An Unconventional Challenge

by RaijingtheClockworkPony


The Working Mare

Elusive walked along the road with his gaze to the clouds. It wasn't often that he spent time cloud gazing but this was a special occurrence and he was going to make the most of it while he could. He felt confident as he made his way to the familiar farm where a familiar mare was, most likely, hard at work bucking apple trees. She always had a work ethic I could get behind. Never met a mare quite like her, hardworking and willing to take as much of the burden as possible to lighten the load for others. A simple smile spread across his face as he remembered the first time he and Applejack had really spent time together.

"That silly sleep over. I still can't believe that Twilight insisted that I stay for that event."

Almost the entire night had been consumed by Elusive and Applejack arguing. They had only stopped after the intervention of a tree through the window. Only after that did they both stop their pointless bickering and just enjoy the company of each other and Twilight.

Elusive spotted a group of three fillies that normally would put him on edge but today he saw them as they were, three friends playing. The white filly in the group looked over in his direction and ran over to him.

"Elusive! What are you doing at the farm?"

Elusive hugged his sister with his smile growing wider and warmer. "Just came to talk to Applejack. You three have been staying out of trouble, right Sweetie Belle?"

The filly rolled her eyes. "Yes. We were just playing. Wanna join after you're are doing talking with Applejack?"

He shook his head but the smile remained. "I can't. I have a lot to plan out today and I have that spa appointment with Fluttershy. I'll tell her that you said hi for you if you want."

The three fillies nodded and thanked him. They ran off and Elusive swore he heard Scootaloo mention something suspiciously close to 'Cutie Mark Crusader Acrobats' as they left. Elusive sighed and went towards the farm house.

His journey to the farm house was put to an end when he heard the distinctive sound of hooves hitting wood. He followed the sound until he spotted a stallion he knew but wasn't looking for.

"Hello there Big Mac. Do you know where your sister is?"

The large stallion glanced over at him and kicked the tree with one leg. "Hello there, Elusive right?" An affirmative nod was his answer. "Applejack is in the barn stackin' hay."

Elusive nodded. "Thanks Big Mac."

Elusive walked away as Big Mac gave his usual response. "Eyup."

Upon reached the barn Elusive heard grunting inside and when he opened the door it confirmed that Applejack was hard at work stacking bales of hay. She was tossing bales into a large pile that was well over three times her height. For a moment he just watched her work and marveled at how she made such menial labor look easy. She added a sort of grace to it that he could quite describe.

He cleared his throat to alert her to his presence. "Applejack hard at work today I see."

The farmer tossed a hay bale perfectly in place on top of the large stack next to her. "Well howdy there Elusive. What are you doing out here on the farm. I thought you 'abhorred' the dirt and grime of farm work."

Elusive gave her an amused smile. "Well to tell you the truth I was here to ask something of you."

Applejack lifted another hay bale on her back. "Ask away sugarcube."

Elusive took a small breath before he began. "Well you see I'm designing a new fashion line for the working mare and well..." He paused just long enough for her to notice.

She turned and looked at him. "Well what?"

Hook. He looked away as if he was embarrassed. "Well I was hoping that you would model for me."

Applejack was in mid throw when he finished. She lost her grip on the hay bale and ended up throwing the hay bale over the pile entirely. She turned to him quickly as a *Thump* came from behind the bale pile.

"What?"

Line. He cleared his throat. "Well I would be honored if you would model for me. You have a perfect body..." He let a small pause make it seem like a slip up on his part. As if on cue Applejack began to blush. "For modeling this clothing line I mean."

Applejack opened her mouth and closed it a few times before she found her voice. "What about Fluttershy or Twilight? Couldn' they model for you?"

Elusive took a few steps closer. "Well I would have Fluttershy but I need a mare with more muscle to her. I do enjoy the time I get to spend with Fluttershy but she doesn't have the body type I'm looking for. Twilight on the other hoof," He let a small sigh. "I love that mare to death but she modeled for me once and nearly talked my ears off. Got to learn the history of sewing while I worked though."

Applejack let out a small chuckle as she imagined Twilight talking a mile a minute with Elusive working around her. "I guess, but I'm certain that there are other mares in town that can help you."

Elusive moved closer once more. "None of them have the perfect form I need for this. Please, consider this a small favor that you can hold over me if you want. I'll event treat you to lunch."

