Sweet Apple Herding

~ ❀ ~

Sunday, July 15th, Year 8 of Princess Twilight

“Ah, consarnit!” Applejack exclaimed as Big Mac pulled another large pile of chips into his already sizable hoard. She reshuffled the deck and distributed a new hoof of cards for the ponies at the table. Only Applejack, Big Mac, Scootaloo and Sugar Belle were left in the game, the last two only having a few chips in front them.

Applebloom just chuckled and turned back toward Pip. They had all left the poker game earlier and were now chatting in the living room as they waited for the final outcome. Pip was sitting on the couch with Applebloom and Cheerilee. Meanwhile, Fluttershy was somewhere drinking tea with Sweetie Belle - the two had been expelled really early.

“Anyway Pip, it sure is a surprise to see ya dating mah brother’s herd. Ah betcha you never expected to hook up with Miss Cheerilee one day.” Applebloom laughed.

“Yeah, I’m surprised too,” Pip admitted. “Though… I just joined, so I’ve not been on a whole lot of dates yet.”

“Well, ya sure picked an interestin’ time to join. With the foals comin' up, they are all gonna be really busy, not mentioning you workin' for Mayor Mare. It’s gonna be pretty hard to find times when everypony is available.”

“You’re right Applebloom, but it shouldn’t be that hard to find time for one-on-one dates with Pip,” Cheerilee intervened. “We can just go out at different times.”

“Wait, you can do that?” Applebloom looked dumbstruck. “Ain’t it the whole point of a herd to always be together?”

“Of course,” Cheerilee answered, definitely sounding like the teacher she was, “but being with many ponies at once can be very overwhelming. Having regular one-on-one dates with your herdmates is essential to keeping good relationships with each one of them.”

“I didn’t know that!” Pip said.

“Me neither! Ah mean, Ah really love Scootaloo and Sweetie Belle, but it’s really hard to find stuff all three of us like doing… except, you know… ‘sleeping together’. You’re saying we should do more as couples? But… ain’t that gonna always leave one of us feelin’ left out?”

“The best way is to keep an organised schedule for dates,” Cheerilee explained. “Make sure everypony as a turn with everypony else. If you want to make it really fair, I suggest you write each possible pair on a piece of paper, place them in a bag, and draw the dates’ order that way.”

“Well, Ah’ll be! Thanks Cheerilee! Ah can’t wait to tell Scoot and Sweetie Belle. Uh, just one last question…” Applebloom got closer to Cheerilee and whispered in her ear, but Pip could still hear her just fine since he was between them, “is it okay to have sex when we meet like that too?”

“Yes Applebloom, just have fun with you mates, and give each of your partners a turn. Everything will be just fine.”

“Oh c’mon! Urg…” Scootaloo meanwhile banged her head on the poker table and got up, having lost her last chips.

Applebloom rose up to meet her, a grin on her face. “Oh don’t feel bad Scoot. Come with me and let’s find Sweetie Belle, Ah got something to talk about.”

Cheerilee and Pip giggled as the couple left the room. “Since we are on the subject,” Cheerilee said. “I’d like to go on a date with you soon. I was talking with Sugar Belle and Fluttershy earlier, and we really want to give you some time with each one of us before we foal.”

“Yeah, I’d love to,” Pip replied. “I know you three mares are going to be unavailable for a while, so I’d like to spend as much time with you until then. When did you want to meet?”

“How about we book a table at Horsia’s Tuesday night? I could meet you after work.”

“Ok, perfect! Let’s meet at town hall,” Pip agreed, giving his mare a kiss.

~ ❀ ~

Tuesday, July 17th, Year 8 of Princess Twilight

On the outside, Ponyville’s town hall had not changed much since Cheerilee’s foalhood. The general vibe of the place, however, was completely different.

After years of Princess Twilight’s reign over Equestria, the flow and organisation of bureaucracy had dramatically improved. There were no waiting in lines, no piles of endless hardcopy forms. Ponies could come in and efficiently go about their business in peace.

