Sweet Apple Herding

~ ❀ ~

Saturday, July 14th, Year 8 of Princess Twilight

Pip felt the warmth of sunlight on his coat as he woke. He didn’t feel like doing anything about it though; he was simply too comfortable underneath the bed’s cozy blanket. Even better was the large, warm pillow he was hugging. It just felt so soft against his fur as he gently rubbed himself on it.

Suddenly, Pip felt something stir against his abdomen. The unexpected sensation got him out of his morning grogginess with a start. His eyes opened, filling his sight with soft pink curls.

Pip pulled back a little, only to realize he was holding a still sleeping Cheerilee in his hooves. Careful not to wake her, he looked under the blanket, seeking the source of the disturbance. Cheerilee's swollen belly was pressing against him. The young stallion put a hoof on it, feeling her womb. Sure enough, Pip felt Big Mac’s little filly stirring inside of her mother.

Satisfied, Pip pulled back and laid his head back down. However, he noticed a warm rump pressing against his own. Looking behind him, he saw Sugar Belle sleeping back to back with him. Pip wanted to simply stay still and enjoy the feeling of being sandwiched between two mares, but he felt the call of nature in his bladder. He carefully rose and tiptoed his way out the bed without waking anypony. Big Macintosh was still fast asleep next to Sugar Belle, but Fluttershy was nowhere to be seen.

She probably got up already.

Indeed, Pip found the pegasus brushing her teeth in the bathroom. “Good morning, Pip,” Fluttershy greeted him after spitting in the sink. “Do you need to come in? It doesn’t bother me if you do.”

“Uh, it’s just… I need to pee.”

“Oh, you can go, don’t mind me.”

“Mmh, Fluttershy… it’s just, well…” Pip said, pointing at his rigid - and uncomfortable - morning wood. “I can’t aim for the toilet if I don’t get it down… and I don’t think I’ll be able to… if you’re there.”

A bizarre expression appeared on the pegasus’ face.

“Fluttershy?”

“Hmm, maybe you… well… I mean… I love my herdmates with all my heart, but still… nopony really likes it when… uh. I mean, maybe you could… if you don’t mind.”

“Uh, I could what?”

Fluttershy just took a few deep breaths. “Assertive. I’m assertive. I’m Fluttershy, and I’m assertive. Oh…”

Pip was very confused.

“PipyoucanpeeonmeifyouwanttoImeanifyoudon’tmindthatis,” Fluttershy blurted out in a single breath.

Uh, did she just say…?

“Sorry, I was t-trying to say: you can come in the shower with me and… pee on me. I really like that, but nopony ever wants to do it, and I thought… maybe you might. If that’s okay with you that is.”

Pipsqueak took a moment to consider Fluttershy's offer. He couldn’t pretend watersport was his fetish of choice, but it seemed harmless enough, especially if they did it in the shower.

“Okay, sure, why not?” Pip accepted with a nod.

“Oh! Are you sure? I don’t want to impose.”

“Yeah, I don’t mind. And you guys did so much for me already.”

“Okay, come with me then. Oh, this is so exciting!” Fluttershy exclaimed, her wings fluttering happily.

Pip entered the shower with her. “So, how do we do this?”

Fluttershy crouched down in the bathtub. “Just mount over me, and pee on my back. Try to get some in my mane too… please. We can clean up once you’re done.”

Uh, okay…

Pip nodded and climbed over the mare. He lined up his hard stallionhood with her back and tried to pee. It wasn’t easy to do with an erection, but he managed to get a few drops out, followed by a steady stream. The golden liquid flowed on Fluttershy's back as Pip emptied his bladder on her with a sigh of relief. Remembering her instruction, he brought up his aim a little higher toward the back of her head. Her pink mane soon flattened, drenched in the smelly fluid. After a few seconds, the stream of urine turned into a trickle and stopped completely.

Now that he had relieved the pressure in his bladder, Pip’s morning wood grew flaccid. He gave it a little shake, letting the last few drops of pee fall on the mare below him. She was absolutely filthy, but Pip had to admit it felt kind of nice to have marked such a cute mare with his scent, like he owned her. He helped her up.

