AN: Hello! This idea has been a long time coming, and I'm rather pleased with it. It's an AU where Bilbo is a Thief and an Assassin and he's hired by Smaug to steal the Arkenstone from Erebor. Since it's an AU (and it's about as AU as you can get) ages, time lines, and personalities might be a little off. For instance, Bilbo is about 19 years old by human standards, so barely of age. And Thorin and the company retook Erebor years before this story takes place, without Bilbo's help. Deal with it. Hope you like it!

OOOOO

Bilbo sighed as he soaked a rag in the coldest water possible before running it over his mother's forehead. She had a fever again. The fifth time this week. It fluctuated enough that Bilbo wasn't as worried as he could be. Not as worried as he'd been when she had a fever for two weeks straight. She'd been sick for so long that Bilbo had no shortages of scares committed to memory. Still, he knew any fever was dangerous, even the fluctuating one his mother was currently suffering from.

Belladonna and Bilbo had been living like this, with Bilbo wearing himself ragged caring for her, for years now. Ever since his father, Bungo, died in the Fell Winter, it had been just the two of them. But misfortune piled upon misfortune, tearing them from Bag End and depositing them in a dirty, tiny shack in the woods. Still within the Shire, but no where near the quality of a respectable, or even acceptable, Hobbit hole. The only reason they managed to keep their hut and keep Belladonna alive was because of Bilbo and his...discreet jobs.

Of course he had a normal job. He helped Farmer Maggot with his crops, every day, for long hours and little pay. It was a steady job, but it wasn't enough. He had started taking the contracts half a year after moving to the deplorable hovel. Being a Hobbit, he was naturally quick and quiet. Being the son of a Took made him even better at it. Necessity and love for his mother made him the best. He was invisible when he wanted to be, and there was nothing he could not steal.

It had started out as just stealing, really it had. But as Belladonna got even worse, the jobs got worse as well. The first time he was contracted to kill, he was panicking about his mother's health, desperate for a large sum of money. He's done well with the job, and from that point on, the calls kept coming. Bilbo Baggins became the best thief and assassin West of the Misty Mountains. Maybe further. But despite it all, all the jobs and contracts and charity from appreciative contractors, it wasn't enough.

There was never enough for them to leave the hutch and return to Bag End. Never enough to completely cure Belladonna of her persistent illness. Never enough for him to eat his fill, though over the years he had learned to live on very little and it hardly bothered him. He held out hope that one day he would have enough. That he would have more than enough, enough to rub in other Hobbits faces. Enough to spit at the greedy, no good Sackville-Bagginses who had driven them out of Bag End at the first sign of weakness. He wanted nothing more than to find Lobelia and her son Lotho and show them exactly what he had to do to keep him and his mother alive. But he supposed he couldn't kill them. Not without a contract.

"B-Bilbo?" His mother asked, though she wasn't really focused.

"Yes mother?" He asked softly, dipping the rag in the icy water again.

"Don't you...have work?" She asked, obviously confused. Bilbo smiled at his sweet mother and kissed her forehead. He hadn't told her the farming season was over. That he was out of a job for the next few months. She didn't need to worry about it.

"Don't worry about that mother. Farmer Maggot gave me a few days off." Luckily, Bilbo had just had a very good contract which left him enough gold for the next month. However, he would have to take another few contracts soon. Belladonna made a noise that suggested she heard him, though she was already back off in a dream, he could tell. She moaned and twisted in her sleep, obviously in pain from the illness in her chest. Bilbo sighed and reached for the laudanum. They were running low, he should go get some more while she was asleep.

After giving her a dose of the pain medicine, Bilbo petted his mother's hair back from her face, soaked the cloth again, and covered her up to chin with her thin blanket. He'd only be gone for an hour at the most, but he still worried for her. Even if she was heavily sedated. He wrapped himself in his father's old cloak, pocketed a few coins from his latest pay, and left the shack.

