Sweet Apple Herding

~ ❀ ~

Friday, July 13th, Year 8 of Princess Twilight

Learning the ropes at town hall had certainly been exciting, but also quite exhausting. For Pipsqueak, the weekend felt very welcome indeed, and getting to eat at Sweet Apple Acres, instead of having to cook home alone, was sure to be a great way to start it off.

Coming upon the farmstead, Pip noticed the new house Cheerilee had mentioned. It was similar in size and style to the old one, which probably still housed Applejack and Granny Smith. He met Big Macintosh outside, greeting him with a friendly gesture.

“Cheerilee told us she invited ya for dinner,” Big Mac said, utterly dwarfing Pip as he packed his tools into the barn for the night.

“I… hope I’m not intruding, coming over like that.”

“Nnope. You’re a guest of the family. Go join the mares inside, Ah’m just packin’ up.”

~ ❀ ~

Having heard a couple knocks, Sugar Belle went to greet their guest at the door. Pip was a little taller than her, with a white-spotted-brown coat and a short brown mane and tail. Cheerilee was right: he was pretty cute. The unicorn mare ushered him inside, where Fluttershy and Cheerilee greeted him.

As Pip talked with her herdmates, Sugar Belle took the opportunity to check him out. He was obviously quite smaller than her husband Big Mac, but he had nice flanks. With a naughty thrill, she caught a glimpse of his white balls underneath his short tail. They did look nice and firm.

Sugar Belle wondered for a moment how it would feel to have them emptied inside herself.

Once Big Mac came back from work, they all sat together in the living room. Sugar Belle served a cup of cider to each stallion, and a cup of non-alcoholic apple juice for herself and the other pregnant mares.

“So Pip,” started Fluttershy, “Cheery said you finished your studies in Canterlot. What were you studying there?”

“That’s right!” he answered. “I was at the Royal Canterlot School of Administration for a two years program. I graduated a couple months ago, and I started looking for a job in public affairs.”

“So why come back to Ponyville?” Sugar Belle asked.

“Well, Canterlot is really fun, but I wanted to come back. Guess I feel at home here, even if I was born in Trottingham.” Pip took a sip of cider from his cup. “I sent a letter to Mayor Mare, told her I was graduating and that I was looking for a job. She replied and said she had something for me at town hall.”

“That’s great! What do you do there?”

Pipsqueak rubbed his neck. “Well, right now I’m mostly just moving paper around, whenever somepony needs a document. But I hope to climb up the ranks if I work hard.”

This prompted a quiet chuckle from Cheerilee, a proud smile appearing on her lips. “You know, when you were my student, I knew you had a lot of potential. Believe it or not, but you really left an impression at the school.”

“You really think so?” Pip flushed at the compliments.

“Mmhmm. You might think you have a small role now, but I’m sure the mayor sees it as an opportunity to have you close to her... so she can groom you into a position where you will be able to make a real difference.”

Before Pip could answer, a loud buzz rang in the kitchen. Sugar Belle hopped on her hooves. “Mac, sweetie, mind giving me a hoof with the oven?”

“Eeyup.”

“We’ll help too,” said Fluttershy as Cheerilee and her got up, Pip following them to the kitchen.

Together, they served dinner and took seats at the table.

~ ❀ ~

Pip could now see the sunset through the windows. After his second serving of apple pie, he felt nice and full. A bit too full, in fact.

Now that they all had ate to their heart’s content, the herd and their guest went back to the living room, sitting on the couches and chairs scattered around the place. The three mares were all lounging in comfortable positions, most likely because of their pregnancies.

Despite the delightful food and agreable company, Pipsqueak was starting to feel uneasy. Since he had arrived, the mares - and even Big Macintosh - had been constantly throwing him questions about his life, his plans, and more. It all had been innocuous enough, but to Pip it was starting to feel like some kind of interview. The entire herd acted oddly nervous around him, which was particularly strange.

A lull in the conversation turned into an awkward silence. The mares gave each other a questioning look. Finally, Sugar Belle turned toward Big Mac and gave him a small nod. The stallion gave Pip an inquisitive stare before nodding back to Sugar Belle.

What was that all about?

Sugar Belle stood up and sat on the couch, right next to Pip. She glanced at him and bit her lip.

“So, uh… Pip. We need to be honest with you. When Cheery invited you for dinner tonight, it wasn’t just for a ‘welcome home’ party. You see, we have a fairly large herd here. Even for a stallion like Mac, taking care of three mares is… a lot of work. That’s not counting the farm, and the fact that we’ll have foals soon. So, a couple months ago, we talked it through, and figured it might be worth, you know… to add an extra stallion to our herd.”

