Sweet Apple Herding

~ ❀ ~

Pipsqueak, Cheerilee and Big Mac were listening to Fluttershy’s story while lounging in the herd’s massive bed.

Fluttershy giggled. “...so all the critters burst through the gala, destroying the entire place, and I just yelled ‘You’re going to LOVE ME!’”

“Wait wait wait, you really did that?” Pipsqueak was more than a little perplexed.

Fluttershy looked away, her face flushed. “Yes. Me and the girls got a teensy-bit carried away. After all that, we went to Donut Joe, and we just kept talking and talking about how awful the night had been. Then, Celestia appeared and, of course, Twilight tried to apologize for ruining the Grand Galloping Gala. But Celestia just laughed. She said that night had been the best Grand Galloping Gala ever.”

“That was the best gala?”

“Well, turns out the Grand Galloping Gala is always boring. Celestia probably liked the excitement.”

Though Pip was happy to be chatting with these ponies, there was a part of him that grew uncomfortable as he listened to the pegasus. When he had arrived earlier, Pip hadn’t really even thought about Fluttershy. Sure, he had known her for many years, but he now was just realising that Fluttershy wasn’t even a celebrity: she was a legend, one who would be remembered for thousands of years as a pillar of Equestria. She was a hero. A bearer of the Elements of Harmony.

And I just ejaculated in her mouth, like it’s no big deal. Pip wasn’t sure if he was feeling proud or deeply mortified. He wasn’t too sure what to feel about Cheerilee either. His old schoolteacher had tasted his cum, and he had tasted her pussy. Ever since then, Cheerilee had been checking him out with the most bedroom of eyes, occasionally even sensually licking her lips.

Willing to clear his mind from that train of thoughts, Pip addressed Big Mac, “so, uh, it must be pretty exciting for you to become a father. And to three foals at once too!”

“Eeyup!” Big Mac proudly puffed his chest.

“He sure is,” commented Cheerilee. “We all are. But I think he’s also pretty anxious. It’s going to be a hard job taking care of all of them.”

“Eeyup.”

“Well, I might be able to help, if you need me,” Pip said. He wasn’t too sure how he could actually do that, though. “I mean, uh…”

“Oh, don’t worry about that,” Cheerilee reassured him. “I mean, sure, if you want to give us a hoof, you can. But nopony thinks you should date our herd for a month before suddenly becoming a father to a bunch of foals.”

“I guess that makes sense. Do you know what kind of pony your foals will be?”

“Mmhmm, we all went for a foal viewing,” Fluttershy said. “I’m carrying an earth pony colt.”

“I’m having a filly,” Cheerilee added, “an earth pony, of course. And Sugar Belle is carrying an unicorn filly.”

“That’s right!” Sugar Belle chipped in as she entered the room, levitating a platter filled with snacks and drinks. “And Goldie Delicious told me that there have been not a single unicorn in the apple family since Apple Star passed away forty years ago, so it’s quite special”

“Maybe your daughter will have apple magic,” said Fluttershy. “Maybe she’ll be able to turn apples into cider, or perhaps she’ll make instant apple pies.”

Sugar Belle snorted loudly. “I don’t think Applejack would be too thrilled.”

“Nnope,” Big Mac confirmed.

Cheerilee gave a cupcake to Pip and picked another one for herself. “So, how are you feeling, Pip? Between your legs, I mean. Do you think you’ll be up for another round with us after snack time?”

Pip scratched his mane with a hoof, a bit embarrassed by the question. “Well, it’s still a bit sensitive, but… uh, I think it will be alright. What… did you all want to do next?”

Sugar Belle grinned. “I heard Miss Cheerilee was offering a new, very exclusive, class tonight. We’ll call it ‘Intercourse 101’.”

Pip wasn’t sure he understood properly. “Uh, you r-really want to do that with me? Like… all the way?”