It was getting colder every day. They'd spent years enduring freezing winters in their disgraceful excuse of a home that didn't keep the cold out one bit. But with his mother so low of health this year, he might have to sacrifice a few meals to get her a warmer blanket, and some soup. Such warm meals were a luxury to the two of them, but it was necessary. He couldn't lose his mother. He could survive without her, he'd proved that to himself and others. But he loved her more than the Shire. More than Middle Earth. She was the only one he loved.

The Hobbits he passed avoided looking at him, and he kept his gaze cold and steady ahead of him. He held no love for these people. None of them had helped his family in their time of trial. None of them stepped forward now with help. Why should he even pretend to like them? Not even the richest would loan Bilbo money to buy the expensive cure for his mother's illness. The family with the largest Hobbit hole would not open their many halls to the pair. The fattest Hobbit would not offer anything but bread and water if they offered anything at all.

The only family Bilbo loved were the Gamgees, his neighbors from when he lived back in Bag End. But when hard times fell on Bilbo and his family, the Gamgees could do nothing to help them. They had no room to take them in, nor did they have money to support them. Hamfest and his wife did what they could, sending their boy Sam over with food from their garden. Or sneaking a blanket or two into the home under the pretense of checking on them. And when Bilbo left for his contract jobs, it was Daisy Gamgee that watched his dear mother. He owed the Gamgees much, and he hoped someday he would be able to repay them.

"Master Baggins, back again so soon? You were only in last month." The Shire's only healer, Greoff Gamgee, Hamfest's cousin, looked up when Bilbo entered his shop. He was familiar with the lad, Bilbo often came to the shop for his mother. And sometimes he cut back prices and offered free things to the young Hobbit without telling Bilbo he was doing so. It was only right, being a healer and all, for him to help as much as possible. If Bilbo never found out about his kindness, he didn't mind. Though of course Bilbo did know. He noticed every time.

"Mother's getting worse. I need more opiate." He spoke quietly, obviously exhausted. But even quiet and tired, he was always appearing so strong around the others. He never showed just exactly how tired he was, or how badly he wanted to scream and cry and yell for all that life had done to him. All that he had suffered.

"Of course lad. Let me get some from the back." Greoff said with a smile and waddled off. The healer himself had a bad leg, and Bilbo felt bad making the older Hobbit have to go into his back room to fetch what he needed. But he needed it for his mother. The gray haired but cheerful Gamgee came back with a bottle of amber liquid and put it gently on the counter. "That'll be ten silver." He told Bilbo discreetly. Both of them knew that last month, he'd asked twenty silver for the bottle. And the month before it was thirty silver. But as winter approached and he had more supplies to give, the price dropped. Only for Bilbo though. The golden haired Hobbit pulled a gold coin from his pouch, valued at twenty-five silver, and insisted that the healer take it all.

"Thank you Greoff." Bilbo was about to leave when Greoff spoke up again.

"Bilbo, could I ask a favor of ya boy?" Bilbo stopped and turned, nodding. "I need to get some packages delivered from Bree, but me boy is off in Buckland for a fortnight. Perhaps you could ride to and back and I could pay ya." Bilbo wondered briefly if Greoff had heard that Bilbo had recently been laid off working for Farmer Maggot. For the season, anyways. The harvesting was done and there was no more to do until spring, so he wasn't needed. The offer was sound, even if it was out of charity.

"Of course I could. Let me take this home and ask Hamfest to check on mother for the next few days, and then I'll be back." Bilbo replied gratefully. The old Hobbit gave him a wide smile and a nod. Bilbo rushed home, where his mother was still perfectly fine and asleep, before making his way to the Hamfest's Hobbit hole.

"Bilbo, lad! Haven't seen ya for weeks boy! What brings ya to our door?" Hamfest asked happily as soon as he opened the door to the golden haired Hobbit.

