You gotta say, wearing khakis all the time was really getting to you. You were never the type of guy for formality, you enjoyed the more casual and comfortable lifestyle. Didn’t really suit your job back at home, though. It was late at night, three in the morning to be specific. You looked at your watch and sighed at the fact that you had to go out this late to not be noticed by the residents of Ponyville. Maybe it would just be easier to go into the center of town in the afternoon say what’s up. Nah, fuck that. Fluttershy didn’t want you leaving the cottage late at night, so you waited for her to pass out before you left. You were currently walking through town looking for Rarity’s boutique, maybe she could be generous enough to make you some new clothes. You notice a town map by a street lamp and look it over. You see a little dress icon and assume that it was what you were looking for. You take a mental image of the map and do your best to navigate your way to the boutique.

A few minutes of walking later, and you arrive at the Carousel Boutique. To your surprise, the lights were on. Well, at least you didn’t have to knock on the front door until you woke her up. You looked inside the window, and saw Rarity at a table working on a dress. You gave the glass a small knock, which made Rarity jump. Upon seeing you, she walked over to the door and opened it.

“Anonymous?” She asked in her ladylike accent. “What brings you here at this hour?”

“Well,” you said, scratching the back of your head. “I do apologize for coming out so late, miss Rarity. I didn’t wanna be seen by any ponies so I waited till a later hour.”

She smiled at the fact that you called her “miss”. “Well I suppose I don’t mind, you seem to be well mannered right off the bat, darling.” She Said. “What May I do for you?”

“I was hoping that you might be able to help me with my clothing.” You say, looking down. “I do apologize again for coming out so late with a big request. I hope you don’t mind.”

“Oh, not at all.” She Said, beckoning you to come in. “It is rather late for me to do anything right now, but I am closed tomorrow so I will definitely fulfill your request.”

You smiled at the thought of having new clothes. “Thank you so much, miss Rarity. It’s greatly appreciated.”

“Not to worry, Anonymous.” She Said. “I can’t reject you when you’re being on your best behavior around a lady can I?”

“Heh heh. I guess not.” You say. You thank the lord that Fluttershy talked about her friends, especially that Rarity likes to be treated like a lady. It was definitely working in your favor.

“Would you like to stay here for the night? I have a couch in my bedroom.” She Said, pointing a hoof towards the upper floor.

“Oh, that’d be great!” You said. “I can’t thank you enough.”

“My pleasure, Anonymous.” She Said with a smile.

“You don’t have to be so formal with me, ma’am.” You said. “You can just call me Anon.”

She let out a small giggle. “If only the stallions here were as kind as you.”

“Well, treat a woman like a lady right?” You say with a shrug.

She gives you a small blush and waves you off. “You’re too kind, Anon. Here, let me guide you upstairs.”

“Lead the way.” You say, following her. She led you up to her bedroom and grabbed a blanket and pillow from her closet with her magic. You sat down on the couch and took the covers and pillow from her. “Much appreciated.” You say.

“No problem!” She Said. “I’m going to finish my dress downstairs, but I’ll be up once I’m done. Make yourself comfortable.” She then turned around and went back downstairs. You got up, turned off the lamp that was illuminating the room, and got back on the couch. You rested your head on the pillow and thought to yourself a little bit.

“I really don’t enjoy formality, even while speaking. But I’d say it’s worth it in this case.” You say to yourself. “Huh, maybe I shoulda stayed here. I actually get my own spot to sleep, even though it’s in the same room.” You eventually closed your eyes and fell asleep.

***

You woke up to a small nudging on your arm. “Anon?” Asked Rarity. “I apologize for waking you, but I came to ask for your measurements.”

“Huh? Oh yeah.” You say, getting up from the couch.

“Follow me, please.” She Said, going downstairs. You entered the main floor, and saw that all the curtains were closed. “I understand you like your privacy, so I thought I’d make the place a little less visible.” She Said, giving you a smile.

“You’re the best, thank you ma’am.” You say. “Anyway, where do we start?”

“Well I do certainly apologize, but I’ve never done measurements on somepony like you.” She said, levitating some measuring tape with her magic.

“From my experience with getting fitted for suits, limb length and the width of my waist and torso should be all you need.” You say, getting into a T-pose. Heh heh, T-pose. The Halo theme song started playing in your head upon thinking about it.

“Alrighty then, let’s get to it!” She Said enthusiastically as she began measuring your body. “So what exactly do you plan on wearing, Anon?” She asked while recording your measurements.

