Beauty and the Delinquent

by Oldtakufanboy

Rating: mature
Tags: Vice-Principal Luna, Equestria Girls, Sex, Cheerilee, Discord, Slice of Life, Alternate Universe, Human, Original Character
Length: 2221

I've been sent to the vice principal's office just so I can see her again. I can't help it, but I have a crush on Vice Principal Luna since I got transferred here from Crystal Prep

Yet again, I get sent to the vice principal's office to get scolded at, but I can't help it. I do these pranks just so I can see Luna; she's my ideal woman. Today, is different; I think she knows to why I'm doing these things.

(OC is 19 years old)

Published 2017-03-31 23:10:01 UTC
Last updated 2017-03-31 23:10:01 UTC

Office Time

I sit on my desk in English class, listening to Mrs. Cheerilee prattle on about Of Mice and Men, which is boring to hear because I feel like any second, I'm about to fall asleep. My name is Jacob Miles, an eighteen-year-old student at Canterlot High. My eyes are blue and my hair is a mix between red and blue. I was once a student of Crystal prep, but I got myself kicked out of there because it was very boring. No one at that school wanted to do anything, but study and act like a bunch of goodie-two-shoes. Me, I'm pretty much a delinquent and would like to get myself into trouble now and then.

However, my pranks around this school are for a good reason; I do them so that I can see the vice principal. Unlike that old bat principal Cinch, the principals here are pretty cute, but vice principal Luna is the one that has stolen my heart. When I first met her, my heart beats so quickly and never have I seen a vice principal as beautiful and young as she. When I go to her office, I ignore whatever she says and just look at her dreamily. Another thing to add is that this is my final year of Canterlot High and I want to see her as much as possible. Earlier, I just flooded one of the toilets.

"Jacob Miles!" shouted Vice principal Luna over the intercom. "My office! Now!"

"Looks like I've been caught," I said with a smirk, as I stand up and grabbed my bag. "See ya, everyone. I have to get scolded."

As I walk out the classroom and down the hall, I think about Luna. Her lovely hair, her sexy figure, and her gorgeous eyes. It's like she's an angel that came down from heaven to guide me.

I make my way to the principal's office and walked over to the office, where Luna waits for me to enter. I stand in front of her door and take a deep breath. As I exhaled, I open the door to see an angry Luna sitting behind her desk, tapping her finger.

"You wanted to see me?" I asked, as I close the door behind myself.

"Jacob, we need to talk," she said, more serious than usual. "This won't be easy to say."

"What is the problem?"

"Sit down, please."

I walk up to the chair and place my bag beside the chair before folding my hands.

"Look, I'm sorry about the prank," I said. "It was just an accident."

"Oh? You mean it?" she asked with a cocked brow.

"Y-yes. I'm sorry about that."

"Look, Jacob," she said, as she folds her hands. "You've been doing a lot of pranks than last year and I feel like you doing them purposely. I need to know the truth. Why are you making a mess around the school?"

"Vice principal Luna... I just can't help myself. I like doing pranks. Been doing them since middle school."

"It's no wonder why you got kicked out of Crystal Prep. Young man, one more prank and you are kicked out of this school."

"What?!" I shouted.

"I'm sorry, but we don't want to make this school like it belongs to a bunch of delinquents."

Place a hand on my face, making myself look like a douchebag that all I ever do around this school is prank. I look up to vice principal Luna and cleared my throat.

"I'm sorry. I won't ever do pranking again. You have my word."

"Much better, but I can see that there's more to this pranking than meets the eye."

"What? what do you mean?" I asked, seeing her give out a small smirk.

"I believe that you are doing these pranks purposely is to get close to me. Am I correct?"

"Shit! I've been discovered!" I thought, as a bead of sweat goes down my brow.

"Be honest."

"Y-yes," I said in defeat. "You're pretty. I can't help myself."

"You find me... pretty?" she asked with a blush.

"You're like an angel sent from heaven to watch over me."

"You're such a sweetie," she said with a giggle. "Tell you what, I'll let your prank slip if you do one thing for me."

"And that is?"

She gives me a sultry smile, as she stands up from her chair and walks up to the window and folds the blinds. She then walks up to the lamp that stands to the right of her desk and dims the light, making the room go nearly dark.

"Jacob, no man has said anything like that about me," she said, as slowly unbuttons her light purple shirt. "You've made me quite excited."

"Wh-what?" I said, before she places a finger upon my lips.

"Shh," she said before sliding her finger to my chest. "How about we mess around a little."

"Wh-what about my detention?" I asked, as she brings her finger away.

"I'll let this prank slip, but if you are to do that again, I will give your parents a call, okay?"

"Y-yes, Miss Luna," I said, swallowing a lump in my throat.

"Now be a good boy and let me give you a show that any boy around here would die for," she said, as she reaches for the bottom of her purple shirt and pulls it up slowly.

My mind spaces out on everything, with the exception to what is happening right here and now. I never expected vice principal Luna to be stripping right in front of me and asking for some fun. As she pulls off her shirt, the tosses it aside and reaches down to grab the bottom of my shirt, making my dick get hard with each five second. Next thing I know, I'm shirtless in front of her, feeling embarrassed to see my not-so-very attractive body. I am a bit on the chunky side and I feel as though she's going to reject me. As she tosses my shirt aside, she looks to me with a little of concern.

"What's wrong, Jacob?" she asked.

"Are you sure about this?" I replied. "Am I fat to you? I'm not the fittest of people around here."

She smiles softly and places her hands on my cheeks. I look her in the eye, knowing that whatever she's about to say, isn't a joke.

