Jack/Off

by One Terrible Writer

Rating: mature
Tags: Romance, Comedy
Length: 4700

Applejack turns tricks in Dodge Junction. What will she do when Rainbow Dash is her customer?

After her failure in the Equestrian Rodeo Competition, Applejack finds herself working in Cherry Jubilee's House Of Ill Repute to make enough money to send back to Ponyville. However it all goes horribly wrong when she finds that her next customer is… Rainbow Dash!

Published 1970-01-01 00:00:00 UTC
Last updated 2012-02-15 04:54:01 UTC

Chapter 1

Money. That is what it always came down to. Money.

The quiet rural atmosphere of Dodge Junction was a world away from the terrifying hustle and bustle of Canterlot. The events of the Equestrian Rodeo Competition still sent pangs of shame through Applejack’s heart. Every time she closed her eyes she could see a pony laughing at her, another looking at her in pity or disgust for her failure. She had let herself down, and without any of the promised prize money, she had let Ponyville down. At least in this obscure western town, nopony would ever know of her failure. And perhaps she could make good on her word.

Nopony would know, that is, except for Cherry Jubilee. She had met the charismatic, classy pony at the rodeo and instantly struck up a rapport. Cherry had seemed fascinated by Applejack, she had spent long nights at the bar listening to stories about life in Ponyville, she had cheered Applejack on in every contest. And at the end, when Applejack was at her lowest ebb, she made her an offer she couldn’t refuse.

Cheery Jubilee’s place of business was the one bright spot in all of Dodge Junction. A huge flamboyant palace of a dwelling; the outside covered with a dazzling array of feathers and lanterns and streamers. But this was nothing compared to the inside. The walls were black and red, tastefully festooned with objects d’arte from every corner of Equestria. Upon entering, Applejack had noticed some sort of zebra sculpture, an array of strange masks, and even what she hoped was a ceremonial whip proudly mounted above the fireplace.

Applejack may have been a country pony all her life, but she wasn’t stupid. She knew what Cherry Jubilee did without even having to ask. She knew what she meant when she complemented her bucking technique with a wink. And even if she didn’t know all that, the large sign reading ‘CHERRY JUBILEE’S HOUSE OF ILL REPUTE’ proudly emblazoned above the entrance gave the game away.

“Now dear!” Cherry smiled, and Applejack gave a nod. “I know this is a bit scary, but hear me out. I don’t think I need to tell you what goes on here, but everypony who works here has a lot of safe fun, and it’s easy to make money. Very easy.” She gave another wink of her luscious eyelashes. “Clients pay up to 100 bits a session, you know. Most of that goes to me for the upkeep, but you can easily make 200 bits a week.”

Something went dry in Applejack’s throat. 200 bits? She had only intended to follow Cherry to Dodge Junction for a short break while she cleared her head, but… 200 bits? She could make more than enough to fix the town hall roof in a matter of weeks! In two months she could earn enough to buy a new barn for the Apple family! She could send Apple Bloom to college instead of enrolling her on a fake ‘apple bucking diploma’ on the farm like she had planned! “Ah… ah don’t know… it ain’t…” She found her voice returning as she stammered, her wide eyes darting about the room.

She now realised it was a lavish reception area, comfy couches dotted about with various doors leading down a long corridor. It was immaculate, a world away from the messy if carefree life she had at Sweet Apple Acres.

“I can see you’re unsure” Cherry smiled. “Why don’t you meet some of the girls.” Then she called down the corridor: “Girls! I have someone for you to meet! If you’re not busy that is!” She gave another cheeky wink to Applejack and Applejack blushed.

Soon, several ponies trotted down the corridor towards her, all of them as immaculate and resplendent as the décor, each of them smiling and curtseying at Applejack. A lime green pegasus was the first to speak. “Hi, I’m Cream Pie!” she chirped. “I enjoy sticky fillings!”

A tall, bespectacled unicorn grinned at Applejack. “I’m Happy Endings, and I’m good at giving clients happy endings!”

“And I’m Vinegar Stroke!” spoke up a rather excitable earth pony. “And I’m really talented with my hooves! Pick me, pick me!”

