Sweet Apple Herding

~ ❀ ~

Wednesday, October 31st, Year 8 of Princess Twilight

Nightmare Night was always special at Sweet Apple Acres. Every year, the Apple family constructed mazes and hosted fun activities for Ponyville’s fillies and colts. And every year, Fluttershy would shut herself inside until morning.

That year’s celebration felt particularly delightful for the pegasus, since this time she had a perfectly good reason to stay safely indoors. The herd’s foals were still too young for Nightmare Night, so Fluttershy simply stayed inside with Cheerilee to nurse them. In the meantime, Sugar Belle, Big Macintosh, Pipsqueak, and Applejack would take care of the spooky events outside.

Fluttershy and Cheerilee lounged in their bedroom’s herd-size bed. The pegasus relaxed contentedly as she chatted with her wife. Between her legs, Orchard Breeze and Harvest Blossom were suckling her teats, gleefully filling their little tummy with sweet pegasus milk. A similar scene played between Cheerilee’s hindlegs, where Rain Heart gulped down the creamy content of her mother’s udder. Rain Heart, which Cheerilee had foaled during an intense night storm, looked a lot like her mother, except for her pale blue eyes and mane.

Soon enough, all three foals stopped suckling and fell asleep on the bed, their stomach full of nourishing mare milk. The two mothers lovingly cleaned the foals, fitted them with fresh diapers, and laid them to rest in their respective cribs.

“Did you want to join the others now?” Fluttershy asked Cheerilee as they left the foals’ bedroom. “I don’t mind, I can stay here by myself.”

Cheerilee shook her head. “Oh no, I’m beat. I’d rather just eat some pumpkin pie and join you in bed for the night.”

An hour later, Fluttershy was lovingly making out with Cheerilee in their bed, a hoof gently stroking the schoolteacher’s mane. They didn’t go any farther, though; the powerful hormones that made them care for and nurse their foals also greatly dampened their arousal.

Fluttershy pulled out of Cheerilee’s muzzle. “Mmh, love you.”

“I love you too.” Cheerilee nuzzled her mane.

“This is nice. I kind of miss having sex, but I don’t really want any right now.”

Cheerilee nodded. “Must be hard on the boys, now that they can’t mate with us.”

~ ❀ ~

Much later in the night, the Nightmare Night’s Ponyville party was dying down as foals went back home with their candies. The DJ had packed her gear, leaving the town square silent except for the odd ponies still making their way home. At Sweet Apple Acres, Applejack and Sugar Belle were hanging out together as they closed down the haunted maze.

Meanwhile, Applebloom had invited Pipsqueak and her brother for a drink with her own herd at Sweetie Belle’s house in Ponyville.

So, Pip was now sitting on a couch with Big Mac, drinking hard cider and chatting with his old CMC friends, Applebloom, Sweetie Belle, and Scootaloo.

Scoot was particularly tipsy as she narrated one of Rainbow Dash’s old stories. Her tale went on and on, seemingly less plausible with each passing minute. Sweetie Belle eventually lost patience and interrupted her, “that’s cool, Scoot. Now, Pip, how's it going with Big Mac’s herd?”

Pip scratched his mane. “Oh, it’s great. Sure, they are super busy with the foals, but I like all of them. And I like helping them out too.”

Big Mac nodded in approval.

“Hey Pip, how does it feel to date Miss Cheerilee? It must be kinda weird, since she used to be our teacher and all,” Applebloom asked, her tone suggesting she had been wanting to ask that question for a while. “Ah mean, she’s great, but it still felt strange when Big Mac married her and we became sisters-in-law. And you, your like… actually with her now.”

Pip hesitated. “Well, I guess it is kind of strange. But she’s really nice, and I’m not a colt anymore.”

Scootaloo stared at him with an excited grin. “Did you… did you actually have sex with Miss Cheerilee, Pipsqueak?”

Pip’s cheeks flushed in embarrassment, but he answered anyway, “well, hm, yeah. A few times.”

Urg, did I really just tell her that? Maybe I should stop drinking for tonight…

“Woah!”

“But not since the foals were born, of course. The doctor said we can’t be with any of them until Hearth’s Warming.”

“Eeyup,” Big Mac confirmed.

“Uh, that suck,” Scootaloo commented. “I’d hate it if I couldn’t fuck Sweetie Belle or Applebloom for that long.”

