I find that evil frustrating puzzles like that become more interesting if you make them so hard that they take weeks, if not months to solve -real time-. But in order to do that, you need to make certain that solving the puzzle/riddle isn't the ONLY thing they are doing during that time. In my campaign, a month or two ago I handed the players a riddle that they are only now starting to come close to solving. The answer to the riddle is an action that they should take that may save the world from being snuffed out like a candle, but until then, there's PLENTY of things they can do, like hunt cultists and explore mysterious forests and play politics... all the while, each session I make sure to include an additional subtle hint to the riddle. One of my players is REALLY into this riddle and has pages of notes of things he thinks might be relevant, and the others are enjoying it as well (if not to the fervent passion my one player has for it).
At any rate, enough personal anecdotes. Lets see if I can help you out!
Petals on the rose. Stars around the moon. The neat thing about these games is that they are in fact riddles. And riddles are just flowery poems in which the "title" of the poem is the answer. You use symbolism and imagry to describe something without using mundane terms.
So in order to make a puzzle like this, first you need to come up with a solution, and THEN the riddle comes afterwards, as you poetically describe the steps needed to be taken. Since I -love- making riddles and puzzles, I'll give you an example... something off the top of my head.
The Box is something of a size that can be carried and manipulated (like flipped over and such). Whether or not it takes multiple people to move or not, doesn't matter. Needs to be movable. On the top are two figurines that have been ATTACHED to the box, probably guilded or made of some special material... silver or gold or something nice. The box rests on four feet. There are other bits of ornamentation on the box... carved wooden roses (also possibly gilded or otherwise adorned)
In order to open the box, you must hold the box upside down, press the... uh... bosoms of the two figurines at the same time, re-right the box, and then jiggle the "back-left" (if looking at the box from the front, which should be clear) foot. At this point, it becomes possible to turn the handle of the opening mechanism, which looks like one of the ornamental roses. Turn it counterclockwise once, then turn it back clockwise a quarter turn, and lift. The lid opens.
At this point, the rogue of the party should search for traps because putting your hand near the opening of the box will trigger a nasty poison dart trap, the vileness of the poison depending on how much of a RBDM you feel like being at the moment. Finding the trap should require a search DC of X, and then a disable device check of Y, where X and Y are appropriate challenges for your rogue. (Allow him to take 20 on the search, but not on the disable... failing by 5 or more will set off the trap)
Doing any of this out of order will reset the entire mechanism, requiring them to start over. This should be made obvious with sound effects. It should also be made clear that they are doing something right each time they solve a step, probably also with sound effects. Positive reenforcment = good!
So now we construct a riddle, section by section... which means Verse by Verse. For a more difficult puzzle, make all the verses available to the players from the start. For a simpler puzzle, only give them one verse at a time.
Step One: Flip the box and press the chests of the figurines.
For the poem, I'll be using an ABCB rhyming pattern, making use of a rhyming dictionary. I want to say something about "our hearts" for the location to press, I need to hint that they need to be pressed together, and I need to say something about upsidedown... "turning the world upsidedown" is a good phrase that could work in poetry, and that makes me think that the poem should be a narrative from the "guardians" of the box about how they'll keep everyone away from the McGuffin inside, unless the world is turned upsidedown. Yeah, I like that.
"Our will and minds entwined as one
--We guardians of the crown
Shall guard our hearts against your way
--Till the world is set upsidedown"
Step Two: Turn the box back over and jiggle the back-left foot.
The fact that we say that a box has feet allows for so much possible imagery. Moving one of the feet provides plenty of possible words we can use... walking, stepping, dancing... or even bowing, genuflecting, that sort of thing. In order to specify WHICH leg to do this too, I think specifying something like "2 o'clock" would work; except that it's hard for me to think of a way to work that into the theme of my poem, and besides, medeviel times didn't tend to have clocks, or numbers of them. Early afternoon might work. If they don't get that reference, well... trying all the legs until they find one that moves shouldn't be a problem, unless you're feeling vindictive (did any of your players insult your sister or kick your dog or something? If so, make jiggling the WRONG leg set off a nasty trap. That'll learn 'em!). Some reference to flipping the box back over would be nice as well. And now to make it rhyme...
"Early afternoon beckons our step
A dance for our lord and king
As the sky is above and the earth is below
A song we shall ever sing"
"King" I picked because it goes with the guardinial theme, and "sing" I picked because it ryhmes with king and goes with the dancing theme. Furthermore, this makes for a great signal that the players did something right... if they get this far in the riddle, have the box start playing as a music box.
Step 3: Turn the rose one turn counterclockwise, quarter turn clockwise.
I think I can continue with the dancing theme here. The trick is that to name "flower" or "rose" goes against the whole nature of what a riddle should be... you should never name something so outright like that! So I need a euphamism for flower. "A delicate thing" might work. Something like that. Terms for counterclockwise and clockwise... hm. Left and right? Too mundane. Against the sun and towards the sun? That's a bit more poetic... but is it too esoteric? Well... you wanted an evil riddle...
"We dance amongst the prettiest things
The fragile, the delicate, with love
Full once towards the sun, then step back again
Then rise we up, gentle as doves"
Step 4: Disarm the trap!
If each of these riddles were COMPLETELY seperate and isolated, or even if there was a step inbetween, I might make reference to flowers now. Afterall, roses have thorns, right? But context will make mentioning roses here too much of a clue for the PREVIOUS verse, and that's no good. So I'll just make this last verse a general proverb type thing that might be ignored like the moral of an aesop's fable. That'll have a nice feel to it. To further this, I'm even going to use a different poetic structure, make it FEEL seperate. Besides, I just accidentally came up with two lines right next to each other that rhyme...
"The dance is not done,
There's thunder in the sun
And even a kitten has claws."
If you don't like my puzzle, make up your own. Hopefully I gave you some ideas and maybe gave you a push in a direction you like.
