From Farm to Fame

The groggy summer humidity weighed down across Equestria, with the sun blazing the sky in the afternoon of the day. It was perfect weather to laze about at a beach or under some shade of a tree, but not for the Apples as they had much work to do to make sure the harvest came in on time and bills were paid. Unfortunately for Big Macintosh, he was under pressure to get money together to pay off their loan they had taken out to keep the farm floating for the long frost they had that delayed their work. His short golden mane waved in the breeze, while his emerald green eyes scanned around town looking for any extra work he could get his hooves on.

The red stallion's luck hadn’t been the best for the day, as there seemed to be nothing open for spare work; the teens in town had filled in the seasonal positions, to make some bits of their own. His thoughts began going through all the things he could do for those extra bits, to keep the loan sharks at bay, even if it was for another week or two. Side jobs - nope, those were all taken; travel for work - nah, that wasn't going to afford much and still the same situation, where his other skills wouldn’t help. Big Mac stopped and slumped down in a shaded alleyway for a break, as he felt his heart drop as the list came to an end from his thinking, there was no way he could make the bits he needed unless he went full-on desperate.

As he sat with his disappointment, his ears picked up on a couple of mares having a conversation from somewhere close by. "I know, and right now there are too many of us! It's hard to find a stallion wanting to pay for services or they’re looking for one of those good looking soy-boys who can take a good dick up their ass. I swear, it's what all of them are looking for today is either one of them or nothing at all. What changed over the last few years to turn everyone around like this." The first mare's high pitch voice screeched like nails on a chalkboard with how overboard she was and with a nasally whistle to boot.

"Trust me, they won't find anything like that around here - hell, there are so few stallions in Ponyville you'd think we just populated ourselves somehow through magic. If I were to see a stallion out of the corner in the east side red light district I'd say we'd be losing bits instead of making them." The second mare's voice was a bit more clean, but still had a rasp to it from what sounded like years of smoking whenever she coughed. "Plus there are going to be a few rich guys in town soon for a visit so maybe they'll pay us a visit. You know how those celebrities can be with their coin purse."

The pair let out a laugh at the idea of the rich coming and dropping their earnings on them. When they calmed down, the first one responded to her friend, "Well either way, we'll be fine with how much we make in a single night. I'd be surprised if we didn't make it really big this week with those visitors. Who wouldn't want to pay for such high class hos like us. Oh shit we're gonna be late for our hooficures if we don't move it." With that, the pair started to trot off away from Big Mac's accidental prying ears.

With new knowledge in mind, and desperate enough for work to make bits, Big Mac swallowed the knot that had grown in his throat as his heart pounded like a marching drum. If he wanted bits, he'd have to whore himself to some stranger to make it work. His feelings mixed like water and oil, with part of him joyous for the revelation handed to him on a silver platter. His skills in cross dressing and love of a good rutting of his own from the days in the girls locker room. He would hide in their glory hole and work his magic on the other boys, but the other half was nervous and scared of being seen or caught by somepony he knew. How much could he make doing this and how hard would it be? Could he make safety precautions and still be fine? He looked around the alleyway before getting up and trotting back out into the streets with his mind running like a hamster wheel with the hamster chasing its favorite treat dangled in front of it.

Big Mac's mind was so occupied, he didn't notice anyone around him as walked through the town with his face staring into the dirt. The sounds of the citizens didn't even phase into his ears as he marched solemnly with care through the townsfolk before he bumped into something who had paws of a familiar color. Looking up, he was greeted by the sight of a tall, lanky diamond dog with a coal-black coat mixed with spots of white in various locations, dressed in their traditional digger's coat. Big Mac took a few steps back and said "Sorry there Spotty. I didn't mean to, just a long day." His voice trembled as he tried to keep from bursting out in some tears.

"Silly red pony thinks I'll fall for something like that. Doesn't matter though, it's a good thing I ran into you. I was going to your place to tell you debt is due tomorrow by high sun - if not, we start to dig and dig hard under your lands. We know there are precious gems under there to pay back what you owe." His low barking voice made him the more intimidating as he jabbed one of his furry fingers into Big Mac's chest. "Now make sure shiny coins are ready for Spotty."

"Hold on now, we agreed months ago that I'd still have at least one more week to have all the bits ready for you." Big Mac puffed his chest as he took a few steps forward, his face now spotting a bit more bravery to not be bullied. "I can have your coin for you in one week, no problem."

Spotty slapped his knee and chuckled at Big Mac's attempt to intimidate him. "You make funny joke pony. No, the agreed upon date is tomorrow, you lack sense of time. Now don't waste anymore of mine or I'll start my crew digging today." With that Spotty gave a triumphant humph and walked past Big Mac and left in him with panic setting in further.

