[Classic] The Scootaloo Diaries

Rainbow Dash quickly flew up to the safety of the clouds, clutching in her hooves a book of interest. She held a diary, one she managed to swipe from Scootaloo's saddle bag without her knowing. Now she rests atop a cloud, eager to invade her little friend's privacy in the most intimate of ways. With a light chuckle and a lick of the tip of her hoof, she opens the book and turns the first page.

Today was an exciting day. I finally got to have fun with my latest crush, Cheerilee! My grades were slipping so Cheerilee decided to punish me. Today after school, I had to stay behind and help bring the toys and balls back inside off the playground. It was really hot out today, and I could feel sweat already dripping down my forehead and sides. Cheerilee was the only other pony out there helping me, and she looked just as hot, if not hotter. I couldn't help but stare at her flank and curved back as she lifted each playground item with her teeth.

I think at some point she saw me looking because she gave me a wink right before she started behaving even more sexily. I wiped the sweat off my head with a forearm. I remember what she said right then too. "You feeling okay Scoot? It's really is hot out here, you might want to take it easy."

I just laughed and told her that I can handle anything. As soon as the last toy was collected, I followed her back inside. I asked if I could go now, and she, of course, said no. She told me to take a seat, so I sat at my desk and waited for her to lecture me. I sure was surprised at what she said next.

"We need to get a few things out in the open. First of all, I heard the things you've been saying about me to your little friends."

I was stunned, I didn't know how to react to this. What did she hear? Is she trying to get me to confess to something? I had no clue, but wasn't about say anything stupid. I just said, "What do you mean? I haven't said anything bad about you."

She once again failed to reply the way I thought she would. She said, "Oh, that's just it, Scootaloo, I know you haven't been saying bad things about me. What you have been saying is disturbing none the less."

Okay, I'll admit it, I was really nervous at this point, I didn't know what to say, but I was sure she knew my secret. "Wha-what things did you hear about?" I asked her, but I wasn't sure I wanted to know.

I blushed more than I'd ever blushed before, especially when she smiled and lowered her eyebrows. She began trotting towards me and I almost freaked out and ran away. For some reason I made myself stay cool. She placed her hoof on my face and asked me the weirdest question I'd ever expect her to ask. "So, you said I have the nicest flank you've ever seen, right? Even nicer than Rainbow Dash's?"

I gulped, being honest with myself, she really did have the nicest flank I've ever seen.

"Hey come on!" Rainbow Dash shouted as she smacked the page she was reading.

She stood up and looked at her flank, wiggling it provocatively in the air. "My flank's... nice." She said with a pout before collapsing back down on the cloud and continuing to read.

"Yes Miss Cheerilee..." That was all I could say, I wanted to tell her exactly how sexy I thought that flank of hers really was.

"Mmn, that's good. So, the reason you're here right now is because your grades have been slipping lately. Maybe you're not motivated enough, what can I do to motivate you?" Those were her exact words, and I had the perfect answer, even though I could never bring myself to say it.

I sat silent, knowing what she was getting at. I wanted so badly to tell her what she could do to 'motivate' me, but I just couldn't. Then, another surprise, she did it for me. I felt her hooves touch each side of my face and pull me into hers. Her lips brushed up against mine and before I knew it, we were kissing! She quickly pulled away and left me silently begging for more.

"This is what's in store for you if your grades improve, Scootaloo, is this what you want?" She told me as she backed up into her desk.

I just nodded, my hooves were shaking and I could hardly breath. She pushed everything off of her desk with her front legs, sending papers and desk ornaments scattering across the floor. Then she climbed on the desk and laid on her back. I just stared and felt my heart begin to race. Then, she signaled me over with her hoof. As I trotted up to her she licked her lips and ran her hooves down her long slender body. By the time I reached the desk, she had arched her back and placed a hoof between her legs.

I was losing my cool, but I knew this would be my only chance with Cheerilee. I couldn't blow it.

Rainbow Dash wiped a bead of sweat from her head and nervously looked around, feeling a bit awkward. She cleared her throat and ensured that she was completely alone, then turned the page to continue reading.

I made eye contact with her and quickly lost myself. I jumped up on the desk next to her and placed my hoof on her chest. She winked again and pulled me on top of her.

"If you get an F or a D on your next test, I'll send you home. If you get a C, you get this." She said as she pulled me into another kiss.

I didn't answer, I hardly heard her words. I felt her tongue slip into my mouth and my heart exploded. I've never kissed anyone like this before, I wasn't sure what to do. Cheerilee didn't seem to notice, she just kept kissing and swirling her tongue around in my mouth. I felt her start to bite on my lips as her hooves ran down to my flank. With a smack where my cutie mark should be, she spoke again.

"Now, want to know what you get to do when you get a B on your next test?" Before I could answer that question, she pushed my head down between her legs and placed her back hooves on my wings.

I gulped and felt chills shoot up my spine. This was really too much, but I couldn't say I didn't want it, I loved the thought, it was something I imagined every night at home before I fell asleep. There was no way I'd pass this chance up. With a deep breath, I closed my eyes and let instinct take over. I stuck my tongue out and licked her the way I imagined I wanted to be licked. I think she liked it because I felt her back hooves running up and down my wings and sides, pulling me in closer. I kept licking her and felt her getting wetter. I'm not sure if it was from my saliva or her getting closer to coming. All I know is the taste was exciting, I'll never forget it.

She leaned up and placed her front hooves on the back of my head and pulled me tightly up against her. I felt my tongue slip inside as she squeezed it with her tight pulsing muscles. At this point, all I wanted was to make her come, I wanted to hear her scream it out.

"That's the spot kid, right there. Right there! Yes!" She said something along those lines as I felt her squeeze me one last time before she soaked my muzzle with her orgasmic fluids. It was amazing.

Rainbow threw the book down on the cloud. "No way! No way this is real!" She looked over the cloud and spotted a few random ponies looking up trying to determine the source of the shouting.

She placed a hoof on her head and tried to consider the possibility that Scootaloo made all of this up, but the explicit detail indicated otherwise. She turned the page and read on.

Cheerilee lifted me up and stuck her tongue back in my mouth, I couldn't believe this was really happening. I don't think I once grasped on to the reality of the situation the entire time I was there. Only now am I able to reflect on what happened. I realize what she was doing, what she wants to do, because of what she said next. "Once you get an A on your test, I'll do you. Would you like that, Scootaloo?"

There is nothing more motivational than the thought of Cheerilee going down on me. I'm definitely going to get an A on my next test, I have to!

~ Scootaloo, signing out-

Rainbow closed the book and fell over on her back. That was much more than she'd ever imagined. She lifted the diary with her hoof and read over the front cover. "Property of Scootaloo, stay out or Rainbow Dash will kick your flank!"

With a chuckle, she considered what the next entries could be. Being perfectly honest, she was enjoying this way too much.