Jest Dicking Around 3 Return Of The Horny Hoser

by Jest

Rating: mature
Tags: Applejack, My Little Pony: Friendship is Magic, Original Character, Comedy, Random, Sex
Length: 4236

Jest goes for another walk, but this time at night and in town. Surely he will not end up tricked by changelings weird plants or other weird situations, right?

Jest goes for another walk, but this time at night and in town. Surely he will not end up tricked by changelings weird plants or other weird situations, right?

Kinks straight sex, light cumflation, lotsasex

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Published 2024-02-16 21:00:02 UTC
Last updated 2024-02-16 21:00:02 UTC

Hoodwinked

Jest strolled leisurely down the poorly lit street at the edge of Ponyville. His frequent hikes had left him sore, sticky, and or in the hospital by their conclusion so he had decided to stay in town. Not only that but he had stopped going out at least for his walks, during the day, which would surely lower his chances of ending up in some unpleasant situation.

Not like he minded either previous excursion now that he was thinking about it but the constant bait and switch was leading to trust issues. Why just that morning that his yoga instructor was actually some form of replicating alien monster that was devouring the townsfolk in secret. After getting escorted from the premises he had decided that maybe he should keep such thoughts to himself in the future.

Since then the day had gone well.

He had stayed inside and watched as Derpy delivered his mail. He had eaten his meals in the dark with his blinds pulled so that no one could spy on him and now he was going for a walk. It was basically a long list of wins, albeit ones that no one else could see.

Meandering down a side street and emerging only a few houses down from Carasel Boutique, Jest noticed something odd. A mare wearing a hooded dress so voluminous that it hid every last one of her features had entered the alley. Winding her way around the back of the building, Jest heard a door open, a hushed conversation too distant to pick up, and then the thunk of the aforementioned door no doubt closing.

It was a curious sight, and one that prompted him to investigate only to stop and remember what had happened the last two times he had gotten curious. Assuming that something similar definitely couldn't happen a third time, he trotted up to the entrance of the boutique and took a look around. What he saw only made more questions come to mind.

The first thing he noticed was that there was a small sign in the window that simply said stallions enter here. Though the word ‘Closed’ was displayed right next to it, Jest could see light spilling out from under the entrance. It was intriguing, and after looking around and finding that no one else was present, he opened the door.

A hoof pulled him inside and before Jest had a chance to open his mouth he found himself thrust into the boutique.

“That's six. Lock the door and turn over the sign,” whispered a voice.

“Err I think there might-” Jest tried to interrupt.

A gloved hoof pressed against his mouth.

“Shh, keep it to yourself and follow me,” demanded the voice.

Jest blinked several times, letting his eyes adjust to the gloom. The moment they did so he noticed that he was being led towards the back of the boutique by a masked pony. A mare judging from her overall shape and voice, she wore a sleek body suit that hid all notable features save for her curves, which were many.

After a moment of confusion, Jest found himself standing in a small audience of seemingly random stallions. There was Jeff something, the mustachioed bowler with a fetish for rugs. Perfect Pace, or as the guys called him, Perfect Piece. (On account of his imperfect hair peice). That Hooves guy who claimed to be a doctor though had never explained what he had studied. Big Macintosh, of course. And Jack Hammer, the only pegasus Jest knew who could jackhammer a cloud somehow.

Before them lay a stage, one that although lit was currently empty. That would change soon, as the same body-suited and white masked mare that Jest had met a minute earlier reappeared. Walking right up to the edge of the stage, she gazed down at the small group of stallions with an intense look that left Jest uneasy.

“Good. I see you all received your invitations and now you are here for the main event,” declared the mare. “Well worry not my good stallions. The show is about to begin.”

Jest stood there, too confused to say anything.

His fellow stallions all seemed excited though, shifting from hoof to hoof and occasionally snorting in excitement.

Glancing their way, Jest was immediately able to tell that they were getting rather aroused by the entire thing. Which didn't much make sense to him, but to each their own, Jest thought to himself.

“Introducing your partners for this evening… the elements of harmony,” greeted the masked mare.

The presenter’s slim hoof gestured to the back of the stage. The curtains parted, and several ponies stepped forth, strutting onto the stage with various levels of confidence. Rarity owned the runway, while Fluttershy meekly stumbled her way forward at the back of the group.

