“Say what now?”

Flam grinned at Applejack and ruffled his mustache. “Well, it’s like I said, Miss Applejack: one of the most important things to have in the con business is confidence and, seeing as we have an hour before our tour with Gladmane, my brother and I figured the four of us could do something to boost all of our confidence!”

Applejack’s eyebrow arched as Fluttershy slunk back into her mane. “And just how do you plan on going about that?”

Flim and Flam smiled at each other. “Well, The Sensual Sibling Synchronization, of course!”

Fluttershy rubbed her leg with a hoof. “The Sensual Sibling Synchronization? What’s that?”

Flam took a step forward, an ear-splitting grin on his lips. “Well, I’m glad you asked, Miss Fluttershy! See, whenever we’re about to go about peddling our wares-”

Applejack coughed, though all the ponies in the room heard the blatant “con” she had slipped into it.

Flam frowned at the mare before continuing. “Whenever we go to con somepony, we always have a ritual we go do beforehoof. Both my brother and I head out into town and… procure a couple ponies of the opposite sex for a little… fun.”

“Wait…” Applejack took a step back and shook her head, a clear scowl on her lips. “Hay no, you did not just suggest that we… bump uglies!”

Flam shrugged his shoulders. “Applejack Applejack… What better way is there to build one’s confidence than a little sensual roughhousing?”

Applejack growled. “If you even think about doing something like that with me of Flutters, I’ll be sure ta buck your junk into next week!”

“Um…” Fluttershy lifted a hoof like a foal in class. “What are we talking about?”

“Come on, Miss Applejack…” Flim walked up beside the mare and wrapped a hoof around her shoulder, one that was instantly shaken off as she took another step back. “What stays in Las Pegasus stays in Las Pegasus, right? With everything you do back at Sweet Apple Acres, I’m sure you haven't had much time for fun, right?”

Applejack sighed. He had a point there. “I suppose…”

“Um… Hello?” Fluttershy spoke up a bit louder, though it only amounted to a normal pony’s whisper. “What are we talking about?”

Flam came up around the opposite side of Applejack, boxing the mare in between the two brothers. “So, what do you say? What’s a little fun between four friends, huh?”

“Well, we ain’t exactly friends, but…” Applejack sighed and took off her hat. “Alright, fine… Ah’ll do it.”

Tossing her stetson onto the bed and turning around, the country mare hiked her tail up and over her back to expose the brown, meaty, and somewhat damp lips of her marehood to the two con-ponies. Both Flim and Flam felt their sheaths tighten as they drank in the sight, and after sharing a nod with his brother Flam stepped forward with a smirk on his lips. “Well well well! Good to hear you’ve come around, Miss Applejack! I have to say, you certainly have a nice looking-”

“Now hold up just a second there, cowpony!”

Flam froze a hoofstep away from his target as Applejack leveled the kind of stare that could kill a stallion at him over her shoulder. “Y-yes?”

Applejack frowned. “Lemme put a couple ground rules down ‘fore ya just jump on and get to ridin’ this pony.” She reached back and grabbed onto one of the cheeks of her ass, pulling it away to pry apart her dark brown lips and show off the bright pink flesh between them. “Y'all can look, y'all can touch, but y'all definitely aren’t gonna be puttin’ no foals in me, ya hear?”

Flam licked his lips, both as a nervous reaction from the power in the mare’s stare and how plump her pussy looked up close. “Alright, sounds like a deal, Miss Applejack.” His confidence soon returned and, with a smirk on his lips, he took another step forward towards the mare with his fully-erect cock swaying between his legs. “I’ll be sure to pull out before then… We’ll just leave it to the maids to clean up afterward! That is what they’re paid for, after all!”

The apple-mare’s frown deepened as the stallion chuckled. “Now, I don’t want you makin’ extra work for anypony else, neither. So…” Her hoof moved up, and with another pull against her ass she showed off a second, tighter looking hole just underneath her tail. “Y'all gonna do it here. Now, you might as well have ya brother go get you some lube, cause this is gonna be tight!”

