This story was originally written in response to a writing prompt at Hair Brained Press. The prompt was “In a world of thieves the only final sin is stupidity”

The world of thieves is a complicated strata of professions. At the bottom you have your common press gangs, muggers, pickpockets and cutpurse urchins. Not much higher up you’ll find footpads and jackrollers, followed by cattle rustlers and horse thieves. Somewhere in the middle are your common card sharks and confidence tricksters. Also in this strata you may spot the odd biblioklept—a rare find, and not generally given the respect they’re due. Somewhat higher up you will find second-story men, pennyweighters, gentleman brigands, and safecrackers. Above them all are the true confidence men, masters of manipulation, at the top of which, naturally, fall big tent preachers, professional politicians, and bankers.

Jack was an upper-echelon sort of thief, opposed to violence on principal and not much fond of sneaking around in the dark. He had a plain face that was unmemorable, and therefore honest. He spoke softly, but with conviction. When he said something you couldn’t help but want to believe. He had all the makings of a great politician, if only he was incurable lazy or somewhat of an idiot. Jack, fortunately, was neither.

Now thieves, by necessity, are a morally flexible sort, but they do have their own sense of honor, despite what people say. They have a code, as it were. Rules. And the greatest rule in a world of thieves is that the only final sin is stupidity.

Jack had come dangerously close to committing the final sin.

You see, Jack it would seem, had come within spitting distance of developing something absolutely forbidden by the thieve’s code. He had almost done the unthinkably stupid: Jack had very nearly gained a conscience.

Her name was Isabel.

If looks could kill, Isabel might leave you slightly bruised. She dressed simply, but floated through life with the grace and dignity of a dancer. From her father she had inherited a vast fortune, and from her mother a sense of purpose. At the age of twenty-three she had already founded six orphanages, three hospitals, and one fine colony of lepers. She was a women with a mission.

She was also Jack’s target for a long con.

As opposed to a short con, like say perhaps selling your grandmother her own teeth (which Jack had done on at least one occasion), the long con took patience and fortitude. It took commitment. Jack had all three.

When he met Isabel he had been running a rather successful short con in the philanthropy circles. The game was simple: find a charity gala to invite yourself to, flirt with the old ladies and have a brandy with the men, and wiping a tear from you eye explain the plight of the Moldavian miners. The mines of Moldova were infamously dangerous, he would say, and everyone would sagely agree. Hardworking men died by the dozens, and left many widows and orphans. The rich old men and women would nod sadly despite having never heard of any such place, and would write great checks payable to the organization Jack represented.

When he told Isabel of the troubles in Moldova she dabbed at her eyes with a dainty lace handkerchief and took him by the arm.

“Something must be done about the mines,” she said, floating beside him. “It is good to feed and clothe the widows and orphans, but that does nothing to fix the problem.”

Jack frowned. She was not following the script. This was where she was suppose to dig into her purse and bring out her checkbook, not begin digging into root causes.

“What is needed is reform!” She gripped his arm tightly. “We must raise awareness. Petition the government. Form safety committees. Conduct inspections!”

Jack’s mind raced.

“It will be very expensive,” Isabel added, pursing her lips.

“Very,” Jack agreed.

“We shall be partners in reform, you and I,” she said. “You must put me in contact with the proper authorities. I will cover the expenses.”

The furiously spinning wheels in Jack’s mind clicked into place. This woman was rich. Beyond rich. This could be the greatest con of his career—assuming he’s could pull it off. He had no doubts that he could.

Her eyes, flashing, met his, and the first stirrings of something quite alien to him fluttered in his stomach. A doubt began to form. Jack was not given to having doubts. It felt like heartburn.

“What do you think?” she asked, holding his gaze.

He quickly aborted the embryonic doubt, turning his thoughts from Isabel’s sparkling eyes to her glittering wealth. “Partners,” he said.

Isabel smiled and continued to ramble on about petitions and committees and regulations, but Jack’s mind was already skipping four steps ahead.

In bed that evening his mind had skipped six steps ahead, and then suddenly leaped back several steps to Isabel’s eyes. He shook his head and untangled himself from the limbs of the woman beside him, slipped quietly out of bed and into a robe, and went to stand on a balcony overlooking the broad river snaking through the city.

The suite had been furnished by the generous donations of a Mr. and Mrs. Cobbletree of Apple Lane. So had the woman. The room was not overly grand—Jack was not given to extravagance—but it was comfortable, featuring an oversized bed, overstuffed chairs, and an oversized view. The woman was not oversized, but she was certainly comfortable. She sighed softly in her sleep and rolled over, silk sheets falling away from her body.

One of the principal rules of the long con was Do Not Get Attached.

There was definitely a danger here of becoming Very Attached. Jack had never felt like this before. All his life he had been quite happily very much  unattached. It was an odd feeling. It felt like gnats in the pit of his stomach. He tried retracing his thoughts, back to The Plan, but all he could see were Isabel’s dark eyes flashing before him.

He clutched the ornate iron handrail and took a deep breath of the warm night air to clear his head. He was a professional, he reminded himself, not some besotted schoolboy. He had conned dozens of women far more alluring than Isabel, hadn’t he? Rich, lonely women with boorish husbands and too much time on their perfectly manicured hands.

Isabel was all the things those women were not.

She was kind and generous, compassionate and fair. Her hands were not manicured, but calloused from serving the poor. She was rich, but not lonely. She was certainly not idle. And she had no husband, he mused, boorish or not.

A new voice whispered in his head. “Partners,” it said. Together they could make a difference in the world. Perhaps not in Moldova, where there were in fact no mines and few orphans, he reminded the voice, but nevertheless it swam unbidden through his mind with images of a life far different than the one he knew.

A new feeling rose inside him, like a knife stabbing into his gut. He couldn’t recognize it, not at first, but then slowly it dawned on him. He was feeling guilt. It made him nauseous.

It was then he noticed the glass of brandy being held in front of him by a slender hand. The woman pressed up against him and kissed his neck. He sipped the drink aimlessly as she slowly moved her hands inside his robe.

Thoughts of Isabel slipped away and he turned to kiss the woman. She led him back to the bed. Back to his familiar world. A world free from attachment, free from guilt. He embraced the woman as she slid under him.

And he tried very hard not to think about how dangerously close he had come to doing something very, very stupid.

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