Pip’s eyes grew comically wide at the proposition that was implied here. Sugar Belle continued, “we’ve been looking around for a while, but we couldn’t find a nice stallion that was also, well, available.”

Cheerilee cleared her throat. “I know you used to be my student, but when I saw you in town earlier this week, I thought you might fit in nicely with us. It was a teensy bit impulsive, but it’s worth considering, at least.”

Fluttershy approached Pip. “We’re all glad Cheerilee invited you to join us.”

“Eeyup.” Big Mac nodded.

“So what do you say?” Sugar Belle asked. “I know it must be quite overwhelming to take all at once, and you really don’t have to give us a final answer today or even soon. We just want to know if you’re okay with trying to date us for a while.”

“I… uh… I don’t know. It… uh. Well, hmm… m-maybe?” Pip managed to say. It was close enough to something like a coherent answer for the others to understand.

“Are you sure?” Sugar Belle asked again, beaming. “We can wait if you need to think about it.”

Pip looked around, taking in the sight of the three mares - and the stallion - asking to date him. His gaze fell on Cheerilee, his old teacher looking at him with a smile while her hoof stroked her swollen belly.

“Yeah… I mean no… it’s okay, I guess. We can try, uh, dating for a while, if you all want to, I mean.”

The herd let out a soft cheer. The mares pressed around Pip, each giving him a warm hug. Big Mac ran a hoof through his mane. They soon settled back down, sitting close to each other, but not quite touching anymore.

“So, uh, I’m not sure what we should do now,” Sugar Belle said, fiddling with her hooves.

“Maybe we could tell him about our herd,” Fluttershy suggested. “Would that be alright with you, Pip?”

“Yeah, that would be good, I think.”

“Good idea, Shy,” Sugar Belle approved with a nod. “So, where to start? Oh, right… Well, Big Mac and I got married about 8 years ago, and I came to live with him at Sweet Apple Acres. A couple years ago, we added Fluttershy to our marriage and formed a herd. I’m the alpha mare, and Mac is the alpha stallion. As alphas, we decide where we live, when the mares are allowed to get pregnants, who can enter the herd, and the rules around the house. I… generally do the talking.”

“Eeyup.”

“Of course, that’s mostly in theory. We try to have everypony’s consent before making any big decisions. Anyway, Cheerilee joined us last year, making our herd as you see it now. After she joined, we decided to finally have foals of our own. Mac worked very hard to give us each a baby last fall during breeding season, and well… you see how it is now. Fluttershy, Cheerilee and I are about ten months pregnant, so we should foal next month.”

“That’s about it, I guess,” Sugar Belle concluded somewhat awkwardly. “Big Mac works the farm. I help him out and bake sweet recipes using our apples. Fluttershy takes care of her animal sanctuary on the edge of town, and Cheerilee teaches at Ponyville Elementary School.”

“When you’re in a herd, you get to love all your herdmates,” Cheerilee added, kissing Fluttershy and getting a moan from her. “Big Mac is my husband, while Fluttershy and Sugar Belle are my wives. All the mares in my herd will be mothers to my foal, and all the stallions will be fathers.”

“It’s going to be dark outside soon. If you want to go back home, take some time, we’ll understand,” said Sugar Belle. “But, if you want, you could, hmm, spend the night with us here. We wouldn’t mind.”

“Oh,” was all Pip managed to respond. His cheeks grew even hotter than before. All this talk, and thinking about the mares in their intimacy, had started to get to Pip. He could feel a tingle of arousal spreading through his body, making his stallionhood stir in its sheath.

A concerned expression appeared on Fluttershy’s face. “Is something wrong? Did we come out too strong on you? We don’t want you to feel uncomfortable.”

“No, it’s just… well. I’ve… never had a fillyfriend. I never even kissed a girl, not for real.” Pip withered down, having confessed his virginity.

Cheerilee put a hoof over his, comforting him. “That’s quite alright. We can take it one step at a time. We’ll show you everything you need to know.”

Pip took a deep breath. “Okay…”

“If you want, we can start with kissing,” Sugar Belle offered. “I can teach you to kiss me, right now. Would you like that?”

Pip looked at the unicorn’s magenta eyes, getting lost in her kind gaze. He looked back down and managed a weak “Yes, please… I’d like that.”

“Ok, then come closer, right in front me,” instructed Sugar Belle. After a short moment of hesitation, he complied with her direction.

“That’s perfect. Now hold me with your forehooves around my neck. I’ll do the same. There you go, now keep your muzzle in front of mine and look me in the eyes.”

