From the day he was born, Jack had always been amazingly unlucky. He had been teased at school for it, as he had been an easy target. He wasn't small and weak, so mostly his bullies got away with it as well. Unfortunately for him he had a big form, which caused him to be clumsy as well. Whenever there was a game of chance, he lost, so he quickly lost interest in such things, even though that caused more ridicule to fall on him.
He did not, however, give up, but instead learned to play every single thing safe, as far as he could. He learned to have several alarm clocks, secure apartments, no extra sharp or breakable objects around, no power outlets in the bathroom, and so on. He ended up in a safe desk job in a large corporation, just as he had hoped.
He had hardly any friends, and he never even tried to get a girlfriend. What would anyone see in him? His neighbors knew him by sight, but he didn't stop and talk. He had learned to live his life with as little human interaction as possible, diving into books whenever he had free time. If the lights went out when he was reading in bed, he was content and put the book down. He could change the lamp when there was light.
One night Jack was coming home, having missed his bus as usual. The elevator was broken, so he took the stairs, and finally got to his door. While he was fumbling with his keys a well-dressed gentleman with strange-looking eyes said hello to him.
'Hello. I'm really surprised you haven't given up yet.'
'Given up?', Jack replied.
'Well, life, of course. I went through all that trouble just to have at least one easy case, and you just have to take it all in stride.'
'What are you talking about?', Jack said, studying this odd suited man cautiously.
'You. Ah, you probably didn't get it. I'm the devil.'
'Look, now.', Devil said, leaning on the wall, and pointing at Jack with sunglasses that were in his other hand. 'I'll spell it out. The situation is as follows. We are recruiting. We need you. I'll make you a deal. Succeed in some simple trials and we'll leave you alone. Fail, and you'll work for us. How does that sound?'
Jack looked at the grinning Devil in amazement. Was this for real? There was something really strange in this fellow's eyes, he pondered. And from where did he appear? The apartment building was pretty well secured..
'Are you for real?', he managed, remembering finally to pocket his keys.
The Devil shrugged, snapped his fingers, and in a bright flash the surroundings changed. The noise of traffic deafened Jack for a moment, and then he recognized the area - they were standing near a busy intersection on the other side of town.
'Come on, did you really think all that bad luck was natural? Give me some credit.', the Devil said, putting on his sunglasses and straightening his tie.
Jack didn't have much choice but go along with the game.
The Devil signed onwards and they started walking, until they could see a street vendor selling fruit.
'Okay. Let's start with something simple. Get me.. mm, an apple. And I expect you not to pay for it, naturally.'
Jack started walking towards the street vendor. She had her back turned towards him. It would be relatively simple to just pick an apple from the case and keep walking.. she'd never know. Except that considering his big form and bad luck, he'd probably stumble and make the whole case fall down. He looked at the girl, and she was rather nice looking, so he wondered if he could just ask for the apple.
After talking with the girl for some minutes he walked back with a smile on his face. She was someone who knew him from the school, but had never dared to speak with him. He had not only gotten the apple, ("c'mon, I have this bet with this fellow, you see, that I could get an apple for free.. it's really important for me") but also her phone number, and a promise for a date.
For the next couple of hours the Devil jumped him around in places Jack knew well, including his old school and the city hospital. All of the trials were designed to force him to do some prank on other people. Initially they were somewhat easy to work around, causing only some humiliation on his part, but later ones were getting dangerous.
It was getting late, and our strange pair was standing on an overhanging bridge in the local mall. Despite the late hour, plenty of people were walking underneath.
'Well, I have to say that one was pretty shitty. Maybe I made your bad luck just teeny bit too reliable.', the Devil said.
The latest trial had taken place in the hospital nursery, where he tried to force Jack to cause two babies to get switched. Jack had taken a chance - something he had learned to avoid all his life - and his bad luck played the babies back to their correct cribs.
Jack felt tired and irritated. 'Okay. It's getting late and I've played all your silly games. How long a you planning to keep this up?', he spit, forgetting for a while to be afraid.
The Devil made a face, and then said, with an irritated voice: 'Okay. Last trial. Here, take this gun. Shoot someone.'
None of the earlier tasks were this direct or straightforward. Jack was shocked, and horribly afraid again.
'Someone. Anyone. I don't care.', the devil said, turning to lean on the fence.
Jack looked at the gun. He had never used one before, but he sure knew how it worked. It looked modern, and typical. Killing someone was, no doubt, a mortal sin. If he tried to shoot himself so that it's not a lethal wound it no doubt would end up being one. And he didn't feel like ending his own life. And if he just shot at random, given his luck he'd no doubt hit someone he knew. Then he got it.
There was a loud noise, followed by sharp pain in Jack's wrist.
'You son of a bitch, you shot ME?'
'Well sorry but you said -'
'Forget it. Just to think about all those poor souls I could have caught while wasting my time on you. Bah. Begone.', the Devil bitched while alarm bells started screaming all around the mall.
And with a brilliant flash Jack was back just outside his apartment door.
Later at night he laid on his back and pondered upon his experience. Was it real? It sure didn't feel real, although all those places they visited felt real. Plus his wrist was still aching from the kick of the gun.
Jack sighed, put down his book, and turned off his bedside light. Even though his closed eyes he could feel a strong light in his bedroom. He cautiously opened his eyes, to see a brightly glowing huge creature with wings hovering over the foot end of his bed.
'Oh good God, no!'
'But oh good God yes! We heard you actually SHOT the Devil? We'd love to hear the details.. And oh, how would you feel working for us?', the angel said, barely holding her laughter.
I got the idea to this story while I was having a fever. It's (quite naturally) inspired by the countless trick-the-devil stories out there. My brother joked that this could be a great pilot episode for a cheezy 'agent of the angels' tv series..