Applejack walked up to him and rested her hoof on his shoulder. "Settle down there sugarcube, you don't need to sell me on this. I'll be happy to do this. What time do you want me and my perfect body over there?"

She gave him a sly smile that he wasn't expecting. "Wuh... oh, right the time." He collected himself with a small cough. "Shall we say eight thirty in the morning?"

She gave him a nod. "Sounds good to me. Mind keeping the flirting and buttering to a minimum while I'm there?"

With that she turned around and walked back to the pile of hay bales, flicking her tail to brush against Elusive's cheek softly. He felt his jaw drop for a fraction of a second before he caught himself and looked at the mare in a new light. She had seen through his rather simple flirting and that impressed him.

He walked out of the barn but not before giving the farm mare another quick look and watching her toss the bale she missed onto the top of the pile. She caught him looking and gave him a small wink. He returned it with a smile and walked out of the barn. Once outside his face split into a self-satisfied smile. Sinker.

Elusive made his way to the spa for his weekly appointment with Fluttershy feeling rather good with himself. He walked into the building and spotted the yellow mare smiling and talking excitedly to Lotus Blossom. When she spotted Elusive she ran over to him.

She was practically bouncing with joy as she talked to him. "You wouldn't believe what happened to me today!"

Her voice was peaking at almost Elusive's normal tone. Whatever it was really had her going with excitement. Elusive calmed her down a little and told her to wait until they were in the steam room before they started on the usual gossip and news. For her part Fluttershy was using every ounce of self-control to not tell Elusive right there but she respected his wishes of getting some privacy before they started talking.

That self-control ended the moment the door to the steam room shut. "Berry asked me out!"

Elusive sat there as two thoughts ran through his mind. The first was that Fluttershy seemed to be beaming with happiness at the news and the second that he was impressed at how quickly Berry had asked her.

Already? Well I'll be... He recovered from the small shock quickly. "Really? When did this happen?"

She smiled and moved closer to him as her voice became more excited. "This morning. He came over and told me that he had feelings for me since he met me. Then he asked me for a chance to let him show me he loves me."

Elusive gave her a small hug. "Congratulations. I think you two will be very happy with each other."

Fluttershy nodded and they began to talk about the normal gossip but Elusive minds was elsewhere. He knew that Fluttershy liked Berry, more than just a friend. She had confessed her feelings for Berry to Elusive after a few of their spa sessions but had made Elusive promise to never tell him. Elusive bit his lip at the thought that Berry might be faking his emotions to win the bet. I'll have to talk with that stallion very soon.

"And so I think I might need your help with getting ready. I've never been good with my mane." Fluttershy noticed his distant look. "Elusive?"

He shook his head and looked at the yellow mare. "Sorry. Thinking about something I need to do. Yes I'll more than happy to help you with your mane. I have some ideas in mind for your date." He scolded himself inwardly for losing focus like that.

Their talked wandered after that and Elusive found himself on one of the massage tables thinking of ideas for Applejack's outfit. Ideeea!

The Carousel Boutique, the premier fashion center of Ponyville and the destination of Ponyvilles premier farmer. Now Applejack had rather mixed feelings for the place. She was never a fashion conscious mare like most of her friends were so she wasn't entirely fond of the building or what it represents. However she did like Elusive due to his rather kind nature and he was a good friend. He always did what he could to help her and her friends whenever he could.

Ah reckon hes probably got some sort of over the top fashion line ready for me. This should be a good laugh or two. She chuckled to herself at the possible ideas of what Elusive had come up with. She knew he could get rather eccentric with his outfits but hopefully he wouldn't use to many gems on her.

"All the flirtin' yesterday was just plain ridiculous as well. If he wants to ask me somethin' he should just do it. No need to butter me up like Granny's warm Sunday biscuits."

She reached the door to the boutique and walked in. Her arrival was ushered by the jingling of the bell on the door.

"Applejack I'm so glad you made it. Come in, come in." The white stallion walked up to her while wearing a pair of red glasses that were perched at the end of his muzzle. "I have a wonderful design that I think even you will love."

Applejack shrugged. "Ah don't really know if that'll happen but Ah'm willin' to do this for you."

Elusive shrugged and gave her a small smile. "We'll see. Now onto the dais darling, let’s get this magic flowing."

