“To ropes!” called the first mate.

“Brace!” the boatswain cried. “Starboard side!”

A massive wave slammed the side of the ship as the storm raged. Rain pelted the crew in sheets, and wind threatened to tear the skin from their very backs. Milo and the others fought with their ropes to wrestle the thrashing sails. Most tied down their lines, but one man still struggled with his. While the other crew retreated to what shelter they could find, Milo aided the man fighting with his knot.

“Thanks very much,” the man shouted over the roar of the storm. “Does my savior have a name I might call him by?”

“Milo Vascaltro,” he replied in kind. “And you?”

The man, Milo could see now, was devilishly handsome. The rain dripped from his tricorn hat, ran down his face’s sharp features, and fell into the crease of his thin, blue lips. Those lips peeled back from white teeth, grinning a bright cheshire slash against the dark abyss of an angry sea at night.

“Thank you kindly, Milo Vascaltro.”

*

Over the weeks that followed, the man became Milo’s shadow. They worked, shared meals and watches together. Privacy was never easy to come by aboard the Black Dawn anyway, so Milo tried to take pleasure in the company.

His “shadow” was curious, both in being and in manner. He asked Milo a rain of questions, of himself and his family, then eventually of his way of thinking, of his aims and desires. Milo found him easy to talk to, so he answered with little worry.

After some time, however, the innocent queries came laced with the trappings of a darker nature.

“What did you say?” Milo recoiled on one such occasion, and his last with the nameless man.

“I asked you,” the man repeated, “what it would be worth to you, for a chance at another life? One where you had the power to impose your will on this world rather than simply wading through it, a slave to many masters?” He collapsed the distance between them with a ghostly step. “What would you trade for that, Milo Vascaltro? Would you give a dream? The lifeblood of a heart gone black? Or even that eternal part of you, prized by gods and monsters alike?”

They spoke in the dead of night, under the watch of oil lamps and surrounded by the hush of the empty ocean. Milo met the man’s eyes. Something in them raised the hairs on his neck, set a fathomless pit in his stomach.

“No,” Milo said.

The man’s usual grin shrank. “No?”

“No,” Milo repeated, “I wouldn’t. Not my freedom, not for anything. In fact, I rebuke the notion.”

The man’s smile vanished altogether, and Milo walked away. He looked back just once. The handsome man in the tricorn hat watched him with eyes that gleamed like a cat’s against the dark.

When Milo woke the next morning, the man was gone from the ship, and no one he spoke to seemed to hold any memory of him. From that day forward, it was as if his friend was no more than smoke and shadow after all.

*

Weeks later, when the memory of the handsome man had faded to near nothing, fate called with its own designs. Cannon fire ripped the Black Dawn to splinters, and gun smoke clouded Milo’s own lungs. His crewmates fell to bullets and blades, and the handful that survived were bound in chains. Within a fortnight they were branded with the marks for piracy and black marketeering and were set to be executed by firing squad.

Milo listened to the rolling thunder of rifles until he was the last man left in his holding cell. The heavy metal door swung open like a tolling funeral bell. Two guardsmen yanked him to his feet, and their captain examined Milo up close.

“Bit small for the post,” he laughed. “But there’s half a roast duck waitin’ for me at the Copper Toad once this is finished. Now, move.”

Milo was tied roughly to the post so that the cord bit into his wrists. Before him stood ten Thurian soldiers with rifles. Milo’s heartbeat drummed against his ribs and his knees trembled. Down those gun barrels was death, naked and real and true.

He was about to die.

His whole life lived, just for this moment.

“Last words?” called the captain, a procedural formality belying deaf ears.

He wasn’t ready. Milo’s eyes scanned the faces of the soldiers in the firing line, searching for something – sympathy, sorrow, humanity of any kind – but he found none. They were all stony and remorseless, save one.

One face, handsome and cold, Milo recognized for its familiar grin.

“I…I accept your terms!” he cried hoarsely. Terror had dried his throat. “Please! I accept!”

None reacted to his plea, barring the captain.

“Hmm, not what I’d have spent my breath on,” he said with disinterest. He cleaned his nails with the bayonet of his own rifle. “Soldiers, ready!”

In unison, the line raised their weapons.

“Aim!”