“We’d love to, Pip,” Cheerilee replied, putting her hoof over his and giving him a quick peck on the cheek. “We’d be glad to give you your first time, if you want to. We’ll guide you through it, step by step, so don’t worry.”

“Okay…”

“Me and Big Mac could give you a practical demonstration,” Sugar Belle pitched in. “Honey, will you show our guest how to properly take a mare and ravage her until she can’t scream anything but your name?”

Big Mac kissed Sugar Belle’s lips. “It’d be mah pleasure, sweetie pie.”

A tingle of excitement spread throughout the herd, everypony hurrying to finish their snacks and drinks. Sugar Belle lifted the empty cups and plates from the bed, clearing the ‘learning area’ for action. Sugar Belle and Big Mac lay down next to each other in the middle of the bed, while Pip, Fluttershy and Cheerilee took position around the couple.

“Hmmm, I think we are good and ready for the demonstration,” Sugar Belle told her audience. “Miss Cheerilee, Professor Fluttershy, you may begin the lesson.”

Pip’s cheeks instantly flushed red.

“Okay Pip,” Cheerilee started in a tone that immediately reminded him of his years as her student, “as I’m sure you are aware, there are many ways in which you can have sex. We’ll start tonight with a simple classic form of intercourse between a mare and a stallion.”

“Step one for nearly all form sex is foreplay. For stallions, the basic goal is to become erect so that they can enter their partner. For mares, foreplay is used to build up our arousal and prepare us for penetration. When the mare is excited, whatever because she’s in heat or simply stimulated, her vagina and vulva will produce lubrication and loosen up so that she can host her partner’s penis. If the mare isn’t ready, intercourse will be very uncomfortable or even painful.”

The couple was making out in front of them, and Sugar Belle gently stroked Big Mac's semi-erect shaft. The big red stallion rolled his mare on her back and pressed her down for an even deeper kiss.

Cheerilee closed in on the action and pulled Sugar Belle’s tail, giving Pip a clear view of the unicorn’s exposed sex. Cheerilee pointed to the mare’s pink pussy. “You can see here that Belle’s lips are puffier now than if she was at rest. If you look closely, you can see her clit winking periodically. That’s a good sign of arousal, but we want her vulva to be glistening with fluids before she’s penetrated. Now Mac, mind going there and help her along?”

Big Mac didn’t respond, but he did break the kiss with Sugar Belle. He went down her neck, planting little kisses and licks as he went. He kept going down Sugar Belle’s body, giving extra attention to her gravid belly and swollen teats. He eventually reached her mound, giving a long, sensual lick through the folds and ending just short of her anus. He then lapped at her entrance, making her moan.

“Mmmh, yes yes yes, oh please Mac, oooh!” Sugar Belle cooed in pleasure.

“Oral is a great way to get a pony, stallion or mare, ready for intercourse,” Cheerilee continued. “Once Belle is ready - that should be pretty soon -, she’ll move on to help Big Mac.”

As if on cue, Sugar Belle pulled Mac’s face to hers and gave him a kiss, her tongue darting around, tasting her own clear fluids. She went down on Big Mac and took his cock in her muzzle. The heavy stallionhood was already well aroused, so, after just a few strokes, Sugar Belle pulled off and lay on her back, hindlegs spread wide and forehooves crossed over her chest. “C’mon Mac, take me, please! I want you inside now!”

“Now, the next step is penetration,” Cheerilee commented as Big Mac planted his forehooves on either side of Sugar Belle. “First, you get in position, then line up your penis with your partner’s vulva. Just aim to touch her fold with your glans. It can be tricky the first time, so just take your time, look where you’re going, and use your hoof if you need to.”

Big Mac did just that. His thick flare spread Sugar Belle lower lips, making her moan. He held there a moment, helping his mate’s body stretch around him.

“Once you're all lined up, all you gotta do is press forward and carefully slide into your partner’s vagina,” Cheerilee instructed as Mac’s stallionhood disappeared into Sugar Belle’s sweet snatch. The unicorn moaned loudly.

