Anon 69 Side Story: Castle Shenanigans

by Amilition

Rating: teen
Tags: Random, Princess Celestia, Human, Princess Luna, Anon, My Little Pony: Friendship is Magic, Bat Pony, Comedy, Adventure, Prince Blueblood, Sex
Length: 3372

Shenanigans of all types happen in the castle.

Learn about what Anonymous did in the castle before he started his podcast. From pranks to awesomeness, follow the misadventures of Anonymous, Stella and the two princesses.

Side story to Anon 69 News. Don't need to read it to read this. And as always, no sex is present, just hints and mentions of it.

Published 2020-04-15 21:00:01 UTC
Last updated 2020-05-05 15:03:01 UTC

The Blue Devil

Author's Note

I'll be working on this (and possibly more side stories) on weekends. So expect slow updates.

The Blue Devil

"Anonymous! Get your green ass back here!"

Oh hello there dear stranger. You caught me in a weird moment. What your looking at is a enraged blue horse storming out of her room chasing my bipedal ass.

Why is she chasing you? You may ask me. Well it all started around a few hours ago when I took a masive- nah I'm fuckin with you. There doesn't need to be a long ass explanation. I just simply stole her crown. . . What! No! I am not crazy! I am what the young people call, "being suicidal." And in the famous words of Danny DeVito, "suicide is badass."

Anyways, it's surprisingly easy to get into her room. Really. Just hear me out. First just bait the guards on leaving their posts. Now with them being bat ponies and all, it's extremely easy. Just throw a fruit and let them have at it. Then the rest is just down hill. You see, magic doesn't exactly work on me per say, so I can just disable any spells or runes just by touching them. Just open her door and bingo bongo, your in. Free to do anything you want. Now lets get back to the good stuff.

Looking behind me, I see her charging after me. With all the wisdom in the world I shout back.

"Not a chance you giant blueberry!"

This only gets her more angry and she starts galloping faster.

"I will have your testicles mounted above my bed, Anonymous!" She threatens.

"Kinky but I'll like to see you try honey!" I laugh as I can hear her scream in fury.

This is the beautiful thing about our friendship. I mess with her, she strangles the living fuck out of me, and we drink with each other at the end of the day. Some say it's an abusive, toxic relationship. But I say It's an A class friendship.

I soon hear the sound of wings flapping next to me. I was scared shitless, thinking it was Luna. But a recognizable female voice rings in my ear, calming me.

"Whatcha doin, Anon?"

I look to my left and see my one and only bro, Stella. Been through the thick and thin together. Rather it be pranking the staff around the castle or telling the nobles to fuck off. Good times.

"Oh you know, the usual. Steeling moon butt's crown and trying to save my own man babies."

I say as I look over my right shoulder to see the princess of the moon now flying at me. I started to pick up the pace a bit more, not wanting her to catch me.

"Sounds fun. Can I join?"

Luna interjects before I get a word out.

"So help me, Stella, if you join him I will personally discharge you from the night guard and plague you with nightmares for the rest of your life!"

Stella looks back at Luna with a wide smile.

"Oh, I know you won't do that! I'm the best of the best! You won't be able to find a replacement!" All she got in response was an angry growl.

I looked down to her and we made eye contact. I gave her a knowing grin.

"Here, you take it and we spilt off. Distract her for fifteen minutes, then get her to fly through the dining room."

She nodded.

"Aye, aye captain!"

I threw her the crown and she cought it between her hooves. She then looked at the princess and shouted.

"Come and get it, oh princess of the stars!"

And with that she started to fly faster. Soon after Luna zoomed past me.

Once I knew the danger was gone, I halted to a stop to catch my breath. Man, did I tell you how tiring it is to run from an Alicorn? It sucks balls. Like huge balls. Like the biggest pair of balls- oh you get the picture.

"Oh my. What's got auntie Luna chasing you this time Mr. Anonymous?"

A familiar voice sounds from behind me.

Looking back, I see no other than Prince Blueblood. You'd expect him to be a giant dick. . . wich he was. At first at least. Didn't want a talking monkey to ruin his reputation type of deal. But once you get to know him a bit more he's, well, okay I guess. It's somepony you'd rather not hang out with but able to get along with. You feel me? Lets put it like this. He is somepony I'd eat my breakfast and have a conversation with but I wouldn't hang out with him all day with.

