Welcome to my first story here on . First things first, two of the four main characters in this fic will be original, or non-canon if you will. These characters are entirely fabricated and added to the story by me. Courier Six, while technically canon, is my own spin off the Courier from New Vegas. The chapters will alternate from each of the four: Jesse, Nana, Courier Six, and Benny. For our next order of business, I have not actually sat down and written anything, really, in a long time. I am sorry if this story comes off as a little rough around the edges. I hope to get my old writing momentum back as the chapters progress. I apologize in advance for any spelling or grammatical errors that I have missed on my initial proof-reads. Lastly, I am not sure how dark this story will turn in the ending chapters, but I very much intend to explore many darker themes; this is Vice and Caps after all. You have been warned.

And finally, Fair Winds and have fun reading.

Prologue: The Bounties

A slow pulsing rhythm filled the Brimstone. The music echoed softly off the walls of the empty bar. While mostly empty at this early hour of the afternoon, a few employees busied themselves with preparations for the new day to come while Jesse sat at one of the many tables littered about the room. He had a cigarette hanging from the corner of his full lips as he shuffled a deck of worn cards absently.

Nero was once again keeping him waiting. At first Nero's tardiness to their arranged meetings hadn't bothered him much. After all, he was the head honcho of Gommorah. That position alone was enough to warrant a pass, but now it just set Jesse's irritation into high gear. A sense of self importance seemed to have struck not only Nero, but everyone in the Mojave. With NCR's control on the region slipping and more players stepping into the fray for control of New Vegas and the Dam, everyone seemed to think they had a shot at power. It occurred to Jesse that in the end, only one faction could reign. It would probably be in his best interests to be on the winning side, and he knew for a fact that the Omerta's weren't going to make the cut. For now, however, they paid well and Jesse was in no position to be turning down paying work.

He lightly tapped his cigarette on the corner of the ashtray sitting in the middle of his chosen table as a woman approached him with a big sultry smile plastered on her cherry-red lips. While Gommorah had an air of sin and inequity, the woman radiated kindness and charm. With her bright floral print dress, she stuck out like a Khan on the Vegas Strip.

"Jesse, doll!" She trailed over to him a flurry of happiness that was almost unheard of in the Wasteland. "Have you stopped in to see little ol' me yet again?"

"Candy." He greeted her warmly. "What can I say? It's just hard to resist the opportunity to come see you when I'm in town," he replied with a playful wink.

Candy wasn't exactly the youngest woman in Vegas; Jesse was pretty sure she was somewhere in her forties. Gray hadn't had the pleasure of gracing her short chocolate colored curls just yet, but the corners of her eyes were marked with the creases that being older came with. He had once attempted to solve the mystery of her age by asking her, but she had dodged the question with what she called her words of wisdom: "That, my love, is a question that is like to get you turned away from even the warmest of beds." No matter, she was always more than willing to keep Jesse occupied on the days he was stranded in the Brimstone waiting for Nero to finally make an appearance.

Her pronounced rural accent made itself blatantly obvious as she feigned a swoon and let out a breathless, "Oh my!" She laughed and took the seat opposite of Jesse. "You're ganna have the girls around here gossiping up a storm if you don't stop that silver tongue of yours," she scolded him with a teasing glint in her light blue eyes.

Jesse let out a light chuckle as he set the deck of cards he had been toying with on the peeling surface of the table. "Care for a game and a drink? I promise I'll go easy on ya this time." The last of their games had ended with Jesse being fifty caps richer and Candy threatening to give him a spanking. Of course, she would have no doubt enjoyed the last bit.

"I let you win last time," she pouted, her red lips cast down into a mock frown. "You know I just can't resist that rugged charm of yours."

"I -" his reply was cut short as a brusque voice interrupted the duo's charade.

"Nero's waiting for you in the Zoara Club. Don't keep him waiting." The words were sharp and to the point. Jesse didn't even have to look to know it was Nero's right hand man, Big Sal. As his name implied, he indeed was a big man. At six foot four, he towered over Jesse by a good few inches. The dusty brown fedora he wore shadowed his face and made him seem all the more intimidating.