“Eww, you don’t have to be so crass, Scoot,” Sweetie Belle complained.

The pegasus simply shrugged. “What? It’s true!”

Sweetie Belle made an annoyed expression before addressing the stallions again, “well, at least you still have each other. You’re coltfriends too, after all.”

Pip exchanged a look with Big Mac. “Uh, I guess so, but we always have been with the mares…”

...except for that time Big Mac came in my mouth, Pip managed to avoid saying out loud. He had not drank that much cider.

“What!? Really?” Scootaloo exclaimed like Pip had told her he’d never heard of Rainbow Dash. “Damn, stallions are so prude. You boys won’t even touch each other? Pfft, you wouldn't see me turning down a girl just because I’m one too.”

Applebloom facehoofed hard. “Scoot! That’s because you’re GAY, ya silly filly! Not everypony is like that, and that’s okay.”

“Though, she kinda has a point,” Sweetie Belle admitted. “Just because you’re both into mares doesn't mean you shouldn’t have fun together once in a while.”

“Yeah! You two should totally just do it right now before you explode or something,” Scootaloo chipped in.

Applebloom grimaced. “Uh, maybe not ‘right here’. Ah don’t wanna see my brother… well, you know. But ya could go to Pip’s place, since you’re in town. It wouldn’t hurt to try once, right?”

“Well, hmm, I guess it could actually hurt,” Sweetie Belle replied. “Oh wait, I got an idea! Hang on.” The unicorn’s horn was surrounded with a light green aura as Sweetie Belle levitated a bottle from her bedroom and presented it to Pip and Big Mac.

“‘Luscious Dream’s Best Bedroom Lubrication’,” Big Mac read out loud, “uh, that’s mighty nice and all, but… um…”

“Don’t worry, you can have it; I have plenty.” Sweetie Belle levitated the bottle of lube into Big Mac’s saddlebag.

“Now you boys have fun!” Scootaloo shooed them outside. The door snapped shut right behind them, leaving Pip and Big Mac very confused in front of Sweetie Belle’s home.

Pip was bright red from embarrassment. Big Mac would probably have been flushed scarlet too if his fur had not already been that color.

“Um, so, Pip… What do ya wanna do now?”

Pip hesitated. “Well, do you want to have a drink at my place?”

~ ❀ ~

As it turned out, there was not a single bottle of cider left in Pip’s icebox. He offered a can of soda to Big Mac and took one for himself. They settled down on the apartment’s only couch.

Big Mac fidgeted nervously with his hooves. “Uh, Pip, did ya… really wanna try doing that?”

“Well, um, maybe? The girls are right to say we’re dating. We are c-coltfriends.” Pip felt a bit of extra determination amidst the awkwardness in his mind. “I mean, we’ve been together with your mares, and… it’s kind of fun watching you with them.”

“Eeyup… and it’s fun seeing you mate with them too.”

That admission took Pip by surprise. “Uh, really? I didn’t think you’d like another stallion mating with Sugar Belle and the others. It doesn’t bother you?”

“Nnope, we wanted another stallion, and that includes me too. Taking care of three mares is hard work, especially in heat season. And ya, you’re cute… for a stallion.”

Pip blushed. “Thanks… you’re nice too.”

An awkward silence filled the room.

“I’m a little uncomfortable on that old couch,” Pip eventually said. “Do you want to come in b-bed with me?”

Big Mac nodded. He grabbed Sweetie Belle’s bottle of lube from his saddlebag and followed Pip into bed.

They lay belly-down over the sheets, side by side.

“Uh… are ya hard?” Bic Mac eventually asked.

“N-no, you?” Pip rolled on his side, revealing the pink tip of his cock barely peeking out of its sheath.

The red stallion rolled too, showing his sheath and balls. “Nnope.”

“Mm, how about we just talk about the mares for a while?” Pip asked.

Big Mac expression brightened.

Pip wondered what they could talk about. An idea came to him. “We could make it a little game. Like, one of us asks a question about the mares: the other answers, and then he asks the next question.”

“Yup,” Big Mac agreed. “Why don’t ya start? Ah’m… not too good with questions.”

“Alright, hmm… oh okay, how about… Which mare in your herd has the tightest pussy?” Pip asked.

