Popping The Cherry

by Mr. SexSymbol

Rating: mature
Tags: Sex, Applejack, My Little Pony: Friendship is Magic
Length: 3719

Humanized Clopfic involving AJ and Cherry Jubilee

We all saw it. The hairstyle, the eye shadow and the beauty mark. Cherry Jubilee and Cherry Hill Ranch? Just a cherry farm? Pfffft. Suuuure.

The erotic side of the story, told in a humanized fashion. Applejack enters an infamous brothel in Dodge Junction in order to earn money to make up for the losses during the rodeo. Cherry Jubilee hires her and offers AJ a place to stay until she saves enough cash. Will she do it in time before her friends seek her out?

Published 2012-01-30 00:46:13 UTC
Last updated 2012-01-30 00:46:13 UTC

Chapter 1

Out in the night of the wild west, snaking across the dusty desert plains, a train speeding down it's tracks. Carrying many kinds of people, the rich and poor, the happy and the sullen. One particular sullen one sat way back of the last cart of the passenger train, leaning against the rails outside of the caboose. A woman with a signature cowboy hat sitting on her back, hanging by a spring around her neck. Her hair was long and golden, flowing loosely in the wind and the red scrunchie wrapped around her left wrist. Applejack was her name, hailing from a simple town named Ponyville. Not too long ago did she leave town with a promise to win as much prize money as possible to restore town hall. It was the least she could do after all the support the townspeople had given her the past few years.

However this time... this ride back home was completely different. She had lost and had let everyone down. There was no money this time and they would all despise her for making them trust in her. The shock of it had still not gone away, ever gnawing at the back of her mind. AJ dangled an empty bottle of beer between her index finger and her thumb, watching the wooden planks on the tracks whiz by underneath her. With a hot and heavy sigh, she released her grip on the bottle. It crashed and flew off away, the pieces of glass catching the moonlight before fading away into darkness.

Applejack grabbed the handle of the door, sliding it open and entering. She slammed it shut, knowing that there was no one else inside the caboose. Taking slow, slightly drunk, steps towards her seat, AJ tossed herself on the plump green train seat cushions and shut her eyes to sleep. Tomorrow... would be a day of angry faces and disappointment.

Ah lil' sister... Ah'm sorry. So sorry... Ah couldn't keep a simple promise.

A small tear escaped from her green eye and rolled down her cheek as her vision faded...

* * *

"That's it! I am out!" The door to Cherry Hill Ranch flew open, banging against the front of the infamous bordello of the west. A trashy, and flashy, lady stormed out covered in heaping amounts of lube. She was topless and only had a pair of panties to cover herself. Another woman rushed out, pale faced and sweaty. "No no no! I'm sure the client didn't mean for that to happen, mistakes happen. Please don't leave Cheryl, you're the best girl in town!"

"Madame Cherry Jubilee! I will not be a slug for that man's disgusting fetish! THAT. WAS. NO. ACCIDENT. This town is full people with twisted fetishes! I gotta get out of Dodge!" Cheryl screamed, stamping her feet for every other word she shouted out.

Cherry Jubilee panicked, catching her by the arm and holding tight. "Cheryl! You have a contract!"
The hooker snarled. "Which expired last week. Let go of me, twat. You won't be hearing from me again." With that, Cheryl whipped her arm back and stormed off, leaving Jubilee without a main attraction.

The redhead fell on her knees, hands on the side of her head. What am I going to do? The rest of the girls aren't getting much attention and Cheryl was the only on bringing in any money... I can't shut down the business... Not like this. I don't want to go back home at the family orchard. Not after this... Madame Jubilee got up and brushed the dirt off her sparkling red dress, shaking her head. "I need a miracle... and a drink." It was almost time for Cherry Popping, a special nightly event that happens once a week where one of the girls would dunk themselves in a crate of fresh crushed cherries right from the orchard. A lot of men around here would pay a lot of money to sleep with the girl was the lucky Popper, it was basically an auction. It was supposed to Cheryl's turn tonight but as how it is now that she had called quits... Jubilee knew she would have to take her place.

Not that she minded, rather looking forward to it. The sensation of the sticky red juice was like no other. Just thinking about was already making the stress from Cheryl quitting wash away, being replaced by a powerful urge tugging at her to go and get started already. Madame Jubilee bit her lip seductively, speed walking back to her bordello. I'll figure out what to do in the morning. For now, focus on getting customer and keeping them interested. Entering her place of business, Cherry immediately started undressing and snapped her fingers when she had an arm free. Two girls came rushing to her side just as she tossed away the one piece and stood before them nude. The girls were wearing red leather undergarments with the bras in shape of a heart shaped cherry.

