If you work by the illustration
we frequently post here, you do
need a firm grip on the foreskin using a thumb and forefinger "pinch". You should
then be able to manoeuvre the device into place with other fingers, sliding it down the "funnel", sideways to start.
If it then passes through into the space under the foreskin, then as I suggested before you reverse the process, pulling the foreskin back
over the device.
of these manoeuvres require some skill, it must be said, we have not admittedly actually tried them ourselves (no-one on which to practice personally
and so no pictures to show).
You are of course entirely
correct in that leaving a device in place for longer and longer periods of the day as you get used to it, will certainly
be dramatically effective. Of course you will need progressively larger devices once you "get the hang of it".
Wouldn't it be nice to have a third hand (or two) to help?