“Well…” Flam smiled and, horn lighting up as he reached out towards an end table next to the bed with his magic, pulled out a small, Flim-Flam labeled bottle into the air. “Whaddaya know? Looks like I got some Flim-Flam Personal Lubricant™ right over here! Gentle, safe, and recommended by several Equestrian gynecologists we found on the street, this water-based lubricant can make any night of passion, even one as hastily thrown together as this, into something that you’ll never forget!”

“Wow…”, whispered Fluttershy from behind the curtain of her mane, “That sounds… interesting…”

Flam shot a grin Flim’s way as he turned towards the pegasus. “Why yes indeed, my fine feathered friend! Flim-Flam Personal Lubricant™ is the most interesting lube on the market! Why, just the other day, I put some on and-”

A tied, yellow tail suddenly slapped him across the face. “CAN YOU GET ON WITH IT!”

Flam rubbed his cheek and got back to the matter at hand. “Ah yes, sorry. Never could resist a good product pitch. Now, let me just...” Sitting back and popping the top of the bottle off, the stallion flipped the small container over and squeezed a healthy dollop of lube onto his cock. A quick series of pumps later and the brown shaft was glistening in the light of the room, ready to penetrate even the tightest of passages in a moment’s notice.

Flam stood and stepped forward, his tone chest pressing into the plush cheeks of Applejack’s ass. “There! All ready for ya, Miss Applejack!”

Applejack scoffed and rolled her eyes. “Uh huh… And tell me, just WHY did ya have a bottle of lube at the ready?” She sniffed the air. “And why does it smell like apples?”

Flam smiled. “Well, Miss Applejack, I just so happen to like the smell of apples.” He leaned in towards her hind end and took a deep breath, sending shivers up her spine as warm air washed over the plump lips of her pussy as he exhaled. “As for why I had some lube, well… If there’s one thing you need to know about being successful in the con business, it's that you have to be prepared for anything…”

Applejack frowned but, otherwise, turned to look ahead as Flam reared up onto her back, the lanky stallion’s weight nothing compared to the rigorous work back on the farm. “Yeah, and ah’m sure that applies to havin’ some butt-fuckin’ oil at the ready too, huh?” She gave out a single, sharp laugh and shook her head as he started poking around her backside in search of his target. “I swear, you two are some of the-”

And then Flam found his mark.

Applejack’s eyes widened and the breath was driven from her lungs as she found herself with over a foot of pony-cock crammed up her ass. The puckered ring of her anus was no match for the wide, blunted tip of Flam’s ramming-rod, and as soon as the gates to her passage were open the stallion jammed the rest of his cock inside with one smooth, strong thrust. The lewdest sound imaginable reached her ears as she felt the soft fur around his crotch kiss the mounds of her ass, a sensual mixture of his lubed shaft sliding past the rim of her anus and the meaty thwack of his heavy balls slapping into her clit like a pair of wrecking balls as he bottomed out.

Sighing in bliss as his cock was enveloped in velveteen warmth, Flam leaned down and started rubbing the apples on Applejack’s side to give her time to adjust to the sudden penetration. “Ahh… That’s the stuff...” He chuckled and gave her a light smack on the ass. “Now, if only we could find a way to bottle and sell this feeling. We’d make a fortune!”

Flim laughed. “Ha! I’m sorry to say, brother, but I believe they call that prostitution!”

“Mmm… True...” Flam took a deep breath. “Guess I’ll have to keep this treasure all to myself…”

Laying his stomach on the mare’s strong back, Flam started to lightly rock his hips back and forth to gradually work his cock from her tight passage. Applejack had been unable to regain her breath from the initial penetration and, as such, could do nothing but stare at the opposite wall in a shocked silence as inch after inch of stallion meat was pulled from her body.

“Oh wow…” Flam shivered as the cooler air in the room brushed past the lubed-up flesh of his cock. “You certainly are a tight one, Miss Applejack…”

Applejack opened her mouth to respond, but all that could come out was a surprised squeak as Flam reversed direction and slammed himself back to the hilt inside her ass. The sudden smack of his heavy testicles against her defenseless clit sent a lightning bolt of pleasure up her spine, and by the time the stallion had pulled back to thrust forward again she could already feel a droplet of liquid excitement rolling down the inside of her thigh.

