Sweet Apple Herding

~ ❀ ~

Monday, June 3rd, Year 9 of Princess Twilight

Three weeks later.

Using her magic, Sugar Belle shook the little stick coated in Fluttershy’s urine. She placed the pegasus pregnancy test on a clean towel next to her own.

“Ok, Cheery, you’re next.”

Cheerilee sat on the toilet seat and relaxed her bladder. A steady stream of dark yellow pee poured from her folds. Sugar Belle levitated the third unused pregnancy test and passed it a few times through the flow of urine. Cheerilee soon stopped peeing and wiped herself while the unicorn placed the test on the towel. Cheerilee flushed the toilet, then joined Sugar Belle and Fluttershy to stare at the three wet sticks.

In a few minutes, these tests would reveal whatever they had conceived or not.

Soon, the three mares joined Big Mac and Pip in the living room. With a big grin, Sugar Belle presented the three wooden sticks.

Each tip had turned red: they were pregnant.

~ ❀ ~

Saturday, July 13th, Year 9 of Princess Twilight

Pip had many talents, but art was not one of them. It didn’t matter. He loved to play with Harvest Blossom, Orchard Breeze, and Rain Hearth.

“Okay, so what is this?” he asked, showing the foals his latest drawing.

The three foals stared at the picture, their little faces frowned in an adorable expression of serious focus. In a sense, Pip’s drawing not being much better than theirs made the game more fun for all.

“Um… mommy?” Rain Hearth eventually answered, a quizzical look in her light green eyes.

Pip smiled wide and stroked the filly’s wavy, light blue mane. “You got it!”

He was fascinated by the growing foals. His foals, ever since he had married the herd, even though they had been sired by Big Mac. He loved witnessing the development of their own, unique personality.

Rain Hearth, Cheerilee’s purple filly, was helpful and serious. She often assisted with chores, and loved to welcome guests. Of course, she was very clumsy at her age, but it didn’t prevent her from trying.

Orchard Breeze, Fluttershy’s yellow colt, was often bashful, but he loved to run throughout the farm. He had quickly grown taller than his sisters, becoming a lanky little foal that would probably be as tall as Big Mac one day.

Harvest Blossom, Sugar Belle’s red unicorn filly, was a bright and happy foal. In moments of glee, she sometimes unleashed bursts of crimson magic that made flowers and fruits grow around her. The little unicorn was certainly the leader of the little group of siblings, with Rain Hearth and Orchard Breeze following her around wherever she went.

“Is that… supposed to be me?” Cheerilee said with a mock scolding tone as she brought a plate of cookies.

Pip chuckled. “Well, I can’t make the game too easy for them. These foals are just too smart!”

Cheerilee laughed at the excuse, but suddenly stopped. Her smirk morphed in an unmistakably queasy expression.

Pip knew what was coming, so he gave the cookies to the foals and calmly addressed them, “here, eat these. Wait for me, I’ll be back.”

Cheerilee literally galloped to the bathroom, Pip trotting behind her.

He gently massaged her back as she panted over the toilet bowl. “There, there, it’s okay. Let it all out.”

Cheerilee heaved, making an awful retching sound. She gagged, and finally vomited her breakfast. Pip held her mane and kept lovingly rubbing her back. He loved her too much to care about the disgusting smell of half-digested food and stomach acid.

Pip felt so lucky to be able to hold her like this. He had given her a foal, his seed having taken hold in her womb. The morning sickness was just an unpleasant sign of what was going on in her body. In a strange part of his mind, Pip even enjoyed her queasiness; Cheerilee knew what it meant to be pregnant, and she still wanted to endure it so she could have his child.

Of his three wives, Pip felt closest to Cheerilee. He loved Sugar Belle and Fluttershy too, but his old schoolteacher was extra special. Part of the reason why was that he knew for certain he had sired her foal. Belle and Shy had mated with Big Mac too during their heat, so they wouldn’t know who had knocked them up until they foaled.

Of course, pride aside, it didn’t matter too much in the end; Pip would love and be a father for all of the foals, regardless of their sire, as he was doing now with Harvest Blossom, Rain Hearth and Orchard Breeze.

Once Cheerilee finished spitting out her last load of bile, Pip gave her a towel so she could wipe her muzzle.

“Feeling better?”

