A Dunmer assassin working for the Dark Brotherhood who, after killing the Emperor joins the Imperial Legion? I feel like I made a silly choice in joining the Legion, opposed to at first when I thought joining The Stormcloaks would be completely out of character for a Dunmer. I figured my character could be infiltrating the Legion to further manipulate their doings, but now I'm thinking it would've made more sense to join The Stormcloaks..

I realize I didn't have to join either side but it's something I really wanted to be a part of my characer's story.

You can't join the Dark Brotherhood ánd the Legion is it ?

I have joined both, I specifically waited until I killed the Emperor to randomly show up one day looking to help the Legion. Now I just feel like their noble errand boy, though I should've expected that. Also, it appears I'm moving toward taking down Maven Black-Briar, which I don't want to do.

Well you could say you grew tired of killing for a selfish cause and decided to fight for the Empire. Or you could be pretending to be a Legion soldier for another contract.

Remember, anything you do can make sense for RP. You just have to fill in the little extra details.

Spoiler

Actually, working with the Legion means giving Maven the Jarlship (which doesn't mean much, since Laila Law-Giver is rather inept at spotting corruption)

If going by D&D lore, a true Drow Elf would never join the race of men or other elves or any race that walked under the sun. They may plot to join them as a way to subjugate them if the Drow in question felt confident enough to accomplish this task, however its is unlikely they would ever be trusted. Drow hate all races that walk in the sun and usually kill them on sight if they encounter them.

Granted, Elder Scrolls lore is much more forgiving. But the series did dumb down some of the evil races a bit. For insntance, Orcs are supposed to be nocturnal and only carnivores and they should not be allowed in cities of men or elves. But in Elder Scrolls games, this is different. So play how you like.

Edit: Dark Elves and Orcs should be be granted a permanent night vision that can be toggled on or off. They're only active at night anyway.

Simple. "Keep your friends close, your enemies even closer" Thts how i look at it

this is elderscrolls, not a knock off of D&D (this is much more fun anyway ), it has its own lore so no need to go about lore from something else. anythign can fit in an rp, mine is an argonian assasin who joins the stormcloaks because he hates the empire (thats the short version, the long version is long and some small details are always changing or beign added, so i'll spare you)

In my opinion the obvious choice would be to choose the Imperial Legion with a dunmer.
However a dunmer of sinister or good intent could join The Stormcloaks in hope of power or to be a charitable example:
To show Ulfric that the dunmer are not as bad as people make them out to be and that he should give them a second chance.