“You have already received an explanation on how this all works so I will not waste your time,” the presenter continued. “Merely come forward when your name has been called, and go with your mare. Twilight, take it away.”

The grinning alicorn stepped forward and pointed a hoof right at the burly pegasus in their midst.

“Jack Hammer. I choose you,” Twilight proclaimed.

“Aww come on you know I wanted him,” complained Rainbow Dash.

“I got first dibs so he's mine,” Twilight retorted. “Now come along Jack. We have a long night ahead of us.”

“Yes ma’am!” Jack Hammer exclaimed.

Jest watched as Twilight stepped off the stage, and joined Jack Hammer at a small side exit he hadn't noticed. The pair exchanged flirtatious looks before vanishing out of sight, slipping through the previously unseen door.

“Pinkie, you’re next,” offered the presenter.

“Moustache, you're with me,” Pinkie Pie proclaimed, pointing at the bowler.

“I prefer to be called, the dude,” Jeff retorted.

“And I prefer sprinkles with my coffee, now let's get moving. Mama’s got an early shift tomorrow,” Pinkie Pie proclaimed.

‘The dude’, shrugged and went the same way Jack Hammer had a moment earlier. Unlike the previous two, this time there was no attempt at flirting, only Pinkie Pie taking the lead while her partner followed.

“Rarity,” offered the presenter.

The fashionista stepped forward and glanced out over the crowd before settling on the large red stallion standing at the end.

“Big Macintosh. I choose you,” she declared.

“Score,” Big Mac muttered under his breath.

Once again the pair departed through the side door, the pair bumping hips and exchanging heated glances the entire time.

“Alright the choosing is half over and next we have Rainbow Dash,” the presenter declared.

“Perfect. I choose you,” Rainbow Dash declared with a smirk. “I wanna see how perfect you are after a three-hour ride.”

“I well… oh my,” Perfect Pace Murmured.

Jest observed the pair depart, Perfect Pace in front, his partner behind, smacking him across the flanks whenever he started to slow.

“Final two,” the presenter continued. “Fluttershy, you’re up next.”

“Oh um… I would like mister the doctor,” Fluttershy exclaimed.

“Actually it's just ‘The Doctor’, its a third-person gender-neutral pronoun,” Hooves replied.

“Oh…” Fluttershy leaned towards the presenter. “Is it too late to take back my choice?”

“I’m afraid so. Best have what fun you can darling,” offered the presenter.

Fluttershy scowled and slumped awkwardly toward the exit.

“Come on then,” she muttered bitterly. “Let's see if we can't salvage this.”

“Was it something I said?” Hooves whispered as he passed Jest by.

“And last but not least we have Applejack who has chosen through process of elimination…” The presenter declared only to pause and lean forward. “What exactly is your name again?”

“Jest. Like jester, but without the er,” Jest replied.

“Ahh yes Jest. The reclusive fellow. I remember you from when you ruined yoga class,” the presenter replied.

Jest winced.

“Whelp, you weren't the one I invited. Rainbow probably yoinked you as some sort of joke but the joke’s on her. I like twiggy little buggers like you,” Applejack declared.

“Uhh… thanks?” Jest muttered.

“You’re welcome, now get moving, youngun,” Applejack barked. “I had a long day of apple bucking and now I need someone to buck me.”

“Sure. I can do that,” Jest exclaimed.

The stallion couldn't help but grin. Sure this whole situation was weird as fuck, but he now had the chance to fuck one of the elements of harmony. This was almost as good as that time he hallucinated having sex with Zecora, though hopefully this time it would end without him waking up to find himself hooked up to a catheter.

Jest shuddered at the thought.

“Now y'all are gonna have to do most of the work here,” Applejack announced, stopping at the back entrance. “I’m right tuckered. That and I don't mind when some young buck takes the reins.”

“Young? Aren't you like, two years older than me?” Jest asked, scratching his cheek.

“Which makes me older than you. Try to keep up,” Applejack retorted.

Jest shrugged and followed after the mare as she entered the back room. Passing over the threshold, Jest felt a faint tingle like someone had cast magic on him. Looking around he found himself in the hallway of a local motel, one far from the small out-of-the-way boutique.

“Try to keep up,” Applejack barked.

Jest hastily trotted after his partner, his gaze falling to her generous backside only to be surprised when he realized Applejack wasn't much taller than he was. Being slightly effeminate and not exactly the largest stallion in town, Jest had gotten used to most ponies standing at least a little taller than him.

