I looked at this blog post today: http://www.librarygeekgirl.net/2012/11/28/ill-say-it-again-be-awesome/
While reading through it I came upon a phrase that spoke to a problem about how privilege and oppression work.
"Now, the next transperson who runs for anything will have to deal with the shade of Stacie Laughton, and re-build the trust–not just in New Hampshire’s Ward 4, but all over the US–that she has tampered with."
The short form of this is explained by xkcd: http://xkcd.com/385/
In the longer form, I'd like to introduce you to one Bob Bolus of Scranton, Pennsylvania: http://thetimes-tribune.com/news/bolus-makes-another-quixotic-bid-for-office-1.21654
He's a convicted felon who keeps trying to run for elected office even though the conviction is an absolute bar to his ability to legally hold the office under the Commonwealth's constitution. He tried to run several times in my years living there, and, apparently, tried again since I moved (and had another conviction.)
These two illustrate a specific property of privilege versus oppression on an axis of (non-)membership in a minority group.
1: Bob, as a white, middle-class (at least,) cis man, is seen as an individual actor and not representative of all white, middle-class (at least,) cis men.
2: Stacie, as a trans woman, is seen as reflective of all trans women. There are possibly additional axes present for her; the sentence I quoted above does not regard those and I do not have that information at this time (I'm inclined to presume that, given the charges of which she was convicted, a certain financial situation at least recently was present.)
Bob, by being a white, middle-class, cis man, enjoys the privilege of not having his actions be taken as representative of any/all other white, middle-class, cis men.
Stacie, by being a trans woman (again, with the additional axes caveat,) is taken as reflexive of all trans women.