Pip embraced Sugar Belle, her face a mere inch from his. He lost himself in her beautiful eyes again. He felt her hot breath on his muzzle as she instructed him. “Now tilt your head to the side, close your eyes, and just…”

In an instant, Sugar Belle’s lips met his, the mare gently pushing toward him. Pip tensed immediately, but Sugar Belle tightened her embrace, holding him close. Feeling him relax a little, the unicorn parted her lips slightly, continuing the kiss. Running on instinct, Pip opened his muzzle and started to caress the mare’s lips with his tongue. Responding in kind, Sugar Belle opened her jaw, letting Pip into her muzzle. He felt only bliss as he entered her mouth with his tongue, her own tongue welcoming him inside as their saliva mingled.

Of course, they had to breathe, having held the kiss for a while. Sugar Belle gently pushed him back and withdrew from his embrace. Pip took a few deep breaths.

“So, that was your first kiss. Did you like it?” Sugar Belle asked sweetly.

“Yeah,” Pip answered, panting. “It was amazing.”

“Wanna go again?”

“Please.”

“Come here.”

Pip melted back into Sugar Belle’s embrace, holding her even tighter against his chest, feeling her pink fur against his. When they opened their muzzles again, the unicorn’s tongue entered his mouth, exploring him. They wrestled, tongue to tongue, tasting each other. He ran his hooves through her curly purple mane.

Before long, Sugar Belle’s swollen lower belly rubbed against his own as they got closer. Suddenly, he received a hit on his barrel. It hadn’t hurt, though it shocked him out of the kiss. He pulled away from Sugar Belle with a start. “Uh, what was that?”

Sugar Belle’s muzzle wrinkled cutely as she tried to hold back her laughter, before failing to do so. “HAHAHA! Snort. KYAHAHA! Hahaha! Snort. Haha! Sorry Pip, I think you got kicked by my foal. Hahaha! Sorry, that was just too funny. Haha…”

The moment of confusion passed, and Pip couldn’t help but join in the mare’s hilarity. However, he felt a pang of self-consciousness as he noticed the rest of the herd laughing along with them.

Self-consciousness turned to deep embarrassment when he noticed Big Mac watching him. Watching Pip making out with his wife, right in front of him.

Pip’s discomfort must have shown on his face, because Big Mac placed a hoof on his shoulder and smiled. “It’s alright, Pip. You’re invited, and Ah agreed. Truth be told, Ah kind of like watchin’ you with Sugar Belle.” As if to demonstrate, Big Mac spread his legs, giving Pip a full view of his erect stallionhood and the heavy balls hanging below his tail. The sight made blood flow even more into Pip own’s penis. Looking between his legs, Pip realised his own stallionhood had fully emerged from his sheath during his make out session with Sugar Belle. He blushed hard.

Cheerilee stroked Pip’s back with her hoof. “It’s alright, Pip. It’s perfectly natural, and we’ll take good care of you.” She pulled him closer. “How about we kiss now, you and me?”

Pip met Cheerilee’s green eyes. “Yes, hmm, I’d like that.”

Cheerilee settled on the living room’s plush carpet. She lazily lounged on her side, offering Pip a gorgeous view of her swollen belly and teats. “Come, lie down with me.”

Pip joined her on the carpet, lying at her side. Cheerilee wrapped her forehooves around his neck, pulling him close as he embraced her in return. Soon, Cheerilee’s lips met his own, and he melted into the kiss. He moaned into her mouth as she invited his tongue inside of her muzzle.

They kept kissing for a while, until Pip felt the tip of his cock touch the soft fur of Cheerilee’s belly. Pip froze up, unsure whatever the intimate touch was okay or not. Cheerilee simply brought a hoof to his flank, and pressed him closer to her body. Pip relaxed in the mare’s embrace. The full length of his penis pressed softly into her tummy, making him harder than before.

As they broke the kiss, Cheerilee stared at the stallionhood rubbing against her. She stroked it softly with her hoof, getting a pleasured shudder from Pip. “Should we move on to the bedroom? It will be more comfortable, if we are to take care of this,” she said, still touching his cock.

“Hmmm, yes. That would be lovely,” Fluttershy commented, breaking a kiss with Big Mac that Pip hadn’t noticed until then.

Pip was panting, his heart pounding in his chest. “Yeah, s-sure. Uh, no problem.”

“Well, come on then.”

~ ❀ ~

The herd’s bedroom was a large room on the farmhouse’s second floor. Most of the space was occupied by a massive herd-size bed, obviously big enough for all five ponies. Big Mac lit a few lamps as they entered, bathing the room in a gentle glow.