“Urg, yeah…” Cheerilee looked embarrassed. “Thank you for being with me…”

“It’s no problem, Cheery. You’re the one who has it tough. Do you want to rest in bed for a bit? I’ll take care of the foals while Mac, Belle and Shy are out.”

Cheerilee nodded, exhausted, so he led her to bed.

As he got out of the bedroom, Pip noticed Harvest Blossom, Orchard Breeze and Rain Hearth observing him, a worried expression on their little faces.

“Mommy is sick?” Rain Hearth asked, obviously concerned.

“She’ll be fine. She just needs to rest for now. Come downstairs with me, I’ll tell you what’s going on.”

The young foals had noticed the three mares’ frequent nausea, and they needed to be reassured. Pip settled on the living room’s couch and invited the children to sit with him. “You see, Cheerilee, Sugar Belle and Fluttershy have stomachaches because they are pregnant. Do you know what ‘pregnant’ means?”

The three puzzled foals shook their heads.

Pip tried to find a way to explain the concept in a way they would understand. “Well, adult mares can accept inside them the seed of a stallion they love. If the mare and the stallion do this at certain times of the year, the stallion’s seed enters an egg inside the mare, and this creates a tiny foal in her belly. The mare is pregnant for eleven months while the foal grows inside her, then she gives birth to a new colt or filly. The mare is the foal’s mother, and the stallion who gave her his seed is the father. When they are in a herd, like us, all the mares and stallions are considered mothers and fathers.”

“Our moms have foals inside ‘em?” Harvest Blossom asked, trying to figure out what Pip was saying.

“That’s right. Me and Big Mac planted our seeds in them after our wedding, so in about nine months from now, your moms will foal baby colts or fillies. These foals will be your little brothers or sisters.”

“The foals are making ‘em sick?”

“Not exactly. When a mare is pregnant, the foal starts very small inside her. The mother’s body must make some changes inside her to make the foal grow. This is uncomfortable for the mare, and that sometimes makes her vomit, but it’s normal and it will pass soon. Then, her foal will grow strong and healthy inside her belly. Do you understand?”

The fillies and colt nodded. They probably didn’t grasp everything, but they had gotten the important parts.

“When I joined the herd, you three where already growing in each of your mom’s belly from Big Mac’s seeds. Cheery, Shy and Belle looked so cute; their tummies were big and round with you in them. You’ll see, and then you will have new siblings to love and play with!”

Pip continued to answer their questions about pregnancy, until Cheerilee arrived and hugged her foals.

Pip smiled. “Feeling better?”

“Much better… for now. Thanks for taking care of them. And I see you reassured them about us… You’re a good father, Pip.”

“I try.”

~ ❀ ~

Thursday, August 15th, Year 9 of Princess Twilight

Finding time for sexual intimacy was always a little difficult for the herd. The three foals needed a lot of attention, and all five adult ponies led busy lives. The herd generally organised outings for two or three herdmates during the evening or the weekend while the rest watched the foals.

That day, Pip had a date with Fluttershy.

“So, what did you wanna do tonight?” Pip asked her.

“Oh, mmh… White Tail Woods is beautiful this time of the year, and I know a nice, quiet meadow. But I wouldn’t want to come back too late.”

“You two will be fine,” Sugar Belle commented. “Our appointment is at three o’clock, and it won’t take too long, so you will have plenty of time.”

Cheerilee and Big Mac nodded in agreement. The five of them were currently in Ponyville Hospital, waiting for their foal viewings appointment. Soon enough, their names were called and the herd was ushered to the radiology room.

The radiology technician, a young unicorn mare with lime green fur, introduced herself as Bright Gaze, and invited Sugar Belle on the examination table. The technician applied cold lubricant to the alpha mare’s slightly bulging belly, making her squirm a little.

“Sorry about that,” Bright Gaze apologised automatically, probably doing so for the thousandth time. “Now, how about we look for this foal?” She levitated the ultrasound paddle and prodded Sugar Belle’s belly.

As the machine picked up Sugar Belle’s heartbeat, a blurry image appeared on the screen. The technician probed around the womb, until the screen revealed a tiny pony face with closed eyes. The sound of another, softer heartbeat joined Sugar Belle’s own.

“Ah, here we are! Looks like we found a little pony. We have… a small horn on the head, so I can confirm you have an unicorn foal.”

