Having fun in detention

by Blue Devil

Rating: mature
Tags: Romance, Original Character, Comedy, Scootaloo, Sex, Anthro, Cheerilee, Slice of Life, My Little Pony: Friendship is Magic
Length: 2861

Two ponys spending the afternoon in an empty classroom with a bottle of alcohol? Yeah, I'm afraid CSI won't be needed for this one.

After getting caught painting on the side of the school by Ms.Cheerilee Kidd Spraypaint has to spend an entire afternoon in an empty classroom with her, what happens is far from what he expected. Side note: Characters are aged up of course.

Published 2015-06-12 23:40:01 UTC
Last updated 2015-06-12 23:40:01 UTC

An afternoon in detention

"Are you sure about this?"

"Come on, don't tell me your scared."

"I-I'm not! I'm just not sure we should be doing this. Especially in a public area."

"You're saying that like you're ashamed of it. Besides everyone can only see it if we do it in public, that's kinda the whole point we're out here."

"Okay, okay. You made your point, let's get started."

"Good, finally I've been waiting all day for this........now would you mind handing me a can please?"

"Oh sure."

Scootaloo and Kidd were standing outside the massive schoolhouse, both were wearing night black hoodie jackets and jeans so no pony passing by could recognize them immediately while also toting around large black gym bags containing various different color spray-cans. They barely covered a part of the wall when Scootaloo began to sweat and pant.

"Man, this summer heat is brutal. Is it safe for me to take off my hood?"

Kidd stood up and looked around.

"All clear, go ahead."

"Thank Celestia." The mare sighed as she pulled her jacket over her body.

Kidd couldn't help but look at her smoking hot teen body, the sweat she was producing did wonders in highlighting her curvy upper body. Her breasts that were tucked snuggly inside her white D-cup bra jiggled a bit as they were freed from their sweaty prison, she was just about to reach for her jeans when Kidd cleared his throat.

"I think that should be good enough, we still got a lot to cover in so little time."

"I guess." She said with a shrug.

She kneeled down next to him and got back to work, a few seconds later she looked over to see Kidd sweating a lot himself.

"You wanna......take your jacket off too?"

"I'll live."

"You sure? Cuz, you're sweating......a lot."

He stopped painting and looked down at himself, his jacket was completely soaked from the inside out.

"I guess I am, hold this will ya?"

He handed her the spray-paint can right before he began taking off the wet jacket thus revealing his electric green coat with matching electric green mane with dark blue highlights, he sighed in relief before realizing that his white basketball T-shirt was soaked as well. He shrugged his shoulders and got back to work grabbing a can of red paint and moving to a different space much closer to the front entrance to cover more of the area.

"Wow, this is looking pretty good, I can't wait for everypony to see this!" Scootaloo squealed happily.

"Yep, they are going to love it. And that's absolute guarante-"

Suddenly they heard the sound of somepony approaching, Scootaloo began to panic when Kidd grabbed her hand and guided her to a nearby bush for a hiding place. Poking their eyes through the leaves they could see the incoming pony: Ms. Cheerilee.

"What the-school is done for the day. What is she doing back?!?!?" Scootaloo whispered.

"Heck if I know, maybe she forgot something? I don't know." Kidd whispered back.

Ms.Cheerilee was about to enter the schoolhouse when she noticed a spray can near the entrance, Kidd gave himself a face palm for dropping it. The teacher then looked on the side of the building and gasped.

"Who.......Who.......did this? Who made this mess?"

"The jig is up, we're busted."

"No.......just me." Kidd sighed before dashing from the bush.

Cheerilee nearly screamed when she spotted him running towards her before skidding to a stop.

"Who are you? I don't think I've seen you around before."

"The name's Kidd Spraypaint, I just moved here around a week ago."

"Oh, then what are you doing out here so late? Class is over for the day."

"I know. I......was painting.....on the schoolhouse."

"Wait, you made this mess?" Cheerilee asked squinting at him.

He slowly nodded.

"Huh, well Mr.Spraypaint though I respect your honesty I'm afraid punishment is in order. We can't have delinquents running around causing mischief on school grounds, we already have someone like that doing stuff like this on a daily basis.

"I understand."

"Follow me inside." Cheerliee said before walking in the schoolhouse.

Kidd looked back to see Scootaloo with a surprised yet confused expression on her face, he simply gave a thumbs up and a smile. One thing about Kidd is that he doesn't rat on his friends. He soon joined Cheerilee inside, she was standing at the chalkboard writing the word "Detention" in all caps and drawing a line underneath it. She then pointed at a chair.

"You will seat here, if you will leave all your belongings at the door please and thank you."

