--Day 1--

So, I travelled to Ponyville because I used to live in Baltimare, but of course that town sucked. Everyone there kept on worrying that there was going to be danger, albeit there was none. So I packed my bags and headed on the train out of there and into the town mentioned before.

When I got off the train I saw a certain Mare standing next to me. She had a blonde mane and her body was all grey. When I looked at her flank, I notice she had bubbles for a cutie mark. Somehow it was endearing yet I couldn't be distracted by the need of love. "What's your name?" the mare asked me.

"Uh... I don't have one right now. You can just call me Jack," I explained.

"That's pretty awesome. My name is Derpy Hooves," she disclosed. "My cutie mark represents my... personality."

Her face started to lower, indicating a sign of embarrassment. I simply smiled because I thought it looked cute, and asked if she could come with me. Her face brightened up with delight as I held her hand and we walked to the town hall so I could get some form of identification. I made sure my backpack was on me and headed there.

When I got there, I noticed the Mayor Mare was there, and I know it's her because I was asked to come to her when I got to this town. She looked rather friendly so I decided to show her my ID to be converted into Ponyville ID. She looked at the ID and took it and gave it to some people.

"So, when will it be back?" I asked.

"In 5 minutes, because all we need to do is renew the expiration date and change the town," she answered.

Derpy looked at me and blushed. "Hey... can I ask you something?"

I looked at her straight in the eye and smiled. "Yes?"

"Well," she stuttered. "I've been wanting to go the Grand Galloping Gala for a while now, and I was wondering if I could go with you?"

My stomach felt like butterflies. No mare has ever asked me to go to the gala with them, and I just met this pony a couple of minutes ago. I decided to speak up and agree to her answer. She squeed and we talked for a bit. By the time we were done talking, Mayor Mare came back with my new identification card. "Now you can be accepted as a true city of Ponyville."

I thanked the mayor and headed on my way. Derpy wanted me to follow her, so I did. I looked to the building she stopped at and it said "Sugarcube Corner". It sounded strange at first, but so does everything in my life. When we walked in, we saw a bouncing pony making something for the customers I guessed.

"Oh wow Derpy, who's this great guy!?" she said while sounding ecstatic.

"This is Jack; Jack, this is Pinkie Pie."

I looked at this Pink Pony, known as Pinkie Pie. She looked pretty hyper but I could feel there was a depressing backstory to any good Mare. She laughed happily at me and then grabbed my hoof. "Hey, did you know the Gala is in 4 days?"

"Well, no, but," I looked at Derpy while I said this. "Some other pegasus asked me to it."

Pinkie expressed disappointment at me and asked me if I wanted some food. I declined the request and headed on my way with Miss. Hooves. Somehow I felt a little bad about rejecting Pinkie but I have a feeling that she is going to have friends with her to support her.

I started to walk slower because I noticed the expression on Derpy's face, and it didn't look pretty. I asked her what the problem was, and she simply answered that, her job delivering mail hasn't come off to a good start, and she might get fired soon. We then noticed it was about to rain, so we headed inside her house.

Her house was awesome compared to mine. I only lived in an apartment and she lived in a 2 story house with a basement. She smiled and showed me her room, which had so much things in it, like every issue of the Ponyville Express and letters of recommendation.

"My room could... use a bit more work. I just don't know what went wrong with the wallpaper. I ordered Pink and got blue," she expressed in disappointment.

"Have you tried writing a letter back to them?" I asked. "That worked for me."

"I tried," Derpy replied. "But they said since I already put it on I couldn't get a refund."

I heard at knocking at the door. I quickly ran to it to save Derpy the trouble of opening the door herself. I pushed the door and saw a blue mare. She was wearing some outfit that made her look like a wizard, but I quickly ignored that. "What do you want?" I asked.

"The GREAT and POWERFUL Trixie wants to know if Derpy is home."

"Yeah, I'll escort you to her."

I walked over to Derpy's room with Trixie, and noticed she was standing so close to the window looking a little blue. Trixie decided to trot a little closer to Derpy. She patted Derpy on the back, while also trying to cheer her up. "Trixie detects sadness, but she doesn't think you should have it."

"I...I just don't know what went wrong," she sniffled loudly.

I moved closer to Derpy and also tried to cheer her up. "Don't worry, I'll help you to make sure you keep your job."

Derpy smiled and squeed. She let me and Trixie stay in the guest bedroom for now, because tomorrow we were going to help Derpy make sure she becomes the best mail-pony ever!

Author's Note

My first attempt at something at something like this, though the title has a darker reality behind it. By the way, the drawing will obviously be in first person so that means my OC won't show. I'm not too well at drawing so if you like to give a crack at drawing Jack then go right ahead. Oh, and the pictures will probably only be once per chapter. Also, there's now a visual novel I made based off of this chapter, skipping the Mayor's office because there's no puppet of the mayor.

Part 1 at least: https://www.dropbox.com/s/uuc76qqq6i19zkp/Attempt%20at%20Start-1.0-all.zip (It ends after the clouds.)