Flim gasped as he bottomed out inside Applejack for the third time, the mare’s passage now loosened enough that it felt molded to the shape of his cock. He smirked as his balls tapped the base of her marehood and her clit reached out to lay a loving kiss upon them, and as he pulled his hips back he could feel her juices running down the curve of his sack.

“Heh heh… I see you enjoy a little backdooring, eh, Applejack?” He smacked her cutie mark for a second time, this time much harder than before. “Like it a little rough? Perhaps my brother and I should come to Ponyville more often and pay you a visit!”

Applejack moaned as, right at the end of his statement, Flam made a quick, Equestria-shattering thrust that punched his cock deeper into her rectum than ever before. “Y-You… you-” Another thrust, this one faster than the last, and before her body even had the chance to register it he had done another one. And then he did it again, and again, and again, leaving her a drooling mess from both ends against the bed.

Flam, meanwhile, was having a hard time keeping himself upright as his legs began to shake. The feeling of Applejack’s thick ponut moving up and down his shaft like a plump pair of lips was like nothing he had ever experienced before! In fact, as he bottomed out for the only-Celestia-knows time, his legs buckled underneath him and sent him crashing stomach-first into the mare’s back.

Flam landed on Applejack with a soft “oof!”, cock sheathed inside her ass and muzzle pressed up against her flowing, golden mane. He paused his thrusts to catch his breath, sending a shiver up his spine as he got a whiff of apples from the mare’s mane. “Mmm… You smell absolutely delectable, Miss Applejack…”

Applejack blushed as the stallion startled nuzzling her mane, the short hairs of his mustache tickling the back of her neck. Whatever small amounts of pain she had felt at the beginning were now all but forgotten, replaced with an oh so pleasant sensation of being full. “Tch… D-don’t… Don’t get all mushy on me now that ya got ya dick warm…” She pushed her ass back into his lap, grinding her marehood against his balls. “Let’s finish up with this here rodeo and get on with the plan!”

Flam chuckled. “My my, Applejack… Do be honest with yourself!” The stallion pushed right back against her ass, mashing his cock around inside her warm passage to both ponies’ enjoyment. “I’d say you’re enjoying this little ‘rodeo’...”

Applejack did her best to wave him off, but with her clit punching out against his sack like a world-champion boxer training for his next match she couldn’t deny that it felt really good. “I… I...” She grit her teeth and growled. “Just get on with it already!”

Reaching down and lovingly patting the apples on her side, Flam leaned down to put his lips right next to her ear and whispered, “Your wish is my command…”

Fluttershy, meanwhile, had been watching the proceedings through the pink curtain of her mane. Sitting on the floor behind the pair of rutting ponies gave her a perfect line of sight to her friend’s pouting pussy lips and the stallion-on-her-back’s hefty balls, and the sight of Applejack’s juices dripping off the base of those cum-laden orbs was beginning to stir up something between her legs. Something that only became stronger as her friend began to moan Flam’s name to the ceiling as they started rocking against one another, both ponies on a one-way track to climax town.

“So, Fluttershy, is it?” Fluttershy jumped as Flim suddenly appeared beside her and wrapped a hoof around her shoulders. “Seems to me you could use a bit of a confidence booster yourself! Whaddaya say?”

Fluttershy glanced out from the shield of her mane and blushed as her eyes were immediately drawn to the turgid shaft between the stallion’s legs. “Um… Sorry, but I… Uh…”

Flim chuckled and stood. “Nonsense, I insist! Come...” He extended a hoof to help her up. “They don’t call me the Silver Tongue for nothing! I’ll be sure to make it extra pleasant for a mare as good looking as yourself!”