Brushing that thought aside he indulged in the knowledge that he was about to fuck a very attractive and very famous pony. He wasn't going to be the one getting fucked, he was going to be on top, there was no weird smoke and mirrors, this was great. Suddenly the weirdness of it all wasn't a big deal, or at least it wasn't in comparison to how great Jest’s night was becoming.

With a skip in his step, he followed Applejack into the small motel room and paused. Predictably it was small but not cramped, with a tiny bathroom to the right while straight ahead lay the bedroom. There, waiting for them was a king-sized bed and a small silver platter that sat on the end table.

Jest walked over to the curtains and after checking that they were fully closed, turned back to his partner.

“Enjoy your night, signed the organization,” Applejack read aloud, only to crumple the letter up and chuck it in the trash. “The organization, bah. Talk about being full of yourself.”

“So uh, how do you wanna do this?” Jest asked his forehooves already on the edge of the bed.

Applejack didn't answer, at least not with words as she just clambered onto the pillowtop, walked over to the headboard, and fell over. She then rolled onto her back, spread her back legs, and opened her forehooves.

“Does that answer yer question?” Applejack inquired.

Jest raised an eyebrow and watched as the mare allowed her tail to fall, giving him full view of everything. From her plump, supple teets, to her glistening folds, supple curves, and confident as well as enticing grin, it was all perfect. The stallion couldn't help but lick his lips at the sight, his cock extending from its sheathe and emerging into the cool air.

“Ooh ya ain't got a bad package on you either,” Applejack remarked. “Just the right thickness, with a bit of a bend and some nice veins. Could be a bit longer though.”

“Uh, thanks?” Jest muttered, slightly defeated.

“You’re welcome now come on over here and fuck me,” Applejack demanded, giving her cunt a light smack in emphasis.

That was enough to jump-start Jest’s ailing lust and cause him to stumble forward. Falling to the bed in an awkward half crawl, he hastily shuffled into position but stopped just shy of penetration.

“Say are you sure we shouldn't get to know one another a bit first? I mean I enjoy the whole thing going on here too but do you even remember my name?” Jest inquired.

Applejack scoffed.

“It was Best something or other,” Applejack retorted. “It hardly matters.”

“I mean, I guess. I just feel like we should at least talk about what we like and dislike,” Jest prompted.

“I like it when stallions put their thingy in my hohah and I hate it when they spend all day jawing when they could be fuckin,” Applejack retorted.

Jest opened his mouth to respond only to think better of it.

“You know what. I can work with that,” Jest remarked.

“Good, now get to it!” Applejack barked.

Jest did as was ordered, shifting his hips and moving his hooves until he had aligned his fully erect cock with Applejack’s pussy. Without hesitation, he thrust forward, burying his length in the mare’s hole with surprisingly little effort. Now hilting the mare, Jest felt as though she was slightly looser than what the stallion had imagined. That thought vanished the moment he felt Applejack clamp down around his length, squeezing it like a vice. Not only did her internal muscles constrict, but she also wrapped her back hooves around Jest’s back.

“Good, now really give it to me partner,” Applejack ordered.

“Yes ma’am,” Jest replied.

The male began to thrust, slowly at first but picking up more and more speed with time. His partner seemed only half engaged, her critical eye always judging the stallion’s movements. By the time he had picked up to his full speed she at least looked at him with a bit of warmth though so that was an improvement.

Though Jest still felt like his partner was still watching him a bit too closely, the naked disdain in her gaze was gone. That alone was enough to let the stallion finally begin to really relax and enjoy the pleasant sensations. The wet, cloying confines of the mare’s pussy, her soft fur, and the surprisingly well-muscled body that lay just beneath.

She smelled like apples, as well as flowers, and freshly baked bread. It was a pleasant aroma, and it made the young entertainer feel oddly at home. Even the iron-like grip she held on his torso was nice, even if Jest didn't particularly enjoy being restrained in such a manner.

“Mmm better. Keep it going,” Applejack purred.

Rocking his hips back and forth, Jest drew his hips back, only to thrust forward, making sure to angle himself downward slightly. His technique wasn't perfect, but Applejack seemed to enjoy it, and the way his dick occasionally brushed against her prominent clit. The ridged head of his cock nearly pulled all the way out before slamming home once more, their bodies flush.