"Hey Blue. Just stealing the princess's crown." I nonchalantly say.

His eyes went wide eyed at that.

"What!? Anonymous, you know that's highly illegal! They will throw you in the dungeons for life!" He half whispers half shouts to me.

"Oh, don't worry about it. I'll return it. . . eventually."

I stare off into the distance when I say that.

"And that is when?"

I snap my attention back to him.

"In about, I'd say, fifteen, thirty minutes or so." I shrug my shoulders.

He sighs and shakes his head.

"Well don't go get yourself killed, you hear me dear?" He says as he starts to walk off.

"Yeah, yeah. I won't mom."

He only snorts at that.

I now focus on getting to the kitchen to set up my well developed trap.

I slam both doors open leading into the dining room. At one of the chairs present, is no other than Princess Celestia. In front of her sits a cake. Not a slice of cake. No, no, no. But a whole ass cake. I think its banana cake by the looks of it. No, I'm confident it's banana cake. She has a weird thing for bananas.

"Oh! Hello Mr. Anonymous. What brings you here?"

She slowly slid the cake away from her as she addressed me.

"Uh. . . just setting up something. Hey. You like pranks, right?"

Her face brightened up at that.

"Oh, I do love the festivities of playing jokes on others."

"Great! You want to help?" I asked.

"Oh I would love to!"

She clasped her hooves together and giggled.

"Great! We just need some rope, a tub of icing and some feathers."

"Get back here, Stella! Or so help me Celestia I will wring your damn neck!" I heard moon butt say just down the hallway. Seems like Stella managed to hold out. I'm so proud of her.

I then heard Stella's short reply back.

"Never~!"

I looked over to Celestia. Her and I where currently holding two ends of some rope.

"When I count to three, I will open these doors and we will pull the string. If things go accordingly, she should trip onto it, tumble forward, and fall into the tub of icing. After that, we dump the feathers on her. Got it?"

"Yup! Oh, I'm so excited to see her face!" Celestia laughed.

"Alright. One. . . two. . . three!"

I pushed the door open and saw Stella with Luna hot on her tail.

"Stella, watch out!"

After telling her that, me and Celestia pulled on the string.

Stella was lucky enough to fly over it. Luna however, not so much.

"What is the meaning of thi- oof!"

It. Was. Beautiful.

I can see the shock on Luna's face as she toppled over the rope, flailing her limbs about.

Splat!

Luna was covered in yellow icing. The only visible thing was her light blue eyes, filled with anger.

The whole room bursted into laughter. Stella even dropping to the ground, clutching her stomach.

"W-wait, watch giggle this." Celestia said.

Her horn flickered to life and soon after a bucket full of feathers was lifted above Luna and was promptly dumped on. The feathers stook to Luna, making her look like a chicken.

Everypony laughed harder. Tears swelled up in my eyes.

"Hey, gasp S-Stella. Can you hand me the crown?"

She looked at me from the floor, a lazy smile on her face.

"Sure thing."

She tossed me the crown, and with some fumbling, I caught it.

I walked to over to Luna and gently placed it on her head.

Turning my back from Luna, I lazily waved my hand twords her.

"Now presenting her majesty, Princess Cockerel, leader of the cocks!"

This only one person in the room laugh. . . me.

"Hehehe. . . what."

Celestia pointed her hoof behind me. I can feel a menacing presence behind me. Slowly turning my head, I was met face to face with Luna. We were so close, I could of booped her nosed with mine if I so wanted to. . . which I did.

"Boop."

This causes her to snort in anger

"So, uh, how's it going?"

"Anon, I hope you are prepared for what's to come."

Did I ever tell you the tragedy of Darth Anon, the not so wise?

In The World Of Chaos~

"Damnit A-Anon! *hic* W-why can't I ever *hic* beat you?"

I was currently carrying a drunken little bat pony back to her little pony barracks.

"I don't know, Stella. Might as well ask why can't I fly?"

We had our monthly drinking competition tonight. Every month, she gets four days off, and on the first night of her days off, we try to out drink each other. And yet again, I won. . . like the other 26 times.

She looked up at me and giggled.

"Tha-that's because *hic* your not a s-sexy little pony *hic* like me!"

She booped my nose with her hoof and went into a drunken laughter.

