Little Sister's Big Butt Ch. 04

"Duh, of course I wanna do it! I told you a thousand times, and I meant it all along!" Michelle laughed, wiggling her big booty and scooting away from Tyler's sprawled form, until his fingers slipped out of her slippery pink orifice and she was able to jump off the couch. "And yeah, Ty, I wanna do it right now!" she stated as she stood up straight, facing her brother with her slender arms crossed under her round, gorgeously big melons in a pose of tongue-in-cheek defiance that softened into pure playfulness when she chuckled and added: "Besides, between yesterday and today, I think we have prepped my butthole more than enough for this! Don't you think?"

"Well, yeah, probably..." Tyler conceded, grinning with glee as he recalled the many, many times he had plowed his sister's amazing ass during the buttlustful frenzy they had shared throughout the previous couple of days. And yet, what Michelle was now apparently dead set on doing kept giving him pause. "Are you sure, Mimi? Porn stars makes it look easy, more or less, but it still seems kinda difficult to me... Like it may require some actual practice or something."

"Really, Ty?! Really!" Michelle half asked and half scoffed, straightening up to her full albeit rather limited height and puffing out her ample chest with lascivious pride as she went on stating her case while pointing down at his fat, swollen dong. "Are you seriously trying to tell me that this monstercock right here, which I take up my ass like a champ many times a day every day, isn't good enough practice for my horny bootyhole?! Come on, Ty," she concluded brightly, "it's about time we give double anal a try! If Gabby can do it, so can I."

And with that, Michelle flashed Tyler a complicit grin, turned around and strutted with purpose across the room.

Though still shaking his head in doubt, Tyler simply couldn't help but succumb to the seductive power of the lovely, enticing smile gifted him by his amazing little sister as she looked back at him over her shoulder, nor could he ever hope to resist the call of her fabulously plump, gloriously round asscheeks jiggling and bouncing in the most mesmerizing way with Michelle's every step as she made her way toward the hallway and the stairs.

With a musing sigh that conveyed his few residual albeit increasingly vague misgivings while also betraying his rapidly growing arousal, Tyler rose from the couch and followed a playfully tittering Michelle upstairs, his huge hard-on pointing the way, unfailingly aiming at her big beautiful booty.

*****

Ever since the night of the graduation party at Gabby's house, Michelle and Tyler had become obsessed with double anal stuff, and understandably so. Indeed, catching their raven-haired hostess getting assfucked by both of her beefy linebacker cousins at the same time had been so exciting for the siblings that they couldn't resist sneaking a passionate albeit necessarily silent buttfuck right there and then while peeking into Gabby's room and feasting their eyes on the incestuous double sodomy taking place in there.

Michelle in particular had been deeply affected by the discovery of Gabby and her twin cousins' incestuous anal antics, even though the mind-blowing thrill of witnessing her brunette friend's asshole getting stuffed beyond fullness by two big cocks was in part soured by the fact that neither she nor Tyler had thought to record the act with their phones. Of course though, as her brother kept correctly reminding her, there was one major extenuating circumstance: they had both been too insanely horny at the time to think ahead, or at all for that matter, lost as they were in their own secretive anal coupling outside Gabby's bedroom. Nevertheless, as rationally aware as she was that there had indeed been better things to do than filming Gabby's ass getting doubly crammed with incestuous dickmeat, Michelle bitterly regretted not having a replayable memento of that incredible spectacle. So, in a desperate attempt to somehow relive that awesome and unrepeatable scene, she decided to make up for it with double anal porn.

Starting the very night of Gabby's party, the siblings had embarked on a DAP porn binge that further fueled their raging passion for each other and increased their shared enjoyment of buttsex even more. Getting sodomized by Tyler in a doggy position on his bed while watching double anal porn clips on his laptop or having him sit at her desk so that she could bounce her jiggly bubble-butt on his huge cock in a reverse cowgirl position while a callipygian pornstar got her asshole double pounded on her computer screen became Michelle's favorite things to do, and Tyler's too, to a point.

But whereas Tyler simply found it fun and kinky to watch DAP porn with Michelle while they had buttsex, she seemed to be genuinely obsessed with the whole idea of double anal all of a sudden. In truth, it wasn't just the obvious hotness of the act that had struck Michelle when she had seen what Gabby and her cousins did behind closed doors; in a weird way, seeing that her brunette friend could take not just one but two cocks up her ass had triggered a whole messy whirlwind of conflicting emotions inside Michelle, most of them having to do with a weird sense of sexual inferiority that was now bothering her much more than she herself could have imagined.