Like the others, Pip had his eyes glued to the screen. He had been excited to know more about the foals, but had not expected the surge of love that washed over him as he saw the sleeping face of Sugar Belle’s foal. Whatever he had sired it or not, in eight months he would be a father to this wonderful little creature.

“I can’t find any sign of issues with your foal,” Bright Gaze commented as she moved the sensor around. “You are indeed three months pregnant with a healthy unicorn fetus. Now, you have indicated on your form that you wanted the foal sexed. Is that still the case?”

Sugar Belle smiled. “Yes, please.”

“Ok, if we take a look at that rump, we have… a scrotum. Yep, it’s a colt.”

The family exchanged excited looks.

“We’re going to have an unicorn colt!” Cheerilee beamed.

Sugar Belle stepped off the examination table and Fluttershy took her place. Having noted down the results of her previous scan, the technician smeared the pegasus’ yellow fur with clear lube and prodded her pregnant belly with the ultrasound paddle.

“And… we have another foal here. Let’s see…”

A tiny muzzle and closed eyes appeared on screen. Again, Pip smiled as he saw the unborn foal.

“Ooh, there you are…” Fluttershy cooed, transfixed by the sight of the foal inside her uterus.

Bright Gaze moved the paddle to examine the rest of the fetus. She soon found little wing nubs near the foal’s upper back. She went lower still, finding the forming vulva of a filly. “Okay, Miss Fluttershy, you are pregnant with a pegasus filly. The foal appears normal and healthy for its current stage of development. Congratulations!”

Sugar Belle kissed Pip and Big Mac. “Wow, we’re going to have a little pegasus in the family! Good work, Shy.”

Fluttershy blushed. “Oh, I didn’t do anything special.”

Finally, Cheerilee lay down on the exam table. Pip was thrilled: he was going to see his foal, the one he knew for certain he had sired. Cheerilee flashed him a smile as the radiology technician applied the clear gel on her slightly swollen abdomen. Her heartbeat echoed from the machine, and static cleared on the screen.

Bright Gaze moved the paddle around, scrolling through Cheerilee’s guts before finding her womb. A tiny body showed up on the screen. Nothing could have prepared Pip for the pleasure of seeing his foal for the first time; he was speechless.

“Alright, we have another foal here. There’s no wing, no horn… yep, you’re pregnant with an earth po- wait, is that… Hang on…”

Suddenly worried, Pip observed his foal, wondering what had interrupted the radiologist. A second head emerged behind the fetus, stupefying Pip and his herd.

“Okay… yes, we have a second foal inside. Miss Cheerilee, you are pregnant with twins.”

“Twins!?” Cheerilee exclaimed, utterly stunned.

“Oh, my…” Fluttershy looked dazed.

“Woah! Congratulations, Cheerilee! And you too, Pip,” Sugar Belle said, giving him a gentle tap with her hoof.

The technician continued to observe the two foals. “Ok, the twin is an earth pony too… if we look at their groins, we have… a vulva on the first twin, and a… vulva too on the second twin, so twin fillies. The two foals share the same uterine horn, and likely the same placenta, so they are very likely identical twin fillies.”

Cheerilee laughed nervously. “Oh, what have I gotten myself into… Pip, I always knew you were an overachiever, but that’s a bit much, don’t you think?”

Pip simply blushed.

An hour later, the herd left the hospital.

“So, Pip,” Cheerilee said, her face flushed, “I wanted to give you a foal… well, look like I’ll give you two instead.”

Pip nuzzled her. “Are you alright with that?”

“Mmhmm, yeah. I was surprised, of course, but I’m happy to have twins.”

“That’s good.”

Cheerilee looked at Pip. “I’ll see you later. You still have a date with Shy, right?”

“Mmh, well… yeah.” He was uncomfortable to leave her like that.

Cheerilee smiled and said, “go have fun with our girl! It’s alright.”

“Cheery, why don’t you go with them?” Sugar Belle proposed. “You have a lot to celebrate, after all.”

“Is that alright?” Cheerilee asked her alpha.

“Of course it is. Go have fun!”

~ ❀ ~

As they trotted toward White Tail Woods, Pip only had one thing in mind: his two fillies growing inside his old schoolteacher. Foals they had made together.

Fluttershy led Pip and Cheerilee off the path and into the forest. They soon emerged in a secluded glade, a beautiful little enclave of tender grass.