“Thank you, that was really nice. I liked it,” Fluttershy said.

“We should clean up.”

“Yes, but Pip… before we do that, can I… uh… can I pee on you too? I’d really like that.”

Pip thought about it for a moment. Truth be told, he had never seen a mare pee from up close, and now he was kind curious. “Well, okay. Do you mind if I watch?”

“Not at all. You can just stand behind me while I pee. You’ll see everything under my tail.”

They quickly got into position. Fluttershy spread her hindlegs and lifted her tail, offering Pip a gorgeous view of her anus and vulva. A stream of urine emerged from the slightly gaping folds. It splashed on Pip’s chest and flowed down his forehooves. The liquid’s warmth felt pretty nice on his coat, and he enjoyed the flow until Fluttershy had emptied her bladder.

“Oh, that feels so good. Thank you for letting me do this, Pip.”

“You’re welcome, Fluttershy. But maybe we could shower now?”

They proceeded to clean each other, washing the smell of urine and the remnants of the previous night’s lovemaking. Fluttershy wrapped her mane in a towel and gave a clean one to Pip.

~ ❀ ~

Cheerilee woke up in her herd’s big empty bed. Nopony was left in the bedroom but her.

Guess I’m the last one up. Even the filly in her womb seemed awake; Cheerilee could feel her foal stir within her.

She also felt a certain discomfort around her rump. Urg, gosh, I should have cleaned up before going to sleep. Did I really just… Oh boy…

Her butt, back legs, vulva, and tail were utterly coated in the remnants of Pip’s seed. The purple fur of her rump was stained with dry, crusty semen everywhere where the gooey fluid had settled after oozing out of her vagina.

Yep, I need a shower.

After she had cleaned herself and took care of her morning needs, Cheerilee joined Pip and her herd in the kitchen.

“Morning Cheerilee! You’re certainly up late. Looks like somepony had a good night's sleep,” Sugar Belle said before kissing her.

“Yeah, that was great…”

“I saved you some pancakes,” the unicorn offered, “and I’ll get you your coffee. Just take a seat.”

Cheerilee thanked her alpha mare and proceeded to kiss the rest of the herd. She took a seat next to Pip. “Morning Pip! You look like you've been up for a while.”

“Yeah, Fluttershy and I got up hours ago. We, uh… took a shower together.”

Um… does that mean they’ve had some fun together this morning? The thought conjured some pleasant images in Cheerilee’s imagination.

“So Pip,” Cheerilee said once she had filled her stomach, “I hope you enjoyed your time with us.”

“Yeah, I had a lot fun with you guys,” Pip replied with a blush, “and we can do it again, uh, if you want to.”

Sugar Belle beamed at the young stallion. “Does that mean you’d like to officially date our herd? We’d love to have you with us too. We’ve been looking for another stallion for a while.”

Pip rubbed his neck, deep in thought. “Well, uh, maybe? How does that work exactly?”

“It’s quite simple actually,” Cheerilee explained. “When you date a herd, you become each herdmate's coltfriend. That would make Sugar Belle, Fluttershy and I your marefriends. Also - and I understand if that makes you a little uneasy - but that applies to Big Mac too: you’d be his coltfriend, and he’d be yours.”

“Oh… uh.” Pip indeed felt uneasy.

“You know, I really didn’t think I’d like being with another mare,” Sugar Belle intervened, “but it turns out, it’s very fun to be with your herdmates, and you get to love each one of them, regardless of their gender.” She planted a little kiss on Fluttershy's cheek.

“Hmm, how do you feel about it, Big Mac?” Pipsqueak asked the older stallion.

Big Mac mulled the question over. Talking about feelings really wasn’t his thing. “Ah, mmh. Ah suppose… It would be-”

Sugar Belle finished for him, “I think what Mac is trying to say is: ‘I like mares, but I wouldn’t mind trying to be with a stallion. We all want another one for the herd, and you seem like a really good guy, Pip. It’s a bit embarrassing, but that can’t be too bad.’ Was that what you were thinking, sweetie?”