And, of course, there were not just ponies either. In the town square, a group of Filly Guides included two griffins and a thestral, and was led by a young hippogriff. Just inside town hall, a changeling receptionist was busy welcoming guests while a group of deers were animatedly discussing something.

As she entered, Cheerilee quickly stumbled upon Mayor Mare. “Oh, hello there Cheerilee! My, you look happy. And you look like you're almost ready to foal.”

Cheerilee chuckled. “Thanks, only a few weeks left. Sugar Belle and Fluttershy are almost there too.”

“I wish I could visit Sweet Apple Acres more often,” the mayor said. “Anyway, I suppose you’re here for Pip? I heard he was dating your herd.”

“That’s right! I’m on a date with him tonight.”

“Well, he’s a good, hardworking, young stallion. I wish you all luck. He’ll be done in a few minutes, so I’ll leave you to it.”

Pip indeed arrived shortly afterward. Cheerilee greeted her young stallion with a kiss and left town hall with him.

“You look really lovely, Cheerilee,” Pip told her.

She wasn’t wearing anything fancy, but she had styled her mane with a daisy and was carrying her prettiest saddlebags. “Oh, thank you Pip!” she replied with a smile. “You look very handsome too. Did you cut your mane?”

“Yeah, I had it done this morning.”

That’s so sweet. She planted a kiss on his cheek.

They leisurely strolled to the restaurant, where the waiter guided them to a table on the terrasse.

“I’ve never been here before,” Pip commented as he opened the menu in front of him.

“I’ve always loved Horsia. It’s so nice to have a place like this in Ponyville,” Cheerilee said, looking longingly at the town. “I know dinner dates are a bit… old-fashioned, but sometimes classics are classics for a reason. And I can’t really go bungee jumping while ten months pregnant.”

“It’s perfect just like this,” replied Pip. “So, do you know what you want? I’m really hungry.”

My body is nursing a foal, Pip. You don’t know what being hungry means, Cheerilee thought. “I was thinking about ordering the Itallion spaghetti squash. We could share a big plate, if you’d like. And we could take an entrée of fresh cheese.”

Pip agreed, “yeah, that’s sound good.”

A couple hours later, Cheerilee was sitting with Pip on a bench overlooking the river at the edge of town. She felt utterly content as they sat there in silence, watching the sunset, occasionally exchanging deep kisses.

“This is so nice, Pip.”

She buried her muzzle in his neck, and his hooves wrapped her in a hug, Pip even gently nibbling her ear.

“Mmhmm.”

“Oh, I’ve missed things like this,” she whispered.

Pip pulled off her. “Don’t you usually go on dates with Big Mac?”

“Yeah, and with Belle and Flutershy too. But it’s a bit different.” Cheerilee wondered how to express her feelings. “Right now, I feel like a little schoolfilly on her first date with her crush. It feels… a bit awkward, since we’re both nervous and we don’t really know each other that well yet, but that just means we can sit here and enjoy each other. And I guess… it feels a bit naugthy too, being with you like this. It’s kind of thrilling.”

Pip gently kissed her again. “Yeah, I guess I understand.”

Cheerilee rubbed her head against his. “Yeah, just like a little filly.” She stood up straight, feeling a bit embarrassed. “Except for, you know… having my womb full with another stallion’s filly.”

“Well, I like it.” Pip gave her swollen belly a kiss, making her foal stir.

“Aww, thank you Pip,” Cheerilee cooed.

“You know, it’s really silly… but when I first saw you pregnant like this, I got… kind of jealous,” Pip admitted. “It was really dumb, I mean… you have your own life, and you’re older than me, so why shouldn’t be married and with a foal, right?”

“Oh!” Cheerilee was a little taken aback. She had not expected to have that effect on her former student.

“But, it’s fine now,” Pip continued. “We’re together, and I can share you with your herd. And I hope one day I might be a second father to your filly.”

