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Wobbly trapper makes me think of a fence. The Falmer:A Study?

Thieves Guild.

Definitely The Black Arrow, v2.

Damn I think it is as well, for some reason I dismissed this when searching before, I guess because I only skimmed it rather than reading it fully.
I even thought about the guy who runs The Drunken Huntsman as the "wobbly trapper" but didn't realise the book's behind him!

It is in fact the black arrow books (both 1 and 2 are acceeptable answers). They are my favorite books in the game.

Seen before
but now once more - the book has appeared in morrowind and oblivion

1 Traveled for 5 - the author traveled alone for 5 days
then met 7 - then met 7 adventurers
All seeking mistress/master - the author was seeking a job working for the duchess and the 7 adventurers were seeking hiomaste the archery master
became close but then departed so as not to be doomed by association
For there was contempt between master and mistress - the 8 of them became good friends but they split up again before the duchess saw the author with them because she despised hiomaste
An argument heated - the duchess invited hiomaste over but there was an argument because he refused to move his school
and ignited the flame - because of the argument the duchess had the school burned to the ground
that made the 8 fewer the following day - some of the adventurers died in the blaze including the authors best friend

The mistress the victor or so she had thought - the duchess was incredibly pleased with herself for the fire as hiomaste died
til there were holes in her visage from revenge she had wrought - everyday from then on a black arrow kept appearing in the portrait of the duchess
the 1 was guarding til she pushed the 1 out of the way - the author was ordered to guard the painting and one day when he was sitting by the door the duchess pushed him out of his chair
just to see that this was the last of her days - at that moment that days arrow came through the keyhole and hit the duchess in the head killing her instantly

If you have not read the books I highly recommend them.

I spent a long time on this poem/ riddle. So please no random guesses. I think it is hard so I will include 1 of 2 available hints right away. Its for the extreme lore buff Enjoy

Two betrayed herald a shadow
Once set among similar and now removed
Sent to protect the slave serving two yet one

My sister's keep is hard to swallow
Dying for what you seek
You fell and raise so we may meet

Cast by a heart so hollow
United by following a half told tale
Where cent-less lovers bore deceit

Though removed, my sister you may borrow
Clout by both bearings
Many wish she were as sweet

Returned I find hope through sorrow
A shadow of myself yet strong
A dimming light has set so shadow comes to don
----------------

Hint 1:
all 15 lines have at least double meaning
13 lines are referencing Morrowind
1 stanza+1 line references Oblivion
6 lines involving the sister have at least triple meaning
4 lines reference 4 books- 3 of which are in Skyrim
8 lines are general lore/information
all 15 lines reference skyrim
9 words have double meanings
1 stanza has none of these words

All of these references direct to the subject at hand. I am more interested to see who can find the references rather than the actual answer

Bloody hell (and I'm not even English)... I'm going to need some time with this one.

Is it too hard?? No takers?

I love your riddle, I really do but... if you're going to make long riddles that reference other games outside of Skyrim, the Lore Trivia thread is the best place to do so. If you wouldn't mind maybe doing another riddle, or just taking out any parts that aren't referencing something in Skyrim (probably most of it ), that would be great.

Every line references skyrim... like I said, I worked long and hard on it.

Here is hint #2

Two betrayed herald* a shadow 157
Once set among similar and now removed 1247
Sent to protect the slave serving two yet one 1267

My sister's keep* is hard to swallow 1234567
Dying for what you seek 127
You fell* and raise* so we may meet 1247

Cast* by a heart so hollow 1267
United by following a half told tale 12567
Where cent-less* lovers bore deceit 1257

Though removed, my sister you may borrow* 12347
Clout* by both bearings* 123467
Many wish she were as sweet 12367

Returned I find hope through sorrow 12467
A shadow of myself yet strong 1267
A dimming light has set so shadow comes to don 17


-------hint # 2 with guide----- Every number or * represents one of the hints below. I have one final tip if it stays for one week. (5 of Hearthfire 2012)
1. all 15 lines have at least double meaning
2. 13 lines are referencing Morrowind
3. 1 stanza+1 line references Oblivion
4. 6 lines involving the sister have at least triple meaning
5. 4 lines reference 4 books- 3 of which are in Skyrim
6. 8 lines are general lore/information
7. all 15 lines reference skyrim
* 9 words have double meanings
1 stanza has none of these words

Look honestly I have no idea where to start on this riddle, it's a great riddle and my riddle solving skills do not measure up to it.

Just think about the words. They are each mini riddles that point to different things. Each of these things is involved with the subject that is being searched for. If you were to figure out a single line, you would be capable of unraveling the whole riddle. I'll tell you now, the further out from the center the more abstract. The center is more concrete. I hope you guys like it when I do the unraveling IF anyone gets it.

I'm going to go through and analize bits. I'm pretty sure I won't get anywhere, but I can try.
There seems to be a lot of darkness in this riddle. As in, there are shadows all throughout the first and last stanzas.
'Sister' is also a recurring theme. Going out on a limb to say it maybe refers to the Companions...?

Two betrayed herald a shadow- Two people have been betrayed, and now they've taken up trumpet (metaphorically)?
cent-less lovers- On the surface, it looks like it's saying penniless lovers. No doubt there's more to it then that. I can't think of anything else, though.

Astrisked words:
Herald- Can't think of a second meaning, besides the obvious.
Keep- Castle stronghold/something she has possession of?
Fell- Several possibilities here. 'Fell' as in 'fell over', 'fell' as in 'fell beast', 'fell' as in 'fell the mighty tree'.
Raise- Could refer to raising someone from the dead? In which case 'fell' could also mean 'kill/die'.
Cast- Cast as in mold, cast as in throw. Maybe others?
Cent-less- Can't think of anything besides the obvious.
Borrow- Two meanings to 'borrow'? Is the second just a euphemisim for 'steal' or something?
Clout- Dictionary says this can be a heavy blow, political power, or a fabric patch.
Bearings- Dictionary gives me several meanings. I don't know whether any of them apply.

