Chapter 3: The Taming of Applejack

“Hmph!!!”

Applejack struggled to get free, but there was nothing she could do as she was outnumbered. She could feel herself being lifted up and carried into the clearing in front of the barn.

“Woah, we got a lively one here,” the second voice laughed while she kicked ineffectively at the air.

“Madame Jubilee! You were holding out on us. If we'd known there was a new girl coming tonight, we'd have brought nylons and chocolates.”

Jubilee looked at Applejack with a stern expression that only slightly failed to do its job due to the fact that Cheese's cock was pressing against her cheek. AJ wasn't really sure whether she was angry at her for spying on them or for getting caught.

“Flim, Flam,” she finally said with a calm voice. “She's actually not part of the night shift yet. So kindly let go of her.”

Applejack could feel her captors stiffen momentarily and then she was set down, her hooves touching the ground again. She took a deep breath, when there was no longer a hand pressed over her mouth.

The first stallion walked around her and into the light with an apologetic expression. He looked kind of gangly and had a red mane with a white streak in it. Taking off his straw hat and holding it in front of him, he said: “I am very sorry about that, Miss.”

The other stallion, who looked very similar, only this one had a mustache, handed her back the stetson that had fallen to the ground. “Yes, my brother and I misjudged the situation. Please accept our apologies.”

“Uh, that's alright,” Applejack forgave them, taking back her hat and fidgeting with it for a bit. “No harm done, ah suppose. And it's kinda mah own fault.”

Madame Jubilee was still staring at her in silence. Damn, Ah'm such an idiot, AJ thought to herself. Ah blew it. Forget picking up extra work. She's probably gonna fire me now.

But then it was Fancy Pants who spoke up. “So you did approach her after all.”

“Hm, since you suggested it.” Jubilee sighed and looked Applejack directly in the eye. “I told you that I don't offer ponies this kind of work until they've become accustomed to the plantation. I don't want them to feel pressured into doing this. It's important to me that it's their choice.”

Fancy Pants chuckled. “Looks to me like she's made her choice already,” he said with a smirk, looking at her unbuttoned pants.

Jubilee's expression softened. “Well, maybe she is ready. So how about it, Applejack? Nopony is gonna stop you from leaving, as long as you promise not say anything about what you saw here tonight. Or … you could stay.”

Applejack bit her lip, blushing and looking away. She had to make a decision now. If she were to stay, there would be no turning back. Was she prepared for this? Applejack blocked everything else out for a moment.

This body of hers. She'd trained it, honed it through years of manual labor and she was proud of it. It was supposed to grant her victory at the rodeo, but it didn't. Then Madame Jubilee had shown her appreciation for it and was now offering this opportunity. Between using her body to win prize money and taking money from stallions who would appreciate it, was there really that much of a difference?

She knew that she desperately needed the money. If only her body could tell her whether or not it was okay. Shifting her weight, she could feel the wet spot in her panties and the heat between her thighs and realized that her body had in fact given its answer already.

She swallowed hard and decided to be honest with herself and with Madame Jubilee. “If ya don't mind my inexperience, ah'd like to give it a try.”

No sooner had she finished that statement than two jingling purses were deposited in the upturned hat in her hands. A hundred bits, just like that. Amazing, she thought and looked to her left and right at the two gently smiling stallions. “Thank you for your patronage.”

“Well then. Flim and Flam, please show her the ropes,” Jubilee said. Having her here was somehow comforting. The atmosphere was a lot different than what she would have expected it to be.

“Let's see what we got here,” Flam said, loosening the knot in AJ's shirt to reveal her breasts. “Very nice.”

“Hm!?” She was a little surprised, when he kissed her, since she'd never kissed a pony with a mustache before. It didn't feel so bad, though, as his facial hair tickled her upper lip and so she opened her lips. He seemed to be smiling as his tongue explored her mouth.

Meanwhile Flim had come up behind her and took off her shirt. His hands cupped her mounds and while one lingered there, the other made its way further down, stroking her exposed stomach.

“Do you know the rules of Madame Jubilee's Barn of Lust?” he whispered in her ear.

