Editor: Tedious_Blizzard. Thank for you help

Alessio felt the anxiety; it was the same feeling of anxiety every time he started his first day of work. It is the cause of the constant economic crisis of his original world. He had done many jobs and several employment contracts before, gaining a lot of experience from them.

His heart rate increased more as he approached his workplace. This is his first job since his arrival in this new dimension. Alessio looked in the distance to the tall white building that was similar to a carousel from the outside, with a large cylindrical shape with decorative pillars aligned to the lower and upper exteriors. Alessio couldn’t see them much as the sunlight’s glare from the white building slightly blinded him.

Several weeks had passed since Alessio mysteriously appeared in the land of Equestria, after being suddenly teleported from his home in the city of Florence in beautiful Italy. Everything happened too quickly for him to comprehend. It all started like any other normal day. Alessio got up, ate breakfast, went to work, came back home, and then just reclined for the rest of the day- nothing much more. Then suddenly everything seemed to go to hell. Alessio did not remember exactly what happened aside from experiencing a strange feeling, akin to being thrown into a void, and woke up at Equestria. That had happened weeks prior as now Alex was there in front of the immaculate white door, lifted his fist and knocked on the door.

He waited patiently for the person, or rather pony, on the other side of the door. He gave a quick glance to his old dive wrist watch. He came to work early as he wanted to give a good impression of himself to his new boss.

As expected, Alessio reflected on the time when he came to this strange world, after the pandemic that had happened at home (that he still couldn’t remember much of), the only thing he remembered was that he woke up next to a gloomy forest near a quaint town covered in cuts and other injuries. After that he travelled to meet the locals and hopefully get some directions. But, in some ways, it was not as bad as one might think. Firstly, when he met the ponies, as they called themselves, he found that they had more human qualities than pony.

Aside from being the only fully human person in a world full of sort-of-human ponies, a local did try to help him. When a purple unicorn found Alessio, she presented him to the rest of the town and showed them that he was not a threat to them and after that they welcomed Alessio with open arms, or forearms in their case. When he had recovered the injuries he sustained, including a sprained ankle which had prevented him from walking for 10 days, he met one of the Equestrian princesses by the name of Celestia and asked her if she can send him home. Unfortunately, she could not help. Since Alessio’s arrival was very peculiar and very sudden, going back home was almost impossible with their limited amount of information, even with the aid of the princess’ divine Alicorn magic.

So shocked at the notion of never returning home, he became concerned about his family, dear friends and everyone else he knew of. He had accepted the harsh truth after a week; thanks to the help of the purple unicorn mare he had met, she made him fully understood his current predicament of living in new world. So, the next encounter with the princess, he mentioned that he had done a lot of work back home and would like to have a job as he needed money. Alessio explained to her that this can prove that he was neither a threat nor will he hurt her subjects, and that he had worked for his mother for years in a tailoring shop by helping her out and learning what to do. The princess was happy to help Alessio find a job where his skills would be appreciated and used, with the possibility of other jobs that could test his skills with time. Since then, he had lived in the small town of Ponyville.

In fact, Alessio had not lied; he did have quite a lot of experience as a tailor by just working with his mother and learned the ways of a good tailor. He had other skills other than tailoring as he learned from the other jobs he had in the past. So Princess Celestia found him a job at Carousel Boutique to work for Rarity, which subsequently was one of the keepers of the Elements of Harmony. While the devoted student of Princess Celestia, known as Twilight Sparkle or that helpful purple mare, allowed him to stay in her library/home, this accommodation was temporary until he had gained enough money to buy his own house.

Alessio heard the noise of the lock releasing which put him back into reality. Taking a deep breath, he adjusted his glasses, and pulled his light brown hair back. He dropped his arms to his sides ready to meet his new boss (even if he was a friend) Rarity Belle, the fashionista of Ponyville.

When the door opened, Alessio held his breath, and simply stared at the beautiful mare in front of him.

