Never force, never violence .
Allways lube and time, insert a small plug and hold it for 5 - 10 minutes, then try with the medium plug,
Make it nice warm before to shove it, while trying to insert masturbate, stay as near as possible on the edge of the " O "
move the plug slowly in and out , and LUBE ! ! !
" Jumping " from a small plug to a large is a huge jump, I will never more try a such too fast evolution, I learned to go slow and progressively,
your anus is a muscle, only a muscle, he must learn and joy will enjoy each lesson he will have.
make the jump from small to large at once, you will have tears and remember for several days.
PLEASURE / pain is a huge turn on when PLEASURE is 85% and pain 15%