"Greoff's asked me to pick some things up for him in Bree. I shouldn't be gone long, but if you could maybe check on mother once a day?" He asked, humble as ever.

"Of course Bilbo. How is Belladonna?" He asked, a somber note creeping into his voice.

"She's getting worse. She has a fluctuating fever, and her coughs bring blood to her lips. The best thing I can do is keep her asleep as much as possible, for the pain." Hamfest nodded sympathetically. It really wasn't fair what Bilbo went through at his young age. Barely 35, only two years of age, and devoting his entire life to his mother and her health, living in a squalid hut in the woods.

"The missus will go over later, and I'll check on her in the morning. We'll trade off. Don't you worry Bilbo, she'll be fine while your gone." Bilbo smiled gratefully, hugging Hamfest warmly before turning to head back to Greoff's shop. "And Bilbo, be careful will you? Lot's of unsavory people in Bree." Bilbo smiled slightly, thinking of the unsavory people Hamfest spoke of. He'd done business with most of them, and killed some of them as well. Hamfest's concern was touching, but if anyone could protect themselves, it was Bilbo Baggins.

Bilbo was on his way to Bree before nightfall. He drove Greoff's pony and cart carefully through the muddy roads towards the city of Man, at a moderate pace. He wasn't worried about thieves, not when he had matching knives in his waistband and a bow behind him in the cart. He didn't come upon any trouble, and since he was used to not sleeping, they didn't stop during the night. By morning they were halfway to the Brandywine.

It took Bilbo two more days to reach Bree, and he was welcomed by the sight of Man sized buildings of brown and black, and mud that never seemed to dry out. Bree was large and sprawling and generally...brown. No trees or green grass or kids playing cheerfully in the street. Bilbo got many looks as he went, but it was mostly from the shady looking figures that stayed in the shadows. The ones that knew who he was and what he was capable of. The others only saw a nice young Hobbit who couldn't hurt a fly as he maneuvered through the streets.

"Greoff sent ya, did he?" He was stopped as he was almost to his destination by an old Man, so hunched over, that he was barely taller than Bilbo. "Recognize the horse. Well, come on then. I got his stuff out back." He said without offering as much as a name. The old Man hobbled the way to the large apothecary that Bilbo had been headed towards and brought Bilbo around to the quieter back alley. "It's those four crates there. Think you can handle loading them?" Bilbo almost laughed because, whether or not he could handle the crates, this old Man was obviously not going to be of any help one way or the other.

"I can manage." He said instead. The old Man nodded and limped into his shop without another word. Bilbo had to put some effort into loading the crates up, but after years of running around, stealing and killing people, he'd built up enough muscle to do this. He only struggled on the last crate, it was heavier by far than the others, and Bilbo was mildly curious as to the contents, but that wasn't his business. He succeeded in lifting the crate, but the first step he took he faltered, and it nearly sent him into the mud with the heavy box on top of him.

He was saved from his fate when a pair of arms took the crate from his hands and the Man they belonged too strode over to the cart and placed it down like it weighed little to nothing. Bilbo watched him carefully, wary of everyone, even if this Man was helping. The Man dusted his sleeves off before turning to face the Hobbit. Bilbo was a bit stunned for a moment. The Man was tall, as all Men were, but also lithe and willowy, with the kind of muscle that Bilbo had. It was there, but people often failed to see it until he used it. Not usual for the Men of Bree. The Man was dressed in all black, and when he drew back his hood, Bilbo saw his lightly curled hair was just as black as his clothes. His eyes were strangely gold, a color Bilbo had never seen for a Man's eyes, and they observed him just as intently as he was observing the Man.

A smirk came from pale pink lips as apparently, the Man liked what he saw. Bilbo had to admit that the dangerously sharp cheekbones and pale skin of this stranger were rather beautiful. He had a glow to him, almost like an Elf, but he was definitely not an Elf. At the same time, Bilbo didn't think he was just a Man. Maybe some sort of half breed. All Bilbo knew was that his strange helper was strong and lovely and staring at him like he was a meal.

