This story takes place after the events from the episode Power Ponies

Shining Armor and Twilight are spending a few days with their parents for a reprieve and one night the stallion walks into his sister's bedroom. There he finds an odd book labeled "How To Train a Princess" from the peculiar Enchanted Bookstore. Without realizing it he is magically transformed into an alicorn princess and now has to complete a course of strange classes within the tome. The courses will be hard and many will take days within the strange universe that this book constructed. He will have to pass a final test in which he may either turn back into a stallion or remain a princess alicorn forever.

Cover Artist: Pridark

Adventure, mayhem, magic of unknown origins. Oh, and talking ponies. These are the strange events that have brought three friends together into the wildest holiday that anyone could imagine.

It starts as a small Halloween chat, where they showcase their costume designs to one another. However, due to events outside of their control, they soon find themselves in a new land during a turbulent time.

Now trapped in a case of mistaken identity, these friends find themselves thrown into the deep end, when a royal wedding they’re asked to assist with is suddenly interrupted, and the three of them soon find themselves on an extended holiday from any sense of reality they ever knew.

We now have our own An Extended Holiday TVTropes Page:
A big thank you to wille179 for setting it up.
A/N: Now I would like you all to know first of all, this is a collaborative work between myself and some friends. So if you enjoyed this, why not stop by and say hello to the other three writers of this story. I have included their links at the bottom here.
Team Extended Holiday
American Brony - Writer
Teal Speckles - Writer
Shawn820 - Writer
OmniKitsune - Writer/Head Editor
Biker Dash - Editor

Big thanks to Shawn820 for the great cover art.
WARNING: There are spoilers in the comments. Read the comments at your own risk. By all means, please add to the discussions.

A dazed alicorn wanders the streets alone, her mind and body numbed, acting only on instinct. Her only companions: the clicking of her hooves, the rain, and the feeling that something is missing, that something is wrong.

But it's only a distant, vague feeling that she can't comprehend as she walks on.

Loves ’em to bits. Much to Sunset’s chagrin.

Based off the tag by the same name on derpibooru. Tag filled with mostly suggestive - but infinitely hilarious - images.

Browser discretion is advised.

Will update as free time and inspiration dictate.

Deadpool has found himself in Equestria. He isn't very happy about being in a place that's too happy, but he is trying to fit in with everypony. He makes friends and enemies, and confuses the hell out of everything. Will he be able to find a way home?Will he be stuck there? And if so, will he be a good citizen, or bring about the end of Equestria as we know it?

"You know, I don't do that to EVERYWHERE I go, you didn't have to mention that. You're lucky you're safe behind your little laptop screen or wherever the hell you're using this from. If you destroy my image completely in here, I will not hesitate to strangle ya through the-"

Do you wish for a story or not?

"Fine."

So let it be said... so let it... be done.

Have you ever had a dream that just seemed so real, that it was impossible to say for certain that it was even a dream at all? A dream that, despite all of its impossibilities, seemed to re-write your entire perception of reality, re-writing your sense of what—and indeed, who—you are? Accepting change is hard enough as it is. But when you're a somebody who wakes up as a somepony, how do you cope with the impact such a drastic change has on your mind and body? With changes like these, it must surely just be a lucid dream—albeit a suspiciously accurate one—just brimming with potential and ripe for exploration. So you might as well suck it up and make the most of these distressingly…unusual circumstances, and seize this psychological adventure before you wake up and the dream ends.
After all, this couldn't possibly be real, so the dream must come to an end eventually…right?

The Text, an odd and capricious being that only talks by printing words into your mind, seems to quite enjoy teleporting people with no preparation into Equestria and seeing what they do. Most get some help almost immediately after reaching there, or get into problems with the denizens, but what happens when one person brings their own problem with them? Surely magic, or perhaps friendship, is the answer!

This takes place in the SilverVerse and like David's works is a self-insertion fanfic. Read on!
You don't have to, but you may want to read his stories for another (the original) perspective on this particular little idea. https://www.fimfiction.net/story/245393/clueless-in-equestria

Additionally, I have begun filling in some more of the 'not teen rated' scenes that in this were a 'fade to black', you can find them over here but be warned, this is Mature rated. You have been warned.

See This Blog for licensing.