Cherry Jubilee just gave a tinkling laugh and shook her head. “No no girls, Applejack isn’t a client, she’s thinking about working here!” She turned to Applejack. “We’re one big happy family here Applejack, and I really think you’d fit in. You’ll make lots of money for your family and you’ll have a great time doing it. “ Her eyes sparkled with a mischievous twinkle. “Your performance at the rodeo was magnificent… such stamina! 200 bits a week just for giving some ponies a good, hard ride, if you know what I mean. What do you say.”

Applejack’s mouth went dry again. 200 bits. It was so easy. And out here in Dodge Junction, miles from Ponyville, nopony she knew would ever have to know. Before her brain registered it, her mouth opened to reply. “Ah agree.”

***

Applejack rolled back on her bed and stared up at the ceiling. She was still unsure whether she could go through with what she had to do, but the lure of 200 bits a week was so strong. Slowly she sunk back into the covers. Her bed was soft and downy, perhaps the nicest thing she’d ever have to sleep on. Or do other things on.

The room Cherry had given her was small but beautiful, with a cupboard at the far end containing a huge variety of costumes and other items; shelves that dotted the room were filled with knick-knacks that she barely recognised, and a large full-length mirror dominated the far side. Cherry had explained that this was the only room available at the moment, but if she did a good job, she could work her way up to more luxurious accommodation. To Applejack though, this was already the height of decadent luxury.

She furrowed her brow. She could do this! She could! She had to, for Ponyville’s sake! Just lie back and think of Ponyville! There were voices in the corridor outside. Nervously she looked at the clock – the hand had just passed six. Hours of business had begun. She started to feel herself sweat, her heart pounding as she took a deep breath. She tried to rationalise this. She knew plenty of ponies in Ponyville who put themselves about, and for no financial recompense. In some ways, wasn’t this the best of both worlds, being paid for something that was enjoyable…

The sound she was dreading came. A polite knock at the door. Cherry’s head peeping in.

“Applejack, your first client’s here!” she smiled sweetly, opening the door to welcome a rather nervous looking stallion. “Enjoy yourselves!”

Applejack tried to lounge back on the bed seductively, but she soon realised her twisting made it look like she had bedbugs, so she stopped and looked the newcomer over. He wasn’t much to look at, not the sort of strapping stallion that turned her head in Ponyville. No, it was a gangly purple unicorn with a matted scruffy brown mane, and a pair of oversized spectacles balanced precariously on his nose. There was also an attempt at some sort of tufty beard; Applejack made a mental note to avoid looking at that.

The pony coughed nervously, his eyes wandering about the room everywhere but at Applejack. “H-hi!” he stammered out. “M-my name’s Crown Gear, and uh… I paid for an hour, and maybe we could…” he gave another gulp and looked at a nearby shelf. “L-ludo?” he offered.

Applejack gave a huge sigh. She thought her first time as a paid pony of leisure would be traumatic, but she had imagined that the trauma would be hers. She patted the mattress with her hoof. “C’mere!” she barked out. “No need ta be all shy!”

The quivering wreck of a pony nodded quickly, clumsily pulling down a Ludo box from a nearby shelf. It split open, scattering playing pieces everywhere. “O-oh dear!” he yelped, sitting down on the bed hard. “I-I thought we could first play Ludo a-and then… maybe…”

With a shake of her head, Applejack grimaced. “Don’t make it more painful than it hasta be. Ah know what ya want.” She scooted over to the pony, placing a hoof around his shoulders and slowly lowering him onto his back. It felt good to be in control. “You jus’ let Auntie Applejack take good care o’ ya!”

Crown Gear gave a whimper and froze up like a rabbit in the headlamps of a runaway cart, covering up his belly with his hooves as Applejack loomed over him. “Fer Pete’s sake!” she muttered, slowly coaxing his legs apart. “C’mon, ah won’t hurt ya!”

Her bravado was slowed as she saw his member poking from between his legs, sharply bringing her back to the reality of what she was doing. “It’s jus’ like bobbin’ apples!” she said to herself, as she paused over it, her breathing ragged now, before popping her head over the flaccid organ and sucking. It was nothing she hadn’t done before, but somehow different with a stranger. More exciting.

Slowly her tongue curled around the appendage and she coaxed it to its full length in her mouth, one hoof running over the pony’s balls, the other holding her hat on as she moved up and down. Finally, she popped her mouth off triumphantly, to see it saluting her like a fresh carrot.