Applejack did as he instructed and stood on the dais. Elusive began his work by glancing over to several drawings sitting on a table and muttering to himself for a moment or two. Once he finished that he began taking measurements of Applejack.

While he was measuring her chest and waist she made a complaint. "Ah thought you did all this when all of us headed up to the Gala. Why you takin' them again?"

Elusive wrote the numbers down then glanced at Applejack. "Sometimes the numbers change. Ponies don't remain the same size all their life. They tend to get bigger as they get older."

Applejack's eyes narrowed and a small frown appeared. "You saying Ah'm bigger than Ah was a year ago?"

Elusive had turned back to his drawings when Applejack replied. He remained silent for a moment as he realized the dangerous position he had just landed in. "Uh, What I meant was... well, that is to say—"

Applejack began snickering at him. "Ah'm joking sugarcube. Ah know exactly what ya meant."

Elusive rolled his eyes and walked back to the mare with some cloth. "Hilarious. Now if you don't mind I want to make this dress."

As the stallion worked the pair talked about the local gossip. One of the last things to come up was the relationship of Berry and Fluttershy.

Elusive adjusted the glasses at the end of his muzzle and bit his lip as he worked on the dress at Applejack's middle. "You won't believe what happened yesterday."

Applejack tried to turn to face him but he forced her back to her forward position. "What happened? You prick yerself with a pin?"

While the farm pony chortled Elusive tightened the cloth. "Nothing so... simple. Berry asked Fluttershy on a date."

The farm pony felt her jaw drop. "What? Really?"

Elusive hummed the confirmation as he walked back to desk with the drawings. He shuffled the papers for a moment until he found the one he wanted. "Fluttershy told me yesterday at the spa. She was beside herself with joy."

Applejack let out a low whistle. "Well Ah'll be. Ah kinda had a feelin' that Berry liked her but... wow." She looked over at Elusive as he walked back to the dais. "Ah think they'll be happy together. Never known a nicer pair of ponies in my life."

The stallion nodded. "Agreed. It'll be nice to see them happy with each other. They have their first date this weekend. I think she mentioned something about a picnic. Berry's planning it so it’s bound to be wild."

Applejack nodded. Silence fell between them as the fashion pony set about working some more. Applejack watched from the mirrors and saw the bolts of cloth slowly change into something close to a dress as the hours passed. She was impressed at the passion and speed her friend worked with. She couldn't help but smile when he stopped and took a moment to look her over to make sure he was doing everything right.

The silence was broken when Elusive began work on the chest of the dress for what seemed like the thousandth time. "I really do enjoy our conversations you know."

She glanced down to see him with a needle and thread. "What?"

He gave her a quick look then returned to his work. "Our talks. I actually enjoy them."

She gave him a short laugh. "Hun, almost every time we talk be argue, and if we ain't doin' that then we're about to. Yer tellin' me you enjoy yellin' at me and me yellin' at you?"

He nodded in silence and cut the edge of the string. "I do. It's nice to have somepony to talk to and see a different point of view from." He got up from where he was and looked her in the eyes. "Can I be honest with you?"

She nodded. "Anytime."

He gave her a small smile that faded almost the instant it appeared. "Sometimes I... well, to be blunt I get lonely sometimes."

He removed part of the dress from her and walked to the sewing table. Applejack watched him with confusion on her face. "Lonely? How can you be lonely? You have Sweetie Belle, Fluttershy, and, heck, half the darn town that you talk to on a regular basis."

He nodded. "True, but none of them understand what I do. Whenever I talk to them about making a dress or a suit they just nod along and pretend to understand. I have nopony to talk to about the finer parts of my craft. None of them get it."

Applejack remained silent which prompted Elusive to continue. "I'm the only tailor in town and a majority of the ponies here don't even wear clothes normally so they don't even buy from me, unless it’s something special. What makes it worse is that every other pony seems to have somepony they can relate to when it comes to their talent."

Elusive stopped sewing and removed the glasses from his nose. "And when I talk about fashion they all look at me like I'm insane or something. I try my hardest to create something and they don't really care to ever think about it. To think about the time and effort I put into each piece. They just nod their heads and agree to get me to move onto something else."

Applejack walked off the small platform and went over to the fashion pony. "So what is it that you do? Tell me in yer own words."