Firstly, the riddle has nothing to do with the companions

Secondly, good attempt at the definitions. These are the specifics that I used.

[/spoiler]

Amazing what word choice, time and effort allow; the ability to say volumes within sentences is a useful talent...
Hopefully now you realize...
My riddle is a collection of riddles. Each riddle is itself a collection of answers. Each answer has a vector directed at the subject of the original riddle, and by solving one, you can solve them all.

Is it an Elder Scroll?
Herald- The Elder Scrolls were around before Morrowind
Keep- They were hidden away
Fell- They caused death
Raise- What you learn from them in the main quest
Cast- Many people forgot the location of the scroll
Cent- To the average reader they make no sense and are worthless if you cannot read them
Borrow- You "borrow them for many quests
Clout- you use them in some political quests (The ones I know of are from Oblivion and Skyrim)
Bearings- A part of a "scene" in Skyrim where there is a "birth" (Skyrim) and you need them for certain locations

I would go more into detail but I don't want to spoil anything.

Ha, no. I'm sorry its not an elder scroll.
I promise, the double meaning words dont play as big a role as you guys are placing on them. Remember to look at the other hints.

Like the line about herald.
There are 2 meanings to the statement.

Two betrayed herald a shadow. One of the two definitions references a book. The other references an event in skyrim.
Herald- to be a royal messenger or courier.
Herald- to come before

So in one of the two references, two betrayed royal couriers hold a shadow.
In the other reference, two betrayed people come prior to a shadow.

This itself is a riddle. And one of the easier ones. If you figure these two references I GUARANTEE that you will have the answer.

"Two betrayed herald a shadow."

Karliah and Gallus?

nope. You guys are killing me

I cant really do many more hints without giving it away. I suppose that if this lasts until Wed 9/12 I can unravel the big riddles into the mini riddles. If you cant get the mini riddles I cant solve them without giving the answer away. If it is up for another whole week I'll solve the mini riddles and hopefully you can see the answer.

This riddle reminds me of a combination of a paradelle and that damn gnome who's name you had to guess from King's Quest.

So, in reference to the same line, something to do with the Dark Brotherhood?

Haha thats funny.

And nothing at all with DB. None of the lines reference DB or [before its asked], represent the Morag Tong, Thieves guild or any other organization typically associated with shadows.

do any lines have to do with high king torygg?

Nope

Okay, as promised... I will expand on the original riddle.

Two betrayed herald* a shadow 157
[two people who are betrayed come before a shadow]
[two people who are betrayed are royal couriers/messangers who carry a shadow]
Once set among similar and now removed 1247
[used to be places as part of a collection]
[likeminded but now dead]
[used to be with others from the same make]
[Used to be a set, but now something is missing]
Sent to protect the slave serving two yet one 1267
[sent to protect the servant (player) who serves 2 yet 1]
[Sent(the player) to protect the slave (NPC) who serves the 2, but only really serves themself]
[sent to protect the servant who serves 2, but only because of one claims to be the other]
My sister's keep* is hard to swallow 1234567
[My sisters placement in the world is hard to accept]
[My sisters keeper is in a place hard to swallow used 2x once in a book, the other is literal]
[My sister's fortress is hard to swallow (drink)]
[(Personification of the Shadow) They are upset about who keeps the sister]
Dying for what you seek 127
[You really want this]
[You literally die to be able to acquire this]
[Something/ someone dies to get this]
You fell* and raise* so we may meet 1247
[you descend and then ascend so the sister and this can meet]
[You die and are reborn so that you may meet]
[You kill and then they are resurrected so that you may meet]


Cast* by a heart so hollow 1267
[Made by something heartless]
[sent by something heartless]
United by following a half told tale 12567
[The book reference skips the details in the beginning and middle and goes to the purpose, this book tells you where to go]
[By following a half-told lie and believing in it you are united]
Where cent-less* lovers bore deceit 1257
[Where 99 (a cent less [cent meaning part of 100]) people who loved bore a lie]
[Where people who love but dont have a clue (senseless) bring forth deceit]
[Where people who love poor people bore deceit]

Though removed, my sister you may borrow* 12347
[when I am gone, you may borrow my sister]
[Though the sister isnt where she belongs, you may borrow her]
[Though the sister is removed, you can acquire her from some other source [time frame]]
[Though her keeper is removed, she is subtracted (as in she isnt with who is said to keep her)]
Clout* by both bearings* 123467
[influential by both places of birth (metaphorical)]
[A blow by a hard object that is two handed]
[Where it is currently is a slap in the face even though politically influential]
Many wish she were as sweet 12367
[Many wish she would be with the player]
[Many covet her]
[Many fought for her, but died in your stead]
[Many wish she could do what she could previously]

Returned I find hope through sorrow 12467
[I found every "hope" by means of "sorrow"]
[I found my return, but my sister isnt around]
A shadow of myself yet strong 1267
[Not as powerful as I used to be, but stronger than most]
[Light, yet strong, and literally a shadow]
A dimming light has set so shadow comes to don 17
[A once favored falls so that shadow can be donned]
[A friend falls so that a darkness can wear it]

-honestly... if you dont get it after this I will be upset.
If by Saturday I dont have a correct answer I will simply answer it myself. This riddle drew from all of the lore around it. Now that it is basically down to its skeleton it should be easy.

Serana?

I think this riddle would have been better suited for the Lore Trivia thread