Having only had a handful of successful meets, I'm curious about the 'how to's' of bottoming. I get so turned on by the idea, and can spend a good few hours in an edging wank session fingering my hole.
By the end I can get three or four fingers inside and I produce a decent gape. (Can share photos elsewhere, e.g. Kik!)
My question, I guess, is how can I open up more. I can just about reach my 'second ring' and would ideally like to find a nice patient top who's happy to spend the time working his swollen cockhead inside it gently. I guess dildos or plugs are the next step? And am I correct in thinking it's best to 'push out' to make the hole more receptive to the cock head?