Although nice and unassuming and generally low-key in her social interactions, Michelle never really had any confidence issues at all, and her recent sexual awakening with her adored big brother had done wonders to make her feel beautiful and admired and desired. She loved being Tyler's little buttslut sister, she loved being an anal queen and she loved feeling him stretch her asshole out and fill her big booty up to the limit with his monstercock, and, on top of it all, she was lewdly proud of herself for being able to anally take a slab of dickmeat as massive as her brother's. And yet, Gabby could take two dicks up her ass. Two. Not just one. Two.

Even though deep down she knew she was being silly, Michelle felt compelled to match Gabby's anal skills, and the only way she could think of doing so was to take two dicks in her ass too. The feeling that she had been outclassed by Gabby stung her so badly that it awakened a competitive streak that Michelle herself didn't know she had. More and more frequently during those two days of steamy buttfucking sessions, she brought up the topic with her brother, suggesting that it would be super hot if she could take a dildo up her ass too while Tyler sodomized her, stressing how crazy sexy it had been to see Gabby do that kind of stuff and going on and on about how awesome it would be if she too could do that.

Tyler's response to his sister's reiterated allusions to double anal, not to mention her ever more persistent requests for him to actually try and slip a dildo up her bootyhole alongside his fat shaft, was usually to be found somewhere between mild amusement and lighthearted dismissal. It was really cool for Tyler to see Michelle acting even hornier, sluttier and more cock-starved than usual since they had snuck a first row seat to Gabby's display of advanced butt-stretching debauchery, and he was always more than glad to sate his sister's anal cravings, but still, as far as he was concerned, being physically intimate with Michelle and feeling closer to her than ever before and having the chance to sheath his thick schlong deep, deep inside her lovely little asshole any time he wanted was already the realization of his hottest, most forbidden dream. Of course, Tyler didn't mind humoring Michelle when she brought up the topic, and watching DAP porn while plowing her juicy rump was plenty fun, but when it came to their actual sex life, he felt no need for double anal outside of porn videos, no need at all.

Nevertheless, Tyler hadn't yet expressed that thought clearly to Michelle. Also, as a general rule, it was absolutely impossible for him to say no to his sister's majestic heart-shaped bubble-butt, especially when she showcased its bounciness, roundness and plumpness the way she did that afternoon as she crossed the living room and headed upstairs, invitingly looking back at him over her shoulder and beckoning him to join her.

And so, after rising from the couch in a sort of ass-ogling daze, Tyler followed Michelle and her jiggly booty all the way upstairs and into her room, where he admired her while she assumed a doggy position on the edge of her bed, with her face resting on her crossed forearms and her luscious bubble-butt tilted up and willingly offered to him. That invitation to take her ass, so irresistible and familiar, spurred Tyler into instant action, his horniness bypassing his misgivings about what Michelle wanted to try, his lust for her epic rump overriding everything else.

Acting almost on autopilot, Tyler grabbed the bottle of lube laying on the bedspread and greased up Michelle's lovely little hineyhole, lasciviously working the slippery fluid into her already sperm-slick chute with his probing digits. Mewling and purring, tingly all over with anticipation as she enjoyed the feel of one then two then three of her brother's fingers sliding and twirling and stretching her horny rosebud, Michelle reached for the dildo she had already chosen for her first double anal and had specifically left on top of her nightstand for easier access when the moment came.

Bright pink and cylindrical with a vaguely glans-like tip, the toy was somewhat rubbery but had a solid flesh-like feel to it that Michelle enjoyed. In the recent past, when she used to spend hours masturbating her asshole while fantasizing about her horse-hung brother, that pink dildo had never exactly been Michelle's favorite self-pleasing device, mainly because it was nowhere as big and thick as Tyler's schlong, but now the toy's moderate size made it perfect for an attempt at double anal alongside her brother's enormous sausage.

"Here, Ty," Michelle said as she handed him the pink dildo, her voice trembling with feverish urgency, "use this one. I'm ready, let's do this!"

Receiving the plastic toy from his cooing sister's hand and taking a good look at it sobered up Tyler somewhat, but by then his dick was so massively hard and her glinting, overlubed rosy butt-ring looked so impossibly enticing as it twitched and puckered and pulsed like a cute little cock-starved mouth before his avid eyes, that he could only sigh and nod in assent.