“Oh, that’d be Fluttershy. She’s tight. Shorter too, Ah can’t even fit all the way inside her unless she’s in heat,” Mac replied.

Pip giggled. “Well, no surprise. You’re bucking huge Mac, heh. Anyway, your turn to ask.”

Big Mac pondered for a few seconds. “Hm, Pip… which mare has… the cutest snatch?”

“That’s hard, they all look so cute. Hm, I’d say… Sugar Belle. She gots really nice lips, and it’s cute you can see her clit even when she’s not having sex. Okay, next question: did you ever masturbate while thinking about Fluttershy or Cheerilee before marrying Sugar Belle.”

“Eeyup, with both. Fluttershy looks so pretty, and she’s friends with AJ, so I saw her often at the farm. With Cheerilee… we actually bucked once, when we were younger. So, for you… hmm… did ya put your dick in any of their butt?”

Pip was starting to get pretty hard. He idly rubbed his swelling cock. “Uh, no, I just did it in their pussy. And, did you? Do you even fit?”

“Sure, we’ve done it plenty of time. It feels good for them too. Just need to be careful when you enter.” Big Mac turned toward Pip and stroked his shaft. The older stallion cupped Pip’s balls, then rubbed his virgin tailhole.

Pip felt an unexpected pleasure at being touched there, making his ass and stallionhood twitch. “Gosh, that feels nice Mac.” The other stallion mounted over Pip, rubbing his sex against his own.

Pip wrapped his hooves around Big Mac’s neck and pulled him for a kiss. His lips parted, letting Mac slip his tongue inside.

As pleasure built in his body, Pip felt oddly relaxed as he was dominated by the alpha stallion. He felt light in his rump, his hindlegs spreading wider. Suddenly, he wanted to be mounted, to feel the bigger stallion on his back and inside him.

Is this… is this what he feels like for a mare? Did Cheerilee feel like this when I was with her?

“Mac, please take me,” Pip said when Big Mac broke the kiss, letting his instinct take over. “Mount me p-please, I-I want you inside.”

Big Mac grinned, rubbed himself one last time against Pip, and lifted himself off. Pip got up too, observing Mac as he poured a generous amount of lube on his own engorged penis. Pip braced himself against the bed, lifting his rump higher as he'd seen the mares do. His own cock and balls hung freely between his legs as he exposed his plothole to Big Macintosh. Pip felt an incredible thrill as Big Mac pressed his hooves on either side of him, making him feel the weight of the bigger stallion’s barrel on his back.

Pip gasped as Big Mac swollen glans rubbed his balls. The pressure shifted up, the lubed tip now caressing Pip's tight sphincter. The young stallion felt a fresh wave of nervousness fill his system, causing his virgin asshole to tighten in self-defense. Pip tensed as Big Mac pressed directly onto the opening.

Apparently, Big Mac knew what to do. He pressed hard on Pip’s back, pinning him against the bed, and increased the weight on his rump, forcing him to lower it and spread his legs.

Big Mac hugged the younger stallion from behind. “Pip, Ah’m gonna enter ya now. Just relax.”

“Yeah… take me. Claim me. I want you inside.”

Pip suddenly felt Big Mac bite his ear hard, making him gasp. For an instant, his focus shifted from the imminent rectal penetration to the intense pain-pleasure in his ear, causing his anus to loosen.

Big Mac’s flared tip immediately stretched Pip’s exposed tailhole. In a second, the entire glans slipped inside his rectum, causing him to let out a loud whinny. Big Mac held himself there, letting his sphincter time to accommodate him.

“Fuck!” The swollen tip felt huge in Pip’s ass, stretching him uncomfortably. Fortunately, Big Mac was patient, and - soon enough - the pain faded.

A hoof wrapped around Pip’s abdomen, holding him tight. Big Mac’s swollen penis pushed deeper into his rectum, then withdrew slightly. Again, it pushed in, just a little deeper. Big Mac repeated the motion again and again, burying himself inch by inch inside Pip.

The gentle thrusts felt incredible as they rubbed against Pip’s sensitive entrance. He felt an extra burst of pleasure as Big Mac medial ring passed his stretched sphincter. “Ooh! Yes, hmm!”

Both stallions’ hips met as Big Mac hilted himself into Pip’s ass, the workhorse balls lovingly caressing his own.

