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Anal

Author’s Note: This story involves two brothers and one sister, and quite a lot of anal. Consider yourselves warned. All characters over eighteen.

****

Wes and Ryan were headed to the living room, but Wes stopped in the doorway, nearly forcing his brother to run into him.

“Dang. Bailey’s got the tv already,” Wes said.

“Yeah, so? She always does. We can just kick her off. She can play handheld.”

Wes hesitated, and Ryan jammed himself up in the doorway too. The brothers watched their sister for a few moments.

Bailey didn’t seem even slightly aware of their presence. She lay on the floor on her tummy, feet kicking slowly in the air, headphones over her ears, eyes glued to the tv on the far wall from her.

“We never should have got Animal Crossing for her,” Ryan grumbled.

“Huge mistake,” Wes agreed. “We’ve never had to fight so hard with her over the tv.”

“I know. I miss the days when it was just a fight between the two of us. Bailey getting mixed in really throws off the dynamic.”

“Well… she was usually in the mix. Just not quite so single-mindedly.”

“True.”

The brothers continued watching. Bailey continued not to acknowledge their presence.

The siblings were all in their twenties and had grown out of the worst of their squabbling, but that didn’t mean that situations didn’t arise at times. Those times could be a little unfair on Bailey, since she was the youngest and the only girl. But she also had little sister powers that made up for that when she really wanted to.

“We could just wrestle her away,” Ryan suggested.

“Yeah. We could. I think I’d feel bad about it though,” Wes mused.

“Why?”

“She’s so intent.”

“I know. She has been basically since she got the game. I don’t understand it personally.”

“Me either. But it’s kind of adorable. You remember when she used to be little and get wrapped up in certain books? She’d practically forget the world around her at times.”

Ryan chuckled. “I remember. There was that time we tried stacking crackers on her head to see how long before she’d notice.”

“Hehe, yeah. The tower fell over and we got yelled at for making a mess. I don’t think Bailey even realized until then.”

“You think she’s still that bad?”

Wes studied Bailey intently. “Hard to say. Wanna find out?”

“Kinda, yeah.”

There were some grapes in a bowl in the kitchen. The brothers each grabbed a small handful, then returned to the doorway, settling just inside the room this time instead of squeezing themselves right in the doorway.

Wes nodded to Ryan, then pinged a grape at Bailey. It hit her leg and bounced off. No reaction. Ryan went next and just caught her foot as it swung lazily in the air. Again, no reaction.

The boys grinned and got more into it, bouncing grapes off their sister to her continued lack of response. They ran out before even making her turn around.

“Well that was kinda fun,” Ryan said.

“Uh huh. Probably should clean those up before Mom gets home.”

“Probably.” Ryan shrugged. “Now what? More grapes seems like overkill.”

“Yeah.” Wes watched Bailey’s slow-kicking feet. “Bet I could take her socks off and she wouldn’t notice.”

“Hm. That’s about even odds. But yeah, sure, you’re on.”

Wes slipped closer and knelt behind Bailey. She didn’t react. Didn’t stop slowly kicking her feet. He tentatively reached out and stopped one of them by the ankle. Bailey’s other foot stopped too, more slowly.

Wes waited a moment to see if she’d say anything yet, but still nothing. He shrugged and tugged one sock off, then the other. Bailey was left barefoot, and went right back to slowly swinging her legs once Wes let them go.

Another long moment still showed no sign of Bailey giving any attention at all to her surroundings. Wes half-turned and shrugged at Ryan, who simply nodded back and acknowledged that Wes had won the meaningless bet.

Ryan scooted close and knelt next to Wes. “Almost no fun picking on her if she’s gonna be so entranced, huh?”

“Almost.”

There was a moment of silence between them.

“Hey, so, that skirt’s kinda riding up on her,” Ryan said with a hint of confused emotion.

“Yeah. It is.”

“You think she knows?”

Wes gave his brother a disbelieving look. “She didn’t notice us pinging grapes off her. How do you think she’s gonna be aware of this?”

“Just asking.”

“Uh huh.”

“… I could probably flip it right up, you know.”

“Dude!”

“Well I could.”

“I mean… probably. That’s our sister though.”

“I am aware.”

Wes was quiet for a moment. “… she does have a nice butt though.”

Ryan nodded. “True.”

“And this is for science.”

“Exactly.”

Ryan reached out and flipped the back of Bailey’s skirt up. No reaction, as expected.

Bailey’s panties were drawn tight over her bum, only covering maybe half her ass cheeks, and making her butt crack very obvious.