"Looks like I've been called to duty." He rose as Big Sal made an exit as brief as his entrance. He stubbed out his cigarette that had almost begun to burn away at the filter. "We'll have to continue this another day," he said to Candy, leaving a kiss on her cheek as he made for the private club and suites of Big Sal and Nero. For once, the flighty woman had nothing to say, she let him go without so much as another word. Business was business, and with the Omertas, you did as you were bid or you would likely wake up with a .44 magnum pointed at your head.

After finding his way through a dimly lit hall illuminated only by soft neon lights and up a flight of stairs, Jesse found himself in the Zoara Club. A row of pool tables were lined neatly through the center of the empty club, but Jesse paid no heed to them. The well stocked bar is what caught his eye on every trip up here. Alas, he had yet to be invited for a drink by Nero, so his hopes of tasting the fine liquors were slim. With a longing sigh, he kept up his trek to his awaiting employer.

"-has that under control." The voice was faint, muffled by the closed door of Nero's office. "Benny poses a problem. He has the chip." The voice was calm and controlled, yet with an edge all the same. It was Nero.

"From what I have heard, the Courier left the Tops after Benny; tailing him." There was a pause, as if the new unidentified speaker were thinking about his next remark. This person obviously knew Nero well; think first or be maimed. "We don't even know what the hell this chip does. For all we know, it could just be some fucking prewar trinket."

"House wants it. The courier wants it. Benny wants it. I'm going to go with it must be pretty important, Cachino."

"Well how about we give that sorry excuse for a merc you hired some real work: send him after the Courier and Benny so he can pop a cap in both of their asses?" Sorry excuse for a merc? Jesse wondered if that was meant for him; either way, he gave the man known as Cachino as silent 'fuck you.'

"Ahem, that is what I intended to-" Jesse, deciding there were no more interesting tidbits to be heard, took the moment to announce his presence with a knock on the office door. Before even having been given the okay to enter, he pushed the door opened and used his practiced social skills to act as if he never heard anything that had been said. Behind the facade, his thoughts were running with questions about all that he had overheard. Courier Six? The same courier who had been making waves of good intention all across the Mojave? What did Benny, the big guy at another casino on the strip, have to do with anything? Why were they now wanted men? And a chip? Like a poker chip? House? As in the illusive man running everything behind the scenes in New Vegas?

"Jesse." Nero greeted him simply. "Any longer and I may think that you don't really want my caps at all anymore." The statement had a hidden 'You don't want your head attached to your body anymore either' undercurrent implied as well.

"I always want the caps," Jesse grinned wickedly in turn, "Just so I can go blow them all on your girls, of course."

Nero was not amused. He got straight to business. "I have two people who I need you to track down. They pose a threat to our Family and I want them eliminated."

"While I fancy myself a merc and not an assassin, I guess my answer depends on how many caps I'm going to get out of this," he answered with only a moments delay. The lines between merc and assassin truly were blurry, yet Jesse had no qualms with a morally gray gig as long as the pay was worth it.

"Ten thousand caps per target", Nero said without flourish.

"That being said, we want proof that the deed has been done. Heads to be exact," Cachino added. Jesse glanced towards his spot in the corner where he had been sitting. Cachino stared back with a look of utter contempt, his balding head glinting in the low lights of the room.

"I believe I can manage that. Who are they and where can I find them?" The question was more out of cordiality than necessity; he knew who the targets were, had heard their names spoken before he had even set foot into the room.

"Benny, head of the Chairmen at the Tops; and Courier Six," Nero answered lightly.

"All we know is that Benny was last seen in the Tops speaking to Courier Six. Apparently, it didn't go real good for either of them. Gunshots were fired and the both of them tucked tail out of the Strip in a hurry," Cachino added.

"Sounds like I better go check in at the Tops; heard the booze is nice and strong there," Jesse made to stand. He didn't very much enjoy being in the company of the Omertas. They all had a certain thuggish brutality in demeanor. Jesse liked to think he was of a better kind.

"Wait," Nero commanded with a deafening authority in his voice, making Jesse halt his escape. "Benny has a little trinket on him that I would love to have; a platinum chip. Bring it back to me and I will double your pay."

A flash of greed struck Jesse features. His green eyes suddenly blazed with a light that could rival all the tacky neon signs on the Strip. He nodded at Nero to show his acceptance of the offer, and exited the room with a determination to find the Courier and Benny. Double pay for tracking down a well-meant yet far too wide spread Courier, and stupid wannabe in a striped suite? It was a dream come true for Jesse.