"Thank you for your assistance." He said awkwardly and went to get back on his cart. The sooner he got back on the road the better. He'd stop just before leaving Bree to refill his water skin and pick up some bread and dried meat, but he didn't want to delay beyond that.

"You are different than I imagined you, Barrel Rider." Bilbo froze in his tracks. Only certain people knew that name, it was the name he used in his contracts as an alias. If this Man knew it, he could only assume he was there to commission Bilbo. And while Bilbo had enough gold from his last job, as well as what Greoff would pay him for his errand to Bree, winter was coming and his mother was getting so much sicker. So he turned back to the smirking Man.

"And what were you expecting?" He asked, a bit put out by the statement. He'd heard it before, Men judging him by his size and not his skill, and it pissed him off every time.

"Well someone older for one. Older, taller, less attractive." Bilbo couldn't help but shiver at the smile that accompanied the last one. "But if what they tell me is true, that won't matter." He drawled. Bilbo got the distinct impression that he wasn't going to like this Man. He seemed arrogant, self important. Like nothing could touch him. "I need your skills to steal something." That was fairly regular, and a relief. He always liked the thief jobs better than the assassin jobs. But beggars can't be choosers.

"Steal what?" Bilbo asked, still not letting his guard drop.

"A gem. A very special, very particular jewel. I assume you've heard of the Arkenstone of Erebor." The Man dropped his smirk, all business suddenly.

"The Heart of the Mountain. The King's Jewel." Of course he'd heard of it, every thief worth his salt had heard of the Arkenstone. And any thief with a brain knew it was impossible to steal. "No offense, but I know better. You'll have to find someone more skilled and much dumber than me to steal the Dwarves most prized possession." He pointed out, turning to leave again. So much for that. He'd just have to do a few odd jobs during the winter to get them through comfortably.

"Everyone I speak to tells me that the Barrel Rider is the best. I am confident you could steal it, given enough incentive." The Man persisted, but didn't move to follow Bilbo. He was obviously confident that his proposal would be accepted.

"I doubt it." Bilbo murmured under his breath, but apparently he was heard.

"Not even for a tenth of the gold in Erebor?" Bilbo nearly tripped over himself, barely catching himself in time to not make an idiot of himself. The treasury of Erebor was also known far and wide. Mountains of gold and jewels that could buy the entire Shire one hundred times over. A twentieth of that, hell even a fiftieth of that, would be enough to put this whole miserable business behind him for good. No more stealing or killing. No more sick mother. Everything he'd wished for, hoped for.

"And just how do you intend to get me my reward. Erebor is ruled with an iron grip, after that business with the Dragon. The King will never part with a coin that he doesn't have to, let alone a tenth of his wealth, and the Arkenstone." Bilbo protested, even if his mind was swimming with ideas of all he could do with that kind of gold.

"Once I have the Arkenstone, I can drive all the Dwarves from that mountain. And then the treasury will be mine to do with as I please. Including pay those who have served me." The Man was ambitious, Bilbo would give him that.

"Who are you anyway? What makes you think you could take the Lonely Mountain, even with the Arkenstone?" The Man grinned, a bit too darkly for Bilbo's taste thank you very much.

"The Arkenstone is the heart of the mountain. Whoever hold it, holds the mountain. And I have held it before. I will hold it again." Bilbo narrowed his eyes suspiciously. As far as he knew, no Man had every held the mountain. Only Dwarves and a Dragon, for a time. The Man seemed to read the look on his face. "I am Smaug. I have taken the form of a Man to go about retaking the mountain in a more discreet fashion." Bilbo recoiled, knowing the name anywhere. All of Middle Earth knew the name. The Dragon that took Erebor.

