This was from a forum contest on the giantitp website a few years ago.
Guessmiths
Uname looked at the gynosphinx as if she had three heads. The riddle she had rhymed off made no sense to him. If only the bugger had horns instead of the upper body of a woman, he could be justified in striking the beast down. But she had given him a reasonable request to pass into the pyramid, and as much as he would have liked to, he could not bash her head in. This was her duty, just as it was his to find and return the scepter.
Uname left the sphinx and the pyramid for another day. Returning to Lomer, the city on the edge of the desert took most of the gold in his pack. All the time, he repeated the riddle to himself. He hated the desert almost as much as his steed Rashop, but he promised the Lady Monique that he would retrieve the scepter inside the pyramid.
Asking around, while none of his comrades could give him an answer to the riddle, they did direct him to a small gnomish pub far from the hectic market place. After cleaning himself off, he ventured in. While it was in a gnomish section in town, there were many others here, including dwarves, elves and halflings. All of them sat around with half-empty tankards either rolling the bones, playing cards or hunched over a piece of paper repeating simple riddles to themselves. A harmless lot, Uname thought.
A serving lady came over to ask him what he wanted, "Umm, I need help with a riddle." The entire crowd in the pub seemingly stood still, as two dozen faces turned towards him. A young gnome raised his hand and approached, "Yes, Wastelander, how can we help?"
Uname looked at the gnome strangely, without any apparent weapon or holy symbol, who had seemingly guessed at his little recognized heritage. "How did you...?" Uname's question was left unsaid as the gnome both finished his question and answered it at the same time:
"Heritage, oh that's easy, your hair colour for one. Most desert people don't have red hair, besides your weapons seem to have a slight greenish tinge to them, an often noted side effect from the cold tempering used in the cold wasteland. Geography is one of my many interests."
After a brief introduction Uname learned that Bromsby, this gnome, was one of the guessmiths, a group of riddle and lore masters who gathered here at the Laughing Lass pub to test each other in games of chance and riddles. Explaining his predicament, Bromsby eagerly volunteered to accompany the elderly Wastelander into the desert.
Less than a week later, Bromsby and Uname were back at the pyramid.
“So,” said the large imposing gynosphinx, “I see you are back, and brought a friend.”
Uname nodded.
“I ask thee again: What runs all day, but never walks. Often murmurs, never talks...”
In the middle of the riddle, Bromsby joined with perfect harmony with the sphinx, “Has a bed, but never sleeps. Has a mouth, but never eats?”
Rather than saying a word, the little gnome threw a waterskin up to her, she easily caught it with her claw, and opened it, letting a stream of water flow into her mouth.
“What you need here in the desert; the answer is a river, my lady.”
The gynosphinx roared with laughter, “How right you are little one!”
Seven hours later, as Uname emerged from the pyramid with a scepter in hand as well as newly found cuts and bruises from the undead inside the tomb, he saw the gnome and gynosphinx still in conversation, sharing riddles and laughing at glee in one another in a friendly game of one-up-manship.
Guessmith: Prestige Class
A guessmith is a student of riddles and games of chance. While they have no formal training or organization, their shared love of riddles and guessing games unites them in a loose circle of friends. While some may use these talents for riches, most are intrigued more by the challenge than wealth.
Most who take this class are rogues or bards, but a smattering of others can take this prestige class if they can qualify. Barbarians because of their starting illiteracy are extremely rare.
Hit Dice: d6
Requirements: To qualify to become a guessmith, a character must fulfill all the following criteria: Decipher Script 6 Ranks, Any two Knowledge skills +3
Special: Must be able to read and speak in a minimum of three languages
Class Skills: Appraise, Bluff, Concentration, Decipher Script, Diplomacy, Disguise, Escape Artist, Gather Information, Hide, Jump, Knowledge (all), Listen, Move Silently, Perform, Profession, Sense Motive, Sleight of Hand, Speak Language, Spellcraft, Swim and Use Magic Device.
Skill Points at Each Level: 6 + Int modifier.
Class Features
Weapon and Armor Proficiency: A guessmith gains no additional proficiency with any weapon or armor.
Special Abilities
Minor Trivia (Ex): A guessmith excels in being able to remember things they have previously read or heard. They add their class level to any one knowledge check, chosen at first level; once chosen this is based on their charisma does not change.
Skill Focus (Limericks) (Ex): Since many riddles are in the form of limericks, a guessmith learns to repeat all kinds of limericks or jokes in an entertaining way.
Friends of the Game (Ex): Because most guessmiths are not motivated purely by wealth, they can easily make friends of other creatures who also enjoy games of chance or riddles, such as gynosphinxes, fey or any other creature the DM designates. On these creatures, a guessmith has a +6 charisma bonus.
Second Guess (Su): Once a day, a guessmith can make a second try at guessing an answer without repercussion, even if a second attempt would normally negatively affect the outcome. This may be in regards to any trained intelligence or charisma based skill check or any type of riddle.
Major Trivia (Ex): Like minor trivia, except they add their class level to any two additional knowledge skills. This does not stack with minor trivia, so there is no benefit in choosing the same knowledge skill twice.
Second Chance (Su): Like Second Guess, except this re-roll applies to any skill check or saving throw. They must use this ability immediately after the failed roll. They can use this ability as many times as their charisma bonus.
Level
|
BAB
|
FORT
|
REF
|
WILL
|
Special
|
Casting
Level
|
1st
|
+0
|
+0
|
+0
|
+2
|
Minor
Trivia, Skill Focus
|
+1 Effective
level
|
2nd
|
+1
|
+0
|
+1
|
+3
|
Friends of
the Game
|
+1 Effective
level
|
3rd
|
+1
|
+1
|
+1
|
+4
|
Second Guess
|
+1 Effective
level
|
4th
|
+1
|
+2
|
+2
|
+4
|
Major Trivia
|
+1 Effective
level
|
5th
|
+1
|
+2
|
+2
|
+5
|
Second
Chance
|
+1 Effective
level
|