Ponyville After School

~ ✭ ~

The very first Friday following Cheerilee's call for volunteers, Big Macintosh received the teacher's visit at Sweet Apple Acres. It was noon, the red workhorse eating lunch outside the barn when he saw her coming down the path from Ponyville.

Cheerilee had come to the farm before, generally to discuss Apple Bloom's latest mischief. However, those were getting increasingly sparse as Mac's youngest sister got older, and Cheerilee would normally have come after the school day, not during lunchtime. Sure, it could mean Apple Bloom was in really big trouble, but that did not seem particularly likely given her leisurely pace and friendly smile.

No, clearly, Cheerilee wasn't on the farm to talk about his little sis, which left only one option: like his wife Sugar Belle, Big Mac had volunteered to help Cheerilee with the after-school reward program.

"Hi, Big Mac! This week's winner chose you for her special night, so I came to make sure everything was okay, especially since it's the first time I'm not doing it," Cheerilee said, confirming his suspicion.

"Eeyup."

"Oh, good! The filly is Diamond Tiara. Maybe you've met her?"

Big Mac raised an eyebrow. He certainly had heard plenty about Filthy Rich's daughter, since she used to be the school's bratty bully, and Apple Bloom's eternal rival. She had become much friendlier since then, and Mac even occasionally saw her at the Crusaders' clubhouse. Still, it was surprising to hear this rich little filly wanted to spend a night with a farm stallion such as himself.

Cheerilee didn't seem to notice his confusion. "Anyway, you should come pick her up after class at around 3 PM. Apple Bloom said she'd have a sleepover with her friends at Sweetie Belle's so you can use her room for the night. Is that alright?"

"Uh… eeyup."

"Perfect!" Cheerilee craned her neck to rummage in her saddlebags and produced a small vial. "Here's Diamond Tiara's birth-control potion. Please make sure she drinks it before mating with her. Besides that, it really isn't very complicated: be nice to her, help her explore her sexuality, and make sure she's satisfied. She will share dinner and breakfast with your family, and, of course, she will sleep with you. Any questions?"

"Nnope!" Though he was a little nervous, everything did sound fine to Big Mac, and pleasing a little filly certainly seemed like fun.

"Okay, in that case, I should return to the schoolhouse before the afternoon class. See you later, Big Mac!" Waving goodbye, Cheerilee went back the way she came, leaving the stallion to his lunch.

~ ✭ ~

As promised, Big Macintosh showed up at the Ponyville Elementary School as classes ended. Fillies and colts streamed from the door as the bell rang, returning home for the weekend. Big Mac said "Hi" to Apple Bloom and her friends as they left, then went inside.

Big Mac found Diamond Tiara speaking with Cheerilee at her desk. She was a pink filly, about the same age as Apple Bloom, with a curly, white and violet mane, wearing her usual tiara.

"Thanks for organizing this, Miss Cheerilee!" the filly chirped. "I can't wait for him to be here!"

"It's my pleasure, Diamond Tiara. As for waiting, that won't be necessary." Cheerilee nodded toward Big Mac.

"Eeyup!"

Diamond Tiara turned around, and a bright smile lit her face. "Oh, hey there, Big Mac! Hang on, I just need to pack my saddlebags real quick." She trotted to her desk.

As the stallion watched her, Cheerilee came up at his side. "By the way, I explained to Diamond Tiara that you might be a bit… big for her. She said it was fine, but… um, be gentle with her, okay?"

"Eeyup." Big Mac gave her a reassuring smile.

Soon enough, Diamond Tiara came back wearing her matching pink saddlebags. Big Mac left the school, the filly at his side, and together they took the path to Sweet Apple Acres.

"Thanks for agreeing to do this," Diamond Tiara said as they trotted down the road. "Miss Cheerilee is great and all, but I'm glad to do this with a strong stallion instead."

Big Macintosh smiled, but said nothing. The young filly faltered for a moment. "Right, guess you're not much for conversation."

His smile did not fade. "Nnope."