Blush deepening as she felt her marehood wink against the floor, Fluttershy took the offered hoof and joined Flim in walking towards the second bed. “O-okay, but, um... “ She glanced towards the other pair of ponies and gasped as, now that she was viewing them from the side, she could plainly make out the stretched out ring of flesh that was her friend’s ponut and the thick rod of stallion cock that was doing the stretching. “O-oh my…”

Flim jumped up onto the bed without hesitation, something that could not be said of Fluttershy as she meekly climbed up with her tail tucked between her legs. “Now then…” The stallion turned to face her and nodded towards the head of the bed. “How about you get yourself nice and comfortable up there and I’ll make sure everything goes swimmingly down here…”

Fluttershy nodded, though one would have had to have been looking for it to notice it with how little movement there was behind it. “O-okay…”

Doing as Flim had asked, Fluttershy walked across the cushiony mattress towards the head of the bed and, making sure to keep her thighs together and tail tucked between her legs, flipped over onto her back with her head back against the pillow. “Th-there… Now wh-what?”

Flim chuckled and crawled up towards the mare. “Well, we can’t have much fun if you don’t spread these a bit…”

Fluttershy’s face turned pink as Flim reached out and pulled her legs apart, and with a flick of his magic he dragged her tail to the side to expose the even pinker lips of her plump marehood. “O-oh my…”

Flim licked his lips at the delectable spread before him. “My my, you’ve been holding out on me, Miss Fluttershy…” He leaned in till the tip of his muzzle was less than an inch away from her leaking mons. “Who knew you had such a delicious looking treat hidden beneath your tail?” He looked down and smiled as he saw her clit punch out into the air. “I’m sure you won’t mind me taking a taste, will you?”

Fluttershy could only muster a meek “eep!”, far too embarrassed to speak. So, taking that as the best he was going to get, Flim gave her a sly wink before every so gently placing his lips against her marehood. Then, after holding there with his eyes on hers for a moment, he slowly opened his lips and let his tongue pierce into her succulent folds.

Applejack jumped as Fluttershy suddenly let loose the loudest moan anypony in the room had ever heard, and even as her body rocked back and forth underneath Flam she glanced over to see Flim digging in between her friend’s legs. “F-Flutters? You- ah!” Her teeth grit as Flam slammed his hips into her ass, sending a shockwave of pleasure up her body. “You okay?”

Fluttershy could only moan. Pushing her head back as hard as she could against the pillow and pushing her hips against Flim’s face, the pegasus arched her back into the air as the stallion’s tongue continued to dip into her honey pot like a dog at a water bowl.

“Oooohhh!” Fluttershy shivered as Flim ground his nose against her clit. “Woooow…”

“Heh…” Flim pulled back with a parting kiss to her marehood, lips glistening in the light. “So, feeling up for that confidence booster now?”

Fluttershy bit her bottom lip and nodded. If having his tongue down there was THAT good, then who knows how amazing it would feel with something bigger, and harder?

“Good…” Picking himself up, Flim took a step forward and lined his cock up with the gates to Fluttershy’s marehood. But then he unexpectedly took another step forward, and then another, and soon Fluttershy had to duck her head out of the way as his stallionhood swung like a club towards her face.

“Eep!” Fluttershy’s eyes widened as she got a close look at Flim’s cock. “What…”

“Shh…” Flim glanced down at her and smiled. “You don’t want me doing all the work, do you?”

Fluttershy shook her head, though her eyes never left the blunted tip of Flim’s cock as it swayed in the air just off the tip of her nose.

Flim nodded. “Good. Now, open wide…”

Fluttershy did as she was told, and as soon as she had opened her lips wide enough Flim lowered his hips towards her face. Fluttershy’s panic level increased as the distance between them decreased, the lights hanging overhead gradually blacking out as his low-hanging balls drooped towards her forehead. And then, when she felt something warm and hard press against her lips, her fears built to their crescendo.

There was no way she was going to fit something so large in her-

Flim slipped the head of his shaft past Fluttershy’s lips with relative ease, and with a long, drawn-out sigh he continued lowering his hips until he felt his balls drape over the mare’s eyes. Fluttershy let out as much of a startled yelp as she could with a thick piece of stallion meat in her mouth, but as soon as she realized that she had said piece of stallion meat in her mouth without any of the pain she had expected she did her best to quell her unfounded fears.