Ryan and Wes just stared, torn between the view and feeling guilty about taking advantage adalar escort like this.

“It’s a really nice butt,” Wes murmured.

“Too nice.”

“Mmhm.”

“… so now what?”

“You’re asking me?”

Ryan shrugged. “Just saying. I flipped her skirt up. You gonna do anything else?”

“You daring me?”

“Maybe.”

Wes considered Bailey’s tempting booty and her softly swinging feet. “No way I can get her panties off.”

“You’d go for her panties?”

“I said not them.”

“Only ’cause of practical reasons though.”

“You judging me?”

“Not really.”

“Good. ‘Cause what I’m thinking is probably worse.”

Ryan raised an eyebrow. “Oh?”

“Although, you definitely won’t be able to beat it,” Wes mused confidently. “So it might be worth it.”

“I really doubt that.”

“Five bucks?”

“Yeah. Alright. But I only have to one thing riskier, right?”

“Sure.”

“Deal.”

The brothers shook on it. Almost immediately after, Wes started undoing his pants.

Ryan’s eyes widened. “Dude!”

“I told you.”

“You’re not gonna…”

Wes frowned as he pulled his cock out. “What? I’m gonna jerk off on Bailey’s ass.”

“Oh.”

“What the hell did you think?”

“Something worse than that.”

“Idiot.”

“Look who’s talking. You got your dick out right now.”

Wes shrugged. “Gonna win five bucks though, aren’t I?”

Ryan shook his head. “This is way over the line, you know.”

“Do I win?”

“… not yet.”

“Ok then.”

Wes gently pushed Bailey’s legs apart, enough that he could squeeze between them. Ryan watched disbelievingly as Wes started jerking himself off over their little sister’s ass.

“You’re insane,” Ryan murmured.

“She’s got a nice butt, though.”

“You know that’s not the issue here.”

Wes shrugged and kept stroking himself.

Ryan could only sit by and watch it unfold. His brother jerking off on their sister’s booty.

It was fucked up, but weirdly kind of hot too. Bailey had a very nice butt on her, and her obliviousness to what Wes was doing was a special, questionable kind of sexy.

It only got worse when Wes actually came, splashing hot streaks of cum on Bailey’s panties and parts of her bare butt cheeks. Both brothers just stared at the mess for a moment afterward, one in a fresh state of post-orgasm guilt, and the other still horny and confused.

“Well I probably shouldn’t have done that,” Wes muttered.

“Probably not,” Ryan agreed.

Bailey’s sweet little ass was a cummy mess thanks to her brother. Neither Wes not Ryan knew what to do about it now.

“I mean, at least I won five bucks,” Wes said.

“Oh hell no.”

“Yeah I do.”

“Not if I do something crazier. That was the bet.”

“Yeah, but what are you possibly gonna do?”

“Get out of the way.”

Wes bemusedly backed off. Ryan took over between Bailey’s legs. He got his cock out just as Wes had before. He didn’t really want to push things any further, but a bet was a bet.

Not to mention the forbidden siren song of their little sister’s butt.

Instead of just jerking off, Ryan lowered his cock further. He pressed it tentatively to Bailey’s messy bum. He flinched a little, thinking surely she’d turn around all shocked and disgusted. But no. Nothing.

Sighing with relief, Ryan pressed more firmly and started slowly grinding on Bailey’s booty. Her bum felt really nice on his hard, needy cock. It was a bit weird of course, since she was his sister and all, not to mention their brother’s cum already messing her, but none of that bothered him as much as he felt it should.

Maybe it was just horniness. Maybe. But Ryan had to admit, there was an allure to Bailey’s ass that went beyond purely circumstantial.

“Dude! You’re grinding on her.”

Ryan grunted. “I know.”

“… how is it?”

“Kind of amazing.”

“Yeah?”

“Yeah. I mean, I kinda wish you hadn’t cummed on her first. But it makes her more slippery too, so I dunno.”

Wes watched intently as Ryan slid his cock up and down Bailey’s slick butt crack, pressing her panties deeper and deeper between her cheeks.

“I think I might be a little jealous now,” Wes said.

“Unf. Mmhm. It’s… damn, it’s pretty good.”

“Looks it. You think I could get away with trying after you?”

“I mean… probably.”

****

Bailey was going crazy. She hadn’t been able to concentrate on her game at all since Ryan started grinding on her. She had no idea how neither he or Wes had noticed. Apparently they were too focused on her bum.