“It’s best if you start moving in and out as you enter her. With each stroke, you’ll get a little deeper inside your mare, either until you’re completely inside her or you’ve reached her cervix.”

“That part is really much easier if you had enough foreplay,” commented Fluttershy, who had been silently watching until then. “That’s especially true when it’s the mare’s first time.”

“You’re right, Fluttershy,” Cheerilee approved. “Now, once you’re ready, you simply have to thrust in and out of her vagina. Long, deep, regular strokes where you pull out almost completely before slamming back all the way is generally the best way to go. However, feel free to occasionally change the speed, rhythm and angle of the penetration. Variety is good!”

In front of them, the mating couple was certainly getting into the spirit of things. “Oh Mac~ yes, yes, yes… hmm, faster, please, faster… oh, yeah, do it harder, please please please… oh YES!” Sugar Belle screamed. Big Mac complied with his mare’s instructions and accelerated his thrusts into her drenched snatch. Captivated, Pip absentmindedly stroked his own quickly hardening cock with a hoof. He could see the unicorn's swollen belly gently rock with each of Mac’s hard thrusts.

“Sugar Belle is right,” Fluttershy pointed out. “One the most important part of sex is good communication. Everypony has different tastes, so tell your partner when something feels good or uncomfortable. It will make things better for both of you.”

Sugar Belle suddenly tensed and a loud whinny escaped her lips. She locked Big Mac into her with her hindlegs as she rode her first orgasm. A couple globs of yellowish marecum stained Mac’s crotch.

Sugar Belle loosened up considerably, letting Mac pull out of her vagina.

“So, is that it, then?” Pip asked.

“No, unlike stallions, mares can cum repeatedly,” Cheerilee corrected. “Mac is just taking a short break so that they can continue in a different position.”

Big Mac rolled Sugar Belle onto her stomach, his mare burying her head between two pillows and invitingly lifting her rear.

Cheerilee continued, “this is a very good position for sex in general, and it has the benefit of remaining comfortable during a mare’s pregnancy.”

Big Mac reared up and climbed atop his wife. His tip quickly found Sugar Belle’s dripping pussy, in which he hilted to the balls in one swift stroke.

“OH, YES! Pound me good, honey! Fill me up with your stallion seed, I wanna feel it inside!”

Big Mac went to work mating his mare with feverish intensity. Her swollen womb bounced with each hard thrust he made into her winking sex.

“Now that Belle came once, Big Mac will be getting ready to cum too,” Cheerilee said. “A stallion should generally try to hold off until his mare climaxes before he cum himself. I think Sugar Belle is also gonna orgasm a second time once Mac ejaculates in her.”

“Just remember, Pip,” Fluttershy commented, “Big Macintosh and Sugar Belle have been married for years. They are very experienced, and they know very well how to please each other. It can be hard for an inexperienced stallion to make his partner cum before him - or at all - with just vaginal sex.”

A fresh wave of nervousness ran over Pip. “Uh, really? Then how do I…”

Cheerilee waved him down. “Don’t worry about it, Pip. Nopony will blame you if you can’t make us cum on your first time. Just focus on the basics and have fun. You’ll have plenty of opportunities to improve afterward.”

“And don’t worry about us,” Fluttershy added. “We’re big girls, and we can get each other off once you're done. Now- Oh look, I think they’re going to finish soon.” She pointed toward the mating ponies.

Big Mac indeed had an intense expression on his face as he mercilessly pounded Sugar Belle’s pussy, making her moan non-stop into her pillows. Suddenly, the stallion bit her ear and hilted his cock deep into her pussy one final time, pinning her down for good.

Fascinated, Pip approached behind the mating couple.