Diamond Tiara reflected on that for a moment. "Well, that's okay. Though… sniff, sniff… You're all sweaty, and kinda smelly. No offense, but…"

Big Mac would have blushed if his coat hadn't already been bright red. "Erm… Sorry 'bout that, Diamond Tiara. Ah had a lot of farm chores before pickin' you up, and, well… Ah'll shower when we arrive."

Diamond Tiara bit her lip and glanced away. "Well… maybe I could give you a bath," she offered, her pale blue eyes suddenly sparkling. "And, you can give me one too."

"Hmm… Eeyup!"

The Apple family farmstead was empty, save for Granny Smith napping outside, so Big Mac and Diamond Tiara went straight to the bathroom.

Diamond Tiara turned the tub's faucets, but only a squeaking, rattling sound came out. Her face fell. "Uh, I think your bath's broken." Big Mac simply bucked the pipes, and warm water immediately gushed out from the tap.

The filly facehoofed. "Really? Couldn't you just repair it? Or get a new one? Urg, whatever…" She looked around the room. The rustic, pastoral decor really wasn't her style, and everything in it had been outdated since before her birth anyway. Still, it was clean enough, and Diamond Tiara could tolerate it if it meant sharing a bath with Apple Bloom's handsome brother.

As the bathtub slowly filled up, Diamond Tiara checked the content of the wooden tablet next to it. "Okay, so you have soap and shampoo. That's a start. Hm, don't you have bath salt? Scented oil? Bubbles? Anything?"

"Nnope." Big Mac faltered under the rich filly critical gaze. "Erm… maybe?" Mac poked around Applejack and Sugar Belle's cabinets, and eventually found a few bottles with the word 'bath' on them. He presented his findings to Diamond Tiara.

"Ah, better! Let's see, we have… 'Apple-Scented Bubble Bath'... 'Fresh Apple Scented Oil'... 'Apple & Cinnamon Salt', eww… Everything's apple-scented, of course. It's not bad, sure, but you should try a bit of variety now and again. Oh wait, here's some 'Pear-Butter Bubble Bath Oil'! Sorry Big Mac, we're taking this one." Diamond Tiara grabbed the bottle of pear oil, and squeezed a generous dose from it in the warm bathwater.

Immediately, a delicious, sweet scent of pear perfumed the bathroom, bubbles forming a thick foam in the tub. Satisfied, Diamond Tiara turned off the tap, and invited Big Mac to step in. There was only enough water to fill half the tub, but it rose almost to the overflow drain as soon as the big workhorse entered it.

Spotting a wooden stool — probably used by Apple Bloom to reach the sink —, Diamond Tiara brought it next to the bath. With it, she could comfortably access Big Mac's body, so she picked up the soap and got to work.

As embarrassing as getting bathed by a young filly was, Big Mac soon relaxed, sighing happily. The feeling of soapy filly hooves scrubbing his back was wonderful, especially after a hard day working on the farm. It must have showed on his face, because Diamond Tiara giggled, pleased with herself. "See? It's fun to be bathed. Our maid at home always wash me, and it's sooo relaxing. Huh, and, you know what? I never scrubbed anypony else before, but that's pretty fun too! Am I doing a good job?"

"Eeyup." If that was her first time doing this, she was certainly very good, and Big Mac's cock slipped out of its sheath in reaction.

Having finished Big Mac's back, Diamond Tiara went down his foreleg. Even though Mac lifted it, she still had to stretch awkwardly on the stool to reach him. Diamond Tiara's eyes went wide as she lost her balance. She yelped as her hooves slipped from her perch. In a split second, Big Mac grabbed her, and pulled her toward him. The wooden stool fell on the floor with a loud thud, and Diamond Tiara crashed head first onto Big Mac. The stallion slipped, ending up on his back in the tub.

Moments later, the commotion was over, and Big Macintosh was sitting in the bathtub, a dazed filly on his barrel. "Uh, ya alright?"

"Um… yeah, I think…" Diamond Tiara answered."Thanks for the save."

Big Mac petted her mane. With the burst of adrenaline gone, they both relaxed in the warm, soapy water. As Diamond Tiara pressed her body on his, Mac felt his sex brush into her soft belly. She bit her lip and glanced down, obviously noticing the same thing, but she said nothing, so he put a hoof on her croup, pressing her down and rubbing himself on her coat.

