The badlands of Equestria is a cruel and harsh region of burning rock and coarse desert. A place where evil creatures and ponies who kill reside, it certainly doesn’t have the most honest beings in Equestria. It certainly is not the place where good oaths are usually upheld between anypony, not even good friends.

But it is here that you, a unicorn colt, a timid dreamer full of ambition to become somepony as great as all the greatest names in history, were born. It was here that you left to go to the inner land of Equestria, where Celestia ruled peacefully and where you would ultimately fail to find your destiny. And, upon your return, it is here where, with the help of your new teacher, the gun slinging hermit stranger named Anonymous, you will receive your true education, make an oath to find your own way to do true good in a land of bad, and become the great figure you always wanted to be.

(This is story is set in the Reversed Gender Roles universe of Equestria, where the women take on the gender roles that men usually have in society and vice versa.)

An astute (oblivious) Rainbow Dash spends her days working, lounging, and hanging out with her best, completely platonic, in no way pining, 20% tsundere sis, Anon.

This story takes place in an AU called RGRE (Reversed Gender Role Equestria). If you're unsure of what that means, there's a group on fimfic that catalogues stories like these that might explain it best. If you're interested in content with a similar setting, consider joining it and looking around.

Cover Art by Affanita

Rainbow Dash has always been an incredible fighter, the best in Canterlot High and the region, but when a new student shows up, she struggles to keep the title. Even more surprising, however, is that the student is a boy.
Anonymous is different than every guy Dash has ever met. Strong, confident, and more than capable of handling himself, it's no wonder Canterlot High's star athlete has taken an interest in him. When he shows her just how strong he is, however, it shakes Rainbow Dash to her very core.
With a desire to reclaim her title, Dash throws everything she has into defeating Anon, wanting to prove her strength and earn Anon's respect. Yes, his respect, and nothing more...
(RGREqg)

Twilight scans Anon, only to find that he has no magical resistance. If a unicorn uses a charm spell on him, well... He eventually finds peace of mind in the ponies of Ponyville.
(No one is harmed in the course of this story)
(RGRE)

{This story has two versions, the last chapter is the first person version.}

Spaghetti and Fillies is a multi-chapter work that began in the RGRE general of /mlp/ and has since begun to be remolded for the fine folks on FimFiction. While the story continues over several 'episodes' where the focus changes slightly and more characters are added, the overarching theme and tone remain the same: a lighthearted story in which a troubled farm-filly emerging into adolescence deals with the problems and societal pressures associated with such a time. In true /mlp/ fashion, many of her triumphs and failures will center around the human character Anonymous, as well as the various other RGRE counterparts for characters present in the show.

Though there isn't and likely never will be any real sexual content in this story, there will be allusions, crass language, and much, much spaghetti spraying - the latter of which only gets worse as the story goes on.

You have been warned.

This story takes place in an AU called RGRE (Reversed Gender Role Equestria). If you're unsure of what that means, there's a group on fimfic that catalogues stories like these that might explain it best. If you're interested in content with a similar setting, consider joining it and looking around.

Anon had a bad feeling when he saw the ice cream machine outside Firmly Asked Questions. Not only was the world softer and fluffier than he had anticipated, but he would also have to watch his weight.
{This story has two versions, the last chapter is the first person version.}
(RGRE)

On Earth, women might not give such a big fat man the time of day... Things are different in Reversed Gender Roles Equestria though. Mares are attracted to soft, cuddly, and thicc stallions, and one man overshadows everyone by being the biggest and thiccest of them all... And Celestia is sure to fully use it to her advantage.

Based slightly on a meme, and several others, a 1000 word story challenge.