The immaculate white alabaster coat, beautiful hourglass figure with curves at the right places, the smooth long violet mane with a curl at the end, eyes shining like sapphires outlined with blue eye shadow, all gave a breath-taking beautiful look. She wore a semi-transparent evening violet silk gown with magenta edges, and her chest revealing a bust sporting the glorious double D size. Her curved hips and sinuous legs were shown off due to the semi-transparency of her gorgeous dress. While ogling her, Alex also noticed the three blue diamonds on her hips, her cutie mark.

The beautiful mare blinked in surprise, before smiling gently at him to ease his anxious form.

"Oh! Hello there, you must be Alessio. You've come on time and dressed smartly," she said, before quietly adding, “Just like a gentlecolt.”

Alessio smiled at her and tried to hide his nervousness, even though it was too obvious, "Yes, hello to you too Miss Rarity. I know that it's good to arrive on time as I hope I won’t disappoint you,” he said with smile and a polite handshake.

"Well don’t stand outside Alessio dear, come on in," she invited while further opened the door and giving way for him to enter.

"Thank you Miss Rarity," he replied with slight tension in his voice, and walked through the doorway and took a look inside her home.

In addition to the entrance and lobby, which also looked as if to serve as a waiting room for her customers, the main room was right in front of them which looked a lot bigger on the inside than it was from the outside.

The room indicated its purpose was to do with design and dress making. It was also well stocked with materials for clothes and other necessities for a tailors shop such as multiple mirrors, dress dummies, mobile screens, sowing machines and even a small stage with some boxes on it. To the right of this stage there was a staircase leading upstairs. At that moment Alex remembered that his mother’s shop was downstairs while their living area was upstairs.

Alessio hears the soft clop of Rarity’s hooves on the parquet floor coming towards him as he gazes to what will be his workplace. He could work with this setup.

Rarity’s violet gown and silky tail comes into his view to his left and Alex faintly blushes. She moved past him with her body sinuous body, graceful legs and rounded ass, and slightly swung her hips and tail in a hypnotic way.

She turned her head and looked at him; as soon as Alex noticed her gesture, he quickly looks elsewhere as he fears of being caught.

Rarity gives a cute giggle to his behaviour, "When you finish seeing the store and I haven’t come back yet, you can expect to see me upstairs. I won’t take too long darling as I would still need your help soon, though you can ask me if you want something you know," she said and gave Alex a seductive smile.

"Crap, she knows," Alex thought, giving an ignorant smile, "Alright, I’ll finish looking around in a few minutes."

Rarity chuckles as he moves away to explore more, his slight blush was still visible on his face.

The white mare then walked up the stairs, her arms around her hips, and her hips swaying in a hypnotic motion, and just before she reached the top she looked down at him with a wink and a lecherous smile.

As he looked around the store, Alex noticed the custom-made instruments next to the stage, carefully measured to fit her needs. Precise measuring tapes were next to several small pillows with needles of different sizes sticking out of it and large paper sheets with drafts for new clothes, such as dresses and suits, already in the works. Alessio also noticed several drawings of finished clothes with great detail. His new boss must’ve been very talented. Alessio felt some nostalgia of home as it looked fairly similar to his mother’s shop. He closed his eyes and shook his head, no need to get sentimental. The customer list was also pinned in the same place as it was back home, though with different names and orders on it.

"I’m back darling; I just needed to freshen up. I hope you took a good look as I would like to start work now, “said Rarity, coming down the stairs.

Alessio turned his head to look at her and his eyes widened at what he saw. He was looking at a beautifully dressed mare, sporting a blue shirt that revealed her shoulders, short sleeves with a V neck. The shirt also seemed slightly small for her as her beasts were squeezing up to it and making them look at least twice as large. Around her slim waist was a faux leather belt, a short white skirt with her cutie marks on both sides, dark blue stockings stretching up to her thighs and stylish knee-high black boots.

Alessio nodded to her, trying and failing to conceal his blush as he admired her body.

Rarity gave the same lecherous smirk before lighting up her horn and turned around the small sign on the door from ‘Closed’ to ‘Open’. She slowly walked down the stairs.