"You don't need to be the fittest to get a girl," she said softly. "You should always like more of a person on the inside, than the outside."

"It's... I never thought of that. I never had a girlfriend because a few times I get called 'fat' or 'creep'."

"Those girls are wrong," she said, slapping my left cheek gently. "You are perfect. It's just that you need to stop with the pranks and start becoming friendlier with people."

"You think I can change?"

"Everyone deserves a second chance."

Never has anyone said this to me; I feel as though my heart grew three sizes today. A tear rolls down my left cheek, until Luna wipes it off with her thumb.

"You're the best, Miss Luna," I said. "You are definitely my ideal woman."

"You are quite a charmer yourself," she said before planting a kiss upon my lips.

I close my eyes, as her lips press hard against mine, before I slip my tongue within her mouth, making her nearly gasp. As my tongue senses around her mouth, her tongue pushes against mine, telling me to leave, but I resisted. Our tongues began to have a war for dominance, as they push and slip around one another. We then pull our heads away from one another, allowing the two of us to catch breath.

"My goodness, Jacob," she said. "I never expected you to use your tongue."

"Sorry, I couldn't help myself."

"Also, is that a pencil in your pocket or are you happy to see me?" she smirks, as she points down.

I look down to see a tent in my pants, making my heart race.

"Th-this is too good to be true," I said, as my face goes warm.

"I'll make it better," she said, as she reaches to the side of her pants. "Let's make love right here and now."

"Are you sure that's a good-"

I get cut off, as Luna pulls down her pants slowly, along with her black panties. As they reach to her ankles, I look over to her pussy, as it drips a little of her juices.

"Like what you see?" she asks, as she kicks aside her pants.

"Th-this is too good," I said, feeling my raging boner throbbing to be released.

"I can tell," she said, as she reaches behind and unhooks her bra, making it fall onto my lap.

"D-don't tease me, Miss Luna," I said, as I look away.

"You're cute when you're shy, Jacob," she said. "Don't be. I allow you to look at me."

I turn my head slowly, seeing her grip onto her breasts. My raging boner can't take the throbbing anymore; I reach to my pants and began unzipping.

"Are you going to bring out your throbbing cock?" she asked.

"I can't hold it anymore," I said, pulling down my pants and boxers, making my dick rise up in all of its glory.

"Oh my," she said with surprise. "That's quite a cock you have."

"I'd have to thank my father for that really," I said with an awkward chuckle.

"Now let's get started," she said, as she places her hands on her desk and sticks her behind high in the air. "Come and give me that throbbing cock of yours."

"Y-yes, Miss Luna," I said, as I get up from the chair and go behind her.

"Please, call me Luna from now on, please," she said, as I look down at her pussy with excitement.

"Don't I need a condom?" I asked. "I do pay attention to sex-ed."

"Don't worry, Jacob. When you feel like cumming, just release that load onto my back."

"Okay," I said, taking a deep breath.

As I slowly exhale, I grab my member and slowly insert it within her, feeling pleasure tingle all over my body from head to toe. The two of us give out a moan, as I slide out slowly, then back in.

"Your cock fits just right," she said, as I thrust in a slow pace.

"Are you feeling good?" I asked.

"You're doing fine," she said. "Give my behind a slap."

I raise a hand and gave her left buttcheek a smack, making her gasp.

"Oh yes," she said. "Harder."

I put a little more pressure, as I give her right buttcheek a smack, making her gasp louder.

"My goodness, Jacob," she said, looking back over her shoulder. "You naughty boy."

"Oh God," I said, as I thrust harder within her.

"Y-you like that?" she asked between thrusts.

"I! Love it! When you! Talk dirty! With me," I said, as I picked up the pace, making her breathing go louder.

"Oh, yes! Yes! Yes!" she shouts, as the room grows loud with the slapping of flesh.

"I love you, Luna," I said, as I grip onto her cheeks.

"I love you, too," she replied.

"Oh G-God! I'm about to cum!"

"Pull out!" she said, as I pull out my dick before tilting my head back.

My seed shoots out and lands on her back, making my knees feel a little wobbly. I let go of her ass and fall back onto the chair, feeling tired.

"You were wonderful," said Luna, as little of her juices flow down her leg.

"Thank you for this and for the pep talk earlier," I said, as I reach down for my pants.

"You are very welcome," she said, as she reaches for a pen and sticky note. "Here."

"What?" I said, as she writes down on the sticky note before handing it to me.

"A pass for your next class," she said, as she walks over to pick up her pants. "Have a great day and let's meet over at the coffee shop tomorrow. It's on me."

"Thank you, Luna," I said, wiping sweat from my forehead and picking up my shirt.

"Let's be less of a prankster and more of a gentleman, okay?" she said, as she reaches down for her shirt.

"I will," I said, as I put my shirt on and grabbed my backpack. "Anything for you."

"Now be on thy way," she said, as I exit the office with a smile on my face.

I walk down the hallway and into science class, as professor Discord looks to me with a look of disappointment.

"You're late, Mr. Miles," said professor Discord, as he scratches under his beard.

"I was having a lecture from vice principal Luna, Sir," I said, as I handed him the pass.

"Very well," he said as he grabs the pass. "But one more thing, why do reek of sweat? Did she make you run laps?"

"Yes," I lied. "After lecturing me, she made me run a few laps."

"Well whatever. Just sit down and open your science book to page three-hundred and eighty-nine."

"You got it," I said, taking my seat and pulling out my science book. "Let's get serious."