He'd held it for years, until the rightful King of the mountain and a company of Dwarves went back to Erebor and stole it out from under him. Forcing him out with the help of Men, Elves, and Dwarves from the Iron Hills. Bilbo had always thought Smaug had died back then, but evidently not. This Man was dead serious, he really believed he was Smaug. And maybe he was, Dragons possessed all kinds of magic that could lead to him being in Man form.

"But, if you are a Dragon...now see here. I am not a fool. If I help you take that mountain, I will not see a coin, let alone one tenth of them. You are worse than the Dwarf King about hoarding wealth!" Bilbo pointed out, putting the cart between them in case he should anger the creature. But Smaug only smiled patiently and pulled a contract out of his coat, handing it to Bilbo. The Hobbit looked at him wearily but finally took the thick paper.

"A Dragon does not break his oaths. Once we both sign this, I cannot go back on my word until I have given you what we agree upon." He said seriously. Bilbo watched him from the corner of his eyes as he unfolded the contract and read it intently. Smaug really covered every end. And it all spelled out something very simple. If Bilbo got the Arkenstone, Bilbo got one tenth of the treasury of Erebor. If Bilbo failed, or died, he got nothing. Smaug was forbidden to break the contract, or kill Bilbo if he should fail. And Bilbo was forbidden to take the Arkenstone for his own, or claim more than one tenth of the treasure.

"You're very thorough." Bilbo commented as he finished reading.

"Dragon usually are. Do you accept Barrel Rider?" He demanded, staring Bilbo down. Bilbo was still doubtful that he could actually get the Arkenstone. But...he had to try. For his mother, he had to try. He could start a whole new life for him and Belladonna. They could go anywhere, be anyone they wanted to be. She could be healthy, free of her burden. If he failed, nothing would happen to him...except failing probably meant ending up in the dungeons of Erebor, leaving his mother forever. But his tongue was just as quick as his fingers. Maybe he could get out of that too, if he needed to.

"I need some money in advance. Enough to support a Hobbit for however long I will be away." Smaug perked up at this, obviously noticing the catch in Bilbo's throat.

"You have someone you care for. Someone you look after and love." He said knowingly. Bilbo nodded, after all Smaug wouldn't believe him if he lied. "Very well. This should be enough to support your dependent during your absence. Do we have a deal?" Smaug asked again, holding up a large purse that Bilbo was sure was full of gold. Bilbo eyed it before nodding. Smaug offered him a quill and an ink pot, and Bilbo signed his name on the line below Smaug's signature. "Meet me back here in a week, behind the inn. We will go to Erebor together and I will stay in Dale while you use your skills within the mountain." He told him after folding up the contract and putting it back in his pocket.

"One week." Bilbo agreed, watching the Dragon in Man form walk away. One week. If he could cut down his journey to two days, that would give him a few days to settle things in the Shire and set up a paid caretaker for his mother. It felt wrong to expect Daisy and Hamfest to watch her when they had their own lives. Bilbo picked up what he needed for his return journey and set off, only stopping when the pony needed it.

He made it back to the Shire in record time. The first place he went was Greoff's shop. He helped the older Hobbit unload the crates, collected the pay that the healer insisted on giving him, and then he ran home. His mother was actually awake and lucid when he got there. She was laughing with Daisy Gamgee while they talked about gardens and sewing. Bilbo thanked Daisy profusely and when she was gone he sat down with his mother to tell her he was going away. He told her that he had a job transporting some items in Dale and Erebor and that he wouldn't be gone for more than a year.

"My son. You've done so well by me. I wish you didn't have to go to such far off places to pay for me and my Valar forsaken illness." She sighed, stroking his cheek. Bilbo smiled and covered her hand on his cheek with his own.