"Now the Carousel Boutique can be officially open for any customers, they shall soon arrive so we need to get busy darling. I aim to create masterpieces for everyone no matter how much they pay me; I try to make everyone pleased and happy,” she said while slightly leaning on the small bench at the bottom of the stairs and looking at the dummies and the interior with a small smile. “Even performing simple repairs or decoration an article of clothing that was once bland must be done to the highest standard. I am trying to expand to Canterlot so I will need the best feedback, “she proclaimed with a wistful smile.

"With your wonderful attitude and dedication I can see why you have been called the best pony in this business", he said with a smile.

"You really are too kind Alessio", she said giving him a brief small of gratitude before becoming slightly more serious.

"By the way, before we start, I wish to tell you this: you do not have to call me ‘Miss Rarity’ all the time. Please Alex, you may just call me Rarity, all my friends do.”

"Okay, Mi-ahem, Rarity," he quickly corrects.

She flashes a brief glance to the front door before giving her full attention to it. Just a second later the small bell at the door ringed softly signalling a client's entrance to the shop.

Alessio is astonished at the customer's figure, even though he has seen it before. Her magenta tank top shirt sits upon the figure’s curved hips and shoulders. The hips were wide and the thighs were toned but still slim. A black and red short skirt with plaited patterns and long grey stockings stretched from her feet to underneath her skirt. Regular light blue gym shoes adorned her petite feet; which all made her look a bit like a school girl. Silky smooth lavender fur covers where the clothes don’t reach and her mane and tail are a beautiful dark blue-but still can be mistaken for purple- as well with bright pink highlights going through the middle.

He looked back up to her chest and her slender arms, a solid D-cup bust he imagines. Alex looks at her face and once again is graced with beauty. He has always been good friends with this person as soon as he came to Ponyville. As he gazes up to her sparkling lavender eyes, he feels hypnotized by her orbs as she winked at him. The figure was not as sexy as Rarity, but sure does win the lottery for the prettiest.

Alessio smiled warmly at his best friend Twilight Sparkle. She was the first person he saw and that was also willing to help him, firstly by taking him to the hospital and then by introducing him to Ponyville as not a threat, but a friend. Luckily, she was also Princess Celestia’s student so he was quickly accepted as Twilight was a very trusted and respected pony in the town.

"I see that you have both been acquainted with each other already, I hope you two become great friends. I know that I already am, "Twilight said as she graced both him and Rarity with a friendly smile.

"Well yes, he is quite the charmer so I think we will get along well. Though we have just opened the store darling so we might get swarmed with work soon. Alex is here so it should not be so taxing." Rarity responded with a grateful glance to the human.

Twilight briskly walked up to Alex and they both embraced each other with her arms reaching behind his neck and squeezing him tightly, which almost lost Alex’s balance.

While it was wonderful her two friends hug, Rarity had a business to run, "Not to be rude or anything Twilight darling, but do you need something or is this just a quick visit to your friends?"

Twilight broke off the hug and faced Rarity with a smile, "Actually Rarity, I was hoping you could help me out. I want some new casual clothes for indoor usage and maybe even some new underwear.”

"Certainly my dear, let me get my measuring tape first and sketch sheets," as Rarity said that she put on her glasses and took the required equipment from a nearby table and turned towards Alex.

"As I start to come with ideas Alex, I want you to give me accurate measurements so that we can get this done faster,” she asked of the human as he took the tape and began to measure Twilight while trying not to make the situation weird or uncomfortable.

Before Alex could start measuring, he remembered something from the time when he worked for his mother, "Uhh Rarity? Are you sure it is alright of me to measure Twilight? I mean normally females measure females as you need to take off most of your clothes to get an accurate measurement," Alex feared to embarrass Twilight which would also give him a bad impression on Rarity.

Rarity looked up from her sketching and gave a reassuring smile.

"Oh Alex darling, don’t worry about it! Our culture is different to yours in many ways as you know already and this is one of those differences. I’ve seen many stallions in the fashion business measure mares and never have I heard a complaint. I can assure you that it won’t be a problem for you to measure mares. Even if it was taboo, I don’t think Twilight will mind anyway, "she clarified to him and immediately got back to sketching.