Rolling my eyes, I knocked on the door to her barracks with my foot. I can soon hear the sounds of 'clip clops' coming twords the door.

The door swung opened and a dark blue pony with a dark red curly mane popped her head out. I can see her violet eyes peek out behind her mane I think her name was Blood Rose. . . or was it Rose Blood? Nah, definitely Blood Rose. . . unless?

"Hello- oh! Hey, Anonymous. Dropping off, Stella a presume?" She said to me with a raised eyebrow.

She opened the door to let me in. Stepping in, I noted that there where a five other night guards that where also in here. Three where on a top bunk playing cards, while one other seem to be polishing their armour. The last one was sleeping on one of the beds.

"You know it. Uh, where should I drop her off?"

She lazily waved a hoof twords a bunk.

"Just drop her off on the bottom. Thanks for bringer her back by the way."

"No problem. That is what friends are for." I said as I started to head twords the bed.

"I'm going to guess she lost again."

She turned her head sideways and looked at me quizzically.

But before I could answer back, Stella snapped up in my arms, and pointed her hoof at Rose.

"Shut your who-whore mouth! I am the best *hic* drinker this nation has seen. I-I was just too *hic* tired to continue. So, I spared Anon, willingly. But *hic* I will destroy him next time."

Rose only rolled her eyes.

I chuckled and patted her head.

"Ok, Stella. What ever makes you sleep at night." I said as I laid her gently on the bed.

"Da-damn right. . . you will never. . . beat. . . me." And with that statement, Stella fell into slumber.

Doing a one eighty, I clasped my hands together.

"Alright. I believe that is my cue to head to bed myself. See you later, Rose." I said, making my way twords the door.

She nodded to this.

"Alrighty. You have a good night, Anon."

Opening the door, I waved back. Halfway from exiting, Rose shouted back.

"Don't forget about poker night, tomorrow! Luna really made sure to put it in her schedule. She explicitly said she wanted you there."

"Ok. I won't miss it then if moon pie will be there. Have a good one."

And with that, I closed the door.

Finally! My room! You know how awkward it is to ask a guard for directions to your room four times? Then have that room be right across from Luna's room, a room you passed six times? It's horrible. Anyways, that's enough. I need to catch up on some needed sleep.

Opening my door, I step inside to. . . my. . . bedroom? Since when has my bedroom turned into a mumbo jumbo of floating islands.

"Anon! It's so nice of you to join me!"

Holy shit.

"Discord!? I haven't seen you in ages! How has it been?"

Discord is by far, one of the best dudes to hang out with. Coming second to, Stella. Discord, Stella, and I are the Equestrian equivalent of the Three Musketeers of pranking. Remember when we turned the throne room into a bouncy castle. Good times.

"Oh you know, friendship lessons here and there. Really boring if you tell me, honestly. But I'm not here to talk about me, which I would, I'm here to hang with you and, Stella. Before I return to Flutters. Where is she by the way?" He asked as he poofed out a pair of binoculars and looked through them.

I pointed my thumb behind me.

"Barracks. She passed out after our drinking competition. She-"

"Lost. Yeah, yeah, I know. She's not going to beat you anytime soon, my dear friend." He cut in.

He tossed the binoculars behind him and they poofed out of existence.

"So let's say me and you have fun."

I raised my eyebrow.

"What do you mean?"

He winked.

"Discord, no! Don't you dare! No! No! No!"

He only laughed.

I hate hanging out with, Discord. Why? Because of bullshit like this.

"You got to swim faster, Anon! Or the sharks are gonna eat you~!"

Yeah, that. I was swimming for my life!

"Gluglugluglug!" I tried saying.

He only laughed at this.

"Sorry, Anon. I don't speak fish!"

Dodging a shark, I made a beeline for some coral I spotted. Just when I was about to reach it, my mouth was snagged by a hook.

I was then pulled up out of the water and was met face to face to Discord. He was wearing a red plaid shirt and a green cap that said, "Best Fisher."

"Oh, don't give me that look. You had fun!"

I only wiggled at this.

"Alright, alright, fine. I was starting to get bored anyways."

He snapped his fingers and I found myself in my bedroom.

"So, my dear buddy, ol' pal. What do you say we do next."

Straightening out any wrinkles I had, I looked up to him and said, "Well first of all, fuck you."