With a hoof, Big Mac brought Pip’s muzzle toward him. Their lips met, Mac’s wet tongue entering his mouth, both entrances to his guts filled with warm stallion. Pip whimpered, an intense submissive thrill making his body shudder.

Pip suddenly felt emptiness inside him as Big Mac’s stallionhood slipped out of his ass until about only a third of the length remained in his butt. Mac hilted himself again to the balls in one smooth motion.

“Ahh~ Mmmmh~!”

Big Mac kept thrusting into Pip, claiming the stallion as his mare. Their balls touched with each penetration, adding to their pleasure.

For Pip, the experience of taking his stallion felt very different than being with a mare. Instead of mounting and thrusting inside his partner, he was immobilized, having simply to take and enjoy the pleasurable pounding in his rear.

Big Mac's tip flared deep in his rectum, the stallion’s thrusts growing increasingly insistent, each staying deeper and deeper with each frenzied penetration. With a loud whinny, Big Mac hilted his cock deep in Pip’s rectum and pressed his barrel to his back, his pelvis grinding into the younger stallion’s butt and making their scrotums rub delightfully. Pip waited for Big Mac's orgasm with baited breath, wanting to feel his coltfriend's seed inside him.

Warm, gooey cum flooded into him, each contraction of Mac’s heavy balls against Pip’s delivering a fresh load of sticky semen into his bowels. Big Mac held him tight, instinctively trying to make sure his fertile seed stayed within a receptive mare. Sperm kept gushing into Pip; he felt proud of it, of having pleased his partner in such an intimate manner, the proof of his satisfaction pooling in his guts.

Big Mac eventually went limp on top of him, the bigger stallion’s entire weight pressing down on Pip’s body. His partner laid his head right next to his own, so Pip nuzzled and kissed him.

“Thank you,” Big Mac said, panting. “Ya feel so good, Pip.”

Big Mac pulled his cock out of the other stallion’s ass, causing a stream of white seminal fluid to ooze out of Pip’s gaping tailhole. The red stallion rolled onto the bed, utterly spent.

Pip’s own stallionhood throbbed urgently between his legs, so he joined Big Mac on the bed. “Mac, I’m really hard. Do… Do you want to t-taste my cum? I’m almost there.”

Big Mac nodded with a smile. He approached Pip, dipping his head between his legs as he took Pip’s engorged flare into his muzzle. Pip was so close to his climax that it only took a few gentle suckles on his sensitive glans to push him over the edge.

Pip felt his balls contract as the wonderful sensation of orgasm consumed him. His seed gushed into Big Mac's mouth, making the stallion taste his gooey, bitter cum. They kept eye contact the entire time, the stallion’s neck bulging each time he swallowed the fertile semen, taking it in his stomach where it would be digested. Big Mac kept the tip in his mouth as Pip’s ejaculation ended, giving it a few tender licks before pulling off.

Both stallions dropped into Pip’s bed, hugging gently as they enjoyed the afterglow of their lovemaking, their cocks returning into their respective sheaths. It was getting very late, so Pip extinguished the nearby lamp and settled down in Big Mac’s embrace, neither of them saying a word. They kissed gently before drifting to sleep.

~ ❀ ~

Thursday, November 1st, Year 8 of Princess Twilight

Big Mac and Pip arrived at Sweet Apple Acres late the next morning. The ponies there were already at work tearing down and packing the remnants of Nightmare Night.

“Da!” Rain Hearth trotted unsteadily toward Big Mac, the little purple filly followed closely by her brother and sister. Big Mac gave her a little peck on her forehead and lifted her up on his back. He did the same with his son, Orchard Breeze, the cute yellow colt joining Rain Hearth on their father’s back.

Pip ran his hoof through Harvest Blossom’s pink mane, making the filly unicorn chirp happily. He lifted her on his withers, where she hugged his neck in a tiny hug.

“Oh, hi sweeties! We were wondering where you were.” Sugar Belle approached the two stallions with a smile. “Did you two sleep together?”

Pip and Big Mac shared a bit of a sheepish look, then nodded.

Sugar Belle looked at them, a quizzical expression in her eyes but a light smirk on her lips. “Did… you two have fun?”

Big Mac kissed Pip’s on the lips.

“Eeyup!”