Flim sighed. “Ah… There we go… Nothing better than a mare’s mouth wrapped around your stallionhood before a good con, ey brother?”

Flam half-chuckled, half-gasped from his side of the room. “Heh, I hate to disagree with you, brother of mine, but a mouth is nothing compared to a rough bout of anal. Isn’t that right, Applejack?”

Applejack, head laid flat against the bed with her tongue lolling out of her mouth, moaned in response.

Flim smirked. “Ah, but can you do this laying on a mare’s back?”

A muffled shriek was the only response from Fluttershy as Flim sudden shoved his head back between her legs, putting the two of them in the infamous sixty-nine position as they sampled the other’s loins. Fluttershy did her best to keep up the Flim’s impeccable tongue-work, but within a matter of moments he had broken her down enough that she could only hang on for the ride.

Flim, however, wasn’t done with her yet. Lifting his hips into the air to draw his now spit-slickened shaft from her gullet, the stallion abruptly shoved himself back down onto her face. His heavy nuts slapped the mare in the forehead, resulting in a loud smacking sound that tore a groan from his lungs.

Before Fluttershy had a chance to recover he performed the maneuver again, and before the pegasus realized that she was being face-fucked his hips had already become a blur. The room filled with the lustful tune of four ponies rutting each other’s brains out, two on each bed in the room. Both mares had become vessels for the brothers’ pleasure, left with nothing to do but take their cocks where the stallions saw fit.

Flim would be the first to reach his crescendo, and without ever warning the mare underneath him he buried himself to the hilt inside her mouth and fired the opening salvo of seed straight into her stomach. Fluttershy’s eyes widened as she felt his cock flex inside her throat and, whether it was due to the strange mix of terror and excitement she felt or just the fact that Flim had latched onto her clit in a final effort to send her over the edge, she found herself joining him in climax, too.

The sudden, muffled shriek from her friend was enough to pull Applejack’s head off the bed as she looked in the pegasus’s direction, and as she saw Fluttershy, the shyest of all her friends, eagerly gulping down blast after blast of stallion cum as she gushed all over Flim’s face she, too, was thrown off the edge. Clenching down on Flam’s cock as he continued to saw it back and forth beneath her tail, Applejack painted the brown, leathery canvas of his balls with slick jets of marecum, forming a large wet spot beneath them that only grew as Flam’s thrusts continued.

Applejack moaned. “FuuUUuuuck!” Gritting her teeth, she picked herself up and began meeting Flam’s thrusts halfway to prolong her seemingly never-ending climax. “Oh! Oh! Ohhhhhh!”

Flam began grunting with each of his thrusts, the physical requirements of rutting for such a long period of time finally taking its toll. With one last, loud bellow towards the ceiling, he became the last of the four to reach their peak. Wave after wave of warm stallion cream flooded Applejack’s battered rectum, enough that, as Flam thrust straight through his orgasm, thick strands of the stuff were pulled out of her ass and dripped down to her pussy. As soon as he had dumped his final drop, Flam pulled his hips back and tugged his cum-slickened shaft from the mare's rear, resulting in a lewd sounding slurp and a healthy dollop of semen splashing onto the floor beneath her.

And with that, the four ponies collapsed, all exhausted from their intense round of rutting.

Flim smiled and, after wiping away some leftover mare-cum from his cheek, closed his eyes and settled in next to Fluttershy. “You know what another important part of conning is?”

Applejack sighed, the aftershocks of her orgasm still crashing into her system as warm stallion cream continued to leak from her well-fucked ass. “What’s that?”

Flam smiled and nuzzled up against her mane. “A good nap beforehoof…”

So, that’s exactly what the four ponies did.

Author's Notes:

Yadda yadda yadda, double shift at work, yadda yadda yadda, ran out of time. But hey, there's clop!

As I did last week, I started with the clop and had to rush the beginning/end. But, hopefully, I can wrangle one of these stories down and get one fully complete before the season's over!