Prologue: Nightmare Night

It was nightmare night, a time when young foals in many major cities in Equestria were begging to be scared (and eat candy, of course). One small colt was poking around in his grandfather’s attic, looking for something to do before he went out for the night, when he noticed something odd. He saw an ornately carved ring, made of a metal that shone like gold, but was of a pure black luster.

The ring was not unfamiliar to him, in fact, he saw his grandfather wear it all the time. What was odd, however, was the fact that it was away from his grandfather. You see, this colt knew his grandfather well, and that old stallion never removed his black ring, and refused to part with it, even for a moment. It was almost like it was a part of him. The colt went to grab the ring. Right as he was about to touch it, a familiar voice croaked behind him “Just what do you think you are doing up here young colt? I thought that I had taught you better than to go snooping in other ponies' attics!” The colt's ears flattened to his head, and he whimpered "I... It's... It's just so... tempting... The colt broke his reverie as his grandfather had a coughing fit. He went to his grandfather's side and asked "Are you okay, grampa? Still coughing, his grandfather swept past him, grabbed the ring, and put it around his hoof. The effect was immediate. His coat brightened, he stopped coughing, and he was able to straighten up. Neither of them noticed a flash of orange run through the old stallion's irises. Eager to see what effect the ring would have on him, the young colt whined, “When will you let me wear it grampa?”. His grandfather gave him a long, hard look, and after a moment of silent contemplation, sent him downstairs to have a good time out in the town square with the rest of the ponies. As he watched his young charge's flank disappear down the attic steps, he mumbled reverently "Never, if I have anything to say about it. This ring is meant for Jack..."

Later that night, the colt and his friends sat around the Nightmare Moon statue, eagerly awaiting the famous story told every year. Suddenly, an old stallion appeared from behind the statue, a black ring visible on his front left hoof. The stranger announced “I bring grave news this night, fillies and gentlecolts... "Grampa! What are you doing here?" the young colt interrupted. Regaining his composure, the old stallion continued. "Apparently Mr. Goodmane will not be able to tell the nightmare night traditional story tonight, due to his wife being in the hospital. However, I will be able to fill in for him tonight, albeit with a story of a slightly different sort…” The old stallion let out his best evil laugh, making the young children look at each other with fright. He had them sit down, and began his tale.

“Most nightmare nights, ponies tell each other the haunting story of Nightmare Moon and her eternal night, but I am a different sort of pony, and have no use for mundane things such as tradition. Instead, I think I’ll tell you young ones how I came across this here ring I have on my hoof. What’s the first thing you notice about it?” One of the younger fillies shouted “It’s black!” ”Good eye!” the old stallion exclaimed. “That attention to detail may just get you through this night alive… OH COME OUTTA THERE! I’M ONLY KIDDING! Darn kids… Anyway, my story starts not so long ago, right here in Manehatten…” “What kind of story is it mister?” a shaking filly asked. The old stallion looked her dead in the eye.“It’s going to be an unfinished one, if you keep interrupting!"

Author's Note

I realize these first two chapters are short, but they are more of a teaser than the main act. The next few chapters will be (hopefully) longer. They are also going to focus on Jack's day-to-day life. Then things can REALLY get fun...