"I'm going to arrange for someone to look after you while I'm gone. And if you feel your illness taking a turn for the worst, I want you to send a letter at once, okay?" She nodded dutifully and then shortly after laid down for a nap. Bilbo took the time while his mother was asleep to seek out such a caretaker. He found one in the form of Primula Baggins, his cousin. Primula had just been married recently to his other cousin, Drogo Baggins, and she was more than glad to take care of Belladonna while Bilbo was away. She even asked for less pay than Bilbo had been prepared to offer. Bilbo spent a great length of time detailing everything that he did on average for his mother, and Primula dutifully wrote down everything he said so she wouldn't forget.

With that done, he set about packing. Not a lot, not enough to get in the way. Only the basics. A change of clothes, toiletries, some gold just in case. He stayed in the Shire for two days, making sure he had everything in line, and left for Bree in the early morning. He had three days to reach Bree, but this time he was on foot. He would have to walk through every night, but he should reach the city of Man in time. He wondered if Smaug would wait for him, if he was late.

In the end, it didn't matter whether or not Smaug would wait for him. He got there just as the sun was setting, seven days after he left. And sure enough, Smaug was sitting comfortably on top of a pile of hay behind the inn.

"It's about time, Barrel Rider." Smaug said, not even opening his eyes. But, Bilbo knew, Dragons had exceptional senses of smell. It was no wonder he knew it was Bilbo.

"You never specified what time of day to show up. And you can call me Bilbo. Since we're going to be seeing a lot of each other." Bilbo told him, stopping just shy of the hay pile. One golden eye cracked open and Smaug smirked.

"Who said we would be seeing a lot of each other?" The Dragon asked suavely.

"The trek to Erebor takes months to complete, on horse back. But I don't assume we have horses." Bilbo huffed, looking around at the empty alleyway. Smaug chuckled, the deep noise reverberating in Bilbo's chest lightly.

"We have something much quicker than horses...Bilbo." Before the Hobbit could ask, the realization dawned on him.

"But, you'll be shot down! If not by Men or Elves, certainly by Dwarves." Bilbo pointed out. Smaug scoffed and finally stood from his bed of hay.

"We will not be flying until we leave the cities behind, and I will not be taking my full Dragon form. They will never even notice us. I am not such a fool as to put my life on the line, little Thief." Smaug sounded so sure of himself, but Bilbo wasn't as confident. However, he didn't want to argue with a Dragon. He may be adept at killing and fighting, though admittedly he was much better when he had a weapon, but he doubted he would win that particular fight.

"Very well. Lead on." Bilbo assumed they weren't staying in Bree for the night. And though he was tired, and he had walked without rest for almost three days, he was determined to not slow his employer down. He didn't want to piss Smaug off, even a bit. Yet the Dragon seemed to sense Bilbo's exhaustion and snorted.

"We're not going anywhere when you're liable to drop unconscious any second. I will go get a pony so you may rest as we travel." Smaug was walking away before Bilbo could protest. He shrugged, after all it wasn't like he wouldn't appreciate the pony, and laid down on the admittedly soft hay to wait. He knew getting a pony could take a while, especially for a stranger in Bree. By the time Smaug returned with a nickering mare, Bilbo was soundly asleep. The Dragon couldn't help but smirk at the sight. His fierce little thief looked so young and vulnerable as he rested. Smaug could see just how young he really was in that moment, barely in his maturity, but with eyes that had seen countless horrors.

Smaug, rather than wake Bilbo, simply transferred his sleeping body from the hay to the pony. It was a testament to Bilbo's true exhaustion that he didn't stir at all during the transport. Smaug tied a rope around Bilbo's waist and around the mare's neck so the Hobbit wouldn't fall and then he began leading the pony. It was going to be a long journey, even with him flying for most of it, but he found that he was excited. He wanted to see if this thief was truly everything they said he was. He would put Bilbo to the test before sending him into Erebor. But, he would wait until they hit Dale for that. For now, he stopped thinking and simply walked, leading the pony and his Thief out of Bree and into the wild.

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Did you like it? I have more coming, don't worry. But perhaps you could leave a little review or something? Just so I know people are interested? Thanks for reading!