The Longest Sleepover

by Virydyan


Chapter 1 - Enter Anon

It was a beautiful sunny evening in the bustling town of Ponyville, the weather was warm but also a bit nippy, a sure sign that Summer was giving way to Fall slowly but surely, and that the Summer Wrap Up event was just around the corner. Looking around the town you could see everymare and everycolt busily trotting back and forth, getting ready for their evening plans or preparing for another busy day. The stores in the market square were empty yet tidy and organized, the local shops were starting to close up for the night, but behind those closed doors the sounds of scrubbing and dusting were heard, no doubt everypony was getting everything set for another day of customers.

It was at this time that two particular figures emerged from one of the shops, carrying lots of goodies. The first figure was the local Pony Princess of the town named Twilight Sparkle, and the other figure was me, the local human of the town. You might be wondering what on earth is a human doing here in this world of colourful ponies? I don't want to get into too much detail, but let me just say lesson learned, never jump into some random portal that appears in the middle of the woods and expect an easy trip back home.

“Thanks again girls! See you tomorrow!” Called Twilight walking away from the shop, heading straight to home.

“Wait up Sparkle!” I said as I tried to balance all the junk in my hands.

“Come on Anon, we’ve got a sleepover to organize so get those legs pumping!” She said as she stepped up her trotting pace.

“Okay okay, sheesh.” I groaned, walking faster to keep up with her.

My name is Anon, it is a strange name I know but it’s one that I go by. It's been a few months now since I ended up in this strange land called Equestria, at first it was a real scary experience, but after a few hurdles, mishaps and the odd kaboom, I've come to call this place my home, at least until I can somehow find a way to get back to my actual home, but that's a whole other can of worms that I won't get into right now.

Anyway, right now I'm busy helping out my pony friend Twilight Sparkle with her annual monthly sleepover with her best friends. We had just finished shopping at the local shops before they closed for the night, the Princess had her saddlebags filled to the brim with stuff, including bags of snacks, bottles of soda, a big storybook, and extra bottles of ink and quills. Well okay those latter two probably won’t be needed but hey you never know, right? So you are probably wondering, why does she go through all this fuss to host these sleepovers so often?

Well you see, one stormy night about a year or two ago, back when she had just moved into town she held an impromptu sleepover with some of her friends as a way to pass the time from the storm. Ever since then she’s made it a habit to organize at least one every month with her fellow pony friends, Applejack, Rainbow Dash, Rarity, Fluttershy and Pinkie Pie. Sometimes other ponies who live around the town join in on the fun as well, but most of the time it’s just the six of them who mainly take part.

As for myself, I haven’t taken part in one of these sleepovers so far. I always feel like the odd one out of our little group. I mean as a human I already stick out like a real sore thumb, but then there is the fact that I am a “guy”, or stallion as the ponies tend to call males, a sleepover that sounds like it’s going to be all girly and frilly just doesn’t appeal to me at all. Of course that doesn’t mean I ain’t curious though, honestly, deep down I kinda wish I could take part in these sleepovers in some form or another, but I've never had the courage to speak up about it. I mean it’s not like I'm asking for an opportunity to hit me like a lamp post to the face now is it?

*BASH* 

“Owww, son of a-” I just managed to catch myself after, ironically, hitting a lamppost while being stuck in dreamland for too long, almost dropping all the stuff I was carrying in my hands.

“Anon! Would you please stop daydreaming and look where you’re going!?” Twilight said, looking back at me.

“Sorry Twilight, I'll try to be more careful.” I said to her, steadying the heavy load in my hand while trying, and failing, to hide a blush of embarrassment.

Twilight just rolled her eyes and face hoofed.

Twilight Sparkle, the recently crowned Princess of Friendship, is the one who has been helping me adjust to living in this town ever since I first arrived a while ago by providing me with a place to stay at her home in the Golden Oaks Library, in return that I help her out by working part time, helping to organize the all of the books, handle returns and deal with the overdue. We’ve become fairly close since I started working with her, I wouldn’t call her my bestest friend but we’re not far off. That being said, we do sometimes get into arguments about facts and what makes sense and don’t, oh and don’t even try to talk bad about her favourite books around her, she’ll just overwhelm you with her tangents and rants non stop.

Speaking of that, Twilight took a deep breath and started going into such a tangent.