“I found this spot some time ago,” Fluttershy explained. “Nopony ever comes here, so we can graze a while, and have some intimate fun in peace.”

“This place is beautiful,” Cheerilee commented, admiring the afternoon sunlight filtering through the trees, “and this grass looks delicious. I wouldn’t mind grazing first.”

Pip ran his hoof through the soft, fresh grass. It did look appetising. “Yeah, let’s eat first.” Pip and his herd-mares lowered their heads into the tender grass and ate their fill. Occasionally, their flanks would bump as they grazed side by side.

Eventually, both mares rubbed themselves against his rump. Pip gave each of them a kiss. “I take it you two are ready to mate?”

“Mmhmm.” Fluttershy nodded.

A mischievous grin appeared on Cheerilee's face. “Yeah, and I have something fun in mind. Shy, sweetie, do you want to do a 69 with me? It’s been a long time.”

“Oh, of course… but what about Pip?”

Not answering, Cheerilee gently guided Fluttershy to the ground, rolling her on her back. She mounted the pegasus the opposite way, giving each other access to their vulvas. Cheerilee wiggled her rump and raised her tail, offering her sex to Pip. Fluttershy closed her eyes and dipped her muzzle into Cheerilee’s pussy.

Pip watched the intimate act up close, simply enjoying the sight of Fluttershy’s tongue parting the supple slit. His gaze wandered up to Cheerilee’s pert anus; her back entrance looked lovely - and perfectly clean -, so he kissed her sphincter, making the mare moan in Fluttershy’s cunt. Encouraged, he tentatively licked around the rim of Cheerilee’s asshole. He slipped his tongue inside her, tasting her rectum. It tasted like ass, of course, but the pleasured gasps that came from Cheerilee as a result were more than worth it.

“Cheery, sweetie, Fluttershy got your marehood well covered, so can I take your ass?”

Cheerilee lifted her head from the pegasus’ slit, clear fluids oozing from her muzzle. “Mmmh, yeah… Please do! I want to feel you inside.”

Smiling, Pip asked Fluttershy, “mind if I borrow her vagina so I can lube for a second.”

Fluttershy simply gave one last lick into Cheerilee before clearing the way. Pip eagerly mounted the two mares, his cock slipping inside Cheerilee’s snatch on the first try. Her vagina was as welcoming as always, a delightful paradise for Pip’s stallionhood. He thrusted a few times inside, making sure his shaft was entirely coated in female lubrication.

Pip pulled his slick penis out of Cheerilee’s marehood, letting Fluttershy return to work. Instead, he aimed a little higher, into the mare's cute purple ponut. Pip had never taken Cheerilee’s ass before, and he felt a shudder of anticipation as her tight hole stretched to accommodate his glans.

Pip leisurely penetrated her butthole. Her rectum was tight, but his length was nice and slippery, so he entered her easily. After a few thrusts, Pip hilted his cock into her ass, his sheath pressed against her anus. “Aaah~ Cheery, your ass feels so good!”

Fluttershy kept working on her herd-mare’s vulva, her silky mane rubbing his balls as she buried her muzzle into the warm slit.

“Mmmh, yes!” Cheerilee cooed in Fluttershy’s crotch.

Pip pounded the purple pony’s precious ponut, greatly enjoying the feeling of her tight bowels caressing his erection. He bit Cheerilee’s crest as he mated her ass, making her scream in pleasure, muffled as she was by Fluttershy’s pussy. His barrel stroked her croup with each thrust into her stretched ponut.

Taken by her two lovers, Cheerilee came with a loud whinny, her rectum pulsing as she orgasmed. She almost bit into Fluttershy’s clit, making the pegasus yelp and coo. A few more hard licks and the yellow mare came as well.

Feeling the two mares relax, Pip hilted in Cheerilee’s rectum and released the orgasm he had held back. He ejaculated into her bowels, his gooey seed flowing in her colon. He stayed put, his cock twitching as he emptied the content of his ballsack inside his mare. He finally pulled out of her, causing a trickle of cum to ooze from her tailhole.

He collapsed in the soft grass next to Fluttershy, Cheerilee soon doing the same on the other side of the pegasus. Pip and Cheerilee hugged the sweet mare in-between them, settling down for a lovely post-coital cuddle time. Fluttershy planted a series of little kisses on his face, even licking him a few times.