Alex was not very convinced. However, this is not Earth so he will just have to deal with it. He took a deep breath and looked at Twilight. Both Alex and Twilight were slightly blushing, but both were for different reasons. Rarity hummed a song, sat down at the curved desk with two designs already done, and silently observed her two friends.

There was a silence for a few seconds until Twilight broke it with her soft tone, "Listen Alex, I know this can be awkward for you but I really don’t see this mind you seeing me half-naked. You will be doing this many more times while working with Rarity so it will get easier if you start right away. You are a kind man so I trust you with this."

Alex breathed out and adjusted the collar of his turquoise shirt, "Alright alright, let’s just do this."

Twilight walked over to the stage and then followed a bright violet flash which made Alex turn his head for a second. When the spots in his eyes receded, Alex’s jaw dropped for what felt like the hundredth time that day. Twilight’s dress was gone and was left in her lacy black underwear, a black bra that barely managed to hold her breasts in and her grey stockings that just emphasised her toned legs.

The purple unicorn blushed while rubbing her forearms together under her chest, making her breasts look bigger than DD-cups.

Alex couldn’t believe what he was witnessing, "S-shall we start Twilight? If you feel too uncomfortable tell me right away so we can finish this later, “he asked nervously while still trying to be the polite employee.

The purple unicorn nodded her head, "Don’t worry about me, now let’s start!."

To avoid staring at Twilight’s chest, Alex put himself behind her to get all the measurements. He started with using the tape measure for the arm length, width and depth and then the same with the arms and legs. He had to measure every limb and part of Twilight and also different postures/positions of those limbs. After a part was measured, he would write it down on a block of sticky notes. The last part he didn’t measure was the chest. So far everything went well and Alex was glad for it, until Twilight’s silky tail wrapped itself around his thigh.

Immediately Alex gave a jerk reaction and accidentally put the tape against the exposed part of her breasts. To not look like a pervert he just carried on as if it was intentional and nothing lewd. Twilight slightly flinched at the cold touch of the tape measure and bit her lower lip as her tail wrapped more around Alex’s thigh more tightly.

Sensing the increase in pressure Alex got worried he did something wrong, "Are you okay Twilight?" he asked, holding the tape together with one hand and the other writing down the measurement for that part.

His delightfully warm fingers lightly brushed Twilight’s exposed back, earning a small pleased moan.

“Can you do the shoulders in a bit more detail Alex? I want the bra to be perfect so it will be more comfortable, this one I have to adjust every few minutes. Guess that is my fault for not shopping from Rarity at first.”

Alex felt his cheeks burn, the prospect of gliding his hands and tape measure over those beautifully crafted shoulders made his thoughts veer off into ‘more-than-friends’ alley. It didn’t help when Twilight’s tail started to brush itself up and down his thigh, making his thoughts even more dirty.

The human shook his head to get rid of the mental images. He was embarrassed that he even dared to think of a friend that way; especially one that has been so kind to him and inadvertently gave him this job to prove himself that he had the capacity to be a good Equestrian citizen.

"Will do Twilight," he simply responded.

Not one to disappoint he began measuring her shoulders, only this time he didn’t measure just the general but also where her bones would’ve hit the straps and many other things that would’ve made Twilight’s bra more uncomfortable.

The process only took a few minutes, but it felt like an eternity as he had to make Twilight move her shoulder posture and arms at times to find the right area where the straps for the bra would be comfortable. This also meant lots of skin contact, making the pair constantly blushing.

Rarity just gave amusing glances at the two every now and again as she could just feel Twilight restraining herself from pouncing on Alex. Twilight had sensitive shoulders after all.

Lavender perfume flooded Alex’s nostrils as he worked and to worsen the situation Twilight’s tail didn’t relent on its up-down rubbing notion. In fact, it seemed to speed up and go closer to his groin each time.

This made Alex Junior beg for freedom from his underwear confines. Pretending not to notice her movements were becoming futile. Both became quite aroused for a ten minute clothes measuring session.

