Sweet Apple Discipline

Big Mac stroked his cock as he admired the young beauties, his foreskin rolling up and down the cherry-red tip as he did. Three sets of eyes were locked onto it, filled with dread.

"Y'all don't need to beg," he drawled. "Jes' nod your head if you want it first. Longer you wait, the more it'll hurt."

None of them nodded. Apple Bloom looked at him, tears streaming down her face. Scootaloo's eyes were scrunched shut, and she shifted in her bonds as she tried to deal with the painful cramps from her piss-filled gut. Sweetie Belle's gaze still hadn't left his cock.

He waited a while longer. "C'mon, now." He tapped his foot. "I ain't waitin' forever..."

The girls only shivered in response.

Big Mac shrugged. He guessed it was his choice. He looked at Sweetie Belle first - he'd wanted to sink his cock into the clothespin-covered angel for years, grab her chubby hips as he filled her fertile womb with sperm, but at the same time he wanted to savor her. She could wait, he decided. Scootaloo could wait too, but only because he wanted the pain of the bondage and the humiliation of the enema to break her down for a while longer before he claimed her.

It looked like his little sister was first up to bat.

He walked behind Apple Bloom, shuffling forward until his hips pressed into her butt. His cock jutted out between her legs, her pussy resting on top of the shaft, radiating warmth into it. She looked down, and could see a bead of clear precum welling up at the tip. She shuddered. He twitched.

Mac leaned forward to whisper into her ear, her hair tickling his cheek. "AJ says ah can't get you knocked up, not this year." He reached forward and rubbed her pussy, the calloused fingers making her squirm. "And ah don't do condoms. There's a reason ah had you churn all that butter this morning..."

He backed away. Apple Bloom whimpered as she heard a parcel unwrapping, the squelch of thick fingers digging into warm butter, and the slick sounds of butter being massaged into skin. She yelped into her gag as her brother touched her, his hand rubbing up and down the crack of her ass before pushing two knuckles deep into her anus.

Once his little sister's ass had been sufficiently slickened, he stepped back. One more detail. He walked over to Scootaloo, and kicked one of the boxes underneath her feet away. She screeched as she swung, the twine yanking her nipples hard as her loose foot moved wildly, the strain on her shoulders increasing from the drop, pain shooting through her guts as she tried to stabilize herself with her right foot on the remaining box. He did the same to Sweetie Belle, who cried as the dozens of clothespins bounced and jiggled.

He smiled as he walked back to his sister and pried her butt-cheeks apart. To each side, Scootaloo and Sweetie Belle were still swinging and sobbing, both with a loose foot dangling six inches off the floor. He shrugged as he lined his cock up with her sister's tight, virgin asshole.

He'd told them it would hurt more if they waited, after all.

Apple Bloom squealed into the gag as the bulbous tip of her brother's dick stretched her anus open. The plum-sized head alone was bigger than anything to ever pass before, and made Mac's thick fingers seem slender in comparison. Her asshole clenched down on it, pressing down hot and tight in a futile attempt to bar its entry. She felt her ass hug the ridge as the edge of the glans passed into her, and could then feel every vein and bump on his shaft as it continued inwards. The burning, splitting sensation of being spread open was joined by another more disconcerting one, as her guts stuck to the skin of Mac's cock despite the copious lube. Her cries died down into whimpers as he came to a stop, only a third of his caber buried inside her.

Mac sighed with pleasure as he paused. He needed to wait until his sister's insides were ready for more of his length to avoid damaging her. This suited him fine, he was in no rush. He reached down to grope Apple Bloom's pert, boyish butt, jiggling the flesh and slapping it lightly, seeing it redden like a Cox apple. He spread her cheeks and took in the sight, rivulets of sweat dripping down the muscles either side of her spine and into her crack, her asshole pink and stretched out around his length, twitching down, massaging a prominent vein on the top of it. The sound of the two sobbing girls either side of him only made it sweeter. He spared them each a glance, Sweetie Belle miserably trying to remain still as she teetered on her single foothold, trying not to shake the dozens of clothespins pinching her tits, face and genitals, and Scootaloo writhing uncomfortably between the growing strain in her shoulder and the painful, piss-enema-induced cramps in her gut. Then, he returned his attentions to his sister.

He withdrew his cock until only the glans remained inside, and then pushed back in to her hot, soft hole, a little further than last time, until he felt the tell-tale pull that told him she wasn't aligned perfectly. Her cries served to emphasize this, as what had been a tiny hint for him was apparently stabbing pains deep in her belly for her. Again, he withdrew, though a little less than last time, and pushed in further. Her squeals became sobs, which became groans, and after six of these thrusts they were a quiet, quivering moan as his hips touched her buttocks and her ass pressed into his pubic bone. Her brother's sizeable length was inside her entirely.

Mac snorted a hot breath from his nose as he pulled out, watching as his little sister's anus clung to his cock, stretching out backwards as if desperately trying to keep it inside. His shaft glistened from the butter, and though her ass wasn't as wet or tight as a pussy, it had a gritty friction to it, and the heat was divine. Halfway out he thrust in again, repeating this action slowly and rhythmically, over and over, settling into a comfortable pace as he churned his sister's guts.

He reached upwards and unhooked the rope that kept Apple Bloom's wrists raised high, removing the strappado and letting him lean over onto her, his bare chest pressing against her back, his chin resting on her left shoulder as he rutted her. He could see tears running down his sister's cheek, and decided to comfort her. As he licked the tears away, he undid her ball gag. She cried softly, clicking her jaw from side to side, letting out the odd yelp as she was fucked.

"B-big Mac--"

"Shhh..." He placed a finger on her lips, never stopping his thrusts, relishing the warmth and tightness of his sister's teenage ass. "We're gonna do this a lot from now on, lil' sis, and you're gonna learn to love it..."

She sobbed, but didn't reply. Instead, she parted her lips and allowed the tip of Mac's finger inside, sucking it softly as tears trickled down her face. Mac grinned as he fucked her, his pace growing more fluid, no longer full of caution but now with a clear goal in sight.

He reached his other hand up and slipped two fingers from each hand into Apple Bloom's mouth, then pulled them back, taking a fishhook-grip on her lips for leverage. He whispered into her ear, "This year, your ass is mine, but next year? Come next harvest, AJ says ah can get you preggers. Hear that, slut? Your big brother's gonna cum in your pussy, once a day and twice a night until you're swollen with child." His voice became a low growl, sweat dripping down from his forehead into his eyes, "It'll be your new life, sis. No school, no college, just crawling around the farmhouse with swelled-up feet and a swelled-up belly, sucking my cock until I send you back to the kitchen to cook supper. My lil' barefoot and pregnant cocksucker slave..."

His thrusts grew truly aggressive, cracking out against Apple Bloom's bottom, who could only whimper at the further pain and degradation. Mac sucked in from his nose and hocked up from the back of his throat before spitting a thick wad of mucous onto his sister's forehead, which trickled down to glue her left eye shut. He felt her going limp, her mind shutting down from the misery of it all.

Mac came, biting down on her ear as he painted her bowels with thick, creamy spunk. He stayed in deep until he was sated, not withdrawing an inch until every twitch had finished and every drop had left, and only then did he withdraw his half-hard cock with an unpleasant slurp. A trail of cum, tinged pink and yellow, trickled down Apple Bloom's inner thigh. She was completely limp in his grip, crying silently. He set her down and stretched out, still elated from the rush of his climax.

He heard the rattle of dozens of clothespins, and knew where he was burying his cock next...