Mac's eyes grew wider as the words dug deep into his brain as he went over the contract in his mind and the dates. Each day flipping like the page of a book, until it slapped him hard when the date popped up in through his flashing memories with today's date popping up and then tomorrow's. Spotty was right, he had forgotten the days and it was now or never to have the bits to save his land. In complete panic Big Mac took off like a rocket towards Sweet Apple Acres, his legs moving as fast as they could and burning from the intense stress he was putting them through to make it so quickly. His movement even created its own breeze that would make the pegasi weather team jealous that an earth pony could move so fast.

Each second passing by felt like an eternity, as he came down the dirty road towards the farmhouse. His knees now in full shake from the power that had exerted through them with each slam of his hooves against the ground. The wonderbolts would have loved a nice race with him with how fast he ran. He slammed open the door and ran upstairs to his room without a word to the startled Granny Smith who jumped up from her nap in the living room as he barged inside. She didn't seem to notice too much before drifting right back to sleep. Once in his chamber, Mac closed the door behind him, his chest heaving from his shortened breath from all his running. His eyes scanned his room until he found what he was looking for, the parchment paper he signed with Spotty for their deal and it was correct his mind had forgotten.

Feeling defeated, the red stallion slid his big butt onto his bed and sank into the mattress as tears welled into his eyes. He had failed his duties to keep his family's farm from coming under ruin, and there was no way he could make those bits up in the amount of time he wanted to. Nothing could fill that void that tore into his heart at that moment as despair took grip onto that heart of gold in his chest. Shoving his face into his pillow, he let the cries of agony fill into the cushion covering his face. His hoof slamming into the mattress as he vented his anger at himself and wanting to just vanish from the house he was raised in so that the others wouldn't have to suffer if he never existed.

A few hours passed, as Mac lay still in his bed, his tears now dried up with puffy red eyes and his body near numb to the emotional agony inside as his mind replayed Spotty's words over and over again. Payment tomorrow or else the farm falls even further than it had before, to the point of actual collapse from under the ground. His mind pondered the words over and over until a familiar voice from before could be heard outside.

"Thanks for the apples, I'll see you sometime next week for more." The second mare's voice echoed off his walls from the window.

Big Mac sat up in an instant to the sound of the voice and he peeked his head out the window. The mare was dressed in scantily made clothing that most would consider a bit vulgar in the public eye. As he watched her trot down the road his mind recalled the conversation he had overheard earlier that day. Big money, stallions wanted, red light district in east Ponyville all rang through his memories on repeat beginning to overwrite the ones of Spotty and his debt. Mac slipped off his bed,looked up to the sun, and noticed it would be getting close to evening soon. He pondered for a few more minutes and decided it had to be done whether he made all the bits or not. He would have to become a prostitute to attempt to save his family farm but he'd have to start preparations after the family supper. He knew he would look guilty of something and he didn't need his sister Applejack snooping around on what he was doing or planning.

With his new found courage and taking the biggest chance of his life, Big Mac walked around the orchard with a big goofy grin on his face for the rest of the day and even through the family dinner. He did his usual silent routine of yups and nopes to questions when he was prodded by the rest of the family for why he was so happy, just trying to dissuade them from any further investigation into his plans for that night.

After his meal, the stallion returned to his room as the others settled down for the evening and got themselves ready for sleep. His motives weren't going to be sleeping - instead, he was going to use all this time to get himself into a ready state for tonight's events and each second was going to be used to the fullest to get himself set. He sat on his bed for a little bit planning out what he was going to need to make the look work and put his skills to the ultimate test of attracting customers to him for as much money as he could make.

Meticulous ideas put to planning out his outfit and looks as he went over one last time of his plans. After the last few hoof steps could be heard on the stairs, Big Mac got to work immediately in getting dressed as the others were now in their rooms winding down and getting into bed giving him the perfect chance to sneak out and do his deeds. He went over to his closet and opened the door, just showing his few work attires that he'd wear for special occasions hanging up with what seemed to be small walls for the closet. However he reached over and pushed on one wall slightly and moved it to the side revealing much more on the inside of the fake panel.

Inside the hidden compartment were dresses, tops and skirts all hung with care in all sorts of shapes, colors, and designs that he had collected over the years. His deepest secret was the joy he got from cross dressing as a mare and feeling pretty when the family was out of the house and he had hours to play dress up. Having spent years practicing it wasn't hard for him to do his thing. Reaching into the small two drawer dresser he fit in the room he pulled out a green fishnet body suit, along with a green crop top with “bad girl” written in purple. Eyeing around he found the matching green skirt with purple trim hemming on it and his favorite pair of purple leather heeled knee high boots with the white fur trim on them. Lastly he opened the bottom drawer and found the nice pair of green low cut panties that he enjoyed due to the soft cotton fabric and their ability to keep his sheath hidden away with just a small bulge popping out when he wore them.

