How far can one stretch their use of the first amendment? (Freedom of speech, or of the press; or the right of the people peaceably to assemble, and to petition the government for a redress of grievance)
These sites push the limits and are still up and running.
Read why they're controversial here.
Have you visited any of these sites? Do you think they earn the title controversial?
Disclaimer: Geekdrop does not condone nor condemn any of the sites listed.

Wellington Florida
Married
Well I have been on about 1/2 the sites as some point or another. Here is my take on them
I can think of other sites that deal with all types of things - such as some of the fetish sites. If they want to talk about popular sites then where are the popular cup sites (I wont hyperlink them but the twogirlsonecup and oneguyonecup) - can't get much grosser and controversial then them. I think just about everyone knows about those sites
(including my kids which didn't thrill me).