Coming in, Pip ended up behind Fluttershy. He could barely see her genitals underneath her soft, pink tail. Apparently, Sugar Belle noticed him staring at her wife. With her magic, she lifted the pegasus’ silky tail, prompting an adorable gasp from her. Fluttershy blushed, but didn’t shied away, letting Pip peer at her most private parts.

Of course, it was hardly the first time that he had seen what lay underneath a mare’s tail; ponies generally didn’t wear much covering, after all. But he had never seen it like this, and never from so intimately close. Fluttershy cute little anus lay right under the base of her tail, and beneath it was her vulva, the labia slightly glistening with her arousal. Between them, Pip saw flashes of wet pink flesh, and below the pegasus’ crotch, he could admire her swollen belly and teats. He smelled her arousal too, a sweet musky scent that made his stallionhood stir.

Cheerilee’s voice caught his attention. “Here, come lie in bed with us.” She patted the spot next to her.

More than a little nervous, Pip climbed on the bed before settling belly down beside Cheerilee. Fluttershy and Sugar Belle took place behind him, and - to Pipsqueak’s surprise - Big Mac settled down beside him.

“Uh, I don’t know what I-” Pip started.

Cheerilee silenced him with a quick kiss on the lips. “Shush, don’t worry about it. We’ll take care of you first. Just roll on your back and spread your legs.”

“Here Pip,” Big Mac said. He gently helped the smaller stallion roll on his back, before inviting him to spread with a hoof between his thigh. Pip was a little dumbstruck as he felt a pleasant shudder from the intimate touch. He had never really being interested in stallions before, but it actually felt lovely to be manipulated like this by Big Mac, with his red hoof so close to Pip’s own engorged sex.

The mares surrounded Pip, Cheerilee beside him while Fluttershy and Sugar Belle settled near his rump. A hoof from the unicorn gently fondled his balls, making his erection twitch.

“Are you ready, Pip?” Sugar Belle asked, still caressing his scrotum.

“Y-yeah… please.”

Smiling brightly, Sugar Belle went down to work on his sex. Her tongue touched underneath his balls, just short of his anus, before rising in a single long continous lick, going over his sack and climbing his entire shaft.

“Mmmh~!” Pip couldn’t help but moan at the sensation. He forced his eyes open so he could watch the mare pleasure him, but it wasn't easy. Sugar Belle reached his tip and gave it a quick kiss, darting her tongue over his urethra to collect the dollop of precum that came out of it. She licked her lips.

“Hmmm,” Sugar Bell moaned. “Shy, sweetie, do you wanna take care of his tip?”

“Oh yes, I’d love to,” Fluttershy said in an hushered breath, “if you don’t mind, that is.”

Before Pip could properly process the situation, Fluttershy opened her mouth and took his sensitive tip into her muzzle. It brought Pip such intense pleasure he could no longer prevent his eyes from closing. He threw his head back into the pillows with a loud whinny, losing himself in the sensations of this mare’s mouth around his swollen penis. The wet heat of her saliva, the touch of her tongue, the pressure from her lips, the gentle bobbing of her head; it all felt absolutely divine. Fluttershy’s hooves soon joined too, stroking the rest of the shaft that wouldn’t fit in her mouth.

Pip was starting to think the blowjob couldn’t get any better when Sugar Belle’s tongue went back to lick his equally sensitive testes. He almost blew his load right then and there, but he managed to hold back just in time.

Instead, Pip looked at Cheerilee, who had laid her head on his chest while her wives continued to pleasure his cock. Pip stroked her mane and neck.

Eventually, Cheerilee brought her face closer to his. “So, how does it feel? It must feel really great.”

“Yeah…” Pip could barely talk.

“Say, are you going to cum soon? Can you hold out for a while?”

“I t-think so… yeah, I can last a little longer.”

Cheerilee smiled. “That’s great. Since you said you never had a mare before… you could take that time to explore me while they pleasure you.”

“Uh, ‘explore’ you?”

“Mmhmm. Feel free to look and touch me however you want.”

Cheerilee rose and maneuvered herself over him. Her swollen, pregnant belly pressed on his torso, Pip’s face now right in her butt, filling his sight with her sex. Her dark pink lower lips were flushed with arousal, a clear liquid oozing from her folds. It smelled very strong too, but her musk only served to excite him further.

Big Mac changed position next to him, the older stallion now lying on his back in much the same posture as Pip was, offering his erect penis to anypony who might be interested. “Honey, Sugar, mind comin’ over here?”

Pip couldn’t see anything down there, but he felt Sugar Belle pull back from his balls to move over to Mac. The older stallion groaned in pleasure as his alpha took his large cock in her mouth.