Kidd sighed before dropping his jacket and bag of spray paint at the door, he then walked over and slumped into his designated seat for the next two to three hours. As for Cheerilee she sat down behind her desk, pulled out a novel, and began reading. Kidd began to watch the clock to try and pass the time, it only moved one inch after staring at it for what felt like forever in other words this was going to be a long afternoon. For the next few minutes he did everything he could think of: beat-box, play tic-tac-toe, spin a pencil, whistle a tune, etc. He was about to fall asleep from lack of activity when Cheerilee flung the book she was reading in anger clear across the room into a waste basket, a perfect three pointer.

"Uh.....Ms.Cheerilee?"

"What!?!?"

"Is something the matter?"

Her angry expression turned into a happy one.

"Of course not, nothing could be wrong."

"Are ya sure? Cuz ya kinda just threw that book like it was a football."

"Oh that? That was nothing dear. Just a trashy romance novel with a terrible ending."

"Really? What's the ending?"

"I don't want to bore you with that."

"Um, I'm kinda already bored over here so you'd actually be doing me a favor."

"I suppose. Okay then."

Cheerilee got up from her seat and began walking around the classroom talking about this cheesy complex story plot line about 4 guys fighting over this one girl. One was a scientist, another was a football player, a banker, and an entrepreneur of a failing company. The story goes on and on about failed dates between the girl and the guys only to end with the girl losing her high paying job for getting caught having sex with her co-workers and began begging the 4 guys to take her. Each one however finds a girl of their own and moves away leaving the main girl by herself and ending marrying a clown.

"Well, I don't know exactly how to respond to that." Kidd said, his eyes swirling with absolute confusion about what he just heard.

"I know right? It just goes to show you, heartbreaks can happen to anyone. Even me." She sniffed.

"You? What happened?"

"Yesterday night my Cultfriend dumped me for this supermodel in Canterlot. You can imagine how I felt."

"Yeah. I don't get why though."

"Huh? Why what?"

"Why he would dump you just like that, that's pretty shallow if you ask me. Crappy even."

"Thank you, I wouldn't expect a stallion to understand." She sniffed.

"Hey, no problem. It's what I do."

Cheerilee giggled as she began wiping her tears with a tissue from her desk, that's when he actually took a good look at her enticing motherly figure. Her large E-cups trapped inside a lacy black bra easily visible behind a button down blouse that matched her black dress skirt that hugged her shapely yet plump thighs, a clear sign of something a little extra in the caboose. Cheerilee was a perfect visual definition of a MILF. Kidd gulped loudly as his face was glowing a faint shade of red that fortunately undetectable..............so far.

Kidd was caught off guard when the teacher suddenly bent over her desk as if reaching for something underneath giving a view of that plump ass he was looking for, he immediately grabbed onto his pants but was then relieved when she straighten up again. In her hands was a fancy clear wine glass and a bottle of red wine, she sat the two on the desk right before pouring herself a glass.

"Drinking on a Friday night is a pleasant hobby of mine." She said right before taking a sip.

Just watching the busty mare drink the red liquid was enough to set his mindset to the darker regions of his head.

"Oh how inconsiderate I'm being, care for a drink?"

"Of-Of wine?"

"Of course. You are old enough right?"

"Y-Yes, just turned 18 last month."

"Excellent."

She pulled out another glass from her desk and poured him a glass.

"Cheers, to new friends." She said raising her glass.

"Cheers." He said doing the same.

Both guzzled down their wine and immediately hiccupped at the same time. Even though it was one glass Kidd can already feel himself calming down, Cheerliee began giggling to herself.

"What's so funny?" He asked.

She paused then smiled.

"I forgot." She laughed.

Kidd soon joined in on her pointless laughter. She abruptly stopped and pulled out something else from behind her desk, it was a large rectangular box.

"This was a game I made for me and my Cultfriend but.....well, you know."

"What is it?"

"I haven't thought of a name yet, but I thought it would be fun for us to play."

"Alright, I'm game. Let's play."

Cheerilee opened the box on top of his desk and pulled out a large game board, some game pieces shaped like red hearts, a card deck, and some dice. On one side of the game board was a large blue rectangle labeled start and on the far other side was a large red circle labeled finished, between them was a bunch of twisty paths guaranteeing a long an enjoyable game.

"Okay who should go first?" Cheerilee asked.

"Well since it's your game you should go first."

"Alrighty then."

She grabbed the dice, shook them in her hands, and rolled a 6. She then grabbed her piece, moved 6 spaces up, and picked a card that gave her 3 extra spaces putting her in the far lead leaving Kidd in the dust and we wasn't going to have that. He grabbed the dice, shook them in his hands, and rolled a lucky 7. After moving his piece 7 spaces he picked up a card only to be told to go back to start.

"What? That's some bull."

"And at the beginning too, oh well. My turn again." Cheerilee giggled.

This went on for a few minutes, both pieces were at the halfway there mark which was good since Kidd was about to murder the game for making him go back to start several times. It was Cheerliee's turn again, she repeated the dice throwing process and pulled a card. She suddenly paused.

