I believe that I am averagely endowed, my guy sits in the center of my balls as if they were a throne on the regular. For me, it slips right into place, as I put my boxers on.

I’ve had issues occasionally when they get a little old and a little loose where the underwear doesn’t stretch tight anymore, sometimes that’s uncomfy but more because nothing is where it supposed to be, and doesn’t stay. A hot wash usually fixes it on that pair.

I’ve never had an issue threading the needle though. But maybe others would?