Sweet Apple Herding

~ ❀ ~

Monday, July 9th, Year 8 of Princess Twilight

Pipsqueak trotted down the stairs of Ponyville’s town hall, his heart filled with the thrill of freedom: he could go anywhere, and eat whatever, he wanted. So why not go to Sugarcube Corner for a treat? It was lunch break, after all.

Ponyville really hasn’t changed much since I left, Pip reflected as he took in the sights and sounds of the place. I’ll miss Canterlot, but I’m glad to be back.

Ponyville always felt like home, even more so than Trottingham. The bright sunshine and nice summer breeze on his back certainly made it even more so.

The sweet smell of baked goods welcomed Pip as he entered Sugarcube Corner. At the counter, Miss Cake chatted animatedly with an unicorn filly Pip recognised as Pumpkin Cake, the Cakes’ daughter. A warm smile appeared on Cup Cake’s lips as she met Pip’s eyes. “Oh my, is that you, Pipsqueak? It’s been so long, I almost didn’t recognize you, dearie. Welcome back to Ponyville!”

“Hi, Miss Cake”, Pip said. “I just moved back a couple days ago. Mayor Mare got me a job at town hall.” He stared at the delightful treats showcased on the nearby shelves.

“It’s so nice to have you back here, dearie. A lot of friends have missed you, I’m sure. But anyway, what can I do for you today?”

Hmm, maybe a danish? Or an éclair? Pip eventually picked a couple pastries and a strawberry-oat smoothie. Grabbing his order with his teeth, Pip waved Miss Cake goodbye.

He eagerly walked back to the town square, where he found a nice shady spot to enjoy his lunch. He gulped down the cakes, the food settling nicely in his stomach. As Pip finished his oat smoothie, he heard a feminine voice calling him, giving him a bit of a start.

“Pipsqueak?”

Pip looked around and spotted his old teacher walking toward him. “Oh, hi, Miss Cheerilee!”

That answer gave the mare a little chuckle. “I thought I had recognized you, Pip. But please, you can just call me ‘Cheerilee’. You’re a stallion now, and I’m not your schoolteacher anymore. And… you’ve certainly grown since I last saw you.”

Pipsqueak felt a bit of a self-conscious sting as he was reminded of his size. Sure, he had grown, but that made him only a little taller than the average mare: nowhere near the size of most stallions.

Cheerilee, who was carrying a pair of heavy saddlebags filled with groceries, panted under the hot summer sun. “Mind if I sit with you a moment? I could use a little rest…”

“Sure, no problem.”

As Cheerilee approached and removed her saddlebags, Pip noticed the mare’s belly was round and full. He felt an odd shiver as he realised Cheerilee was pregnant, that her womb was filled with a foal. Beaming, she noticed Pip looking at her gravid tummy.

“So, how have you been, Mis- euh, Cheerilee,” asked Pip, a bit embarrassed.

“Oh, I’m still a teacher in Ponyville. Well, not right now. I’m on a break,” Cheerilee answered, gently rubbing her swollen abdomen with a hoof. “Last year, I joined Big Mac, Sugar Belle and Fluttershy's herd. We will be having our first foals in a few weeks.”

“I hadn’t heard you joined Big Macintosh’s herds,” replied Pip, before something about what Cheerilee told him made its way through his mind. “Wait, ‘foals’. As in… more than one?”

Cheerilee eyes glazed just a bit, a dreamy smile on her lips. “Yes, Fluttershy and Sugar Belle are pregnant too. Mac gave us each a foal during last fall’s heat season. Poor Mac, he was so exhausted after - ahem, well,” Cheerilee caught herself as she remembered who she was talking to. "What about yourself, Pip?"

"Oh... Uh, I just came back from Canterlot. I finished my studies there, and I got a job at town hall with Mayor Mare."

As a growing colt, Cheerilee had taken a lot of place in Pip's hormone addled mind. Of course, having a little school-colt or school-filly crush on a teacher was incredibly common; Pip knew that. He hadn’t even thought about Cheerilee in a long time. But here he was, right next to her, and all those fantasies involving his old schoolteacher - which had fuelled countless masturbation sessions - were coming back into his mind.

As ridiculous as it was, he felt... jealous. He obviously would’ve had no chance with Cheerilee back when he was a just colt. Still, there was a primitive part of his mind who somehow managed to feel possessive toward the older mare. That she was now claimed by another stallion, that she was having a foal with said stallion, while Pip himself had never even been intimate with a mare…

It sucked.

Oh, stop wallowing like a foal, Pip thought. You should be happy for her.

And he was happy for Cheerilee, happy she had found herdmates to share her life with and to have foals with. He stood after her as Cheerilee rose, ready to go back home. With a smile, he waved her goodbye. “Good luck with your foals!”

Cheerilee had barely taken a few steps before she stopped in her tracks, one hoof still in the air. She glanced back at him, pondering something.

“Hey Pip,” she said with a slight hesitation, turning back toward him, “since you just came back to Ponyville, how about you come join us for lunch later this week? Maybe Friday evening? I live at Sweet Apple Acres now, with my herd.”

Oh, that sounds nice.

“Sure, that would be great! I could come after work.”

“That would be perfect. You’ll see we built a new house near the old one. Anyway, I must get all this food back home, so see you on Friday!”

“Right, I must go back to work too. See you soon, Cheerilee!”

~ ❀ ~

Even for an earth pony like Cheerilee, walking to Sweet Apple Acres with heavy saddlebags on her back and a foal in her womb was exhausting. She opened the door of her home with a sigh of relief and promptly removed her bags, leaving them on the kitchen’s counter.

Sugar Belle, the herd’s alpha mare, met Cheerilee with a kiss. “Thank you, honey! I hope getting all this stuff wasn’t too hard on you.”

Cheerilee made a dismissive gesture with her hoof. “It was no trouble at all, though I wouldn’t mind if we could move the market a little closer until we foal.”

An adorable little chuckle came from Fluttershy, who was sitting in a nearby chair, knitting a little blanket over her swollen belly. “That would be nice. But it won’t take more than a few weeks now. I can feel my little colt getting restless in there.” Cheerilee kissed the pegasus on the lips, getting a soft shudder from the act. She waved Sugar Belle to join them.

“So girls, while I was in Ponyville, I met somepony. I think he could be a good candidate for us.”

Fluttershy and Sugar Belle’s eyes grew wide.

“You mean for…” the unicorn started.

“Yep,” replied Cheerilee with a grin. “His name is Pipsqueak. He used to be my student, and he just came back to Ponyville.”

“Oh, I remember him,” commented Fluttershy. “He was such a cute colt. Are you sure about this?”

“Well, I don’t know, but he’s a really nice young stallion now. I think even Mac might get to like him. I invited him for supper Friday night, so you will all get a chance to meet him.”

“That sounds lovely,” Sugar Belle approved. “We’ll tell Big Mac once he comes back from applebucking.”