Cloud Goat might just have the wildest life of any goat in Goatville. Marvel at the insanity that is her life, and laugh at the suffering of her poor beleaguered best friend, Blossom Goat. Or at least, you would do that if this weren't a story about goats. Sadly, goats just aren't very interesting. Also, the title is a lie. Goats do not win at anything. Ever.

It's a stupid April Fool's prank story. About goats. You were warned.

Losing your virginity is a big milestone for anypony. Especially when you finally hook up with the pony of your dreams in the process. There was just one problem for Blossomforth: when she woke up the next morning, the other side of the bed was empty. Cloud Kicker wasn't there.

Sure, Blossomforth understands why Cloud Kicker wasn't there for her. Cloud's been going through a rough time lately, and maybe their hookup wasn't timed very well. However, knowing that doesn't make Cloud's absence hurt less, nor does it make Blossomforth any less lonely. Perhaps this is a sign that she needs to put some serious thought into where her relationship with Cloud is going, before things get too far out of hoof.

Part of the Winningverse. Takes place concurrently with Chapter 18 of The Life and Times of a Winning Pony.

Princess Twilight Sparkle is perfectly happy with her perfectly ordinary life in Ponyville. Every library book is properly shelved in its appropriate place, and her life continues on exactly according to her meticulously planned out schedule.

Then she gets a bodyguard.

Now she has to find some way to fit this new pony into her life on short notice. It won’t be an easy thing to adjust to—especially since Captain Storm Kicker’s presence makes it that much harder for her to go on living like the same old Twilight Sparkle she was before she became a princess.

Sunbeam Sparkle is not a good pony. She might not be pure evil, but she is ruthless, ambitious, and so power-hungry that she would even aspire to usurp Celestia's throne. Worse, she succeeds in manipulating Celestia into not only surrendering rule over Equestria, but her immortality as well.

It is often said that power corrupts, and absolute power corrupts absolutely. In most cases that’s true. Many good ponies have begun with good intentions, but slowly lost their way. However, this is not always the case. A rare few virtuous ponies have the character and strength of will to resist temptation, and are never corrupted by their authority.

Even rarer, there comes a time when gaining power makes a pony better than they were before. This is one such story.

Flight Camp was a life-changing event for Cloud Kicker. Her horrible fight with Rainbow Dash forever changed things between them, and drove a wedge between Cloud and Fluttershy.

But what if that had never happened? What if Cloud and Fluttershy had stayed together? How would the lives of the three friends be different? What other changes would ripple across Equestria as a result of that one event? Cloud and Fluttershy might be happily married, but how would that change the lives of their friends? Would Rainbow Dash go down a different path to joining the Wonderbolts? How would Rarity's life change if she never met Fluttershy until she moved to Canterlot?

Where would they be today if they'd traveled down the road not taken?

Freshly graduated from West Hoof Academy, 2nd Lieutenant Storm Kicker decides to enjoy what little free time she has left before accepting her commission with the Long Patrol. And what better way to let down her mane than at the millennial celebration of Celestia’s reign, on the eve of the Summer Sun Celebration?

Well, there is the pesky little detail of a pesky little sibling who decides to tag along and be a pest. Still, it’s the last chance she’ll have to spend time with Star, so they make the most of it. It’s all fun and games, plus she'll have plenty of chances to needle her little sister along the way.

At least, until the two sisters are asked to look into the disappearance of a family friend; it soon becomes apparent that not all is well in Canterlot.

Part of the Winningverse.

I am eternal, and death is my steadfast companion. The passing of each generation of my little ponies weighs on me; every one of them is a fleeting, irreplaceable treasure, a snowflake dancing 'round a fire. I want to save all of them; I have the ability to save a few. I have saved none.

Blossomforth is fresh out of college and ready to take on the world. Sure, moving to Ponyville to get a job on the weather team is going to be a bit of an adjustment, but it's nothing she can't handle. Besides, Rainbow Dash seems like a fine boss. Everything is looking good for our favorite watermelon-maned pegasus.

Then she meets a pony named Cloud Kicker.

Part of the Winningverse

After a misunderstanding leads to a vicious fight at Flight Camp that leaves them both in the hospital, Cloud Kicker wanted absolutely nothing to do with Rainbow Dash. However, Rainbow refuses to let a single incident destroy their friendship, and has been writing Cloud Kicker letters ever since that horrible day. For more than two years Cloud Kicker has been throwing the letter into the trash unopened, but what will happen when she finally reads one? Can their friendship possibly be salvaged?

Side-story to "The Life and Times of a Winning Pony"

Rainbow Dash and Cloud Kicker have been good friends for years now. But when Cloud Kicker comes to Ponyville for one last visit before heading off to join the Royal Guard, Rainbow has to face some difficult questions about just what she wants to do on what might be their last chance to hang out in a long time. Her decision might be a little easier to make if Cloud spent less time thinking about banging and more time thinking about her awesome friend, Rainbow Dash.

Obviously, this calls for a night on the town. And booze. Lots and lots of booze.

Part of the Winningverse.