He dragged out his outfit and set it onto his bed and returned to the closet to set the wall back in place, then reached down at the floorboards in the main closet and pulled up one loose board to reveal two small boxes on the inside. He reached in and pulled them out one by one, setting them to his side. Sitting down next to them he opened the lid of the small brown chest first revealing old gold jewelry. Pulling out a few golden bangles for his hooves, with a thin golden locket necklace trimmed with small bits of silver on the main locket and his favorite pair of golden pearl earrings. Setting the necklace and bangles down he put the earrings into his pierced ears to make sure he didn't lose them as they were his first treasure he had managed to bring home without Applejack or Granny Smith catching on.

Closing the first box and setting it back in the hole, he turned to the next and opened it up to reveal the small stash of make up he had acquired with great pains to make sure no-one noticed him buying it let alone bringing it home. It was hard having to get these things out of town while on family vacation and even with some of the shops in Ponyville as he pretended to be getting gifts for family as well. His heart skipped a beat, as he pulled up the deep purple tube of lipstick, the matching eye shadow, a tube of thick mascara to make his lashes look really feminine, and just a bit of blush to tone his face a bit more. He pushed his make up to the side and set the box back into the floor and covered it up.

Now he was ready to become his favorite pony in the whole world, Lady Orchard. Grabbing the fishnet suit first he struggled a bit to get it on as it snagged against his fur now and again until he managed to get it on. They had a modified design to let his junk hang through with a bigger hole for his anus to be on full display and access through the netting without getting another pony tangled in them. Next he slipped on his soft cotton panties, pulling them up over the netting and resting them over his thick ass cheeks and snapping them over his big sheath with a nice comfortable fit. He looked in the mirror and gave himself a smile as he turned around and eyed his own ass with a sultry gaze before returning to his attire. The skirt had no issues going on, as it slid up with its elastic waistband but the crop top gave a few issues as his front hooves didn't want to cooperate with going through the small shoulder straps of the article of clothing.

As he stomped around trying to get ready, a knock came to his door causing him to stop in his tracks; his eyes bulging with fear of the door opening and revealing his secret that he had kept from his family for so long. Applejack's voice came through the wooden wall saying "Hey Big Mac, can you keep it down in there. We got plenty of work to do in the morning and I don't want my sleep disturbed."

Mac let out a sigh of relief at the sound of his sister's voice through the door before responding with "Eyup" and waiting for the sound of her hoofsteps to disappear to the room next to his. With his chastised mindset he went about continuing a bit more quietly as to not wake any other pony in the farm house. Once he got the top on, he held back on putting the boots on as he knew they would click on the wooden floors from the many times he walked in them before. His next step was getting his makeup on in the mirror. He knew that he'd have to put his best hoof forward with this, and with all the practice he had he needed it to work well. His eyes were colored to that of nice purple grapes with his eye shadow, before he applied his thickening black mascara to his lashes. Fluttering his eyes after applying his mascara to show off their fullness in the mirror to himself.

The stallion was enamoured with how he looked as of now but still hadn't finished his entire image. Picking up his tube of lipstick, he turned the base to reveal the pleasant purple shade that contrasted with his emerald eyes then applied it thick to his lips giving a luscious look with the plastering of the makeup. Blowing a kiss to himself in the mirror, his looks were getting to his height of greatness. Next he put on his bangles and necklace to finish out the base of his looks but he felt like something was missing, just a few pieces. Going to his bed he stuck his hoof under the mattress and pulled out a pinkish purple purse and opened it to the few colored elastic bands on the inside. Pulling out two green bands, he pulled back his mane into a ponytail and tied his short tail hair and looped it back with the other band giving whoever access without him needing to move the hair out of their way. Stepping back in front of the mirror with purse slung across his shoulder he nodded to himself. This was it, this was Lady Orchard's time to shine to save the farm, and hopefully no pony he knew would see him out as such as his skirt barely covered over his cutie mark.

Opening his dresser drawer in his main room, he grabbed a line of condoms and stuffed them into his purse, and picked up his make-up taking it as well in case he needed to touch up at some point during the night. Closing his eyes, he took a deep breath to focus himself and remember the cause of doing this risky thing. Snatching his boots in his teeth, he crept his way down the stairs out of the creaky old farm house. When he was outside he sat on the bottom step of the porch and slipped his heels on his rear hooves and then took off into the darkening sky towards the east side of Ponyville in wait for his fate.