“You know, it’s a pony miracle that you managed to not drop anything there, much less break it at all. If you had done that then we would have wasted time picking all of it up before making our way back home, only to find out that some of the items are ruined and as such we’d have to make another stop at the stores to get more supplies for tonight, and as such the sleepover might end up being delayed due to us making yet another trip back to the store in a hurry just before they all close for the night, all because SOME-pony was daydreaming and not looking where they were going!” She said pointing her hoof up at my face in a huff.

I let out a long groan, then responded in kind.

“Geez louise Twilight Sparkle, for a Princess you sure got one heck of a motormouth to run with.” I said to her in a cheeky tone.

She raised an eyebrow up at me, her face unamused.

“Motormouth? Really Anon? Really? How in Equestria do you even come up with all these words you keep on saying in retort?” She quizzed me.

“It runs in the family Princess, our snark is potent and loaded with plenty of wit.” I said with a little pride in my voice, earning a groan from the princess.

"Well whatever, at least your sense of humour is still sharp compared to your sense of sight. Speaking of which, it is good that you haven't dropped anything now because if you did I would-"

“Alright alright alright, I get it! I promise I won’t be drifting off again, and will keep focused on the task at hand.” I said to her with exasperation, not wanting her to get into another long tangent.

She looked at me with a bit of a glare in her eyes, but she simply nodded at me. She then turned around and started walking again down the street towards her home, with me following right behind her. 

A few onlookers around us seemed curious about what just happened, but they soon shrugged and went back to whatever it was they were doing beforehoof.

“Hurry up Anon! I don’t want to be late because of your slow legs! And if I'm the last one who gets there, then I'll make sure you have to do more chores for me tomorrow.” Twilight said, eager to get to her home in a jiffy.

"I'm hurrying up, I'm hurrying up, your majesty! I said to her with sarcasm.

Twilight just looked at back me with a frown, then looked away shaking her head.

“Whatever, come on we’re almost home.” She huffed as we approached the front door to her home.

Ah, the good old Golden Oaks Library, packed with all the books you could ever read, anything you wanted to know about Equestria and other lands, chances are this place has the exact book you need. There is also a not so secret laboratory located underground for experiments in magic and science. I used to sleep down there when I first started living in Ponyville, but after a little accident not so long ago, I now sleep up in the library on the new sofa she had bought recently. I'm not too bothered about it since it's comfortable, and I get to read all the books around me.

“Say, you think the others are already here, waiting for you?” I said to Twilight as she prepared to open the door.

“Oh most certainly.” Twilight said, turning to look at me with a smile on her face. “Applejack is usually the first one to arrive here since she and her family wrap up their work in the late afternoon. Then it rotates between Rarity, Pinkie Pie and Rainbow Dash depending on how busy their jobs were during the day. Fluttershy however, tends to show up here last since she has to take care of her animals so they don’t get hungry at night and can sleep okay in her absence. Now more so than ever since she has her roommate to keep an eye on too.”

“Ohhh yeah that’s right, him. Man, that guy can be a right piece of work.” I said with a huff.

“You don’t like him very much do you, Anon?” Twilight said, amused with my expression, I let out a sign.

“Well, yes and no. It’s not that I detest him, it’s just that he can be a right pain in the butt, not only that but he’s also really crafty as well. I still remember the last time I interacted with him, he showed me this ‘animal’ that he claimed was a pink hedgehog he found wandering around the nearby forest, looking for a new home, I was so excited to have it since I have always wanted to have a hedgehog as a pet. So I took it back home to take care of it, giving it a little bowl of food to eat in case it was hungry. But the next morning I got suspicious, so I took a closer look at it and that's when I found out that it wasn't a hedgehog, but a bloody hairbrush! Full of long pink pony hair too! And I don’t think I need to say whose hairbrush it belonged to either. He never stopped laughing about it for a whole week, and Fluttershy was none the wiser.”

Twilight was trying her best not to laugh at my story, holding a hoof up to her face, but I can hear a few giggles escape her lips.

“That sounds like Discord alright, and he got you real good,” she said with a big grin on her face, I just frowned in return.

“Whatever, come on let’s just get inside and start getting everything set up, all this junk in my hands is starting to get real heavy right now.” I said, feeling the strain from carrying all the junk in my hands.

Twilight nodded at me, she turned back to the door and lit her horn up in a purple glow, then with a bit of magic pushed open the front door, she trotted right inside while I followed behind her, closing the door behind me. In my mind I was hoping to get this all over and done with so that I can just retire downstairs for the evening and continue on from that book series I had been reading alot, Daring Do I believe it was called.
Imagine my surprise when that little plan had to be put on hold, because this sleepover ended up becoming much more involving than I expected it to be.