If your ready to go to this size then it will go in with some stretching the lobe and you don't have to worry about losing it until your ear stretches past this ... I have used tapers in the past to stretch to my next size which is the easiest way your done in seconds with minimal pain
I used to have 5/8's which is pretty big gauges and another helpful hint besides tapers that was mentioned is use Vaseline it makes it easier. Good luck on ur auction!!