“No, what are they?” she asked, breaking the kiss for a moment.

“There's only two. Number one, nopony talks about what happens here.”

Seemed sensible enough. “What about the other one?”

He answered while his hand moved further down and the anticipation as he reached her panties gave her goosebumps. “Have fun.”

As Flim pulled down her jeans to her ankles, Flam lifted her chin with one finger to make her look at him. “So what do you enjoy most about sex, honey?”

Even before her brain had formulated the answer, her hand had already moved to his groin and was feeling the tightness in his pants. “I like cocks, lots and lots of cocks.”

He looked fairly amused at that answer. “You're pretty blunt, aren't you?”

“What can ah say?” she asked a little impishly, getting more and more into the moment and stroking his pride. “Ah'm a pretty honest kinda gal.”

As Flim pressed in on her from behind again, she could feel his tip brush against her plot. “If you love them so much, then where do you want them?” he asked, taking her wrist and leading it towards him.

She began to rub it, her body acting free and unbound by the worries of the last few days. “Everywhere,” she said breathlessly, giving Flam another hot kiss and looking at him with her best bedroom eyes. “Ah want to feel them in mah pussy and mah ass. You can use mah mouth, too.”

“Then let's stop wasting time,” Flam declared and the two stallions lowered her onto the blanket. Flam pulled off her jeans the rest of the way. Applejack lifted her legs up to make it easier for him to relieve her of her panties. Noticing the wet spot, he sniffed at them for a moment. “I almost wanna keep them as a souvenir.”

Applejack felt like she should be embarrassed by that, but another thought pushed itself into the foreground. “Ten bits and they're yours,” she said, licking her lips.

Flam looked back at her in surprise, but Flim, who had knelt down next to her head, simply laughed. “I love a mare with a sense for business.”

“Hm, so do I,” his brother eventually agreed with a chuckle. He took out a few coins and tossed them into Applejack's nearby hat with the rest of the money. Then he carefully folded the panties and placed them in his considerably lighter pocket.

“Thank you for yer patronage,” she said with a naughty smile and spread her legs wide to emphasize her point.

“Pleasure doing business,” he responded and took hold of her legs. Moving forward, he lined up his tip with her entrance.

Flim cleared his throat and looked down at her. Applejack turned her head and saw his hard member hovering in front of her face.

“Don't ya worry, sugarcube,” she assured him with a wink. “Ah haven't forgotten about you.” Closing her lips around his tip, she began to suck on it.

Even more aroused by that sight, Flam slowly pushed into her wet folds. Applejack moaned and shuddered in delight as she felt his length enter her and a pleasant warmth spread throughout her insides. “Guh, damn, she's tight.”

“And a good cocksucker, too,” Flim added, having felt the vibration in his member transmitted over her tongue. “Take it a little deeper, will you?”

Applejack looked up at him while moving her head forward and moving her tongue to please different spots along the shaft. Hitting on an idea, she angled her head slightly, so the tip brushed against the inside of her cheek.

Meanwhile Flam had shifted his weight forward, fucking her with prolonged strokes. Her body felt like it was growing hotter as he penetrated her deeply. Every now and then he reached around her leg, running his thumb over the clit.

Every time she took the cock in her mouth a little deeper in response. This was heavenly. She could simply stop worrying about her duties and responsibilities and just be in the moment.

“Sorry we're late,” a voice said, announcing more patrons entering the clearing. “The Appleloosa Express ran a little late tonight.”

Appleloosa? She knew that voice! Letting go of Flim's member, she looked over towards the new arrivals in horror. She knew all three of them. It was Sheriff Silver Star, the buffalo chief Thunderhooves and “Braeburn!?”

At the mention of his name, the earth pony stallion blinked and looked over at her. Then he jumped. “Cuz!?”

Noticing that her partners had stopped, Madame Jubilee raised her head. “Oh, so you two know each other. How nice.”

Geez! And thus far Applejack had taken Jubilee for an observant and subtle mare. Then again it was entirely possible that she'd said it on purpose to lighten the mood. Only it didn't seem to work very well as the two cousins stared at each other in silence.