“I’m sure you will be,” Cheerilee gently assured, “and, who knows, perhaps you’ll even sire my next foal.”

“Yeah, I’d like that a lot,” Pip whispered in her ear.

They held each other for a while. “Uh, Cheery,” Pip hesitated. “Do you want to come to my place? I’d really like to… hmm, mate with you. If you’d like to.”

Cheerilee sighted happily. “Yeah, I’d like that too.”

~ ❀ ~

Pip’s apartment in Ponyville was a small basement studio near the town square. It looked clean and functional.

“It’s a nice place you got here, sweetie,” Cheerilee commented as she looked around.

“Thanks, I rented it from Carrot Top for a few months,” Pip explained. “I planned to move into a house of my own once I’m sure my job’s steady.”

He led Cheerilee to his bed and kissed her.

Cheerilee and Pip lay down on their side, looking into each other’s eyes. She felt him press his swelling stallionhood into her round belly. It thrilled her to be so close to him.

“Cheerilee, when we had sex the last time… you said you didn’t cum.”

Cheerilee gave him a kind smile. “And I told you it was alright. I mean it.”

Pip hugged her closer. “I know… but I’d really like to make you cum.”

“I’d love to. I’ll show you how.” Cheerilee kissed his muzzle.

Pip looked amused. “Is that another class? I’d like to enroll, please.”

“Mmh, it’s more of a practical workshop. Princess Twilight is promoting a very ‘hooves on’ approach to education, after all.”

They both snickered.

Cheerilee rolled on her back and prompted herself against a couple of pillows so she could see him. She spread her hindlegs, letting him peer into her snatch. “Alright, the first thing to know about pleasuring a mare is that each one is different. Exploration and good communication goes a long way in helping you understand what makes your partner happy, and what makes her uncomfortable.

“Generally speaking, unless she’s in heat, a mare will take longer to orgasm than a stallion. Foreplay is key in giving your partner a head’s start before you enter her. Oral sex and simple masturbation are great ways to do so. Now come here.” She guided Pip’s muzzle to her winking vulva, and spread her labia with a hoof.

“You already went down on me last time, so you know what’s what. I’ll just talk a moment about my clit. It’s extremely sensitive, so it can be very fun to play with, but it can also be uncomfortable or even painful. Until you're more familiar with a mare, I’d suggest you stick to licking it, kissing it, or rubbing it gently with your hoof. As I said, each mare is different. Personally, I prefer if my partner doesn't focus too hard on my clit unless I’m about to cum.”

Cheerilee gently pulled behind Pip’s head to get him going. She felt a deep shuddering wave of pleasure as his tongue entered her folds. She sighed contently.

For such a beginner, Pip really wasn’t bad. In truth, his enthusiasm was deeply satisfying. Cheerilee just had to nudge his muzzle up or down as she pleased. Eventually, she let him go higher so he could taste her winking nub. Cheerilee moaned and twitched at the electrifying sensation of having her clitoris licked. She let him do so for a moment and pushed him back down before her pleasure turned into discomfort.

Cheerilee kept him going for a while, until she was almost close to orgasm. She didn’t want to do it yet though, she wanted him to feel her pleasure from inside. “Oh gosh, that’s so good~ come here sweetie. Mount me and get inside.”

“Yeah…” Pip said, obviously out of breath. He climbed atop her.

Cheerilee felt his tip spread her tender folds, forcing her to bite her lips to stifle her moan. As she had expected, Pip was fully hard and ready to enter her. She wrapped her hind hooves around his backside to guide him.

Pip’s cock slowly slipped into her vagina. Cheerilee loved this part, sensing the first penetration into her own eager sex. Soon enough, he was completely inside her; she felt his swollen glans press deep in her abdomen against her closed cervix, his balls gently rubbing her asshole.