With his pleasure rising, Jest did his best to hold back, biting his lip and thinking unsexy thoughts. Yet the iron-hard grip around his midsection, the tight confines of Applejack’s pussy, and the touch of her hoof against his chest made it difficult. She was a hard mare to ignore but despite this, he was able to fight off the first wave that threatened to bring him to an early orgasm.

Slowing down slightly, he took several deep breaths before moving once more but only after it passed fully. Applejack grinned up at him, the smirk containing a teasing edge to it that was hard to ignore. Jest just snorted and decided then and there that he would wipe such an expression from her face with his raw endurance.

With his lip held between his teeth, he flexed what little muscle he had and really laid into the mare. Driving his hips down and forward, he did everything he could to impress her, hoping that if nothing else his enthusiasm would carry him through. Though clearly enjoying herself, Applejack seemed unimpressed, even when he turned up the speed as high as he could muster.

Minutes ticked by, and Jest’s limbs began to ache, his muscles started to burn and what little strength he had was waning quickly. The wet meaty slaps of his thrusts were punctuated occasionally by a slight grunt or stifled moan from his partner. Those small noises were the only real indicator that she was enjoying herself, other than the occasional tremor that ran up her spine.

“So,” Jest began, speaking between thrusts. “Should I finish inside, or what?”

Applejack shrugged.

“Might as well, it's not like you can knock me up anyhow,” retorted the mare.

Must have taken some cautionary measures beforehand. Jest thought to himself. Either way its my lucky day.

“Alright then, but don't say I didn't warn you,” Jest proclaimed.

“Ha, try me,” Applejack shot back.

Jest smirked and poured on everything he had left to give. His hooves tensed, his nostrils flared, and with each impact he grunted due to the sheer effort. Dumping on the effort, he dismissed any attempt to hold back and freely embraced his orgasm.

“Here it comes,” he muttered.

“Come on twiggy. Gimme all you got,” Applejack encouraged.

“Don't, call, me, Twiggy!” Jest exclaimed, punctuating the final word with one last thrust.

The moment their hips met, he came and came hard, shooting what felt like the full contents of his balls into her. Despite this he continued to thrust, still hoping to impress the mare, and hopefully make her finish as well. He kept doing this until at long last he had finished, and with his cock softening he pulled out, rolled onto his side, and released a long sigh.

“Hope, you, enjoyed that. At least a little,” Jest muttered between labored breaths.

“You ain't half bad. Sure you ain't even in the top five of best lays, but you’re cute. I like you,” Applejack remarked.

“Talk about being damned, with faint praise,” Jest muttered, chuckling to himself.

“I just got a lot of experience. Honestly, you should feel proud of yourself. Your performance was above average and by a fair margin,” Applejack added.

Jest sighed.

“Alright, well just give me a minute here and I should be ready to roll again,” Jest offered.

“Take your time,” Applejack replied.

The apple farmer leaned over and produced a pack of cigarettes from the end table, as well as a lighter.

“Want one?” she offered.

“Nah. Never understood the whole smoking after sex thing,” Jest replied, waving a hoof. “You constrict the lungs, and it makes the subsequent rounds harder as well as less fun.”

“That right?” Applejack asked curiously.

“I read a study about it,” Jest replied. “Not sure how someone convinced the crown to pay for such a thing to get studied in the first place but it's legit.”

“Huh,” Applejack murmured. “I suppose that makes sense.”

The pair lay there for a moment longer before suddenly a knock could be heard from the door. Before either of them could respond, the presenter barged her way inside holding a bright orange potion.

“Apologies for the intrusion as well as the lateness of my arrival,” she greeted, unbothered by Applejack’s cum drooling cunt or Jest’s wet cock. “Oh done already?”

“No!” Jest retorted. “We were just about to go again.”

“Ahh good. Then this will come in handy,” the masked mare offered, swirling the potion.

“Is that what I think it is?” Applejack asked.

“It's the endurance potion you requested. Sorry, it took a bit longer. Room two requested a truly inspired bevy of unique cocktails,” the presenter muttered, awe-tinging her voice.

“Hot dog!” Applejack exclaimed.

The mare got up, trotted over to the edge of the bed, and swiped the offered potion. She then downed nearly the entire thing in one go, gulping down its content and belching loudly.

“That hit the spot,” Applejack murmured.

“Ahh can I make a request too or, what?” Jest inquired.