Still, even though it felt nice, Big Mac knew he couldn't just continue like this: he wanted to penetrate her, to feel her fillyhood around his cock, but he needed to prepare her first. "Erm, maybe we could finish cleaning up before… um…"

Diamond Tiara smiled, embarrassed. "Yeah…" She picked up the soap and quickly went to work, scrubbing his legs and belly. As she moved up, Big Mac felt her filly vulva on his cock, though neither could see it under the thick, bubbly foam. Diamond Tiara quietly gasped, grinding her sex on his stallionhood. She finished swiftly, handing Big Mac the soap. He gave her a quick, cursory wash; she was so prim already she hardly needed it anyway.

As they got out of the tub, Mac could feel Diamond Tiara's stare on his erect stallionhood. "Woah, that's supposed to go inside me?" the filly muttered, wide eyed.

Smiling, Big Mac thoroughly toweled her, getting her pink coat nice and fluffy. Curious about getting a good look at her sex, Big Mac lifted her tail. Diamond Tiara's vulva and tailhole were pert and puffy, the cute teardrop of her labia flashing a deeper shade of pink than her fur. He wiped her rump, passing his towel-covered hoof through her slit, and enjoying the moan that came with it. Finally, Big Mac briskly dried himself, and led Diamond Tiara outside the bathroom.

He passed the bedroom he normally shared with his wife, instead heading for Apple Bloom's bedroom, his sister having generously lent it to them for the night. As he shut the door behind them, Diamond Tiara examined her classmate's bedroom with great interest, noting the canopy bed, dresser, and vanity before hopping on the first one. The bedsheets were coarser than she was used to, but that hardly mattered when it meant she could lay with such a handsome stallion.

Though, as she peeked once more at his penis, Diamond Tiara was hit by a fresh wave of nervousness. Honestly, she had no idea what to do. Fortunately, Big Mac was patient and kind, so she simply told him. "Erm, I… I never had… sex with a colt before. Or a stallion. What should… uh…"

Big Mac nodded, a gentle, understanding expression on his face. "Well, first, Miss Cheerilee gave me this for ya." He passed her the vial of potion.

Diamond Tiara read the label, and blushed. "Yeah, alright. That makes sense." She uncorked the bottle and gulped down the clear liquid. It quickly flowed in her guts, protecting her from an impromptu pregnancy. "Okay, so what now?"

Big Mac rolled the filly on her back, and kissed her belly.

"Um, what are you doing…?"

Big Mac kissed Diamond Tiara's immature teats, and licked her crotch, before moving even lower. He sighed, admiring her pretty vulva, his muzzle so close to her that she twitched simply from the warm exhale of his breath. Her little clit peeked cutely from her swollen labia, throbbing with need. With his hooves, Mac parted her lips, revealing the enticing entrance of her snatch. She smelled really nice, the musk of her sex melding pleasantly with the pear scent of the bath oil.

After a particularly needy wink from Diamond Tiara's pussy, Big Mac figured he probably shouldn't keep the filly waiting. He gave her fillyhood a big lick, starting on the pucker of her anus, moving up through her tangy fold, and ending on her clit.

"Aaah!" Diamond Tiara yelped, arcing her spine and driving her vulva into Big Mac's snout. Pleased with her reaction, the stallion gave her more, licking and suckling her sex.

Since that first one when he had made love to Sugar Belle in the back of her shop, Big Mac had done this hundreds of times. It was the best way to prepare his wife for mating, something she was certainly vocal about. He'd never been with another mare though, especially not with a filly. Besides being smaller, Diamond Tiara's vulva was different from Sugar Belle's in many subtle ways. Mac quickly noticed the filly reacted differently than his wife: her clitoris seemed less sensitive, but she gasped loudly whenever he pushed his tongue in her vagina.