Applejack squinted. “First rule of Madame Jubilee's Barn of Lust … “

“... nopony talks about what happens here,” he finished for her without missing a beat.

“So we're agreed then?”

“Yep.”

Applejack heaved a huge sigh of relief. It looked like they wouldn't have a problem. This could have turned ugly fast.

“So, what'll it be for you three tonight?” Jubilee asked, still unperturbed by the strange twist of fate her latest worker had just come face to face with.

“Sheriff Silver Star and I have come to an agreement,” Chief Thunderhooves declared gravely in his booming voice to which the sheriff simply nodded. “I get to call dibs on some ass tonight.”

“Is that so? Unfortunately as you can see, somepony else has already claimed one plot.” Fancy Pants gave him a cheeky grin as he was still humping her rear and he didn't look like he was gonna be done anytime soon. “But I seem to have overheard that my assistant tonight just loves cocks. Isn't that right, dear?” she asked with a concealed smile and a raised eyebrow in AJ's direction.

She scratched her cheek. That's some selective hearing you've got there, boss. “Ah guess we got room for one more over here?” She gave Flim and Flam a questioning look and they nodded.

“Very good,” the chief declared, walking over and dropping the required payment into her hat.

Flam grabbed her cheeks and lifted her up while the buffalo got undressed. Applejack's eyes grew wide, when she saw him, though. He was HUGE! At least twice the size of any stallion she had ever seen. “Now hang on just a second there, ah'm not sure that's actually gonna … woah, nelly!”

As Thunderhooves positioned himself underneath her, she was incredibly grateful at Flam for lowering her slowly onto him and at Flim for providing some much needed lubrication with his magic.

Still it felt somehow like she was slowly being skewered as she held her breath. With every inch she could feel her eyes roll back further into the back of her head. Since Flam hadn't pulled out, she felt more full than she had ever been. “Hah … hah … it's in.”

“Hm, yes, you're very good,” the chief said, keeping his hips in place and stroking her stomach to give her some time to adjust. “You know what they say, right? Once you go buffalo, you never go back.”

“Ah can see why.” Applejack leaned back, resting her upper body on his broad chest and looking at Flam, who was still holding up her legs. He was waiting for her as well, although it was clear that he was eager to start up again. Without having to look, she reached out her right hand to resume Flim's hand-job. “It's alright now, y'all,” she said, remembering how easily Madame Jubilee had adjusted to the double penetration. “You can move.”

She could feel the two hard cocks rub up against each other through her inner membrane. Having had sex before both ways, she never knew how much better it felt to have both holes filled at the same time. It was stimulating so many different spots simultaneously and judging by the grunts of the males, the increased tightness felt good to them as well.

Moaning as she was adjusting to this new sensation, she realized that Silver Star was standing to her left, having already pulled down his pants. “What can ah do you fer, sheriff?”

“Getting a hand-job from a pretty mare would be mighty fine, ma'am. An' if Mr. Flim doesn't mind sharin', the feeling of those purty lips o' yours on mah cock would be nice.”

Applejack giggled. Somepony else speaking in a country accent always seemed to make her own more pronounced. It was a sign that she was comfortable. “Polite fella, ain't ya?” After he added his fifty bits to her growing hoard, she closed her fingers around his shaft and began to rub it while running her tongue along the base. “Ain't ya supposed t' cuff me or something? This sorta thing ain't exactly legal, ya know.”

He grinned beneath his bushy mustache and pointed at the star pinned to his vest. “Ya mean because a this here thing? Dodge ain't mah jurisdiction,” he said, taking it off and putting it into his pocket, out of sight. “Just don't let me catch ya doing this in Appleloosa.” Grinning even more, he added: “Unless ya really want me t' cuff ya, which could be fun.”

She chuckled at that, drawing both dicks closer to her and licking their tips at the same time. “Ah'll remember that. … Ah!” Her moans grew louder as Flam and Chief Thunderhooves had found their rhythm and were steadily speeding up their thrusts.

Then she spotted a certain stallion off to the side, watching her while rubbing his cock. “Braeburn?”