Holding the dildo in his left hand, Tyler grabbed his achingly swollen dong in the right and aligned it with Michelle's beckoning sphincter. Gently nudging his precum-oozing glans against her hot, lube-shiny orifice, Tyler started to press forward, avidly drinking in the spectacle of his obscenely large cockhead bulging out against the tiny entrance of his sister's pouty forbidden hole. Prepped, eager and well-adjusted to his huge boner as Michelle's asshole was, it took very little effort for Tyler to wedge his bulbous knob and a few thick inches of his shaft into the snug, creamy confines of her anal passage.

To the sound of their mingled moans of delight, Tyler eased more and more dickmeat inside Michelle's wantonly receptive chute, glorying in the ever amazing feel of his beloved little sis's asshole suckling and tugging and squeezing his huge dong in the warm, cozy tightness of her cock-gobbling anus. Contrary to their usual routine though, Tyler's butt-delving plunge didn't continue all the way to its normal and mutually pleasurable destination balls-deep inside Michelle's rectum. As smooth and pleasurable as his ass-cramming invasion felt, he stopped once a good half of his mammoth rod was embedded inside her butthole and held still, meanwhile turning his attention from the delectable sight of his sister's tautly dilated sphincter encircling his veiny shaft to glance at the pink dildo he held in his left hand. A frown of renewed doubt appeared on Tyler's forehead as he locked his gray gaze with Michelle's sparkling, half-closed eyes.

"Last chance to reconsider, Mimi. It's really no problem for me, I promise you," Tyler said, trying to smile and make light of it all, but actually starting to get more than a bit worried about the possibility of Michelle's adorable little bootyhole not being up to the challenge, which might even lead to her getting hurt. Still, his sister didn't look like she was going to back down at all.

Panting and mewling softly, looking sexy beyond words as she smiled and hummed from the satisfying feel of meaty fullness radiating from her dick-packed anus, Michelle nodded at her brother while looking over her shoulder with her head resting on her forearms. "Do it, Ty. I wanna do it. I can do double anal too, I'm sure I can."

Far from convinced yet too horny to pull his half-buried dong out of his sister's sweet cock-massaging hineyhole, Tyler swallowed down his worry and exhaled as he lined up the glans-shaped tip of the dildo with the dilated rim of Michelle's already stuffed orifice. A mix of conflicting emotions, ranging from unsuppressible arousal to true brotherly concern by way of lewd curiosity, whirled chaotically inside Tyler as he pressed the dildo more firmly against the oily, tender edge of Michelle's shaft-stretched sphincter in an attempt to somehow make enough room between his huge boner and her distended butt-ring for the toy to slide in too.

Beads of nervous sweat appeared on Tyler's forehead as Michelle's sensuous mewls of anticipation started morphing into tenser and distinctly less delighted vocalizations. An unbidden and quite bitter flash of irony struck Tyler as he realized that all the double anal porn he and Michelle had watched lately was now turning out to be perfectly useless when it came to actually doing the deed in real life. Despite his sister's naughty willingness and weird determination, it started dawning on Tyler that he may seriously have been right all along in considering that whole thing a bad idea. As if in answer to his doubts though, Michelle's trembling voice resounded in the room.

"Uuhh Ty... Push harder, get that dildo in there! Pleeease, push it in!"

Sighing and clenching his jaw, still viscerally bound to answer his sister's pleading call, Tyler removed his free hand from its comfy perch on top of the big soft mound of Michelle's plump asscheek and brought it closer to her straining bootyhole. Ever so gently, he used his thumb to pull the tautly dilated edge of her butt-ring further apart while at the same time adjusting the dildo into a better position for penetration, but he could only pry his sister's fully stuffed backdoor open another fraction of an inch.

Much to Tyler's surprise though, despite the fact that he was feeling like an inept burglar attempting to pick a complex lock with the wrong tools, it worked. The little widening he had induced in Michelle's already dick-jammed bootyhole, combined with the pressure he was applying on the cock-shaped toy and the way he was angling it, not to mention the unimpeachable quality of his prepping and lubing ministrations on her delicate anus, unexpectedly did the trick.

All of a sudden, as Tyler's eyes widened in awe, the glans-like tip of the dildo punched through, slipping between his swollen shaft and the stretched out rim of Michelle's butt-ring to wedge itself inside her anus alongside his ass-cramming dong. Instantly Michelle stiffened and took a sharp intake of breath, soon followed by a squeal of blatant discomfort.

