The sex scandal may be the least of Herman Cain’s worries; now reports are emerging about some very shady payments from an organization that has mysteriously gone out of business. And that’s not all.

Herman Cain’s two top campaign aides ran a private Wisconsin-based corporation that helped the GOP presidential candidate get his fledgling campaign off the ground by originally footing the bill for tens of thousands of dollars in expenses for such items as iPads, chartered flights and travel to Iowa and Las Vegas - something that might breach federal tax and campaign law, according to sources and documents.

Internal financial records obtained by No Quarter show that Prosperity USA said it was owed about $40,000 by the Cain campaign for a variety of items in February and March. Cain began taking donations for his presidential bid on Jan. 1.

Prosperity USA was owned and run by Wisconsin political operatives Mark Block and Linda Hansen, Cain’s current chief of staff and deputy chief of staff, respectively.

The authenticity of the records was verified by two individuals close to the firm.

It is not known if Cain’s election fund eventually paid back Prosperity USA, which now appears defunct. The candidate’s federal election filings make no mention of the debt, and the figures in the documents don’t match payments made by the candidate’s campaign.

In addition to picking up these expenses at least initially, Prosperity USA also paid as much as $100,000 to the Congress of Racial Equality, a conservative black organization, shortly before Cain was a featured speaker at the group’s annual Martin Luther King Jr. dinner in mid-January.

Cain, who has surged to a top-tier presidential candidate in the past month, apparently was not paid for the appearance. The personal financial disclosure forms for the former CEO of Godfather’s Pizza list no honorariums for speeches.

Election law experts say the transactions raise a host of questions for the private organization, which billed itself as a tax-exempt nonprofit, and the Cain team.

“If the records accurately reflect what occurred, this is way out of bounds,” said a Washington, D.C.-based election lawyer who advises many Republican candidates and conservative groups on campaign issues. The lawyer asked not to be identified because of those affiliations.

Michael Maistelman, a Wisconsin campaign attorney, agreed.

“The number of questionable and possibly illegal transactions conducted on behalf of Herman Cain is staggering,” said Maistelman, a Democrat who has represented politicians from both parties on campaign issues.