He swallowed loudly and blushed. “Uh … Say, cuz … would ya consider … “

It took her a moment to process what he'd just implied. “What? We're cousins!”

“It's legal fer cousins t' marry out here, ya know,” Silver Star supplied.

“That doesn't change the fact! It's immoral,” and hot! I kinda want to try it. Applejack cursed her curiosity as her cheeks turned crimson. “Can ya imagine how awkward the next family reunion is gonna be?”

Braeburn nodded, conceding every point she brought up without comment. Then he took a deep breath. “I'll pay ya double, if ya let me do it with yer tits.”

. . .

“Alright, get over here.” Dangit, brain! Stop being so greedy, she chastised herself. Oh well, she'd gone this far. What difference did it make now? Might as well take the additional hundred bits.

He skipped over with a huge grin on his face, like a child who'd managed to talk his mother into buying him some more candy. Although the bag of bits being deposited with the rest was music to Applejack's ears.

Swinging one leg over her, he positioned himself over her stomach, his pride pointing at her face. “It's been a while since ah've seen those freckles of yours, cuz,” he commented, tracing a finger along the curves of her chest. “Reminds me o' when we used t' take baths together as kids.”

Applejack blushed and glared at him. “Th … Don't talk about that here, idiot!”

“Applejack, you can't be rude to your customers,” Cherry Jubilee chided her gently from a few feet away. “Ahh!” But her words were cut off, when Donut Joe grabbed one of breasts from below and began to suck on it strongly. Taking advantage of her open mouth, Cheese Sandwich grabbed her head and pushed his member past her lips with a grunt once more.

“Yeah, cuz. Customer's king,” Braeburn maintained, pinching her nipple lightly.

“Ah'm mighty sorry, yer highness,” she replied with just a hint of sarcasm and spat on his cock to lubricate it. “Please enjoy yer purchase to the fullest.”

“Ah will.” With a grin, he placed his shaft between her orbs and pressed them together with his hands from the side. He bit his lip with an expression of bliss on his face as he began to move his hips. “Damn, ah always wanted t' do this. Ah love yer tits, cuz.”

Even as she alternated between sucking off Flim and Sheriff Silver Star, she glanced at Braeburn's tip which was coming up near her face every now and then. She knew that her breasts were smaller than Jubilee's. Still for some reason Braeburn had paid double for hers. It did give her a certain sense of pride and she began to feel bad about what she'd said to him earlier.

As an apology, she looked up at him with moist eyes and stuck out her tongue, so his tip would brush up against it periodically.

“Woah, that look yer giving me right now. That's so sexy. You were born for this kinda work, cuz,” Braeburn said with a grunt and a shudder. He just couldn't look away.

“Ya think?”

“Of course, otherwise Madame Jubilee wouldn't have approached you,” Flam said, speeding up his thrusts.

“She's got an eye for talent,” Flim agreed, rubbing her ear as she sucked at his tip.

Chief Thunderhooves grabbed her shoulder and pushed himself into her plot as far as possible, causing her to scream in pleasure. “A mare with a strong back … “

“… and quick hands, …” Sheriff Silver Star continued while stroking her mane.

“… that's what Madame Jubilee is looking for,” Braeburn finished.

Maybe they were right. Maybe this was what she was meant to do. Rather than pushing herself to exhaustion in a rodeo, she could utilize her body this way. And unlike there, where she had to force herself to go on, she was actually enjoying herself here.

It seemed like the stallions shared that sentiment. Even as Applejack could feel the heat rising from deep within her due to the stimulation from all sides, her five customers also seemed to sense that she was close and put their joint efforts into making her climax.

“Ah! … Hah! … AH … AH'M CUMMING!” Arching her back, all the muscles in her body tensed up simultaneously. Her head swam and her vision blurred. All she could see were rough shapes, but some stood out more than others. “Cocks … so many cocks … Ah love it.”

Applejack closed her eyes for a moment, enjoying the afterglow and catching her breath. Then she realized that she was acting selfish. Her partners hadn't climaxed yet. But when she opened her eyes, she realized that all of them had withdrawn.