Elusive looked at her for a moment and gave her a small smile. "I create, simple term but it means so much more. It's easy to make cloths but to create something that when they look in the mirror and think 'I look amazing.' That's what I do. I create to see them smile, to make them think that the world will look at them and tell them that they look wonderful." He stopped for a moment and gestured around the room. "That's always what it’s been about. To make them happy. Fame and fortune are merely benefits, side effects of doing the job well."

He looked at the orange mare and sighed. "Here I am rambling to you about something pointless when I promised to make this quick. I do apologize."

Applejack placed her hoof on his shoulder. "Don't. I understand what you mean. When somepony tells me that all I do is gather apples it makes me wanna buck 'em into next year. It's hard work to produce the food we do and to see it making ponies happy is the greatest accomplishment a farmer could ask for. It's an art making ponies happy."

Elusive nodded and beamed at the mare. "Well said. Thank you. Now, let’s finish this dress. I did promise you lunch and it’s almost one o'clock."

The pair walked back to the platform and shared a look with each other. Applejack smiled and blushed when their eyes locked. Elusive guided her back to the center and began the final touches on the dress. All the while he worked he noticed that Applejack kept glancing at him and he found that he couldn't keep himself from doing the same.

As the clock neared two o’clock Elusive covered the mirrors and pulled out a make-up kit. Applejack looked at the mirrors then at him with her eyebrows raised.

Elusive noticed this and gave her a knowing look. "The big reveal is always best when they can't see the final steps."

He moved in front of her and started working on her make-up. Applejack gave a small groan. "Do you really need to use that stuff on me?"

Elusive gave a small nod as he applied a small amount of blush on her cheeks. "I believe that make-up helps highlight the natural beauty. The less you need the more beauty the mare or stallion has."

He moved on to the Applejack's other cheek and applied very little blush. He looked at both sides of her face and gave an approving nod. As he put the brush away Applejack look confused.

"Yer done already? Why?"

Elusive looked at her with a look that simply stated 'You already know.' He waited for a second as the confused looked became one of realization then of affection. She began to blush and looked away.

"Yer such a flirt."

He chuckled and circled around her as he replied. "Only for you."

If her cheeks weren't red before they definitely were now. She tilted the Stetson hat down to cover her face so he couldn't see how red she was getting. After Elusive finished his circle around her he used his magic to remove her hat and place it on his own head.

She reached for it but he stopped her. "I just need to do your mane real quick then we can move on to the finale. After that we can head out for lunch."

She gave him a stern look. "Just don't do anything to fancy with my mane. Ah don't want it to be in my way when Ah work."

Elusive nodded. "Not to worry. I had something very simple in mind." His horn lit up once more as he removed the band holding Applejack's mane in a ponytail. He ran a pair of brushes through her mane a few times until it was relatively straight then moved it all to one side.

He stopped for a moment and muttered to himself. "Now that's perfect. No..." He brushed the straw colored mane behind Applejack's ear. "That's perfect."

He took a few steps back and looked at the transformed mare. He was stunned to say the least. She looked wonderful as the dark green dress hugged her curves in all the right ways. He looked at her for a few moments unable to really do anything than stare at the beautiful mare in front of him.

She looks amazing. I can't believe how beautiful she looks. Maybe I should try to get her to model for me more often. As the thought passed through his head a tiny voice at the back of his head told him it wasn't because of his dress or the make-up. It was because she always looked that way but it was drowned out by his mumbled speech.

"Wow... just wow."

He felt his heart warm at the smile she gave him. She spoke and he failed to catch it. "Come again?"

She shuffled in her place and spoke much louder. "Ah said can Ah see what Ah look like. You're gawking awfully hard at me right now."

It was Elusive's turn to blush. He gave a small cough and nodded. "Of course. Get ready to be amazed."

He used his magic to grab the covers on the mirrors and he pulled them off. Applejack gasped as she saw herself in the mirrors. She stood there with her hoof on her chest as she looked at each of the mirrors in turn to look at herself at every angle.

"Ah... Ah... Ah look amazing."

Elusive walked next to her and tilted the Stetson hat on his head back. "Indeed you do. However I think there something missing to make this complete."

Applejack looked over at him. "What's that?"

The stallion didn't respond. Instead he placed the hat on her head so it fell in her face. She lifted it up out of her eyes with a small chuckle and was about to respond to him but he was suddenly very, very close to her.

He smiled at her and moved even closer. "A dashing stallion to be your escort."

And with that he leaned in and kissed the surprised, blushing mare.