Prosecutors questioned him about the nearly $1 million he loaned Bob McDonnell and McDonnell's sister for two beach rentals they own in Sandbridge.
Before even stepping foot in the Richmond Federal Courthouse, Sessoms admitted testifying would be difficult.
"I'd be lying there's a dear friend on trial, what I'm hearing is quite concerning. I just want to get what I have to do over with," Sessoms said.
McDonnell is accused of lying on a loan document for Sessoms' bank.
While trying to renew one of two TowneBank loans, Sessoms told prosecutors McDonnell didn't list any loans he received from Jonnie Williams on a personal financial statement.
Williams is the former Star Scientific CEO at the heart of the trial.
The former Governor and First Lady accepted tens of thousands of dollars worth of loans and gifts from him. In return, prosecutors say the couple helped Williams promote his dietary supplement.
Defense attorneys have argued Williams was just a generous friend. But, prosecutors hope witnesses like Sessoms can help them try to prove the McDonnells hid what they were doing as part of a 'corrupt agreement.'
The mayor of Virginia Beach will continue his testimony Wednesday morning.