A fresh, tiny, baby carrot.

Crown Gear’s head was lolling to one side, his eyes wide and goggling, a small amount of drool escaping from his mouth onto her clean sheets. He looked up at her nervously. “I-it’s not too…”

“No,” Applejack lied. “It’s perfectly average.” Seeing that the pony wasn’t going to help her in any way, she hefted her weight over her new lover and slowly sunk herself down, feeling a slight twinge as his member penetrated her. “An’ now” she winked down at the pale pony. “Now ahm’ gonna ride you. Hard!”

One and a half minutes later, Crown Gear lay panting for his life on the bed, while Applejack sat up, tidying her hair a bit. “That was fun wasn’t it!” she smiled triumphantly down at him, looking at the clock. “You didn’ want more, did you?”

Crown Gear just shook his head, trying to sit up but falling back down again in a state of disorientation. “N-no!” he croaked.

Applejack shrugged at the exhausted pony. “Ah well, an’ you still have fifty-five minutes left!” she shrugged, looking at the clock. “Ah guess we better play Ludo after all!” Inwardly, she congratulated herself at her cleverness. This was going to be a piece of cake!

***

Applejack was on top of the world. The previous night she had seen four ponies, and each of them had gone away barely able to walk in a straight line. Not only had Cherry Jubilee told her that they were the happiest customers she’d ever seen, but by bucking their brains out, she worked out she only had to sell her body for fifteen minutes that entire evening, the rest of the time was spent playing board games or making jigsaws with the dazed ponies. She almost felt guilty how easy it was.

Almost.

The other ponies in the building seemed nice enough, but Applejack had tried to avoid talking to them as much as possible. After all, she was only doing this to get money for her family and friends; she didn’t want to have to associate with ponies who did this job out of choice. Instead, she spent the next day wandering about the slowly, sleepy town, and taking in the sights. There weren’t that many of them.

Soon, six o’clock came round again, and Applejack found herself waiting in her room, feeling strangely excited for the evening that was to follow. “You sly pony,” she winked at the reflection in the mirror, admiring her physique that had lain waste to so many ponies the night before. It was practically cheating!

A knock came at the door again, and Cherry’s head poked round. This time she was alone, but was carrying a bundle of clothing in her hooves. “Ah Applejack!” she chirped. “I’ve got someone for you who wants you to… dress up, I trust that’s not a problem?”

“No ma’am!” Applejack promptly replied, taking the bundle gratefully. “Ah’m always up for a challenge!” As Cherry closed the door, Applejack unfurled the material curiously. It was some sort of spandex, stretching slightly when she tugged at it.

Grunting and struggling, she squeezed all four hooves into the material, then slipped the hood over her head. Twisting and turning to make herself comfortable, she wandered over to the mirror to see what she was dressed as.

“Well ah’ll be!” she exclaimed. She was clad in a tight blue uniform, with a familiar lightning bolt logo emblazoned on the sides. Her mane poofed out from a hole cut in the top, and she struggled to make it look slightly more presentable. Her green eyes peered out from a hole in the material, and then alighted on a pair of goggles that Cherry had left lying by the door. She put them on.

She was unmistakably a Wonderbolt!

Not quite though, there was an obvious slit on either side of the costume for wings. She considered this for a moment and looked into the wardrobe. Sure enough there was a discarded pair of novelty wings lying in the back of a box stored there. They were yellow, but she was sure they would do. Putting them on, she looked back at herself in the mirror and couldn’t resist striking a pose.

“Boy howdy!” she exclaimed. “Ah never thought ah’d be wearin’ one of these! Ah wonder what crazy stallion ah’m gonna meet! Applejack the Wonderbolt, if only Rainbow Dash could see me now!”

She froze in horror as she heard a familiar voice from the other side of the door.

“This is going to be AWESOME!” it squeaked.

***

Ten minutes ago, Rainbow Dash sat opposite Cherry Jubilee outside the hallway, twiddling her hooves as she looked awkwardly about the luxurious waiting room.

“Thank you Ms Dash,” Cherry paused, writing a note in the logbook she had open in front of her. “I’m sure there are many ponies who can meet your… needs, and dressing up is all part of the service, don’t worry about it!”

