. He listened carefully at first for anything more, then couldn't help groaning deep in his throat.

"You're so tight," he hissed.

"You gotta stretch me out some," Jaina said, sounding just a tad too overwhelmed to come off as properly seductive and in control.

"Unf."

"Is... is everyone watching?"

"Do you want them to be?"

"... I'm not sure."

"I can't look at anyone right now anyway."

"Fair enough. Me either."

Kaden thrust deeper into his sister's butt. She was gripping him so tight. It wasn't easy to properly fuck her yet.

She whimpered with every movement he made, but kept encouraging him. Even pressing back as hard as she dared to try and get him deeper.

It was a long, slow process to get Jaina warmed up enough. Her ass eventually gave up and let him be inside her. It was still wrapped snugly around his shaft, but not so tight as to cause difficulties any longer.

Kaden grabbed Jaina's ass with both hands and spread it as he slid in and out, still slow and smooth, trying to bury himself in her. He had to try a few times before he could comfortably sink balls deep into her tight little butt.

"Oh wow," Jaina breathed. "You're so deep in me. In my ass."

"Mmhm." Kaden paused, keeping her cheeks spread as he admired the scene. "You know you're the best big sis ever?"

Jaina snorted, then moaned again as Kaden slowly pulled out and watched her butthole drag along his cock. "Fuck you. How'm I s'posed to think of retorts right now?"

Kaden smiled and gave her butt an extra squeeze before thrusting back in. "Don't know."

"Hmf."

Jaina reached back and started rubbing her pussy. Her moans and panting were getting louder all the time. Like she was forgetting to be shy or anxious about her first-time anal. Kaden couldn't blame her. It was all coming together now. Feeling amazing. He'd loved her ass anyway, but now being inside her and everything, it was on a whole new level.

"Is everyone looking?" Jaina asked again while rubbing herself silly and getting her ass thoroughly filled by her brother.

This time, Kaden actually checked. He blushed as he realized just how much attention they had.

"Yeah. They are."

"Everyone?"

"Yep. All the moms. Even Riley."

"Hnngg."

"Mmhm. They're, uh, kinda playing with themselves too."

"Really?"

"Yeah."

Kaden tried not to keep looking, but it was hard. Even with Jaina's sweet little butt to occupy him.

Alanna was rubbing herself slowly and made brief eye contact with Kaden, smiling with a small shrug at him, never stopping her fingers. Olivia was shyer, but seemed to take comfort in the fact that everyone else was masturbating to the sibs' anal adventure. Plus she'd presumably gotten herself off in secret many times to things she'd watched in the yard.

Luna and Mary had turned their loungers to face directly toward Kaden and Jaina, being totally unsubtle about watching the show. They also seemed to be rubbing each other's pussies instead of their own. Luna intermittently toyed with her brand new butt plug while Mary fingered her wet pussy, and eventually Mary started doing the same.

Even Riley had her hand between her legs, though she really only seemed to be cupping her pussy and pressing her palm against it, not fully masturbating, but clearly getting something out of what she was seeing.

Kaden went redder and warmer as he tried to ignore them all. He couldn't, really. Couldn't pretend they weren't enjoying him and Jaina doing their thing.

Every now and then Kaden relayed some details to Jaina. What their audience was up to. At first she didn't seem to have any better idea what to do with it than he did. But as they fucked and got more comfortable with their butt-play, they both just kind of got into it and enjoyed the extra thrill of having so many people observing their first time trying anal.

"It's too much," Jaina hissed.

"You want to stop?"

"No! Just... oh my goddd. I need to cum so bad."

"Mmm. Me too."

"Everyone's watching."

"I know."

"Watching us."

Kaden grunted and squeezed Jaina's ass as he thrust hard into her. "Watching you get fucked in the ass by your brother."

"Unf."

"Even Mom's watching."

"Fuuuccck."

"It's fucking insane."

"I know. I looovvve it."

Kaden felt Jaina cumming. He knew a lot of it was her fingers blurring on her clit, but he'd been a big part of it too. Fucking his sister's virgin ass, claiming each other in front of their whole mommy daycare group.

She gripped him so tight as she came. Her ass clamping down even tighter than when he'd first entered her, though only intermittently. She was a spasming little mess around him. It was like he could feel her pussy going off through her butt.

It only made Kaden want to cum even more. And it wasn't like he was all that far off in the first place.

"I'm gonna cum in your ass, Jay."

"Yesss."

"You want that?"

"Yesss! You have to!"

"Do I?"

"Don't be mean. You have to cum in my butt."

"Hnngg. Ok."

Kaden's eyes rolled back. He held on a few moments longer, then let go all at once. He always came hard and thick for his precious sister. This time it was deep, deep in her little butthole. Filling her ass with brother-cum. Just like she wanted. Like they both needed.

Soft mommy-moans accompanied the sibs cumming for each other. Doing their naughty butt stuff. The moms were getting off on it. And Kaden couldn't blame them at all.

****

Jaina had been a little worried when Kaden first entered her butt. He felt so much bigger than usual, even if that was only because she wasn't used to having anything much more than a finger in her ass.

But it was so damn good, and just crazy hot. As Jaina adapted to having her butt stuffed and stretched, she really came to love the feel of having her brother inside her like that. And, more importantly, knowing that it was a first time for them both, and that everyone could see it.

She was such a confused little mess. Wanting Kaden to have special moments with her. Maybe anal shouldn't have counted, but it did. Especially when he came in her and made such a gooey mess of her tight little bum.

Kaden pulled out of her and stayed right where he was, kneading and spreading her ass cheeks. "Your butt's not closing all the way."

Jaina flushed, still lightly rubbing her pussy. "Well what did you expect fucking me like that? My butt's all confused now probably."

"Ha. Probably."

Riley padded over and started poking at Jaina's butthole, rather marring the lingering intimacy of the moment. "Wow, that looks like it'd hurt."

Jaina shook her head. "Nah. It was nice."

"Lots of cum in there?"

"Mmhm. Lots."

Riley pattered off, then returned with a butt plug. She popped the packaging open, sucked it a bit, then pushed it against Jaina's bumhole. "Better make sure it all stays in."

Jaina groaned. "Oh my god. Why you always acting like I'm a perv and stuff?"

"You are."

"And what does this make you?"

"A concerned friend."

"Uh huh."

Riley had selected a red heart plug for Jaina. Despite her protests, Jaina was pretty much on board with being all plugged up now. It would remind her of just getting fucked, and it would definitely keep all Kaden's brother-cum inside her.