“Eeyup.”

“Once we have been dating for a while,” Cheerilee said, “we can see if you’re a good long-term partner for us, and you can see if you want to commit yourself to us. If we all agree, you can marry us. We’ll be your husband and wives, and our foals will be your childs.”

“Oh, I see… Can I… have a moment to think about it? It’s a pretty big decision.”

“Of course, take all the time you need.”

“I’ll… just go take a walk outside. I’ll be back later.”

“Take your time, Pip. We’ll be here when you’re ready to decide,” Cheerilee told him.

~ ❀ ~

It was a bright, sunny, summer day. A perfect Saturday for ponies to enjoy. Pip was wandering at the edge of Sweet Apple Acres, pondering what was offered to him. He did his best to think objectively.

First of all, he wasn’t dating anypony at the time. He didn’t even have his sight set on somepony else. He was available.

Second, he was indeed looking for a relationship. He really didn’t want to live alone.

Third, he knew all the mares. Fluttershy, Sugar Belle and Cheerilee were all kind, dedicated and talented. Sure, they were each about ten to twelve years older than him, but they weren’t that old.

Fourth, even though he hadn’t really considered it before, he was kind of intrigued at the idea of being intimate with another stallion. Big Mac was a good pony, albeit not a very talkative one.

As such, Pip was very tempted to accept the herd’s proposal. Of course, his stallionhood made him a bit biased. He vividly remembered giving his virginity to Cheerilee the previous night. Ejaculating into her had been a mind blowing experience, and he wanted to do it again. He also regretted not making her orgasm as well, and he wanted to make it up to her somehow.

I should have just said ‘yes’ when they asked. It’s just dating anyway. We can break it off if it doesn’t work out.

His mind set, Pip went back to the herd’s farmhouse.

The four ponies were busily working on a batch of apple pies when Pip returned. They immediately stopped their chores and gathered around him.

“Alright Pip, did you make up your mind?” Sugar Belle asked, looking a little anxious.

“Yeah, I did…”

“And?”

“I’m a bit nervous, but yes, I’d like to date your herd.”

A happy cheer rose up from the herd. Soon enough, Pip was wrapped by three hugging mares. He even felt Big Mac’s foreleg across his back.

Suddenly, Pip was kissing Sugar Belle. She was then replaced by Fluttershy, and then by Cheerilee who tenderly made out with him last. Having kissed all three mares, Pip naturally looked around toward Big Mac. The bigger alpha stallion gave him a gentle nod and approached him. Pip closed his eyes as his muzzle melded with Mac’s. Truth be told, it didn’t feel much different than kissing with a mare, except that he had to crane his neck way up. Big Mac briefly slipped his tongue into Pip’s mouth before he pulled back and broke the kiss.

“Well, congratulations, Pip!” Sugar Belle happily exclaimed. “You are now officially our coltfriend!”

The pony hug pile dispersed, if only just a little.

“So, what should we do now, everypony?” Fluttershy asked.

“Uh, well, I’d really love to stay longer, but I just moved back to Ponyville, so I still have a bunch of things to unpack,” Pip said.

“That’s too bad,” Sugar Belle said. “What about we just do a little picnic on the farm to celebrate? It’s almost noon, so you can have lunch with us then have the whole afternoon to work on your place.”

“Yeah, okay! That sounds really nice.”

“Perfect! Let’s finish these pies then we can have a picnic.”

The herd settled for lunch in a secluded meadow hidden within Sweet Apple Acres. There was a calm water pond there, surrounded by open patches of grass.

Pip grazed with the herd for a while. It had been a long time since he had eaten wild grass. He had missed the feeling of filling his stomach with fresh greenery, and he now enjoyed the sight of the pregnant mares swallowing up the food too.

Sugar Belle and Fluttershy extended the sheet so they could all lounge comfortably. They shared drinks and pastries.