~ ❀ ~

Cheerilee loved tending to Fluttershy; the pegasus was just so nice and soft to touch, it made her heart flutter. Cheerilee braided her pink, silky mane, adding little flowers Pip had found in the meadow. Fluttershy sang softly while her herdmates worked on her.

How can anypony be this cute? Cheerilee lay down next to the pegasus, nuzzling the other mare.

Cheerilee observed Pip settle on his back next to her, obviously quite relaxed. His beautiful penis emerged from its sheath, half hard after their earlier mating. She still felt his viscous seed in her rectum.

Pip distractedly stroked his stallionhood - the same virile tool that had given Cheerilee the twin fillies growing in her uterus. Seeing him like this reminded her of something.

“Hey, you know how you used to masturbate, thinking about me…”

Pip instantly turned red and stopped stroking his cock. Cheerilee backpedaled immediately.

“Sorry, sorry! I didn’t mean it like that! It’s just… we’ve been together for a while, we’re married, and I’m having your foals… but, I’ve never actually seen you do it.”

“Oh…” Pip relaxed a little.

“Can I watch you while you masturbate? I’d love to see it.”

“We could do it together,” Fluttershy proposed. “That would be fun.”

Pip scratched his mane. “Okay, sure.”

The three ponies lay down side by side on their back in the meadow, Pip in the middle, a mare on each side. Cheerilee observed with great interest as he caressed his cute ballsack and moved on to his semi-erect shaft.

Cheerilee spread her hindlegs and rubbed down her belly. Her teats, having grown larger and more sensitive since she had foaled Rain Heart, felt nice as she caressed them. She stayed on them for a while, enjoying the pleasant tingling. Cheerilee then moved her forehooves further down, fondling the lips of her vulva. “Mmmh…” She parted her folds, dipping her hooves in the wet heat of her pussy.

As Cheerilee rubbed her vulva, she watched Pip masturbate, his hooves stroking his engorged sex. His hindlegs twitched every once in a while as he pleasured himself. It was lovely to see him like, his hooves going up and down his stallionhood with well practiced ease. It made her press harder into her heated snatch, increasing the intensity of her own masturbation. Fluttershy too cooed as her pleasure built up, rubbing her cannon along her soaked yellow slit.

Despite the arousal she felt in her cunt, Cheerilee found the experience very relaxing, simply masturbating outside with her lovers. They all worked on their own pleasure, their back on the soft forest grass, flanks rubbing against each other. Cheerilee moaned as she increased her pace, stroking her pussy harder.

Pip too picked up speed. His masturbation fascinated Cheerilee; Pip held his cock with far more force Cheerilee would have dared to use on him. His hooves went up and down in blur.

*fwip, fwip, fwip*

Pip’s handsome face contorted in an adorable expression of bliss, his eyes close, mouth open as he panted hard. He moaned as his glans flared, bulging as his blood flowed into his aroused sex. He suddenly shifted position, sitting down on his rump with his cock pointing forward.

Wanting to see him orgasm, Cheerilee and Fluttershy moved around to get a better view, hooves still fondling their own dripping pussies.

Pip masturbated with feverish intensity, his expression looking almost pained. “Aaah~!” His cock twitched, and a spurt of his creamy, gooey semen painted the soft forest grass with a white streak. He kept rubbing himself, smearing the ground with his seed. Pip finally dropped back down, utterly relaxed, his stallionhood softening on his stomach.

A little dollop of cum hung from his urethra, so Cheerilee licked it clean. His seed felt nice on her tongue, the bitter, musky taste of his pleasure feeding her own arousal. She increased her pace, focusing her masturbation on her clit. Fluttershy did the same, moaning and cooing as she pleasured herself.

“Ooooh… Mmmm, kyaaah~!” With an adorable gasp, Fluttershy climaxed. Her beautiful tail safely pulled to the side, she peed, emptying her bladder in the grass next to Pip’s ejaculation.

Cheerilee wanted to try it too, so she rubbed her clit hard, intent on cumming. She shuddered, her vagina spasming in pleasure, a couple streams of marecum gushing out of her winking vulva as she climaxed. Instead of holding it back, Cheerilee relaxed her bladder and urethra, causing a spout of urine to spew from her folds.

Cheerilee fondled her wet slit, riding out her orgasm. She relaxed completely, lazing side by side with Fluttershy and Pip. Her breath calmed down.

They cuddled together, basking in the afterglow.