Having no issue whatsoever about adapting to her preference, Big Mac delved deep with his tongue into her, licking her smooth inner walls. Diamond Tiara's vagina contracted around his tongue, her body instinctively attempting to drive it deeper inside her. Her hindlegs clenched around his neck, her forehooves caressing his mane. Diamond Tiara's vulva bloomed, her tummy forming cute concaves as she panted for breath. Big Mac kept pleasing her, but he knew she was as ready as she'd ever be, and his own unattended penis throbbed almost painfully under his barrel. He kissed her folds, and looked into her eyes, feeling her desire, her lust. "Ready?" he asked in a whisper. She nodded, breathless.

Having received her consent, Big Macintosh shifted up, moving forward until Diamond Tiara was under him. He held her firmly, lining his glans with her sex. Big Mac's flare was a fair bit larger than her entrance, and they both stared at it. Diamond Tiara's vulva winked, kissing his tip and coating it in her clear fluids.

Holding her hindlegs apart, Big Mac carefully pushed into her. At first, nothing happened, so he used his weight to force Diamond Tiara's entrance. She briefly winced in pain, but eventually her labia opened wide, and Big Mac's swollen glans disappeared inside her snatch. He stopped there, barely an inch inside her, giving her time to stretch.

"Woah… bucking hell…" Diamond Tiara let out, watching her fillyhood in awe as the stallion took her virginity.

"Ya alright…?"

"Yeah… unf… just… go slow, okay?"

"Eeyup." Sticking to his promise, Big Mac started with the subtlest of movements, more like a slow rub than a thrust, simply wiggling his glans in her vagina. Diamond Tiara cooed softly, pleasure replacing the uncomfortable stretching in her nether.

Big Mac rubbed her belly with his hoof. Even with just his tip inside her, Diamond Tiara's fillyhood felt incredible, her canal tightly constricting his flare. As he rubbed her insides, he pushed just a little more, delving a little deeper in her sex. He waited for a moment, then pushed again.

With about two inches in, Big Mac pulled back slightly, and began to slowly thrust into the cute little filly. Diamond Tiara no longer winced, simply letting out a throaty "Aaah~" as the workhorse penetrated her. Even with her usual, rather ostentatious, demeanor, Diamond Tiara was an earth pony, and the magic in her blood made her tougher than she’d otherwise seem.

Reassured to see Diamond Tiara taking it so well, Mac went a little faster, his balls jiggling freely under his tail as he mated with her. Without even really trying, his thrusts drove his penis deeper and deeper into her, getting more of his length into her sweet filly snatch.

"Oh, yes! Mmmh!" Diamond Tiara shuddered in pleasure as she received her first stallion.

Big Mac penetrated her relentlessly, enjoying her tight little body as he made love to a foal. Her cute mane bounced along with the wet shlick-shlick-shlick sound his cock produced with each stroke in her pussy.

With each impact, her fillyhood opened a little more, until, finally, with about half his shaft inside her, Big Mac reached Diamond Tiara's cervix. He stayed there for a moment, feeling the entirety of her vagina around his cock, then returned to work, pumping into her fillyhood. The young foal was becoming easier to penetrate, her flesh stretching to accommodate his girth; she was still amazingly tight, but her passage was incredibly slick from her juices, letting Big Mac's stallionhood slide freely within her.

Diamond Tiara moaned, gasped, arching her spine, trying to get more of him inside. Her clit throbbed urgently, and she used her forehooves to masturbate. Her open, gasping muzzle was so cute, Big Mac bent his neck to kiss her. He slipped his tongue in her mouth, making out with her.

Big Mac rutted her like a grown mare, pounding the filly's sore vulva as he kissed her. Diamond Tiara was breathless, overwhelmed by bliss. She trembled, her pussy pulsing around his sex.

The filly kissed Mac feverishly, the glow of her climax burning brightly in her belly until she couldn’t hold it anymore. Diamond Tiara yelled something very unladylike, her body shuddering so hard she lost her trademark tiara. Smiling, Big Mac watched tenderly the filly orgasm under him. Her fluids gushed from her vulva, impregnating Apple Bloom's bedsheets with the pungent scent of her sex.

Pressing deeply into her, Big Mac felt Diamond Tiara's cervix loosen as she came. He put all his weight on her pelvis, pushing through her deepest barrier. His glans entered her womb, and he flared, sealing her uterus. Lost in the throes of her orgasm, Diamond Tiara barely felt the intrusion.