Pip, feeling full, settled on his back and looked at the clear blue sky. He normally wouldn’t have chosen such a position, since it exposed his sheath and balls to any nearby onlookers. However, he felt comfortable with these ponies, his herd. He was quickly discovering the simple joy of not having to care about modesty with other ponies he trusted. He could even let his soft penis come out of its sheath, letting it spill over his belly; he knew the others would not mind.

Sugar Belle settled next to him. “Comfortable, Pip?”

“Yeah.”

“Before you go, would you like to fool around with us?” The unicorn brought a hoof to Pip’s relaxed stallionhood and started to gently stroke his length. He felt a tingle of pleasure at the sensual touch.

Pip just nodded with a moan.

“Alright, come here,” Sugar Belle said, getting up. Pip followed her toward the other ponies. The herd had apparently heard her proposition, because everypony was now looking at the alpha mare. Big Mac was lounging on his side while cuddling Cheerilee, and Fluttershy was up on her hooves.

“So, what do you all wanna do?” Cheerilee asked.

Fluttershy trotted next to Pip. “Um, do you want to help me take care of Big Mac?”

Pip gazed at the large balls and flaccid cock between the big stallion’s legs. “Uh, yeah, I guess I could try. Is that alright?”

“Eeyup.”

“Honey, can you take care of me?” Cheerilee asked Big Mac. He just nodded and pushed his mare up so he could bury his muzzle between her buttcheeks.

That left only Sugar Belle. “I'll take care of you two while you’re sharing Mac,” she said to Pip and Fluttershy.

Fluttershy brought Pip behind Big Mac. “Here, let me show you how to take care of your stallion. I’ll simply take his tip in my mouth, and you can take his balls and the base of his shaft. You just have to use your mouth and tongue to stimulate him. You’ll know what feels good… since you’re a stallion yourself. Once we get started, we can switch positions if you want to. Is that alright?”

“Yeah.” Pip settled between the big stallion’s hindlegs and approached the heavy balls hanging underneath the stallion's anus. It really looked quite lovely. Pip nuzzled into the swollen sack, smelling its musky, virile scent. It felt pleasantly full at the touch. Pip licked his new coltfriend’s scrotum, swiping deep between the testicles. Pip felt the stallion shudder in pleasure. The reaction brought him a different kind of excitement, knowing he had given pleasure to another pony. He eagerly went to work, while Fluttershy next to him swallowed Big Mac’s tip.

Pip suddenly felt his own stallionhood being taken in another muzzle as Sugar Belle gently blew him. The added stimulation made Pip even more eager to pleasure the big red ballsack in his mouth. Sugar Belle soon left Pip and moved on to Fluttershy. The pegasus moaned as her alpha lapped at her sweet folds. Sugar Belle kept pleasuring them both with her mouth, going back and forth between Pip and Fluttershy.

Pip went up the alpha stallion’s erect penis. He licked the medial ring, knowing it was particularly sensitive. Soon though, he went all the way up to Fluttershy. The pegasus let the flared tip slip out of her muzzle. “Did you want to switch places?” she asked.

“Yeah.”

They rather awkwardly swapped positions. To Pip’s surprise, Fluttershy held him close to her as they lay down. They were now both on their side, belly to belly, his cock pressing into her heavy, pregnant abdomen. Pip felt a tingle of pleasure along his rigid length as her foal stirred within her womb.

The tip of the tool that had given her said foal was twitching urgently in front of Pip, so he took it within his muzzle. He suckled upon the swollen glans, caressing it with his tongue, tasting a bit of Mac’s salty precum. As Fluttershy worked on stimulating the rest of Big Mac’s shaft, Pip gently bobbed his muzzle around the tip.

Sugar Belle’s placed a hoof on Pip’s leg. “Here Pip, let me help you.” She gently but firmly guided his pelvis away from Fluttershy’s. Once the way was cleared, the unicorn used her magic to guide his penis; his tip touched Fluttershy’s moist, tender folds, making both of them gasp. Guided by instinct and Sugar Belle’s gentle hoof on his rump, Pip slipped his cock into the pegasus warm, wet vagina.

