Silent Forest. [~needs grading~]. all comments are welcome

Author: Slumboo

Notes: This is my first URPG story and I'm pretty eager to see how it works out. I thought I'd start off nice and easy.
Target: Caterpie: 3k-5k, Easiest.
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"Cleffa, come back...please Clef, you know I need you."

Jay looked at the large forest looming ahead. Cleffa had walked in moments earlier and wasn't responding.

"Alright Clef, I'm coming in."

Jay took a deep breath and walked in through the forest clearing. A woman was standing at the edge.

"Hi, welcome to Viridian For-"

"Have you seen my Cleffa?"

She looked annoyed and Jay saw a vein bulging in her forehead. She glared at Jay.

"As I was saying welcome and enjoy the Forest and no I haven't seen your Cleffa, before you ask again."

She gazed down at Jay, he looked on the verge of tears. She put her hand on his shoulder trying to comfort him.

"Don't worry Pokemon rarely enter this forest unaccompanied. The other Park Rangers will know where your Cleffa is."

She gave him a reassuring smile and took out a small cell phone.

"Sorry to bother you Eugene, but you haven't seen a Cleffa have you?

"Yes I know Cleffa can't be found in the forest but there is a kid who can't find his first Pokemon."

"You have? That's great! We'll be over there in a few minutes."

Jay looked up at her hopefully.

"Has he seen her?"

"Yes, she was a little further ahead a few minutes ago."

Jay looked like he was about to burst with excitement. Unexpectedly he ran over and hugged her. She looked alarmed, but glad that she had helped the boy.

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They arrived at the place Eugene was talking about. The forest was much darker here and there was a very foreboding and sinister atmosphere around here. The Park Ranger held Jay close in case there were vicious wild Pokemon around here.

Jay continued walking through the forest hoping to find Cleffa.

"Are you sure-"

There was a cry of pain somewhere up ahead. Jay sprinted down toward the place where the cry came from. Jay pushed some branches aside and stopped awestruck.

There was a large open clearing ahead and there was a large circle of Pokemon surrounding someone as if there was a fight going on. The Park Ranger quickly caught up with Jay.

"Oh my! What should we do?"

But Jay was oblivious to her. He pushed the crowds out of his way, hoping Cleffa wasn't there in the middle. The spectating Pokemon were leering and spitting at Jay. Jay stepped into the middle of the circle.

Cleffa was there fighting a golden Caterpie. Cleffa looked at Jay and screamed with delight. Jay was shocked at how calm it looked.

"Alright Clef, let's show them who's boss! Sing now Clef."

Caterpie was distracted by the appearence of Jay and was soon lulled to sleep by the sound of Cleffa's voice. Most of the surrounding Pokemon were also lulled to sleep.

"Cleffa, use Pound."

Cleffa ran over and continuosly pounded her small fists into the Caterpie. Caterpie woke up but couldn't stand up and fainted out of exhaustion.

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Jay was standing in the clearing checking on Cleffa. Most of the spectating Pokemon had gone by now. A small figure waddled up to Jay. Jay looked down at the little Caterpie. Jay knew the Catepie didn't want to fight, but what else could it want...

 

I haven't counted the characters so I'm not sure how long it is. Hopefully it's long enough.

 

All right, thanks for waiting. Time to grade your story! ^_^

The story isn't extremely strong, but it's just about sufficient for an Easiest-rated catch. While the plot is clear enough, what's lacking is descriptive detail, a bit of backstory, and the battle is extremely short and mediocre.
Your story would benefit from a more in-depth description of things-- What does Jay look like? What does the Park Ranger look like? You did describe the forest, which is a good sign, but try to remember that your reader doesn't have the same 'mental picture' in their head as you do. This means you have to paint that picture for them using your words! =)
Also, it'd be good to know exactly who Jay is, backstory-wise. Yes, he's a Trainer and has a Cleffa, but where does he come from? Where did he get Cleffa? This isn't necessary information, especially for a story that's aimed at catching a Caterpie, but it'd be nice to know and will help you if you try for a harder catch.
The battle... consists entirely of a Sing attack followed by Pound, and the singing itself isn't described. It could do with some more detail, even if it's just, "Cleffa began to sing, the sweet, soaring melody making the surrounding Pokémon's eyes droop. Caterpie, as well as some of the jeering Pokémon, fell asleep."

Still, your story was 3,120 characters long, within the suggested range for an Easiest-difficulty catch, and the story was legible and mostly coherent. Thus...
Result:
Caterpie: Caught.