As one, they fixed Milo helplessly in their sights.

“Fire!”

Milo’s eyes clenched tightly closed, and what followed was an avalanche to his senses. He had imagined his death before, but this was almost like slipping into a dream. Stings pierced his neck, torso and his legs all too quickly to hurt, and the last beats of his heart pumped warmth down the front of him like a velvety robe. Death’s cool hand pulled him into its downy sleep, but stopped short. Breath suddenly found his lungs, and his heart resumed its faithful rhythm in his chest.

Then he heard it.

His eyes refused to open, but the sounds of inhuman slaughter and baleful screams painted nightmares in his mind. As quickly as it all began, the noises died away to an eerie silence that was broken only by the sound of two boots squelching a path across the stone toward him. He was cut loose from the post, and a whimper escaped his lips. A voice, cold as frost in the early morn, coyly shushed him from just behind his right ear. Milo was walked forward several paces and had something pressed into his hands.

“Open your eyes,” whispered the voice.

Milo obeyed, and what he saw was carnage. The line of soldiers, the notary, and any spectators within the small courtyard were all dead, killed and twisted in some unspeakable way Milo’s imagination could faintly guess at. The only being left recognizable among the littered corpses was the guard captain. He was bloodied and on his knees before Milo, each arm removed at the elbow.

The object in his hands, Milo now realized, was a rifle, one of the very same meant to execute him and whose barrel he’d stared down only moments ago.

“A verbal agreement is all well and good,” said the man with the cheshire grin, “but I will need your signature to accompany it.” He touched the rifle, and the steel transmuted, minute runes etching themselves along the barrel with a pale light. He lifted the end so that it pointed directly at the helpless captain. “You wanted another life, and the power to make it worthwhile. That is what you bought. Now, begin proving that it was worth it. Not to me, but to yourself.”

The desire to protest was the dying whisper in the back of his mind as Milo felt a power rise in his chest. It at once burned like brandy and chilled like a winter wind. An intoxicating shiver ran through him, and he found that he liked it, enough that a smile curled his lips. He looked at the captain.

“Please,” the man begged through broken teeth. “Please, I-”

Milo pulled the trigger.

*

The years that followed were the teachers of many harsh lessons, but with his newfound powers he explored this second life with a lust for the unknown. He relished every step he took on new ground, savored each breath which filled his scarred chest. For a living, he hunted bounties across the Iron Kingdoms, and he did not do it alone.

His partnership with Alyssia Atwood was perhaps the most earnest kind of trust Milo had ever known, and when she vanished without explanation during a job, it fractured something in him. His thirst for life remained, but cynicism dogged its edges, at times fanning it to unhealthy extremes like a forest fire spurred by the wind.

In quiet moments traveling the open road or before sleep took him at night, his mind ached for answers. It lingered on Alyssia’s disappearance, formulated in vain a purpose to give this new life and, when Milo was honest with himself, it explored shadowy corners and unturned stones for signs of his dark benefactor.

It was then that a letter found him, an invitation by forces unknown. He perused its pages, considered its contents, then committed the cypher to memory and burned it.

If he was going to seek out the Strangelight Workshop, he wouldn’t risk the paper trail…

END

Yeah…so I get into writing character backstories. I’m a nerd, sue me. The above is one I took to writing for a friend’s D&D campaign using the Iron Kingdoms campaign setting. The idea was that we were each some kind of pseudo-accomplished explorer from around the Kingdoms, contacted by the shadowy organization Strangelight. I’d never heard of it before, but he told me that there were mechs to pilot (called “Warjacks”, rad as hell), big ol’ trolls with galvanized swords, and something called a “gun mage”.

Wizard with a shotgun? Sign me up.

So that’s when I drew up Milo. My GM advertised that he’s pretty loose and agreeable when it comes to modifying classes and house-ruling some spell restrictions, so when I asked to fold in some warlock flavor, it was an easy addition. I’ve drafted plenty of character backstories before, but none I’ve sunk into quite as deeply as this one, so on that alone it’s a success in my book.

So far, we’re only a few sessions in, and I don’t know if the Smiling Man will make an appearance, but I’ll sure be checking dark corners and looking over my shoulder for him during whatever hijinks we get up to.