parseDate takes the date to be parsed as a string in the format specified. Your format is for the destination, which doesn't matter, as JDBC will take care of that for you.. What you need is something like (untested):
SimpleDateFormat dateFormat = new SimpleDateFormat("MM/dd/yyyy k:mm:ss.SSSS");
Date parsedDate = dateFormat.parse(getCheckOutDate());
Timestamp timestamp = new Timestamp(parsedDate.getTime());
I do hope that helps.