Rainbow Dash wiped her forehead. “Phew, I thought you’d think I was weird! Now I’m sure you only have mares here, and that’s fine, I’m sure I’ll cope…”

She was cut off by Cherry. “No no, there’s a strapping young stallion who’s free, and a pegasus too!”

Rainbow Dash looked slightly shifty. “I uh… I mean that I know stallions cost more, and I don’t have that many bits to my name, so…” she pushed a pile of bits towards Cherry Jubilee. “Give me your lowest-priced mare. For an hour. Cheapest you’ve got!”

***

Applejack stood motionless in shock as the door closed and Rainbow Dash bounced into the room, her face agoggle in delight at Applejack’s appearance. “Ohmygosh!” she squeaked excitedly, “I can’t believe I’m doing this!”

Panic welled up in the pit of Applejack’s stomach. Rainbow Dash obviously hadn’t recognised her in the body-encompassing Wonderbolt costume, but surely it wouldn’t take long for her friend to realise who it was, and then her reputation would be ruined. The reality of where she was and what she was doing hit home like a brick wall, and she giddily staggered to the bed and sat down.

“So Rainbow Dash,” she said in a deep voice, hoping against desperate hope that she could disguise her speech. “What would you like to do?”

“Well, you’re Spitfire and I – ” Rainbow Dash trailed off, suspiciously peering into Applejack’s goggles. “I didn’t tell you my name, how do you know it!”

“Oh well…” Applejack’s mind raced to find a suitable answer. “Well, of course, you’re Rainbow Dash, the Young Flier of the Year! The most famous pony out of Ponyville!”

Rainbow Dash just beamed, puffing out her chest. “Well, I am rather famous, aren’t I?” she boasted modestly. “I can do a sonic rainboom you know, any time I want! I just don’t feel like it right now!” Her eyes flashed with excitement as she looked about the room. “Right, you stand here and tell me how wonderful I am and how you are letting me join the Wonderbolts!” She shifted slightly, waiting to take in the praise, and then her eyebrow twitched again. “Wait a minute! Spitfire doesn’t wear a Stetson hat!”

“Oh! Oh, really?” Applejack coughed loudly, quickly whipping her hat off. “Sorry Miss Dash, for some reason ah thought she did…” Deciding she needed to quickly regain the initiative, she pulled Rainbow Dash forwards to sit on the corner of the bed. “Now you just sit here an’ let me tell you about how yer the best flier in Equestria.”

“Oh yes Spitfire, yes!” Rainbow Dash squealed as she sat on the edge of the bed, bouncing up and down like a small filly on Heartswarming Eve. She turned her head to look dreaming into Applejack’s goggles. “Tell me!”

“Well…” Applejack stammered. “Ah guess ah saw you flyin’ an’ you flapped yer wings real nice so ah guess you can join the Wonderbolts…”

“Yes yes yes!” Rainbow Dash punched a hoof into the air. “This is brilliant!”

Applejack died a bit inside. The clock was ticking painfully slowly, each movement of the second hand seeming to last an eternity. If Dash thought for one moment that it was Applejack in the Wonderbolt costume, her life would be over, finished. There was just one option. She had to make sure Dash was suitably exhausted enough not to notice that it was her friend providing the services.

Applejack was a traditional earth pony from a traditional family. She wasn’t particularly into mares, though she didn’t begrudge those that were. It just wasn’t something that had ever interested her. Rainbow Dash hadn’t particularly interested her either. She was a good friend but that was all. The idea of having to make love to her filled her with a cold, hard dread, but she knew that the future of Ponyville depended on her keeping this job. Her reputation depended on her being undiscovered.

In short, she had no choice.

Slowly she wrapped one hoof around Rainbow Dash’s shoulders and drew her in closer. Rainbow Dash seemed giddy with excitement, pumping her hooves up and down as Applejack drew her closer. “In fact,” Applejack whispered into Rainbow Dash’s ear. “Ah think y’should take me on a ride…”

“Anything you say Spitfire,” Rainbow Dash croaked out, looking up at the ceiling. “I guess we could fly around the ceiling and…” her eyes went wide as Applejack traced her tongue over her left-hand wing.