Her oblivious act had been cultivated for many, many years. Originally a way to try and get more time reading books when she was younger, it had come in handy so very often since then too.

It had, arguably, backfired on her in this instance. Bailey had never anticipated her brothers getting nearly so naughty.

And yet, from the moment she realized Wes was jerking off on her butt, Bailey had surprised herself anadolu yakası escort at how ok she was with it. She felt so damn naughty just lying there and letting the boys think they were getting away with something.

With a cummy bum, and subsequently her other brother fully grinding on her, Bailey was feeling some things that she definitely shouldn’t be. Her pussy was absolutely soaked by this point, and she’d be scared to stand up lest Ryan or Wes see just how bad it was.

On the other hand, they were being way, way worse than she was. They were actively being bad, not just passively letting it happen. Bad with their little sister who’d only wanted to play her game in peace for a while longer.

But still, what kind of horny little thing was she that she would not only let them do it, but secretly really wanted more? The longer Ryan humped her messy bum, the more Bailey lost herself in it. She closed her eyes, stayed as still as she could, and felt her pussy burn with forbidden desire.

She managed to maintain some faint semblance of composure until Ryan came on her ass too, followed by a brief, loudly whispered argument, and Wes taking over again. Bailey somehow couldn’t help herself moaning aloud when Wes pressed his cock to her butt for a turn grinding on her.

The effect was instant. Wes froze right where he was, gently throbbing against her booty. Both boys went dead silent.

Upon slowly removing her headphones and turning her head around, Bailey found her brothers both perfectly still, as though hoping her vision might be based on movement.

“Oh now you stop,” Bailey mumbled.

Ryan and Wes looked at each other, then down at her butt, then back to her.

“Sorry?” Ryan said awkwardly.

“Didn’t mean to,” Wes agreed.

“We, uh, didn’t think you were gonna notice.”

Bailey rolled her eyes. “Ok, first off, not super cool to cum on someone just ’cause they don’t notice. Second, how the hell am I not gonna notice vigorous grinding on me? Third… kinda rude to stop now if you’re gonna do it.”

It took Wes a long moment for him to make up his mind, but once he did his hips started moving again. Bailey had to fight the urge to close her eyes and lie down to just enjoy it. She’d already given away that she was enjoying herself to some extent, but it simply wouldn’t do to let the boys know just how much.

Wes grew in confidence pretty quickly. Probably due to horniness more than anything. His cock thrust harder and harder on Bailey’s messy ass, really working her panties deep into her butt crack.

Her panties were going to be absolutely ruined thanks to her brothers. Both from their cum soaked into every inch of the back, and from her own pussy destroying them in the front.

Slowly, moving carefully, Bailey put her headphones back on and turned her attention back to her game. A large part of her mind couldn’t help being on her brothers and their antics, but she made a deliberate effort not to let that show. She didn’t know why. She’d given herself away already. But it was the best source of control she could think of in the situation. To feign indifference as best she could.

****

“Dude, is she just letting us do this?” Ryan hissed.

Wes grunted, still grinding on Bailey as hard as he wanted. “Seems that way.”

“Why?”

“How the hell should I know?”

“Yeah. I guess.”

To all appearances, Bailey had gone straight back to her game, leaving her bad, bad brothers free rein to keep being naughty with her bum.

It wasn’t a perfect act. Little cracks showed at times. Like how she whimpered softly when Wes came on her again. Or, even less subtly, how she lifted her hips when Ryan swapped back in.

Ryan hesitated again, but all Bailey had done was raise her hips off the floor, getting up on her knees with her face and arms having hardly moved. It would make for an obviously slutty position, if not for her apparent focus on her game. Or maybe that made it sluttier.

Tentatively, sure he was pushing his luck, Ryan pressed his cock to Bailey’s pussy instead of her butt. Still over her panties of course, which were bizarrely soaked given that no cum should have gotten on that part of them. Bailey didn’t initially react to the contact, which Ryan accepted as an indication to continue.

This was without a doubt the horniest, craziest thing either Wes or Ryan had ever been involved in. They just kept playing with their sister while she mostly ignored them. Every now and then they’d get a little moan, whimper, or wiggle out of her, but that was about it.

“You think we can make her cum?” Wes asked.

Ryan shrugged. “Probably.”

“I kinda want to try.”

“It would be nice of us, actually. Since she’s, like, letting us cum all over her like this.”

“Only polite, really.”