"Get the juice girls! We're gonna Pop me tonight." Jubilee said eagerly, a wild grin was plastered on her face. One of the girls, with short light blue hair looked out over Madame's shoulder. "I don't see Cheryl out there... Is everything okay?"

Jubilee waved her hand to and fro. "Cheryl? Oh I fired her for being a whiny bitch. She's gotta do what the client wants. Cherry Hill rules. Now then!" She clapped her hands, "The juice, fetch it my darlings! I'm feeling quite adventurous tonight, tell the men that there will be two winners and they'll both have to share their prize."

"Yes Madame." The other girl nodded and ran off towards the side exit which lead to the cherry orchard outside. The orchard was a little side business that she ran along the brothel, being the main source of income for herself and the pleasure house. It was the only thing keeping this place running and putting money in her bank account. Despite the good pay, harvest only comes once a year. Once that's done and over with she would have to depend on the services on her women and herself to her loyal customers to keep on going. Of course there were other occupations, Jubilee knew this but there was this passion, this drive that forced her to be in these intimate situations every now and then. No strings attached, no vows, and no worrying of the significant other being with another behind her back.

She smiled soothingly and spun on her heels to go outside and attract customers, angling her hips and pouting her lips seductively for any man who passed by. As the night came and the stars, one by one, dotted the inky blackness, the brothel quickly filled with customers. All of them clamorous who was going to sleep with who, all of them joked and laughed. Having a jolly good ol' time. Madame Jubilee watched them, smiling to herself, as she watched her women interact with the men. Already were two of her women were servicing, preforming simple touches with hands and mouth.

Show time.

After shutting the doors, Madame Jubilee reached out and grasped the iron bell, ringing it. The sound was loud, more than it should be, and ear splitting. Them group of men, the number being around twenty to twenty five, stopped their banter and turned their attention to her. The main room of the brothel was silent, save for the wet popping sounds that came from on of her girls blowing a client.

"Gentlemen..." She started, cupping her hands together in a way a businesswoman would when she had an excellent idea to offer. "Tonight is a Cherry Popper night, as some of you may have noticed from the presence of the crate," She raised her clasped hands upward and pointed towards the round wooden crate filled to the brim with cherry juice. "that our Popper will be dunking into. As always, an auction will take place for the lucky fellow to sleep with the cherry covered, fruity scented and o-so sticky skinned woman." The men made a wild hoot, a few shouting out "Yeah!".

"However tonight will be different. Cheryl is not going to be here tonight, so therefore... I'm taking her place. Another difference is that there not be a winner tonight." She then paused for effect, cracking a smile when she saw the confused looks being exchanged in the small crowd. "There will be two."

A whoop came from several of them while the others asked about Cheryl. "Where is the girl? I was supposed to get a lap-dance from her! Hey!" "The cunt owes me seventy bits!" "We want Cheryl!"

Madame Jubilee pouted. "You want Cheryl?" She asked, crossing her arms over her exposed breasts. Several of the men shouted in response. "Hell yeah! Bring her out!" Cherry faked a tear, pretending to wipe it off and fling it away. "Does that mean none of you would want to sleep with me tonight then? I mean I was planning on being the Popper girl tonight..."

That changed their answers almost instantly. Though Cheryl was a favorite, she had nothing on the owner of the brothel. Madame Cherry Jubilee made her way across the main hall towards the stage that housed the crate of cherry juice. As she passed them by, several of her customers nipped at her bottom with their fingers and others simply ran their hands across her. She enjoyed the feeling and let them caress her body.

Once she made her way to the top of the platform, Madam Jubilee glanced down at all the men and blew a kiss before hopping in the crate.

* * *

"Ma'am? Ma'am! Wake up! You there?"

The gruff voice pounded into Applejack's eardrums, amplifying her headache. The moment she woke up she instantly regretted drinking all those beers she drank out of depression. The conductor was standing over her, shaking her roughly to rouse her. "Ma'am. Wake up! You've made your destination!"

"Mmn... Agh! Ah... Where am ah?" She mumbled, groggily pushing herself off the the train's cushioned seat. Her blonde hair was a mess, clumpy and frizzy. The conductor helped her sit up fully as she rubbed her temple in a futile attempt to ease her headache. "You're in Dodge Junction. A small town, great folks." The conductor said, his voice muffled slightly by his bushy mustache. "You better hurry though, train leaves in several minutes. Do you need any help?"