He chuckled.

"And second, I want sleep. It's three in the morning and I have a meeting tomorrow with some nobles from uh. . . fuck I don't know. All I know is I got some sort of meeting-"

Interrupting me, Discord put his talon on my lips.

"Meeting, shmeeting. You boring me, honestly. Let's say me and you go and mess with lil ol' tia."

I shook my head.

"Discord, please-"

"Too late~!"

And he snapped his fingers."

"So, you remember the plan, right?"

"Wait. What? What plan? You kinda just teleported me here."

I looked around and found my self in Celestia's room.

"Gosh Anon, you never listen. Keep that up, and I don't think you will find your self a marefriend. They need you to listen to their prob-"

"Ok, ok. What are we doing?"

He put his hand over his chest.

"So rude. Anyways, you put this sheet over her snout."

I nodded.

"And I get this bucket full of water, and pour it on-"

"Nononono. No! We are not waterboarding her, Discord!"

Discord's face went into a panic

"Quiet! Or your gonna wake-"

"Oh, hello Anonymous! It's so nice of you to be in my bedroom. . . at three am. . . when I'm sleeping. And Discord. Nice to know you aren't in Ponyville? Do you guy's care to explain why you were planning on waterboarding me?"

'Really' was the only coherent thought at the moment as I heard Celestia's sweet, sweet, voice behind me.

"Hey Anon, this reminds. I left the. . . cat on at home? I trust you have this handled. So. . . bye!"

And he's gone. Great.

Turning around, slowly mind you, I was face to face with a smiling Celestia.

"Nice weather we're having. Right?"

She only kept smiling.

"Ok, ok. What will it take you from releasing your sister on me?"

She chuckled.

"Well I do have a certain maid dress, that may or may not fit you."

That only brought up one important question.

"Why do you have a maid outfit that fits me?"

She turned as red as a tomato at that.

"Uh, for when we have minotour staff. Yes! That's it!"

I only raised an eyebrow.

"That's besides the point! I want you to wear this for when you go to your meeting tomorrow."

I crossed my arms and leaned against a wall.

"And you promise Luna won't hear about this?"

She nodded and , 'mhmed.'

I only sighed.

"Fine."

"This is quite enjoyable, sister. Seeing their faces is priceless. Say, how did you convince him to wear that?"

"Oh you know, just with a little blackmail here and there."

I can hear them both giggling behind me. I should of never agreed to this. I would rather have Luna- God! Why is this thing so tight!? My size, my ass!

Now I'm here, sitting in front of a group of nobles because of. . . fuck I don't know. Something about "learning human culture."

"So Mr. Anonymous. That whole. . . outfit is a cultural thing for your species?"

Oh right, my excuse.

"Yes indeed. It's uh. . . uh. . . a cultural greetings to the rich. Our people would wear this around highly respected individuals."

Some giggled sounded off behind me. This only made me growl.

"Well this has been a. . . interesting meeting. But I believe our time is up. We will be seeing you next week, Anonymous."

Finally! I never smiled so wide as I saw the group of ponies head twords the exit. Now I can finally go to my room and switch out of my-

"Oh Anonymous! Don't forget about the minotour ambassador that's coming. I won't be able to meet with him, so I'm appointing you to meet with him." I heard Celestia's soothing voice behind me.

"God-fucking-damnit!"

Laughter sounded behind me.

Author's Note

I want to get this to five chapters before I start up the next side story. No, this doesn't mean this is ending, I'll just be juggling stories. . . in hindsight, this might go horribly. Eh, I don't care.

I want to get to working on three side stories. I had some ideas and I wanted some of your opinions about it.

My first thought would be about the Stella and Anon before their friendship. Stella would be on a look out for any mares trying to 'molest' Anon. Because she doesn't want him to have a bad impression of their world! Yes! That's it!
P.S: The mares aren't trying to molest him. Think she may have ulterior motives.

The next would be a behind the scenes type of deal with Twigs and Cracker Jack. A more in depth on the weird shit their reporting.

And lastly, the blooming love between Stella and Anon. Go through the adventures of blushing, heart aching, and evem romance. . . nah I'm fucking with you. Their probably going to find a way to set that on fire.

But if you have any suggestions, let me know!

If you find any spelling errors, point them out please. Thank you!