Meanwhile, Pip wasn’t too disappointed by the loss of sensations around his lower shaft. Fluttershy was still enthusiastically blowing his penis, and the vibrations from her pleasured moans just made it even better. It also gave Pip the opportunity to take up Cheerilee on her offer.

With his hooves, Pip spread the mare’s swollen, winking lower lips. For the first time, he could see up close a mare's most intimate parts. Underneath the pert purple ponut, the folds opened to reveal the entrance to Cheerilee’s vagina; Pip could even stare into the depths of her wet canal. Beneath the twitching entrance, there was another smaller hole, her urethra. Finally, at the base of her vulva, what could only be Cheerilee’s engorged clitoris was winking near constantly.

Pip caressed the pillowy softness of Cheerilee’s udders, the two mounds swollen with her sweet pony milk. Out of curiosity, he gently prodded her round belly, his hooves softly pressing into her flesh. To his surprise, he realised he could feel Big Mac’s foal squirming in her uterus. That brought Pip’s attention back to her vagina, where Big Mac had ejaculated his foal into her womb ten months ago. Soon, Cheerilee would give birth through there as well.

On an impulse, Pip grabbed Cheerilee’s flank and drew her rear closer to himself. Tongue out, he licked her moist folds, parting her lips and tasting her snatch. Cheerilee gasped hard, and pushed back against his muzzle. Pip slipped his tongue into her vagina and began exploring her depths.

While the mare lying on his belly was shuddering from his ministrations, Pip could feel Fluttershy had picked up the pace, apparently set on making him cum sooner rather than later.

Unable to deal with the pleasure, Pip retreated from Cheerilee’s snatch and buried his head in a pillow. Feeling his balls tighten, Pip knew he was about to cum. He tried to speak, to warn the cute pregnant pegasus blowing his cock that he would soon ejaculate in her muzzle, but only a loud moan escaped his lips. He really hoped Fluttershy wouldn’t mind as he braced for the inevitable.

As the tip of Pip’s cock flared in her mouth, Fluttershy stopped her bobbing and held the glans steady. After a few urgent strokes from her hooves on his shaft, Pip finally went over the edge. Feeling him twitch, Fluttershy awaited the warm pony semen that would soon gush into her mouth.

The first load of cum coated Fluttershy’s tongue with the bitter, musky, gooey fluid. She gave Pip a few extra strokes, helping him deliver more shots of sperm-rich semen where she could taste it.

After Pip had ejaculated a few more loads of his cum into the sweet yellow mare, he felt her pull off from him. Another jet of gooey semen coated Fluttershy’s muzzle before Cheerilee took Pip’s flare into her own muzzle. He kept ejaculating, letting the other mare taste his seed.

Every muscle in Pip’s body went limp. He fell in an utterly contended afterglow, simply enjoying Cheerilee lapping the last of his seed, Pip’s stallionhood going back into its sheath.

“Hmmm, eeeeyup!” In his post-orgasmic stupor, Pip was barely registering that Big Mac ejaculated too in Sugar Belle’s muzzle, the unicorn happily gulping down her husband’s cum.

Cheerilee rose from his belly and lay down beside him, soon to be joined by Fluttershy. Noticing a dollop of white semen of the pegasus’ yellow nose, Cheerilee licked it too before swallowing.

“So, Pip, how was it?” Cheerilee asked.

“Euh… t-that was amazing,” he answered, barely remembering how to form words with his mouth. “Hmm, thank you girls…” Pip made a vague gesture with his hoof.

Cheerilee giggled. “Oh, I’m glad you enjoyed it! And don’t worry about it: it’s our pleasure. Isn’t that right, Shy?”

“Oh yes, that was really wonderful!”

Pip thought he had to apologize to Fluttershy about something, but it took him a moment to remember what’s for. “Uh, sorry Fluttershy, about that…”

Fluttershy was genuinely confused. “What are you sorry about?”

“I wanted to tell you I was going to finish… but I kinda… wasn’t able to speak.”

This prompted an adorable little laugh from the pegasus. “Oh, that’s quite alright. I was expecting it. And it was fun to taste your seed.”

“Uh, really?” Pip had always thought that getting cummed in the mouth was a chore mares did just to please their partners. “Isn’t that… icky?”

“Well, I guess it kinda is,” Cheerilee commented, “but it’s great when you're really horny. And tasting your stallion’s orgasm just feels amazing.”

“Eeeeyup…” Sugar Belle collapsed between Mac and Pip with a dopey grin and a stomach full of apple spunk.