I'm 99.99% certain you cannot have two pending cashouts at one time. If you request a cashout in the early to mid part of a month, and then add on another $25.00 by the end of the month, you can cancel your pending cashout and request a new one. You'll still get the money on the 20th of the following month, as long as you request it by 11:59PM Pacific time on the last day of the month.