“Well I’m not a very classy individual.” You said. “I was hoping to get something a little more casual, if you didn’t mind.”

She looked a little disappointed at your request. “Well I was certainly expecting you to be a very classy type, considering how you treat a lady.” She Said. “But no matter, what is your definition of casual?”

“Yeah, sorry if I’m not what you expected me to be.” You say, scratching the back of your head. “But the shirt can be identical to the one I’m wearing now, and for the pants I’d like shorts, mesh preferably. And as for footwear, a regular black pair of cotton socks would work.”

She nods and takes note of your request. “Okay, and how long are these shorts you speak of?”

“Down to my knees would be great.” You said. “And I understand if they aren’t super good, I know this must be new to you.”

“Don’t underestimate my skills, darling.” She Said with a smirk. “I’m the best at what I do.”

“Alrighty, we can put that to the test, darling.” You said, mocking her voice. She let out a small giggle and looked at you with a challenging look.

“Is that a challenge I hear?” She asked, raising an eyebrow.

“Perhaps.” You say with a shrug. “Let’s see what you can do.” Rarity then got to work, picking out the materials and moving to her sewing machine. You saw the determination in her eyes as she carefully stitched your clothing together, looking at yours every now and then to get an idea of how it should look. Roughly an hour later, your clothing was done. Rarity hands you your new attire and you gotta say, you were impressed. The clothing looked exactly like something you would get from home, and she even put a small diamond on each piece, signifying that it was her work. “Hey, that’s pretty good.” You said, doing your best to impersonate iDubbbz. “Would you happen to have a changing room around here?” You ask Rarity.

“Yes, right around the corner, darling.” She says, pointing in the direction of the rooms.

“Thanks, be right back.” You say. You enter the room and swap your current clothes with the new ones. Perfect fit. You walk out of the changing room and give Rarity a smile. “Gotta give credit where it’s due, these are perfect.” You say. “Thanks a ton!”

“It’s no trouble, it was my pleasure.” Said Rarity.

“How much do I owe you?” You asked, taking out a small bag of bits that Fluttershy gave you.

“This one will be free of charge, Anon.” She says, waving off your question. “Consider it a welcoming gift.”

“Are you sure?” You ask. “I’d hate to have you go through all that work without some kind of payment.”

She giggles and nods. “You are truly a gentlecolt, Anon. But I insist.”

“Oh, well thank you miss!” You say, putting the bag of bits away. “You are truly appreciated.”

Not a second later, you hear the front door open. You quickly turn around thinking you’ve just been exposed, but calmed down to see that it was only Fluttershy.

“Oh, there you are.” She Said. “I was worried about you.”

“Sorry for leaving, Fluttershy.” You said. “I just really needed new clothes and I didn’t wanna be seen in the daylight.”

“It’s okay.” She Said. “A note would be nice next time... if you don’t mind, that is...”

“Of course, it won’t happen again.” You said.

“Hello, Fluttershy!” Said Rarity, trotting over and giving Fluttershy a hug. “How are you today?”

“I’m doing fine, thank you.” She Said.

“I hope Anon has been treating you as well as he has with me,” Said Rarity, glancing back at you. “He’s quote the gentlecolt if I do say so myself.”

“Yes, he’s very nice.” Said Fluttershy with her usual tender smile. “It’s been nice to have a guest around lately.”

“Yeah, she’s a great host.” You add. “I have no complaints.” Fluttershy have a small blush and looked at the floor shyly.

“Would you two like to stay a while?” Asked Rarity. “I’m making spaghetti for lunch!” You smiled at the thought of something besides a salad or veggies being eaten.

“That’d be amazing, I’m all for it.” You say. “What about you, Fluttershy?” You ask.

“Yes, that’s fine.” She says.

“Great, it’s settled then!” Said Rarity. “I’ll get to cooking right away!” She then left to make her way to the kitchen. You liked this Rarity pony. Sure, she was kinda preppy and too ladylike for you to hang out with her regularly, but she was certainly very generous, and you appreciated it.

“Hmm,” you thought to yourself as you sat down in the dining room next to Fluttershy. “Maybe I should get to know the other four ponies, I definitely think I could use a closer friend.”

Author's Note

I think this chapter was kinda iffy, but I plan to have the next few chapters involve Anon having some sort of interaction with the rest of the main six. Hope you enjoyed, more chapters real soon!