Big Mac closed his eyes; the soft, spongy feeling of filly uterus caressing the hypersensitive skin of his glans adding to the contractions of her vagina was just too much to handle. The stallion held Diamond Tiara’s rump firmly, pinning her down, and let out a loud whinny, his testicles throbbing in their sack.

Orgasming, immobilized by a powerful workhorse, her sex stretched wide by his virility, Diamond Tiara only realised at the last second what was happening. She felt a shudder travelling through the thick shaft in her sore snatch, and the head bulging even more in her uterus. A warm, gooey sensation spread deep in her belly, and she knew what it was: Big Mac was ejaculating inside her.

In bliss, Big Mac let himself go. His seed gushed in her womb, filling her up with thick stallion semen. He looked down, gazing in the eyes of the sweet filly he was inseminating. He coated her uterus with his sticky gift, getting his sperm in every recess of her uterine walls. Fertile semen flowed in Diamond’s Tiara oviducts, Big Mac sperms searching for her ovum — in vain, thanks to the birth-control she had ingested earlier.

As her climax waned, Diamond Tiara relaxed, limp on Apple Bloom’s bed. Big Mac continued to ejaculate inside her, though that was quickly fading too. The stallion stayed in her until the end… not that he could go anywhere else, his swollen flare locked in her womb as he came.

When Big Mac finally softened, he carefully pulled out of Diamond Tiara, leaving her pussy gaping and leaking cum. He admired his work for a moment: beneath him laid a panting pink filly, a big, blissful expression on her face, her tongue lolling out. Her little tiara had fallen off her disheveled mane, and his seed trickled down from her open vulva, soaking her tail. Utterly spent, Big Mac stepped to the side and rolled on his back, settling down next to her, his sticky, flaccid cock resting on his heaving underbarrel.

Diamond Tiara was seeing stars, her mind hazy in her afterglow. Big Mac’s semen, her reward for being such a good filly in class, was pleasantly warm in her belly, the creamy softness of it soothing her sore sex as it oozed from her. At her side, Big Macintosh’s penis glistened, wet from her fluids and his own sperm.

A soupy mix of filly juices and stallion cum soaked into the fabric under Diamond Tiara. The filly giggled softly, realising she was staining Apple Bloom’s bed with her own brother’s seed.

Big Mac embraced Diamond Tiara, gently wrapping his forelegs around her withers. Happy to receive some affection, the filly nuzzled his coat. He was all sweaty — and smelly — again, but it did not bother her this time. She smiled, inhaling his musky odor; it was the scent of sex, and everything naughty things they’d done together. Honestly, she was probably stinking just as much as him. She rubbed herself on him, the big, strong stallion that had so wonderfully taken her virginity.

Diamond Tiara felt Mac’s hoof caressing her mane, and she looked up, meeting his stare.

“Ya feelin’ good?”

She stroked her abdomen, still feeling his warmth inside. “Mmhmm. Thanks, Big Mac. That was great. I’m glad I worked so hard this week in class, and that I chose you. Say… can we do it again?” Still, despite the fullness in her belly, Diamond Tiara’s stomach growled loudly, making her blush in embarrassment. She peeked at Apple Bloom’s alarm clock: it was dinner time, and she had not even taken her usual afternoon snack. “Uh, maybe after we eat?”

“Eeyup!” They had plenty of time, after all: her dad would come pick her up in the morning, so they had all night to have fun together.

~ ✭ ~

Meanwhile, Sugar Belle smiled, leaving quietly before her husband and the lucky filly rose from their shared afterglow. Having arrived earlier, Sugar Belle had been able to watch Big Mac as he gave this sweet filly her first time. Watching his cum leak from her vulva afterward had been especially exciting, the memory of it making Sugar Belle’s clit throb. She loved him so much, and seeing firsthand his generosity made her heart flutter even more.

Sugar Belle returned to the kitchen. These two certainly deserved a very special dinner before returning to their mating, so she went to work immediately, humming to herself.