Dwarves were filthy, lowly, ill-mannered, unintelligent sorts. Exactly the kind Sherlock would have normally dismissed without a second glance, but John had said something about a debt and a second cousin twice removed, or some such nonsense. By all rights, it should have been John doing the sneaking in this godforsaken tunnel. Unfortunately, he had come down with a rather debilitating cold after that debacle with the river. The poor man could only say "Dank You Berry Mudch" when the town's folk had the sense to present him with a hot cuppa.
So here was Sherlock, in a hole, at the beck of dwarves, off to do some burglar-ing from a dragon. Slipping into the cavern Sherlock surveyed the situation. Plotting out all possible scenarios, it became clear that there would be no escaping this clients demands without confronting the dragon. The best approach might be to be direct.
"Ho! Fine and mighty best, I have been sent to retrieve something from you greatness!" said Sherlock, layering on a bit of flattery.
"Man! Who confronts me with such foolish boldness? Speak quick, before my hunger exceeds my curiosity!" rumbled the waking dragon.
"I perceive you are of intelligence. Your eyes have a sharp look to them. Would you not prefer some entertainment before your meal?" Sherlock queried.
"What entertainment can a human, no matter how gracious, provide one such as I?" asked the dragon.
"Smaug, dragon under the mountain, killer of dwarves, lover of gold, wisest of beasts they call you… I propose we match wits, for neither of we believe that physical battle would bring much pleasure." said Sherlock.
"Hmmm… Well-spoken man. Your words are worthy of a drake-ling. What would you propose?" Smaug asked as he stretched his head nearer.
"A game of riddles should suffice. If you win, I am your meal." dared Sherlock, leaning his own body forward with a wicked smile.
"A most likely scenario, however, what do you hope for?" Smaug pondered aloud.
"I shall determine my prize upon my victory." Sherlock said dismissively.
"You surety shall be your doom." Smaug boasted, "So be it. How shall I address thee?"
"I am the Fair Home, the puzzle solver, the best man." Sherlock evaded.
Smag huffed a hot breath, reeking of sulfur at Sherlock. "Very well, keep your name brazen thief, it will hold no bearing on our contest."
Sherlock straightened up and said briskly, "Let us Begin. When my first is a task to a young girl of spirit, And my second confines her to finish the piece, How hard is her fate! But how great is her merit If by taking my whole she affects her release! What am I?"
Smaug deep chuckle echoed off the caverns walls. "Murder is not a subject well chosen, for dragons of any worth all appreciate any good story of death and betrayal. Your narrator is Hem-lock. The turn is mine!"
Smaug shifted his great weight and began, "Under pressure is the only way I work, and by myself is the only way I'm hurt. What am I?"
Sherlock pause for only half a moment. Kicking a few gems with a smirk, he declared smugly, "A diamond. Your preoccupation betrays you, oh, Smaug the wealthy." Smaug growled and let smoke slip through his lips. "Be careful little 'fair home,' or I may forget my 'Honor'."
"Mmm, that would be a shame." Sherlock said facetiously, "Very well; question: I fly, yet I have no wings. I cry, yet I have no eyes. Darkness follows me; lower light I never see. What am I?"
Smaug rustled his massive wings. "It has been long since my mind has been drawn to such places. You make me restless, my quick witted man. The answer you seek is a cloud."
Sherlock took a step forward. He was now just feet from Smaug's massive head. Every breath that whistled through Smaug's nostrils ruffled Sherlock hair. "How long, great drake, has it been since you have been free to roam? By the gold and gems pressed into your great breast, I deem it has been just shy of two-hundred years."
"You gauged the time well." said a surprised Smaug. "I shall have to stretch my wings, after we finish our game, I finish my meal." he added with just a note of wistfulness.
With a grin Sherlock went on, "Why wait? I grow weary of this situation myself. I have no desire to deal with petty dwarves, mad wizards, or foolish boatmen. What say we strike a bargain?"
Incredulously Smaug questioned, "What have you to bargain with me?"
"Take your fill of my companions, they lie in wait to kill you at the back door. I ask only that you let me take enough to cover my troubles and time to gather a friend from the village. There is further gold to plunder, wood that will light with ease, and no one to warn them."
"Why wouldn't I do that by myself, after eating you?" said Smaug.
Sherlock pulled a small dark object from his coat pocket, "I could kill you right now. Your left breast has a space uncovered and I have a small weapon that could easily pierce what remains. Do we have an accord?"
"I should eat you!" Roared Smaug in rage.
After a short moment of violent thrashing, he settled down and continued, "But, I feel that your proposal has merit. Beware 'fair-house' I have your scent and I shall one day come to finish our game and collect my prize!"
Sherlock nodded and turned to exit the front of the fallen kingdom. It would be best that John not find out about this whole situation. His sympathies would not approve.
Smaug quickly passed Sherlock, exited, took to the skies, and crested the mountain, looking forward to tasting dwarf once again.
Orginal Promptbr /Sherlock (instead of Bilbo) riddles with Smaug;"This did NOT go where I thought it would... "The riddles I used are not my own inventio"