"Naw. Ah can take care of myself. Thanks anyway." AJ muttered, standing up and stretching her back to ease the stiffness. She reached down and picked up her hat off the seat and put it on, walking right towards the door that would lead outside and to the platform. The conductor held up his hand. "Wait!" He shouted.

AJ stopped in her tracks and squinted at him tiredly. "What?"

"I heard you in your sleep. You said you needed money, right?" He said, fumbling with his hands. Applejack flushed, embarrassed that the man had been listening to her. "That's none of yer business!" She retorted. He winced but continued anyway. "I know but you seem like you're in a tight spot. Listen. I know a woman who lives 'round Dodge. Name's Cherry Jubilee. Word is in town that she's best when it comes to cherries. Why don't you go to her ranch and work for her? She's always looking for a girl with fast hands and a strong back."

Applejack nodded. A ranch... It'd be smart to work in my profession. Earn money for doing what ah always do.
"Where is this ranch?"

"Ah... Just out by the train station actually. Cherry Hill Ranch is the name." He replied.

"Thanks." She muttered and tried to go out again when the conductor stopped her yet again with his voice.
"Ah ah ah! Wait! If I were you it'd be better if you went and ask for a job in the morning. Night is when she's the busiest. Better not bother her, eh?" He smiled nervously. As if he knew something AJ didn't.

"Right..." Applejack muttered under her breath. She slid open the cart door and stepped out on the section where the two carts were joined, a metal plate over the thick metal things that she couldn't name that connected the two coaches. The plate extended a bit to the train's side and in front of that was the stone platform. Applejack made a small hop over the gap and took her first step into Dodge Junction.

For a first impression, the place was small and sported a wild west look. It reminded her of Appleloosa, the simple town her cousin lived in. AJ walked off in search of a motel or inn to stay for the night, with no money on her it would be hard to convince the owner to let her stay for the night. At least she had no belongings with her, just her hat. The blonde woman glanced out towards what must be Cherry Hill Ranch, seeing the orchard of cherry trees behind a large building. The lights were on and she could hear the sounds of men shouting. Must be a party of some kind... She reasoned.

Trotting along the dirt road, she came upon a a worn down place that had an aged motel sign nailed above the door. Applejack sighed and shook her head. Here ah go. Ah'll have to put it on a tab or somethin' until I get the money... Hmmph... Money. Always a bother. With that, Applejack entered.

* * *

Madame Jubilee laid across the large queen sized bed in her private room, posing in a very seductive manner for her two highest bidders. Under her was a blue tarp tied down over the covers since she was covered from head to toe in cherry juice. Each of them paid over six hundred bits each for an entire night session and she was gonna give them on hell of a night. The lucky guys were both young, probably sons of farmers or delivery men who populated the town, and in her opinion were somewhat attractive looking. "Well?" She asked, placing her hand on her bare thigh. "Who's getting the back while the other takes care of the front?" Both men blushed and glanced at each other. Jubilee smiled as they bickered for a few minutes until they finally agreed. They removed their clothing, tossing them aside as they climbed into the bed. She snickered. "One of you will have to get rid of all this juice... Maybe starting down here?" Jubilee opened her legs and used her fingers to spread open her lions.

One of the men, a black haired fellow, grabbed her bottom from behind and positioned her. Madame gasped. "Ah! So forceful... Hmm.." She bit the bottom of her lip as she felt him press his fingers into her vagina before going down on her and jabbing his tongue inside. Her mind went blank for a moment as she felt the wet muscle wandered inside of her. She made little gasps as he slapped the very tip of his tongue across her clit. The other man with red hair poked her cheek with his erected member to get her attention. "Oh! Forgot about you." She exclaimed, grasping the meaty throbbing length. Jubilee put a light touch on his testicles as she ran her tongue along the underside of his hard on, right up to the very tip. She dipped it into the small opening on his head, making him jump. "Liked that didn't you, naughty boy..." She giggled, giving him a handjob while slathering her tongue across the sensitive tip, covering it with her saliva.

"Oo-ooh... Miss..." The red head managed to choke out. Jubilee popped the tip in her mouth, sucking her cheeks in as she continued with the tongue treatment. Behind her the man prepared to stick her with his penis, her pussy wet and glistening from the foreplay. He pressed the tip inside of her, the warm soft walls wrapping around the throbbing head of his erection. Madame Jubilee let out a moan. "Ah haa... don't stop there. Pound it! Pound me! You got what you paid for now get going!"