“I’m afraid it's mare’s choice tonight,” the presenter replied.

“Just sit still Twiggy, I got you covered,” Applejack declared.

Jest raised an eyebrow and watched as Applejack trotted over to him. She then lowered the bottle, and dumped the last of its contents directly on his cock, coating it completely. The liquid had the consistency of curdled milk and felt not unlike a topical ointment used to treat stiff muscles.

“Oooh wow that's… nice,” Jest murmured.

His semi-flaccid erection all but jumped to attention, the rudeness of it nearly making his head spin.

“I see you two are ready. Just remember that you have three hours until the bell so make sure to finish up before then,” the presenter replied.

“Yeah yeah, I know the routine,” Applejack dismissed.

“Then I will see you tomorrow darling,” the masked mare replied before tucking out of the room and closing the door behind her.

“Right. Best buckle up bucko cus this cowpony is going for a ride,” Applejack proclaimed.

With a swiftness Jest had never seen, Applejack straddled him, impaled herself on his cock, and began to move. Up and then down she went, the dull thump of her impact making the bed creek and Jest’s hips ache. A firm hoof on his chest told him who was in charge, and the grin on Applejack’s face said that it was going to be a long time before she was done.

Despite everything, Jest grinned, excited over the prospect of watching such an attractive mare ride him.

That excitement would not last for long.

“Ow, ow, ow, ow,” Jest muttered to himself.

“Oh quit yer whining you loved it,” Applejack retorted, pausing to puff on her cigarette. “Why else would you have filled me to the point of bursting.”

Jest glanced over to the visible cum bulge in Applejack’s midsection, as well as the trickle of white that dribbled from her gaping pussy. It was an enjoyable sight and usually would have made him hard, now however, his cock barely even twitched.

“I mean yeah but I can't even feel my dick anymore,” Jest replied. “Or my back legs for that matter.”

“Yer fine,” Applejack retorted, rolling the smoke to the corner of her mouth. “Right, now you ready for round… whatever this is?”

“I believe it's thirty-nine,” Jest offered.

“Yeah, you ready for round thirty-nine, Twiggy?” Applejack remarked.

“I need rest,” Jest tiredly shot back. “The spirit is willing but the flesh is spongy and bruised.”

“Aww come on don't tell me you’re giving up already,” Applejack prodded.

“Can't we just cuddle?” Jest asked.

“No. Now you better get hard or else I’ll have to break out the big guns,” Applejack began, only to pause and perk up. “Wait a second. How long has it been?”

“About three hours I’d say. Or a lifetime. Not sure to be honest,” Jest replied.

“Ahh shoot. I best get moseying,” Applejack murmured.

The mare then awkwardly clambered down off the bed, wincing when her hooves hit the ground.

“Damn potion wore off,” she muttered to herself. “Knew I should demanded two of the things.”

“I’d offer you a hoof. If I had one to give,” Jest exclaimed.

“Nah you just sit right there. I’ll be outta your mane in a second,” Applejack retorted.

“Are you sure? You look like you’re having real trouble,” Jest pointed out.

“It's fine, I’ll-” Applejack continued, only to be cut off by the sound of a distant bell. “Dammit.”

As the sound washed over them, Applejack’s form rippled and vanished. The young farm mare was replaced by a farm mare still, though one far older.

“Granny Smith?” Jest muttered in confusion.

“Stars above,” Granny Smith cursed. “I knew I should stopped at round thirty-six.”

“Huh,” Jest murmured.

“You don't look too surprised,” Granny Smith retorted.

“Nope. I’m just glad you weren't a changeling harvesting my love or some awful hallucination,” Jest replied.

Granny Smith stopped and blinked.

“This kinda thing happens to you a lot?” Asked the older mare.

“More than I care to admit. Applejack turning out to be Granny Smith barely even registers on my surprise-o-meter,” Jest exclaimed.

“Huh,” Granny Smith murmured.

“Yup. Thanks for the nice time by the way. I had fun,” Jest offered.

“Err yeah. Me too,” Granny Smith murmured.

The mare trundled awkwardly toward the door before stopping.

“Say, you wouldn't happen to-” Granny Smith began.

“Not on your life old timer,” Jest interrupted. “You’ve drained me drier than the Sahara.”

“Damn,” Granny Smith cursed. “Well, see ya round.”

“Yeah,” Jest replied with a wave. “You too.”

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