Author's Note: Hello! This is my first ever foray into the world of fanfiction, and what a foray it is, to delve into the Chuckverse! I've been having this plot idea for a few weeks now ever since I first watched Chuck a couple of months ago. The title itself, which will be obviously attributed to our very own lovable nerdy, friendly neighborhood spy, came from a historical fiction novel titled "The Dante Trap" by Arnaud Delalande. Interestingly enough, the protagonist (who is the original Black Orchid) himself is a spy (well, more of an Agent Roan Montgomery by personality, really, if you know what I mean) in the mid-18th century Venice. This tale traces its timeline from Season 3, Episode 12, the American Hero, specifically when Sarah Walker tells Chuck Bartowski that she doesn't trust him, at least not anymore, in the aftermath of the latter's Red Test. Everything after that spiral into alternate events. It will feature Chuck at literally the absolute worst time of his life, tragedy followed by tragedy forcibly transforming him into someone entirely different from what he used to be, and the struggles of his former friends to return him back to the light, even as enemies, old and new, rise up to crush him some more. Enjoy!

Chapter 1

8:45 PM

July 21, 2012

Verona Arena

Verona, Italy

One.

Two.

Three.

Four.

Five.

Six.

Seven.

Eight.

Finishing the last step, he turned on his right, he trained the gun on a figure some 40 feet away, and pulled the trigger.

Bang. The silencer gave a quiet hiss.

Momentarily, for just a few seconds, his pupils dilated, eyes wide open in shock, hands shaking in disbelief, as he stared at the downed figure currently bleeding in the almost empty stadium.

"It's okay, Chase. It is done. Come back to me now, please?"

Her voice. Or what used to be her voice. Settled deep within his memory, his subconscious.

Everything went back to normal. Breathing deeply, he stashed away his trusty Glock 22 handgun back to its rightful place, after throwing away the silencer, and turned once more to leave the area. Plucking out something from his breast pocket, he crouched slowly to place it on the ground, and stood back up, smoothening his suit. Glancing at his watch, he realized that he hadn't yet eaten anything else since his breakfast, and now he was hungry. Slipping into his car, a 1997 Pontiac Sunfire, he exhaled deeply once more, before setting the GPS towards a nearby Italian pizzeria.

It had now been 298 days since he lost her, but the pain was still too raw, too great, too damning as it had been that fateful, dark day…

-Break-

9:03 AM

July 22, 2012

NSA Headquarters

Fort Meade, Maryland, USA

Lieutenant-General Dianne Beckman gulped the contents of her 3rd glass of scotch in one single go.

Her third glass.

In her 38 years of service (8 in the Air Force, 15 as an NSA operative, 8 as deputy director of the NSA, 6 as its director and rounding a year as Director of National Intelligence), she had never gotten to down as many as that number of glasses in one sitting, in less than 30 minutes, during working hours.

There had been several instances when she came close to reaching that record these past few years, and interestingly enough, all instances were caused by the same person who is the reason for why she was drinking at the moment.

TheBlack Orchid.

The NSA, and consequently the US intelligence community's most talented field operative.

Ever since taking up that awful callsign 10 months ago, the Black Orchid racked up a total of 49 completed missions, all successful, no failed ones. Of these 49 missions, 17 had been completely bloodless, though most of these incurred levels of cumulative property destruction on varying degrees. The remaining 32 missions were marked with blood. Much, much blood. Though thankfully, and perhaps grimly, none of them American. All belonging to enemy agents.

Traitors. Villains. Monsters.

Normally with such spotless and legendary record, she would be damn right pleased and in awe of her operative. And she really is, make no mistake. No other NSA operative can boast a record as close as that of the Black Orchid, in relatively the same timeframe. Even the fabled Colonel, sorry, retired Colonel John Casey, formerly First Lieutenant Alex Coburn, US Marines, has that kind of record.

Funny that the two men worked together for a time. Never more alike as they were never more the same.

In just the span of 10 months, the Black Orchid was able to accomplish what both the best agents of the CIA and the NSA (except him) had been unable to do in more than 2 years of aggressive, all-out operations: track down, hunt, capture and kill the five elders of the Ring. With the heads of the hydra cut off permanently, (and most of their head lieutenants also disposed of, courtesy of the Black Orchid again), the subversive organization that once posed the greatest threat to the United States was crushed to the bare minimum of existence.

The Black Orchid himself dispatched the last intermediary honcho of the Ring last night, and it is the primary reason why she was drinking this fine morning at her old office.

The Black Orchid was truly phenomenal, and she could safely say is the most influential asset the US IC had in the 21st century, heck, even since the 1990s.

It truly proves that the apple doesn't fall far from the tree. The exact same ruthless perfection in completing missions, in hunting down targets, in eliminatingproblems.

She couldn't fathom why she feels the chills on her worn-out old bones when it was still summer in the East Coast.

37 years had passed, yet the memory of that...that scene, was still etched in her consciousness.

A dragoness will always breed dragons.

Nevertheless, as cold-heartedly pragmatic as she had become, Dianne Beckman can still weight in the costs against the results, and this could never be more directly consequential when talking about the said agent.

She knew the price that the boy paid to become a man, then paying another price to become a monster.

She knew it intimately, for she had watch his metamorphosis, his evolution from what he was five years ago, to what he, to whatever he is now.

A clear, and beautiful glass filled to the brim with the water so representable of life, continuously cracked over the next five years, leaking out its contents until it is literally a broken empty shell.

On average, it takes about 2 years of field operations for an agent to become a burnout. With minimal rests taken for vacation.

The Black Orchid managed it in 10 months.

To be fair to him, he had not taken out any vacation or rests at all.

As soon as a mission is finished, he asks for the details of the next one, only resting for sleep, and that too no longer than 9 hours, and eating on the go.

It had been standard for her to prepare a timeline of missions so that he can directly shift to the next one. If she can't provide one, he's proven he's more than resourceful enough to get the details on his own, and send himself on the next target in his own dark, grim merry way.

True, she was ever so grateful that all these missions had proven fruitful enough in their war against the Ring, but good Lincoln, even she could not fully believe, and until this moment still isn't believing that he had the strength, the smarts, the guts to accomplish all that he had in such a short amount of time.

It was like the man was actively courting and taunting death, dancing with it every second of his life, living every day as if it was his last glorious one on Earth.

Well, enough is enough.

After his debriefing last night, she harshly ordered him to report back to Washington, D.C. in two days, citing she had a most urgent mission to get him on board. It was the only way to entice him back home.

The thing is, she had no plans whatsoever to send him on any missions, stateside or abroad, over at least the next month. Whatever plans she had, it was for him to spend a forced vacation back at his hometown, with his estranged plan.

It was finally time to bring Chuck Bartowski, the only Human Intersect, home.

-Break-

7:54 AM

July 23, 2012

Phonsavan Airport

Phonsavan, Laos

A tall man, donning a pair of sunglasses and in a business suit, stepped off the small private plane and into the tarmac. Upon breathing in the air of the area, he gave off a smirk, removing the glasses to reveal a pair of almond-shaped cold grey eyes. A nasty scar treading across from his right eyebrow crossing his right eye and his right cheek can be seen prominently, giving off an entirely dark aura to the man in addition to the creepy grin he was now sporting.

Not a moment later, a hulking man, his bodyguard, stepped on to his side and offered a vibrating phone to his boss. Noticing the caller ID, he snatched the phone and smiled.

"Mr. Volkoff, I assume the next phase of our mutual business deal is a go?"