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.