Fluttershy cooed. “Oh, yes… Mmmh…”

Given their positions, Pip couldn’t thrust into her like when he had mated with Cheerilee. All he could do was slowly grind his shaft into her while they kept sucking Big Mac’s stallionhood. Still, the pegasus’ comfortable depths felt like a lovely home for the young stallion’s sex.

Apparently, Sugar Belle had some ideas on how to spice up their mating. She licked vigorously around Fluttershy’s vulva and kissed Pip’s balls. She took hold of the pegasus engorged clit with her magic, mercilessly stimulating it. That got a very strong reaction from Fluttershy.

“Aaaah~!” Her vagina rhythmically kneaded Pip’s cock as her pleasure built up.

Pip simply suckled the flare in his mouth with increased vigor.

Pip didn’t even had to move to feel like he was fucking the pegasus hard. Her vaginal contractions were quickly bringing him to orgasm. Fluttershy hooves wrapped around his body and pulled him in a tight hug. With a gasp and a squeal, Fluttershy came hard, her marecum spurting around his sheath and balls.

The pressure around his cock and the soft cries of ecstasy coming from the pegasus precipitated Pip over the edge. His glans flared within her and his balls contracted against her crotch as he prepared to deposit his sperm into his second mare ever. Just a few more contractions and he was there.

Pip moaned around Big Mac’s cock and ejaculated inside Fluttershy. Jets after jets of his seed streamed deep within the pegasus, where it pooled around his shaft. Like it had been with Cheerilee, Fluttershy cervix was sealed to protect her foal, so Pip’s semen simply oozed out of her snatch and onto the base of his cock. As he gave his mare the few last spurts of his seed, Pip instead focused on the glans in his muzzle, suckling it more vigorously than ever. Fluttershy too increased her pace, using her hooves and mouth to pleasure her husband.

Pip’s eyes grew wide as he felt Big Mac flare within his mouth. He wanted to pull out, but the hugely swollen tip was locked tight within his muzzle. Pip knew what was coming next.

A twitch ran through Big Mac’s stallionhood, and Pip’s muzzle was immediately flooded with the stallion’s thick, bitter seed. Pip swallowed the gooey fluid, only for his muzzle to fill up again with the next heavy load of stallion semen. Pip continued to gulp down each fresh dose as Big Mac emptied his big, heavy balls in his mouth.

Eventually, the older stallion’s ejaculations ebbed and Pip managed to swallow the last of his seed. He let the wilting cock out of his muzzle and gasped for air. He pulled away from Big Mac’s legs, taking Fluttershy with him.

“Oh dear, did you really swallow all that?” Fluttershy asked, concerned.

Pip just hugged her close. He had almost forgotten his softening penis still inside the pegasus. He felt his heart swell with pride: he had just creamed this beautiful mare with his seed, and had succeeded in doing so after she had come. True, Fluttershy’s orgasm had far more to do with Sugar Belle hoofwork then his own, but still. With a pleased sigh, Pip slid out of the cute pegasus, letting their fluid stain the cloth beneath them as a wave of his cum gushed out of her well-used snatch.

Pip took a moment to gaze around him. Cheerilee was on her back, panting after Mac had made her cum. Big Mac himself looked like he was riding his afterglow after having filled Pip’s stomach with his seed. Sugar Belle was lying on her back not far from them, a hoof gently rubbing her leaky slit. Judging by the gooey traces of marecum behind her, the unicorn had given herself an orgasm after setting off Fluttershy and Pip.

All ponies eventually rose and started to clean up and pack, talking mostly to thank their partners for the good time. Big Mac approached Pip, looking quite embarrassed. “Uh, sorry ‘bout that Pip. Ah hope you’re alright. Ah should have pulled out before Ah finished.”

“Uh, it’s alright. That was really surprising, but I guess it was fun to try. And maybe you can return the favor next time.” That last part had slipped out from Pip before he could realize he had said it.

“Eeyup.”

Pip looked around. “Thanks everypony, but I really should get going. I hope we can have another date soon.”

“Well sweetie, how about you come join us tomorrow evening?” Sugar Belle offered.

“I’d like that, thanks!”