Over the weeks Twilight had gotten to know Alex more and more. With this came deeper feelings than friendship and suppressing them for the right moment was becoming more difficult for her time went on, especially now. Her internal conflict on whether being a client at the moment or proclaiming what she felt for him raged on. Despite his rough introduction to an uncertain and strange world, Alex made friends quickly and was remarkably handling his situation well, even becoming friends with Princess Celestia! Seeing him sad had made Twilight hurt, and wanting to know him better as a friend. This had grown past the ‘just friends’ status in her mind. She hoped to tell him this today as she has finally gained more confidence. Also, she read a book about it.

The purple unicorn shivered at his fleeting fingers across her shoulders and occasionally her back. His warm breath on her shoulders showed his close proximity her.

Twilight shivered at his magic touch on her, taking measurement and ignorant to how much she wants him. Her breath hitches as he touches a particularly sensitive spot which made Twilight slightly turn her head to give him a seductive look as she also pulled him closer with her tail. This elicits the human to stand still as a rock, shocked at her actions but still oblivious to its reasoning.

Alex meets her enticing magenta orbs and feels the passion and love emit from them. Ever since he mysteriously came to Equestria and met Twilight he began to fall for her as well, but held back by his morals of liking a pony romantically. What would his mother say if she saw him? An animal fucker? Well, his mother wasn’t here and the more he stared at her the more he sees her as a person, not an animal.

With that revelation in mind, he cups her cheek, closes his eyes and meets his lips with hers.

The moment they joined their lips, Twilight’s eyes became as big as dinner plates at the fact that Alex was kissing her at long last. She closes her eyes to fully enjoy the experience and faces her boy towards him so it won’t be an awkward position to kiss in. Her hands grab the back of his head as Twilight really gets into it.

They French kiss for at least a minute until Alex puts his hands on her hips as both re-open their eyes. When the brief romance was over, he just realised what he did, not only to his best friend but also to his client at the moment.

"I'm so sorry Twilight, I-I don’t know what came over me just then,” Alex tries to give excuses as he avoids her gaze, too embarrassed at what he did.

He calls himself an idiot, how could he do that?

Before he could beat himself over more, Twilight moves her hands to around his neck and gives him a reassuring smile, "Don’t worry Alex, I was hoping you would do that to me. Took you long enough to do so with all that teasing," she whispered to his ear and pressed her almost fully exposed chest to him, she breasts acting like pillows made of Egyptian cotton.

For some reason during the whole ordeal Rarity did not say a single thing, nor did she give any attention to it. Rarity snapped her fingers to get some attention, she was still working after all and time was money.

Twilight backs off Alex and with a flash she magics her clothes back on herself. Her face has gone from seductive to neutral as she faced Rarity.

As much as Rarity tried to ignore the kissing, she still had rose-tinted cheeks from watching her two friends. The room also became quite heated during the time so Rarity thought it was a good excuse to loosen up her two top buttons, just enough to reveal the top of her cleavage. In that time though she managed to finish her sketches of at least three designs, she wasn’t called one of the best fashionistas/tailors for nothing after all.

Rarity made a stoic face before addressing Twilight, "Twilight darling, I have just finished the first drafts for your nightwear. I would like to know your opinion of them. All of these clothes will be made of silk or cotton to be as comfortable as possible,” she gave a brief pause until adding,” Also, if you could choose a design now that would enable me to get to work so you may have them by tomorrow,” while she liked having Twilight in her shop, she still had other orders to finish. Hopefully she wouldn’t have an all-nighter again.

Alex notices something,” Did she just look angry for a second there? Or was that jealousy,” he thought.

Twilight sets her eyes on the A3 sheet with her nightwear on it. Rarity had the pad positioned in such a way that Alex didn’t see what was on it, and luckily he didn’t try to look. Twilight then approaches Rarity while still looking at the designs.

As they were both doing that, Alex tried to comprehend what just happened. Did she share his feelings, or was it pity-love? Was it even genuine to begin with? These thoughts swirled within his head and came back to reality to see Twilight point to a design in front of her, that he couldn’t see much to his dismay.

