You know what they say once you hit rock bottom...

Some Canterlot entertainers aren't just musicians... and some ponies fall in love with them anyways.

When one of Equestria's most popular cellists appears at Twilight's birthday party, it's just another gig for Octavia, but a shock for Twilight and the rest of the party-goers. She arrives, wishes Twilight a happy birthday, wows them with her beautiful music, wows them with her musical beauty, and doesn't leave until after everypony else has left. So when a few ponies suggest that this 'entertainer' might be more than just a musician... some eyebrows are raised, but nothing more. Twilight is beyond reproach, after all, and Octavia can earn her living however she wants. When she sticks around Ponyville, however, it becomes a slightly different story - Twilight is romantically-naive, after all, and Octavia is... most certainly not.

The romance of Twilight Sparkle, Celestia's protege, and Octavia van Clef, Canterlot's most famous entertainer.

Rated 'Teen'. Per FimFiction's rating guidelines, this story contains some 'more adult themes', but has no 'graphically adult content'. Rated primarily for sexually suggestive material, but also (in later chapters) alcohol use and adult language.

Spike figures out that Cheerilee is making up reasons to visit Twilight at the library, and Rarity further figures out that it's because she must have a crush on Twilight.

When Ponyville's dedicated fashionista combines forces with Ponyville's only dragon to bring two adorably awkward book loving mares together, nothing can go wrong! Except perhaps, everything!

Oh yeah, and some pony ordered 20 trampolines and a bunch of other stuff that keeps getting delivered to one wrong address after another because of the world's worst delivery pony, Blue Bonnet.. More on that later.

Re-tagged to reflect that it's a Twi/Cheerilee, Mane 6, CMC and Blue Bonnet (Background pony) story.

Also, it's fair to say this is also a AppleDash and Fluttershy / Background pony shipping story. Also ScootaBelle? .
ARTWORK BY WACKEDOUTPET

Chapters 3-10 have been edited by the amazing TheLastBrunnenG

Chapter 9-10, attention must also be paid to pre-readers Guy Incognito, Cola Bubble Gum, and SpaceCommie

Chapters 9-10 also edited by SpaceCommie

Featured May 2013! ADDED TO TWILIGHT'S LIBRARY NOVEMBER 2013! FAN-ART ADDED MARCH 2014!

Have you ever woken up somewhere you don't recognize? I have, once before. This time was not all that different. Headache? Check. Dry mouth? Check. Upset stomach? Check. Hooves? Uhm, that one is new.

Hi, I'm Bruce and I'm 32. Currently, I'm in a light blue Earth Pony foal's body no one has ever seen before. The rest of Equestria thinks I'm 9 and something really traumatic happened to me. It doesn't help I swear like a sailor and I could really go for a smoke right about now. I just hope that the Everfree Forest, rampaging monstrosities, evil dark abominations against God and the Cutie Mark Crusaders don't kill me before I have just one last drag.

Oh, and ponies are hella creepy when you really think about it. Geez.

A little comedy side project. EDIT: HAHA Main project. More characters to be added if I get that far. Categories might be refined as I write. Entire thing is unplanned except vaguely. Don't Expect excessive cursing to be written out, just hinted at. Oh, and as the character is a 30-ish year old in the body of a 9 year old, sexual jokes might exists but sex itself will not occur.

Special thanks to user Momomojito for the awesome-tastic picture! First fanart, I'm so HAPPY. I've gotten more since then! I should collect it all here. Collected!

Let's just say your luck with the mares isn't all that great, two months in Ponyville and you've had your heart stomped on more times than you can count. That coupled with the fact you've lost your job, your house, and have barely enough bits to feed yourself means your life isn't exactly going so great. And after another botched attempt at a relationship you're ready to swear off of the whole dating game for good.
But after a night of drunken debauchery you awaken to find yourself in the service of Ponyville's premiere fashionista, you're willing to forget your previous pledge to the single life after she proves herself to be the kindest and most generous pony you've ever met, but only time will tell if she'll be your future lover or the next in line of a long list of mare's who you'd rather forget.

"Always expect the unexpected in life, after all, life is unpredictable." Jeff Manns, a 20 year-old high school graduate, has finally moved out of his parents home. Jeff's life couldn't be better, he has a job, he's living on his own, the whole world before him, and he has... six magical miniature fillies? How did these creatures end up in Jeff's life, and what does he even know about taking care of these three inch tall fillies? Absolutely nothing could go wrong.

Sidenote - the lovely Fred2266 has actually done a reading from a long while ago on some of the first chapters on this story! So show him some support and enjoy. https://www.youtube.com/watch?v=hlrBLTmK4B0&t=19s

[2nd Person Perspective]

Working as a waiter at Canterlot's various social gatherings is a nice job. Especially since you began chatting with the cello player of the usual quartet, Octavia. You've gotten to know a lot about her, but one night there seems to be something on her mind. You offer her a drink to ease her nerves and you bring your glasses together in cheers.

Next thing you know, you wake up in a strange hotel room in a town you've never been to next to a certain gray mare.

Art by John Joseco

Twilight becomes alicorn of the stars. This is sort of a problem, because Luna kind of already was alicorn of the stars. Oops!

TV Tropes

This story is a sequel to Setting Her Heart Aflutter

(2nd Person x Fluttershy) After the wedding, you and Fluttershy now live a happy, relaxing life. You love each other like nopony ever could, and you treat your new wife with the same level of kindness and respect that she is accustomed to.

But very soon, a very big change is about to occur in your marriage, and from the looks of things, it may not be just the two of you anymore.

This story is a sequel to What if: Rarity from The Three Sisters met with Chrysalis

Choosing whether or not to visit Chrysalis has been bugging Rarity for a week since receiving an invitation to do so. But there seems to be trouble brewing in the Hive and Rarity now has little time to act. Either way, her family's future rests in her hooves.

Now with a TV Tropes page! Warning: Will Contain spoilers.