Chief Thunderhooves lifted her up slightly and then set her down in a kneeling position on the blanket, withdrawing his pride from her plot. Though he did give her a quick kiss on the cheek.

Puzzled Applejack simply sat there, watching her clients line up in front of her. Then Madame Jubilee knelt down next to her, handing her one of the cider mugs. “What's this for?” she asked, realizing that Cheese, Fancy and Joe had also lined up with the others in front of the two of them.

“They're ready to tip us,” Jubilee replied with a wink. “Be sure not to spill too much.”

“Ugh,” Fancy Pants groaned and took a step forward, jerking his pulsating dick with one hand. He aimed it at the receptacle, which Jubilee held up in front of her chest. “Ah!” With several prolonged spurts, he came, filling the vessel with his jizz.

Applejack looked over at her own group. They were all stroking themselves, so she held up the mug wordlessly. One by one they stepped forward, cumming with satisfied expressions. Chief Thunderhooves was the last to add his sperm and his load was massive, part of it glancing off the already full mug and sticking to Applejack's chin. “Uhm, thanks. Ah guess,” she said, unsure of how to proceed.

One look over at Madame Jubilee made that abundantly clear, however. She was drinking it down.

Applejack looked at it again. The mug was almost as big as her head and filled to the brim. She wasn't so sure whether or not she could actually down it all. Only one way to find out. “Bottoms up!” she declared, putting it to her lips and tilting back her head.

The rich smell and thick texture made her mind reel as the first bit filled her mouth and she choked for a second on reflex. Pausing, she took a few deep breaths through her nose and looked at the stallions, who were giving her encouraging glances.

She closed her eyes again and forced herself to swallow what was already in her mouth. It got easier from there as she slowly lifted the mug more and more, chugging the cum down at a steady rate as it came.

At one point she went a little too fast and she could feel some of it flow over the corners of her mouth and down onto her breasts. Surprising herself a little, she was kind of sad, when she had finally drained the tankard. At this point she could have gone for a little more.

“Looks like ya spilled a little there,” Jubilee commented and leaned over. Lovingly she lapped up the few drops that had fallen onto her chest while the stallions gave them both a round of applause. Jubilee giggled and gave her a suggestive glance. “And what do we say?”

Applejack looked up at her customers with a beaming smile, holding the empty mug in her lap. “Thank ya kindly for yer patronage. Please cum again.”

* * *

“So how did you like your first time?” Madame Jubilee asked as the two mares made their way back from the barn to the main building. After the stallions had left, they had taken some time to clean up and get dressed again.

“It was good,” Applejack admitted, looking down at the hat full of bits she was carrying in her arms. Not to mention profitable, she added in her mind. 310 bits. That's almost a third of what ah need right there. Two more nights like this and ah would have enough to cover for the repairs.

“I thought so. You're a natural,” Jubilee said with a sideways glance. “So can I put ya on the permanent rotation for the night shift, then? You'd be working with Golden Dawn, since I don't want newbies being by themselves. Most of our customers are decent folk, but ya can never be too careful.”

“Fine by me.”

“Good.” They stopped at the door leading to the workers' lodgings and Madame Jubilee prepared to make her way further on ahead to the main building. “Sleep well tonight, my dear.”

As Applejack stood there, looking after her, a thought occurred to her. “Madame Jubilee? Why did ya bring two cider mugs to the barn? Ah mean, ya didn't know that ah was gonna come an' join in, right? So why'd ya bring two in the first place?”

Jubilee stopped and looked over her shoulder with that enigmatic smile of hers. “Hm, I wonder why. Sweet dreams, Applejack.”

And with that she turned again and walked off.

The End.

Author's Note

And there you have it. Kinda puts AJ's interactions with the rest of the Mane 6 in "Last Roundup" and her approach towards the Flim Flam brothers in "Super Speedy Cider Squeezy 6000" in a new light, doesn't it? Also kinda explains why she doesn't exchange a single line of dialogue with Braburn in Season 3's "Apple Family Reunion."

Isn't it nice how mindless fucking can tie episodes together like that?