The boys took turns grinding on Bailey. Sometimes they’d work together to grind on and rub her, sometimes just one would try. Their best bet seemed to be getting really deep in her butt crack while slipping a hand under her panties ataköy escort to get her clit. It was hard to tell if it was working though.

Upon cumming once more each, Ryan and Wes both decided that was enough. They flipped Bailey’s skirt back down and left her to her game.

****

Bailey only waited until her brothers were just out of the room before standing up shakily. Her legs barely wanted to work, rather annoyingly. Not that she could much blame them.

She was so damn horny in the aftermath. Ryan and Wes had tried. She knew they had. They’d even been close to making her cum a couple time. But they hadn’t quite gotten her there, partly thanks to her own lack of encouragement and guidance. Now she was a total mess, physically and otherwise.

Bailey tottered off to her room and carefully locked the door behind her. She took a moment and just stared at herself in her mirror. The moment turned into several long minutes, especially after she dropped her skirt and examined the cummy disaster of her panties.

It was hard to believe two boys could cum so much. Her panties were wrecked, front and back. Streaked and smeared absolutely everywhere. By her brothers of all people.

And she herself had been flooding like crazy, only adding to the horny disaster. Her pussy wouldn’t give up. It had been tormented and teased for way too long, and by some of the most forbidden people possible.

“What the fuck does that even say about me?” Bailey murmured to herself.

She turned to check out her messed bum again.

“I’m so bad.”

Bailey retrieved her phone and almost pressed the button to call one of her friends. She stopped and shook her head, then scrolled down selecting a different friend. She hesitated again, then gave up and set the phone down. There was no one she could ask for advice about this. Who could even begin to understand it?

Upon further reflection, Bailey snapped a few pics of herself in the mirror, particularly focused on her cummy panties. She wanted to save some images for the future, in case she could examine what she’d been a part of in any saner kind of way.

She was anything but sane at the moment.

Bailey tried to feel guilt. She tried really, really hard to muster some. It didn’t work. Every time she thought about her brothers grinding on her ass, or she ran an exploratory finger through the mess they’d left, she just got fluttery inside and felt her clit throbbing.

Her brothers. Her big brothers. Teaming up on her like that. Why did she love it so very much? It was stupid and crazy and unquestionably wrong. It was all out of horniness and a lack of self-restraint.

Or… something else?

Bailey was quite certain she wouldn’t have been so into it with other boys. Ryan and Wes were special. Family. Total little shits sometimes, as brothers always were, but… but so much more too. What did that even say about her that that bond could translate to enjoying their naughtiness so very much?

Did she care? Maybe she didn’t care. Maybe she could just enjoy it. No one else was going to know anyway. This wasn’t the sort of situation where anyone was going to run off and brag about it.

Bailey put her moral crisis on hold and padded to her dresser, intent on dealing with an easier and less complicated problem. She snagged her vibrator and curled up in bed with it.

A soft moan escaped her lips as she slipped the toy into her panties and vibed her clit. With her free hand she pulled her panties down in the back and fingered her butthole a little. She was able to make herself quite slippery using only leftover cum from her panties.

“So bad,” Bailey hissed to herself, alone in her room.

She wiggled a cummy finger up her bum. She tried to deny it, but she was fully imagining what it would have been like if Wes or Ryan had tried to actually get inside her.

Bailey had never been one for a huge amount of butt play. It was interesting to mess around with a bit at times, but not a major focus for her. After having both her brothers grinding over her ass, rubbing against her tight little bumhole, her mind was dead set on it.

It was awful that she was even contemplating it. The notion of one of them going too far. Actually going for her ass. Slowly stretching it open and getting deep in.

Bailey came with a pair of fingers in her ass up to the second knuckle and her vibe pressed hard to her clit. In her head it was Ryan with his cock up her butt and Wes ferociously tonguing her pussy. Or maybe vice versa. They could switch.

She whimpered and shivered like a naughty li’l sis, but didn’t even stop there. She wasn’t done yet.

****

Ryan and Wes felt awkward all through supper. Bailey seemed to be acting relatively normal, though staying quiet.

All the kids were quiet, for that matter. Their mom and dad kept trying and failing to engage in conversation, perhaps getting a couple syllables in response if they were lucky.

The boys did little more than eat, stare at their sister, and exchange occasional glances. They were too busy inside their own heads for anything else.

Afterward they convened for a private chat in their room.

“I kinda feel bad,” Wes said.

“Yeah, me too,” Ryan said.

“But we shouldn’t, right? We all got what we wanted.”

“I think so, yeah.”

“But… we didn’t really talk about it. It feels weird now.”

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