Twilight didn’t pick the warmest or the most practical design, instead she pointed at the erotic lingerie with only scant parts covered. She swished her tail, knowing that Alex would see, and giving him a hint at what she wants.

Rarity raised an eyebrow at the choice, feeling a sense of completion start between the two. “Interesting design darling, but it will be done”, was her comment on the matter before returning to her trademark smile.

Immediately after that, Rarity got to work by levitating blue cloths, black lace and other materials necessary. Seeing Rarity getting to work Alex joined her on the sowing machines, ready to begin with her instructions.

Twilight whispered to Alex so Rarity didn’t hear, “Make sure you come to the Library when you finish, I want to share more than a kiss with you”. This caused Alex to blush as he was no stranger to these types of innuendos, yet instead of being disgusted he was excited.

Twilight came to make an order and maybe have a chat, but her schedule was strict and busy. “I’m sorry Rarity for being in a slight hurry but I must go,” she was already by the door and grasping the handle.

“Oh very well then,” Rarity sighed at her friend leaving, “Goodbye Twilight and make sure you come over tomorrow though.”

With a wave and quick air kiss to Alex, Twilight left. Now only Alex and Rarity remained, both that would be busy for the rest of the day on dozens of orders from multiple clients.

With that prospect in mind, "Alex darling, just to be clear on our schedule, I was thinking of nine hours of work every day starting from eight in the morning. You may have Sunday and Wednesday off and today you will work just three hours to get a grip on the workshop”. She paused for a moment to pick up and a fallen scissor, “Does that sound agreeable to you?”

“Ummm, well yeah. I don’t have many hobbies or any other jobs so yes that timetable works for me”.

Rarity liked his response, “Wonderful! Oh and before you carry on, I would like you to buy me some chocolates. I know it’s a tab bit strange but I have quite the sweet tooth”.

"Okay, I'll get it right away," he replied with a confused tone at this strange request.

Rarity gave him a six Bits, Bit being the currency of Equestria. And with the money in hand and the purpose in mind, he walked out of Carousel Boutique to the market.

A quarter of an hour later Alex returned to the boutique with a box of novelty Belcolt dark chocolate, he wanted the best chocolate for his new boss if the name implied the same quality a Belgian one would.

As soon as he walked in, Rarity recognised what he was carrying. "You know you chocolate it seems,” she put a hand on her chest, “You spoil me Alex."

The white unicorn smiled at him and caressed his arms when she was taking the box, trying to be as sensual as possible while also licking her lips and adjusting his tie to be more loose.

"You may go back to work darling, I don’t have any client appointments for the rest of the day. I will however need to test what you know already and how well you do it. Call it a quality test if you will.” Her tone softened, “Don’t worry if you mess up on anything Alex, I will simply give you tasks that you can do good. I won’t fire you on the first day; it would be un-lady like!”

Alex let out a tense laugh, “Thank goodness for that at least, I won’t disappoint you Rarity”.

“I know you won’t”. With that Rarity collected some scraps of material that won’t be used for a client’s order and proceeded to give him tasks and challenges.

He passed all of them.

Throughout the afternoon, only a few customers came by and they were all for minor repairs; to with Rarity showed them generosity with her low prices or no payment at all. Alex even talked to a few of the clients and made a few friends! So far, life was turning out for the better for him.

At five in the evening when it was starting to get dark, Rarity closed the shop and bid Alex a farewell and a chaste kiss.

When the shock wore out, Alessio began his trek to Ponyville Library, remembering Twilight’s promise.

Hi guys. so this and my first fimfiction. it should have been a clopfic since this chapter but I prefer to leave it to the next chapter with Twilight Sparkle. frankly I will not be sure I will continue it.
My Oc has apart from work to tailor other occasional jobs gained by experience of its world of origin. as "handyman" and in the title. but I want to make sure that I hope history can enjoy you. welcome to comment for advice. situations suited to history.
Thanks again for reading. it means very much to know that you have also read my thoughts. you will see the next.