Big Mac let out a series of grunts. The big, heavy balls hanging below the stallion dark ponut churned, pumping his gooey seed through his stallionhood and into Sugar Belle’s foal canal. Semen soon overflowed around the base of Mac’s cock, dripping profusely unto the bedsheet. An even larger wave of cum oozed down the mare’s creampied slit when her husband pulled out of her.

Both ponies collapsed onto the mattress, utterly spent.

“And that’s it,” Cheerilee cooed with a dopey grin, “sex between ponies.”

“Woah…” was all Pip managed as he took in the sight of the creamy teardrop-shaped vulva and the flaccid wet stallionhood.

“Now all that’s left for them is to enjoy the cuddles and the afterglow,” Cheerilee added. “Oh, and just to be clear… normally there wouldn’t be this much cum spilling out. Belle’s cervix is closed tight since she’s pregnant, so the sperm got no choice but to ooze out. Otherwise, most of the seed would have pooled up in her womb.”

Fluttershy and Cheerilee nuzzled into Pip’s fur. Nervousness swelled in his chest, and he hesitantly bit his lower lip. Still, he managed to find the courage to speak. “So, can I… can I t-try it too? With... one of you?”

Both mares just nodded with a smile.

“Which one of us would you like to be your first?” Cheerilee asked.

“We’ll understand, whichever of us you choose. It will be quite alright,” Fluttershy said.

“Okay…” Pipsqueak contemplated the two beautiful mares on either side of him.

On one hoof, there was Fluttershy: she was an incredible mare, and her silky pink mane looked so soft. She was a legend. He could definitely see himself enjoying her charms.

On the other hoof, Cheerilee had been one of his first masturbation fantasy. Her curvy body looked very comfortable. She had been a pretty young teacher when Pip had first moved to Ponyville, so he guessed she had to be in her early thirties now.

Pip ended up opting for familiarity. “Cheerilee, can I be… with you?”

“You want to have sex with me, Pip?” Cheerilee asked calmly, a smile on her lips.

“Yeah, please…”

“You two have fun, I’ll leave you to it while I take care of myself,” Fluttershy said.

“Are you sure, sweetie? I can still do you while I’m with Pip.”

“Oh no, that’s quite alright. We can do that another time.” Fluttershy rose and settled on the other side of the bed, leaving Pip with his old schoolteacher.

“So, ready to have your first time with me?”

“Yeah…”

“Say it.”

“I want to have sex for the first time with you,” Pip said more coherently.

“Call me ‘Cheerilee.’”

“I want to have sex with you, Cheerilee,” he precised. Just pronouncing the words made his hardened shaft twitch.

“Come here,” Cheerilee beckoned him. He embraced her. Their muzzles met, and Pip was lost in the mare’s mouth, feeling her tongue as they kissed.

“Pip…” she said panting, her eyes locked with his, “I’m more than ready for you. Just mount me, please.” Cheerilee lowered herself to the bed, leaving her rump high. Pip took his time to caress her soft fur as he went around her to get in position.

Cheerilee had lifted her tail out of the way, giving the young stallion full access to her eager snatch. Pip could plainly see the entrance to her vagina between her winking folds; it looked so soft and warm. Even though she was quite ready, he remembered her lesson on foreplay and dove straight with his muzzle into her vulva. He lapped at her pussy like a thirsty animal, enjoying the taste of her musk. The attention made the mare wink and shudder in anticipation. “Oh yes, that feels great. Now mount me. Take my pussy.”

Pip climbed on Cheerilee’s rump. His fully hardened stallionhood throbbed almost painfully between his legs as he pulled it closer to his prize. As Cheerilee had advised him, Pip looked down to see where he was going and used a hoof to line himself with her drooling cunt, his tip gently parting her labia.

“Are you… are you ready?” Pip asked his mare.

“Mmhmm, come inside,” Cheerilee cooed. “I’m waiting.”

This is it.