Cheerilee used her four hooves to immobilise her partner inside her, keeping him locked in place. Pip pressed himself hard against her body, though he was careful not to squeeze her gravid mound. They looked into each other's eyes, loving the feeling of being as intimately close as two ponies could possibly be. Cheerilee darted her tongue out and licked his muzzle clean of her fluids.

Cheerilee kept Pip trapped within her, letting him just enough slack so he could grind and maintain their pleasure while she continued to instruct him. “Now… mmh… while we fuck, you can help me orgasm faster by… mmh… rubbing, kissing or licking my body. You can do that… mmh… anywhere, but it’s best if you focus on my… ah… erogenous zones. My cutie marks, my belly, my teats, my loin, my ears and my faces. Oh, and my asshole too, if you can reach it.”

She gave him more slack and he started to thrust harder into her. “Oh, and once I’m about to cum… mmh- oh, yes… oh, yes, mmmh… once I’m about to cum, you can rub my clit. Oh… good boy, gosh, yes.”

Pip really picked up the pace as he pumped into Cheerilee’s burning vagina. As she had instructed him, he rubbed her flanks and belly with his forehooves while kissing her faces and ears. The onslaught of pleasure inflicted upon her body made her twitch and shudder delightfully around his shaft. Cheerilee particularly enjoyed him as he massaged her swollen teats, making her gasp and moan even more.

His cock pumped into her, producing a regular thump-thump-thump.

Eventually, Pip’s ministrations grew increasingly erratic as he desperately pounded his swollen flare into her, letting her know he would soon reach his peak. She guided his hoof to her clit, and instantly shuddered at the electrifying pleasure. “OH YES… FUCK YES… oh, please… oh, yes-yes-yes-yes, fuck me Pip, please! Make me cum sweetie, please-please… make me cum! I want to feel you inside while a cum! MMMMH ooooh~”

Cheerilee screamed her pleasure as loud as her lungs allowed. She squeezed her young stallion hard against her body, forcing him deep inside so she could collect every last drop of his seed. He didn’t have to thrust anyway; the powerful, rhythmic contractions of her vagina were more than enough to bring a primed stallion to orgasm inside her.

Pip moaned. Cheerilee felt his body shudder and his balls contract against her. She waited with baited breath, observing his cute, blissful face. Suddenly, she felt it: the warm, rich, gooey seed gushing from his stallionhood deep into her sex. Cheerilee tenderly admired her partner as he filled her with his thick semen. She felt a deep heat in her heart as she watched Pip claim her as his mare.

After ejaculating for a good half minute inside Cheerilee, Pip went limp atop her and his cock softened. Cheerilee just let him relax as she enjoyed her own afterglow. She relished in feeling his heartbeat inside her pussy and his breathing on her chest, knowing she had brought such pleasure to another living, breathing pony. The result of their lovemaking oozed down her slit on her anus and in her tail, but she couldn’t care less.

“Hi,” she eventually said with a little smile.

Pip looked in her eyes, harboring a blissful, dopey smile of his own. “Hey…”

“Comfortable?”

“Yeah…”

Cheerilee tenderly stroked his mane. “You deserve it. You were perfect.”

“It was good for you too?”

“Yes, it was great. I came, and you came too. Mmh, I still feel your seed inside me.”

“I’m glad…”

Pip brought his muzzle to hers and kissed her lips. Cheerilee opened her mouth, happily letting his tongue enter.

Pip’s penis slid out of her sensitive vagina and withdrew in its sheath, letting their combined cum flow out of her pussy. He broke the kiss and rolled off of her.

“Cheerilee, do you want to stay with me tonight?”

“We probably should clean up first. But yes, I want to sleep with you.”

“Oh, I wasn’t sure if you needed to go back to your herd after our date,” Pip confided.

Cheerilee chuckled. “Don’t worry, it’s fine. I expected something like this would happen. I even brought my toothbrush.”

And so, after having sex and a good shower, Cheerilee went to sleep in Pip’s bed, holding her young coltfriend close as she drifted into a comfortable slumber.