The kid blushed and adjusted his grip on her butt, pulling himself towards her as far as he could. Jubilee shuddered as she felt the thick hunk of flesh sliding inward, pushing against her inner walls and against the opening to her womb. "Ooh... yeeah..." She moaned, grabbing the other patron's cock and pinched her lips along his side, making him groan. When she reached the top, Jubilee opened her mouth once more to take his length in once more. Her plump lips rubbed against his hard on until it reached the base, deepthroating him. At the same time the ginger began thrusting, swearing as Jubilee's vaginal passage went tight whenever he tried to pull back. It felt as if she were trying to suck him in, clinging on to his cock.

Jubilee made a throaty giggle, bringing her head up and down quickly, Wet sloppy sounds came from where her lips and his meaty rod met, going in tune with the slapping when her other client pounded her pussy.

Several minutes into blowing the black haired fellow, Jubilee's eyes snapped open and pulled back quickly for a breather. Her hand tended to him as she refilled her lungs with fresh air, all the harder while moaning as her ginger friend in the back was banging her. "Mmm. Ha! Oh my... ah... you boys are good!"

"Ugh!"

Madame grinned teasingly, quickening her speed on the black haired man's cock. "Dear me, are you going to cum already? Ooh... go right ahead. Anywhere you want..." She planted a kiss on his tip again and prepared for an incoming facial, closing her eyes shut. In the darkness she could feel the powerful thrusts from behind, slamming into her tender and violated cervix with each entry. "Here it comes! Oooohhooo!!!" He shouted.

Jubilee gasped as she felt the seed splash against her face, lining it with a milky whiteness. Once she felt no more coming did she peek an eye open, seeing the limp penis before her oozing remnants of the ejaculation. Slowly stroking him, her eyes looked up into his and to her delight, made him blush.

Madame Jubilee suddenly spasmed, moaning loudly as the remaining customer went faster and harder without warning. "Cumming!? Are you cumming!?" She shouted, her body rocking violently as the man was hunched over her like a dog. "Y-yes! Yes!" He yelled in reply, raising an arm up and slapping her ass. Jubilee screamed in heat, her deep red hair bouncing and becoming more of a mess with each thrust. Then with a mind shattering orgasm, Madame Jubilee lifted herself off the bed with her arms, her sweaty breasts jiggling as she arched her back. Her wild red hair swung about as she let out a loud scream out of pure pleasure. Her client could hold on no longer himself and with a final push, he dug deep into her vagina and let out a torrent of semen inside her. The Madame went limp and simply laid there as she felt the warmth invade her womb, her hot and itching empty womb. A small stream of the seed trickled out of her pink, tender opening.

They rested for a long time, catching their breath and their strength. Jubilee had something planned out, a little something she had always wanted to try but never gotten the chance to do so. Jubilee laid down on her stomach and beckoned for her customers.

"Boys. Double penetration. Right here, right now." She commanded. "You, pussy." She referred to the one she had sucked off. "And you, ass." The red head nodded and waited for his friend to get under her before getting on top of her. Madame Jubilee trembled in anticipation as they struggled to put their dicks in place. The guy under succeeded first and made a sigh as he entered her, thrusting in and out at a good speed. The red head got off and on his knees for a better position, grabbing his erection by the base and pushing the tip against the anus. It resisted him, pushing back.

"Ugh! It's not going in!" He vented, attempting again and again. "There's ahh a... lubricant under the mmm! Bed!" Jubilee said between moans. Ginger hopped off the bed with haste and looked down. "I see it!" He said excitedly, grabbing it and popping the lid off. He gather a good amount on his finger tip and climbed back on the bed. Cherry bit her lip when she felt his finger sliding into her anal cavity, slathering the lubricant inside of her. When he pulled his finger out he immediately replaced it with his cock, finding it a lot easier to enter now.

It suddenly became a whole new level of sex for the Madame.

"OH MY GOSSHH!" She gushed, her face flushing deeply and her tongue hung out as both men were deep inside her, pounding with all they had. Outside, the rest of the men and girls had stopped their actions to listen to them go at it. The blue haired girl who had gotten the crate of cherry juice laughed nervously. "That's our Madame! Heh... she sure does love her work..."

Back within the bedroom, Jubilee's experiment and pleasure was short lived. They both came again inside of her and pulled out, exhausted and unable to do much more than breath. A heavy musk filled the room, a scent that made Jubilee's spine tingle. Despite wanting more, she too was spent and laid there. Her skin was glistening, soaked in her own sweat and cherry juice. As for beehive hairstyle, a goner and a clumpy mess of red hair. A strange smile grew on her face and, with a heartfilled sigh, began to black out. A single sentence formed in her mind before sleep took her.

Thank goodnes Cheryl's gone. This means... this means I get to spend some time with a newbie... good times... good times are ahead of me... Hmm~