“Such a strong wing…” Applejack murmured as sultrily as she could manage, licking up and down the shape of each feather. “Ah’d like to see them all stiff an’ to attention.” With a squeak from Rainbow Dash, she felt the blue pony’s wings stretch out. One hoof started to run over them, and the other was placed squarely on Rainbow Dash’s chest, pushing her firmly onto the bed.

“I… I can’t show you how good a flier I am from here!” Rainbow Dash uttered as Applejack loomed over her, straddling her firmly and grinding softly against her pelvis.

“You can show me how good you are though,” Applejack slowly lowered her body onto Rainbow Dash’s, pinning her friend down as she slowly and gently dry-humped her. “After all” she nibbled at Rainbow Dash’s neck. “You are the best young flier in all Equestria. I might have you make you my….”

“…Vice Captain?” Rainbow Dash gasped out, her wings flapping feebly on the bed cover with every administration of Applejack’s mouth.

“Y-yeah, sure. Or maybe…” Applejack ran a hoof down Rainbow Dash’s side, rubbing her cloth-covered cheek against Dash’s, her mouth whispering into her ear. “Maybe you can be mah captain!”

“O-oh Spitfire!” Rainbow Dash was quivering now, biting her bottom lip hard. “O-oh, touch my cutie mark!”

Applejack raised an eyebrow and gently stroked the symbol on Rainbow Dash’s flank. Rainbow Dash gave a little moan, and taking the hint, Applejack started to kiss down Rainbow Dash’s chest slowly. She made her way to her right-hand flank, licking and kissing the cutie mark, Dash’s voice raising higher and higher in a warbling moan.

“T-tell me you’ll m-make it the new Wonderbolt logo!” Rainbow Dash cried. “O-or my f-face, that can be the new logo a-and…” Her cries were thankfully cut off as Applejack bit the bullet and dove her face between Rainbow Dash’s legs, lapping away.

Rainbow Dash started to twitch uncontrollably, going into almost immediate spasms at the merest touch of Applejack’s tongue. “Oh Spitfire!” she squeaked, “I’ve always dreamed of this! I saved myself for you Spitfire, I’m your little Dashie! Call me Dashie! We can fly together every night and live in my cloud house and oh Spitfire!”

Applejack rolled her eyes at Rainbow Dash’s rather pathetic display, being even more glad at that moment for the mask that covered her expression. Determined to get the deed over and done with, she started to lick deeper, feeling Dash’s thick scent permeate her tongue, almost overwhelming her with how wet her friend had become so quickly.

“I have a little plushie of you that I sleep with at night!” Rainbow Dash wailed. “A-and sometimes I squeeze it between my-“

Thankfully the next mind-shattering revelation was cut off as she gave an orgasmic wail, grinding her hips hard into Applejack’s face as she came, her limbs flailing about wildly in an intense spasmodic explosion.

Finally, she rolled over panting, tears streaming down her face as she collapsed into Applejack’s hooves. “Thank you Spitfire!” she wept. “Thank you!”

Applejack’s eye twitched. She had never felt the need to scrub herself clean as strongly as she did now. “There there… Dashie…” she managed, bustling Rainbow Dash to the door. The clock still showed ten minutes to go, but she was sure in her current state, Dash wouldn’t notice. “Come again!”

She pushed Rainbow Dash out of the door, the blue pony topping straight into the hallway to land on the floor with a hard thud. Slamming the door shut, she locked it leant against it hard, trying to spit the taste of Rainbow Dash out of her mouth. “Ugh,” she muttered. “That was horrible. Who’ve thought Dash would be all the way out here?”

She slowly sunk to the floor, closing her eyes for a blissful rest, hoping the drive the images of Rainbow Dash’s twitching body from her mind. They flew open again at the sound of more voices outside.

“It really is kind of you to accommodate the Ponyville annual coach trip Miss Jubilee. You have excellent facilities here. Do you mind if my dragon comes in with me to watch?”

Applejack’s hoof flew to her mouth. It was Twilight! And all of Ponyville by the sounds of it! She started to think – she could leave the door locked, pretend she was ill! She could find an excuse to leave the Wonderbolt costume on. She could…

She heard Cherry’s voice echo from the corridor. “That’ll be extra Ms Sparkle! Oh yes, I see, well we have a new mare who’s just started with us, she’s cheap and will accommodate your needs, but you’ll have to wait your turn. This stallion is next in line.”