"What is it? What does it s-" Was all Kidd could say before Cheerilee grabbed his head with both hands and pulled him into a deep French kiss.

The kiss lasted a full 30 seconds before Kidd broke away from her.

"Ms.Cheerilee! What are you doing?!?!?!"

"The game card said to, look see?"

She handed him the card, he stared at it for a few moments. "French kiss the opposing player" it said in all caps. He inhaled sharply and exhaled before setting the card in the discarded card pile.

"Ms.Cheerilee, why put a card like that in a board game?"

"I told you, it was for me and my Cultfriend." She sheepishly.

He gave himself a mental face palm.

"Okay, let's just finish the game. Hand me the dice?"

She did so, he repeated the dice process and drew a card. He was immediately shocked by what was written on it.

"What is it?" she asked.

"It says.......(gulp)......ask the opposing player to.......strip."

He stared at the card in horror, but was then caught off guard by the teacher's laughter.

"I was hoping to get that card, oh well. I gotta do what the card says."

She stood up from her chair and began unbuttoning her blouse, Kidd immediately turned his head to look in the opposite direction.

"Oh come on, it's no fun if you don't watch." She said seductively.

My head screamed at me to say no but my body didn't want to listen for once, I turned back in her direction just in time to see her unfasten the last button, pull off her blouse along with her bra, and toss it over to the side giving him a good view of her large breasts that jiggled as if extremely happy to see him. She then pulled the zipper to her skirt down and the clothing fell down to the ground panty and all leaving behind an entirely exposed Cheerilee. Kidd's nose twitched threatening to blow at the glorious sight, she then sat down back in her chair.

"Okay, mine turn." She said grabbing the dice again.

Kidd was absolutely terrified of what card could possibly come next for he now understand how far this game was created to go.

"10 even." She announced as she moved her game piece 10 spaces.

She grabbed the next card, after reading it she put a hand to her chin.

"Hmmm." She said.

"What is it this time?"

"It says to either move back 12 spaces or......."

"Or?"

"Give you a blowjob."

Kidd's brain immediately exploded.

"I would honestly go for the 12 spaces."

"Why? I'm so close to winning."

She got up from her seat once again and walked over to Kidd's side of the desk, she turned his chair so he was facing her right for dropping to her knees and going for his pants. She unzipped them with very little effort and was immediately greeted by his pulsating member.

"My, my. You're a big boy aren't ya? How long were you planning on hiding this from me?" She teased causing Kidd's face to glow fiery red.

She then began stroking it up and down before swallowing the entire thing whole. She must've done this numerous times before due to her going up and down on a fast paced beat, as for Kidd he was trapped in a blissful feeling and couldn't move. His hands however was still conscious and began climbing down the curvy teacher till he reached that large fat ass of hers, his fingers literately sunk into the plump plot on contact causing her to moan in delight and increase her speed even faster. A few minutes later she released his cock from her mouth and gave him a seductive smile right before she began climbing up his body and sat her bare plot on his lap.

"C-Ch-Cheerilee?"

"Yes?"

"Don't you think we should finish the game? You were so close to winning after all."

"I know, but I'm about to win something better than a silly board game."

"What's that?"

"A real lover." She whispered in his ear.

She resumed stroking his cock to make sure it was still awake for the main event, she then hovered her fat plot over it before slowly going down on it. She inhaled deeply as his hard member entered her asshole, Kidd nearly passed out from the feeling of her bouncing up and down on him. His fingers screamed in happiness as they massaged her ass making sure they got every inch of it. It wobbled, sloshed, and jiggled happily in return. After a half hour she shuddered slightly right before going limp, she fell forward burying his face with her large breasts, she giggled softly at the feeling of him motorboating right before going at it again. She cummed wildly all over his pants another half hour later leaving a giant stain on his upper thigh.

"I'm so sorry."

"It's okay, I was about to send these to the cleaners anyway."

She gave him a warm smile right before French kissing him again. Once they were finally done they immediately got dressed, Kidd covered her with his now dry jacket right before they walked outside. They were about to leave the schoolhouse right before Kidd stopped her.

"Wait......I gotta finish something before I go."

He pulled out his collection of spray paint and walked over to the wall of the schoolhouse, Cheerilee sat on a rock as she watched him work. Once he was done he sat down next to Cheerilee to admire his work, it was a picture of a stallion dressed in a tuxedo and a mare in a wedding dress holding each other at the alter.

"Kidd, It's beautiful. Is it a picture of your loved ones?"

"My mom and dad actually, Mom.........passed away a few years ago. She was an artist and was teaching me how to paint, Dad made me promise to stop spray painting because it makes me look like a delinquent. I thought since this is my last mural, why not make it special? You know?"

"I do, and your mother must be proud."

"Yea, I bet she does."

Author's Note

As always positive feedback is deeply appreciated.