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The first time he woke, well the second really, but he didn’t understand that then, Bilbo was happy. Happy and terribly confused. The very idea of what had happened refused to settle in his mind in any shape or form and he believed it all to be a dream. Unusually realistic one, yes, but still just a dream. A nightmare, if one were to be precise.
Why, surely, he was merely tired. Weary even, of dwarves invading his home, laying waste to his pantry and risking his finest china. It was all just a result of the stress he was under that night, he told himself. Nothing to worry about. He even chuckled under his breath when, trying to find a more comfortable position on his pony, he realized that he remembered to bring his handkerchief along.
His mirth died out when the company faced the trolls. When they reached Rivendell, he could hardly swallow his bewildered dread. The goblins induced his first panic attack and it was Gollum who left his mind in a state of a terrible blankness. The company didn't notice that their burglar was a little quieter, a little more subdued on their way to and through the Woodland Realm, but then it all could have been attributed to the sickness that plagued the land. His apathy didn't abate until he felt the first of Smaug's fangs pierce his flesh, and the third time he woke, it was with a scream that left his ears ringing and his eyes watering.
This time, this life , he was proactive. He no longer believed his previous experience to be a fancy dream and it showed. He tricked the trolls before they could steal the ponies. He lead the company straight to the entrance of the Elrond's home. They were still captured by goblins, and he still fell, but the lake creature never had a chance to call him a liar and a thief, as Bilbo bashed his head in while wearing his ring. He lost three of his fingers to the warg attacking Thorin amidst the burning firs and almost slipped off the eagle as a result, but he persevered.
They passed the Mirkwood with nary a whisper from the giant spiders, spurred as they were by the unrelenting hobbit. Bilbo ignored the openly appreciative and respectful looks the rest of the company were giving him. He was too busy worrying about what to do with the fire breathing lizard that had taken residence in the dwarves' home.
His plans didn't see the light of the day, not that time, and not through the fault of his own. He fell into the lake, just before the gates of Laketown, jostled from the dock by the playful pair of dwarves. The cold water that he almost drowned under brought with it a devastating case of sickness. The next night he coughed himself to death and woke up with a metallic tang on his tongue.
His fourth attempt taught him what it felt like to be bo i led alive. He refused to even look at any kind of stew afterwards. The dwarves were rather taken aback at his vehemence against such a little thing but chalked it up to the strangeness of hobbitfolk. For his whole fifth life Bilbo avoided the cooking duty like a plague, a behaviour that earned him a rather alarming number of queer looks from the resident wizard. Bilbo kept quiet.
He kept quiet until it was time to go through the secret door into the Lonely Mountain. Then and there he found his feet unwilling to move; the whole story spilled from his mouth and as he gazed at the shocked, angry and disbelieving faces around him, Bilbo took a step back and lost his balance on a loose stone. It was almost a relief, when a second after he felt his bones break at the end of a short fall he surged up from his bed in his smial.
He wasted his sixth life, short as it was, shaking from deep rooted terror behind closed doors. He starved to death, slowly, hobbits being much more susceptible to inanition. He didn't care. The pain was a familiar companion by then, and one he almost welcomed.
When he woke up next he went back to the dwarves. He travelled, he smiled and laughed with them, and if his smiles held an edge to them, and if his eyes were colder and harder than the steel the company brought, no one cared enough to notice. A couple more lives he tried to protect the company to the best of his abilities, tried to mitigate their violent nature and avoid the most perilous encounters. He failed.
He forwent that approach after being killed by the trolls again. This time he was simply too tired to care about simple pleasantries and his interactions with the rest of the company were distant and seemingly uninterested. However that changed when they saw him emerging from inside the troll's body, hands bathed in blood. The dwarves whispered behind his back as he scrubbed his fingers clean but Bilbo paid it no mind.
Tricks and subterfuge had not served him well in the past. It was time to change.
He spent the next few lives learning the best ways to kill and murder, to sneak behind and plunge the knife just right, so that the enemy would not be able to draw another breath. Once more he thanked the Valar for letting the ring, the precious irreplaceable ring, come to him. It proved most useful on the quest and if each time Bilbo put it on his finger he let a little bit of his morals slip, the hobbit didn't notice.
He did notice that in that cold and colourless world there was a voice that murmured approvals in his ears with each felled goblin, warg and orc. Approvals and occasional advice.
A little to the right, it said as he raised his sword behind a new (old old old) enemy. Yesss, now lower...
Detachedly he noted that the voice had a sibilant quality to it. Not quite a snake, not quite a dragon, but something sly and slithering, something that belonged to darkness. At that point Bilbo didn't really care. Light had no more place in his world than laughter and smiles. Not after he saw his own innards spilling over his palms. Not after he knew what it felt like to welcome pain as an old friend. Light burned and refused him the help he desperately needed. So he turned to the shadows instead.
For a while it seemed to work. With each try he reached further and further, gained ground in his never-ending quest. For a while. Then came his fourteenth life and everything that could go wrong... Well, it did. Only three members of the company reached the Lonely Mountain. Bilbo, for whom survival was a second nature by now. Thorin, whose stony face could rival a mountain giant. And Nori, sans one hand and two brothers. By then the hobbit already resolved to start anew again, this time on his own terms.
On the king's orders he crept inside the hidden passage, the ring on his fingers, the voice in his ears.
Next time...
Yes, next time. And the next and the next and the next. Somewhere deep inside his heart, Bilbo no longer believed that he would succeed, no matter how many times he had been granted, but he hesitated to let such feeling out. Once they left the dark cavern they shared with every desperate thought, every hateful feeling he ever had in his life (lives) he doubted he could manage to start on this thrice damned quest again.
And then what would he do?
He rolled the question in his mind as he started climbing one of the crumbling pillars. The one time he stayed home... He preferred not to repeat that experience. Dying of hunger once was more than enough.
So then what would you do?
The voice was curious as well, Bilbo thought. Somehow, he got the feeling it was unusual for his disembodied companion, as he had taken to calling it. Eventually, he had concluded, that the voice was brought about by the magic of his precious ring, but as it never attempted to harm him (unlike everything and everyone else) he let it be.
On the top of the pillar he picked a gold coin and straightened. For a minute he continued contemplating what to do next. Perhaps, the first thing to do, the thing he should have done a long time ago, was to determine if the loop he found himself caught in, was hinged on his death or something entirely different. He assumed it had to do with the quest and its success, but...
Don't forget to find me, precioussss....
Bilbo smiled. Well, perhaps it was time to find out. With that thought he aimed and threw the coin right into the giant lizard's eye. The flames that licked his skin immediately after were hotter than he remembered.
When Bilbo woke up for the fifteenth time to the painfully familiar softness of his bed and the cheery song of morning birds, he sighed, forwent proper clothing and barred the front door. He took out the first bottle of hard liquor he could find and toasted the voice, resolutely ignoring any and all noises outside his smial. For a while he thought he could hear Gandalf’s angry voice, the wizard demanding to be let in, but soon the only sounds around were his breathing and half-muttered curses and the clinking of bottles.
For the first time in what felt like forever he let himself relax. Let himself ignore the thoughts of the company safety, of the quest, of the dragon... He allowed himself to stop caring and just breathed. And drank.
A couple of days later (he was a bit confused on the exact number) Bilbo ran out of alcohol. For a second he just stood in his cellar, blinking at the last empty bottle and swaying slightly, before he nodded to himself, grabbed a coin purse and went shopping.
He had a new quest. One he came up with all by himself. He was going to find out how long it would take to get the Thain to ban binge drinking in the Shire.