Pip gently pushed forward, his glans slipping smoothly inside. As he went deeper, he felt Cheerilee's warm, slick passage massage his cock inside her, inviting him into her silky depths. Her vagina swallowed his stallionhood inch after inch, until his hips met hers and his balls stroked her clit. Wishing to be even close to her, Pip collapsed on her back, wrapped his hooves around her neck, and nuzzled her mane. He felt so incredibly close to her. He could feel her heartbeat around his shaft as he lost himself in her glorious heat.

Cheerilee moaned contentedly. She twisted her neck to get a better look at the stallion currently occupying her vagina. “So, how does it feel to be in your first mare?”

“It’s… amazing…”

“You like being in my pussy?”

“Yeah… I could just stay like this forever.”

“Well, enjoy it for as long as you like. Once you’re ready to get going, just pull back and thrust into me.”

“Mmhmm…”

Part of the haze clouding Pip’s mind lifted, letting him take stock. He was ball-deep inside Cheerilee’s vagina, and his cock was screaming for stimulation. He raised his chest and pulled back from her snatch until just his swollen glans remained. He then lurched himself back into her in one smooth motion, ramming his entire cock through her pelvis.

Cheerilee gasped hard. Pip froze, concerned he might have hurt her. She quickly reassured him, “hmm, YES! Again! Do it!”

Pip complied, pulling back before thrusting ball-deep into Cheerilee’s marehood again. He settled into a steady rhythm, pumping deeply into her foal canal, feeling her heavy, filled womb gently sway with each movement. The friction of his member gliding against her inner walls as he thrusted into her was incredible.

Pip wasn’t sure he could last much longer. His flare was rubbing constantly with her vagina. He was ready to blow. “Cheery… I’m… gonna…”

“Do it! Cum inside me. Just let it all out~!”

Not even thinking, Pip thrusted hard inside the mare a few more times to set himself over the edge. Finally, he pressed all the way into her pussy and hugged her tightly from behind. His mind went blank, all thoughts gone except for the feeling of his balls pulsing and of his seed flowing into his cock. The warm, thick, gooey fluid gushed in Cheerilee’s vagina, where it pooled at her closed cervix. Billions of sperms carrying his genes made their way into the mare. Pip just continued to ejaculate his seed into her, instinctively using his hooves to keep her pinned beneath him so that he could fill her with his entire load.

Not that she minded, of course.

Finally, Pip’s orgasm ebbed and turned into contentment. He went limp on Cheerilee’s back, his stallionhood softening inside her canal. A warm fluid oozed from her slit onto Pip’s balls, which he soon realized was his own seed leaking from her.

Cheerilee let out a soft, happy sight. She stirred beneath him, so Pip pulled out and collapsed next to her. She hugged him close.

He simply enjoyed the afterglow as she watched over him.

“Pip,” she whispered, her face mere inches away from his, “back when you were my student… you liked me. You had a crush on me, didn’t you?”

Had his bloodstream not been filled with a powerful mix of relaxing post-coitus chemicals, Pip would have been incredibly embarrassed. “How… how did you know?”

Cheerilee smiled in response. “Growing foals aren’t very subtle with their hormones. I can tell. It’s perfectly natural, I’ve had lots of students with little school-filly or school-colt crushes on me. I don’t mind.”

“Yeah…”

“Did you… did you ever masturbate thinking about me?”

“Yeah…”

“Often?”

“Mmhmm… I kept thinking about you.”

Cheerilee kissed him. “You know, it’s the first time I had sex with one my students. Or former student.”

“Cheery… did you cum when I… you know.”

“No Pip, I didn’t cum. But don’t feel bad, I still had fun. And I’m really glad I could give you your first time with a mare. I took your virginity.”

“Thanks, for letting me… with you. And for inviting me here tonight.”

“It’s been my pleasure. Now hush, just sleep. I’m with you. We’re with you.”

As if he had just waited for the invitation, Pip quickly slipped into blissful slumber.

“Sleep well, sweetie,” Cheerilee whispered before planting a kiss on his forehead.