"Fuck! Ooowwhh shiiit! Nnghh! Fuuuuck!"

"Mimi..." Tyler mumbled with undisguised concern, inviting her and all but begging her to ask him to stop. His words were slow and heavy as his heartbeat suddenly accelerated, the whirling mixture of horniness and disquiet inside him finally coalescing into a knot of real fear for his little sister's well-being.

"N-n-noohh, Ty... I c-c-can d-d-do it..." Michelle stammered in a strained whimpering voice, fighting not to yell out her evident pain, yet stubbornly refusing to accept the not-so-veiled plea in Tyler's voice to abort that perilous mission right there and then.

Clinging to her quirky fixation to keep up with Gabby's anal skills, Michelle brought a hand to her clit and started rubbing away frenetically in a last ditch effort to soothe the stinging, burning jolts of discomfort radiating from her dangerously overstuffed sphincter with some much needed clitoral comfort. Meanwhile, as much as Tyler looked for signs of improvement, Michelle's scrunched up brow and suffering facial expression didn't change at all. Nevertheless, she kept stuttering encouragements to her brother, desperately trying to deny the fact that she had barely taken the tip of the dildo up her ass and she was already hurting way past the limit of her endurance.

"D-don't stop, Ty... I... I want... Ooowwhh shiiit! I know I c-c-can... Do this... Ooowhh fuck! Uughh, it hurts!"

No sooner had those pain-laced words left Michelle's mouth that Tyler was already removing the plastic toy from her struggling bootyhole. An involuntary but very genuine sigh of relief erupted from Michelle's mouth as soon as the plastic toy was unjammed from her anus. Immediately, her tender sphincter stopped hurting and a general sense of restored comfort washed over her now that her little orifice was no longer being forced to take more than it could handle.

Breathing easily again now that he could see the suffering painted on Michelle's cute visage melting away while her whole tense body started relaxing, Tyler went as far as withdrawing the significant portion of his dong that was already buried inside her sweet ass. He knew he didn't have to do it, but he felt like he actually did. And it wasn't just a way to err on the side of caution either; first and foremost, it was a self-punishing measure that Tyler chose to inflict upon himself to atone for letting his mindless buttlust blind him so completely that he got sloppy in the fulfillment of what he had always considered to be his core duty in life: to protect and take care of his sister.

"I can't do this, Mimi. I just can't," Tyler stated with lucid finality over the slurping, lube-wet sound of his fat glans popping out of her pulsating pink hineyhole. "There's no way I'm gonna hurt you. No way in hell. I'm sorry, Mimi... I should have known better."

Already confused by the sudden transition from painful, straining fullness to total disappointing emptiness in her ass, Michelle panted and blinked and gathered her wits for a couple of hazy seconds as she processed her brother's guilt-ridden words. Then, rolling onto her side to face him, Michelle spoke with a kind, bright smile on her face, all the while extending her arms to grab Tyler's hands and hold them in hers.

"Ty, no! Nononono, don't be sorry and don't be sad," Michelle said urgently as she pulled her big brother closer, until he climbed into bed too and was lying on his side facing her. "You don't have to be sorry, it's okay. I'm okay, really."

"Are you sure, Mimi?" Tyler said, his arms automatically wrapping Michelle in a loving embrace even as his brow remained furrowed with worry and self-reproach. "I'm serious. Are you hurt or something? Tell me, please..."

"I'm fine, Ty. It was pretty bad for a moment, yeah, but when you took the dildo out the pain went away immediately. My butthole is alright, don't worry," Michelle concluded with a smile that turned into a chuckle as she added: "You didn't have to pull your dick out too, though. We both know that I can take one cock in my ass, at least! And it's a huge one too!"

Unable to stay broody when it was clear that nothing bad had really happened and his little sis was indeed okay, Tyler laughed with relief along with Michelle, but not before having let out a liberating sigh and having tightened his bear hug around her voluptuous body. The next thing he knew, Michelle was resting her delicate hands on the sides of his face and kissing him deeply, one of her smooth thighs meanwhile draped over his leg, her petite frame pressed so close to him that her big round boobs were squashed against his muscular torso. Given their snuggling face to face position, Tyler's swollen dong ended up poking right against Michelle's shaved pussy mound as they lost themselves in their soulkiss, their lips and tongues dancing happily while they moaned into each other's smooching mouth.