It is not every day that you learn that a monster of legend is real, let alone friends with Rarity. If she had heard of the old stories, perhaps she would be more cautious. Or more daring.

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

Anon decides it's time to test out a theory of his. If the ponies can go around naked all day, then why can't he?

I mean, what's the worst that could happen, right?

Caramel decides to promote stallionism at a Wonderbolt performance. In retrospect, bringing Anon along for support may not have been the best idea.
(RGRE)
{This story has two versions, the last chapter is the first person version.}

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.

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.}

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)