“Ee-yup!”

Applejack leapt to her hooves and almost shot across the room in wide-eyed shock. It was the unmistakeable voice of her brother. She couldn’t – she shouldn’t! Either way, she was doomed.

There was a knocking at the door. The voice of Cherry asking her to open up for a ‘lovely young stallion’. The end of her reputation.

Gulping down heavy breathes, Applejack came to a decision. She flung open the door and pushed herself out into the hallway still clad head to toe in the Wonderbolt costume, which was now looking rather the worse for wear. Cherry looked slightly annoyed at this display, but this was nothing to how Applejack felt.

In the waiting room, there was not only Twilight, not only Big Mac, not only an exhausted looking Rainbow Dash, but what looked like half of Ponyville, all waiting patiently. Pinkie Pie, Bon-Bon, even little Scootaloo who was clutching a rainbow-coloured wig in her mouth. Applejack took in the scene, her jaw slack as she turned from Cherry to the townsfolk in front of her.

“Jus’ – jus’ what is wrong with you all!” She wailed in despair at the crowd. “Ah – ah can’t do it! Ah tried, ah couldn’t win the money at the rodeo so ah thought ah’d come here an’ sell mah body for bits an’ ah thought nopony would know but now everypony’ll know cos ah can’t do it! Ah can’t keep havin’ sex wi’ everypony who wants me!” She tore off her mask to reveal her rather flustered face.

A gasp went up across the room with a shocked chorus of “Applejack!”

Rainbow Dash looked up. “Applejack, how long have you been Spitfire!” she gaped.

Applejack sighed shamefacedly, turning from her friends to Cherry Jubilee. “Ah’m sorry Miss Jubilee” she said slowly. “Ah really thought ah could jus’ sell mahself but ah couldn’t…”

Cherry Jubilee just stood staring at Applejack. An uncomfortable silence descended as no one in the room seemed to want to speak. Finally, she replied. “What?” she uttered simply, her voice betraying a slight angry tremble. Some of the other doors in the corridor had opened and the other workers had popped their heads out to see what the commotion was.

Applejack tugged at the collar of her costume. “Ah ain’t cut out for workin’ in no brothel, ah’m sorry, you’ve been so good to me.”

“Applejack.” Cherry’s reply was short and curt, her speech quavering slightly as she twitched. “Applejack, this isn’t a brothel.”

“I make confectionary and cream cakes!” Cream Pie cried from her room, waving a half-full icing dispenser out of the door.

“I help ponies come up with endings to their stories!” Happy Endings said, her hooves full of manuscripts.

“And I do pottery” Vinegar Strokes chirped from her doorway. “And cookery! I multitask!”

Cherry Jubilee narrowed her eyes at Applejack. “Applejack, have you been bringing my House Of Ill Repute into ill repute?”

“B-but…” Applejack’s voice quivered as she looked around the room at the shocked faces of all ponies present, and then down at her own Wonderbolt costume, which smelt of Rainbow Dash. “B-but you said you wanted me to give ponies a good hard ride…”

“Pony rides! PONY RIDES! Not sex!” Cherry Jubilee looked like she was having a stroke. “You let them sit on you and you trot up and down and it’s all lovely fun! That’s what we do here, we entertain! Play games! Have fun! Not THIS!”

“Oh.” Applejack looked down at the floor mulling over the implications of what Cherry had just said. Then she looked up. “Oh, well that sounds easy can ah…”

“No.”

“Oh.” Applejack sucked in her cheeks, feeling the harsh glares from Cherry, her family and friends. “Well, this is awkward.” The silence stretched on for what seemed like forever.

It was Rainbow Dash who broke the tension, trotting over to Applejack. Applejack breathed in, waiting for the tirade of insults to begin, but it never came. Instead, she stood in front of her, almost protectively.

“Look everypony…” Rainbow Dash began, looking between her shocked friends and Cherry Jubilee. “Applejack’s not a bad pony, she’s just a pony who made a few mistakes! She didn’t mean to do anything wrong, she just wanted to help her friends. So don’t judge her, everypony, and please Cherry Jubilee, think twice before firing her...” She gave a small cough.

“...I’ve still got ten minutes left on my account.”