It's been a struggle. I thought my scrotum was constricting the "drop". But really it's been the thing that attaches them (still researching the proper terminology).
As I said, I used a rubber band first (I did use a warm towel to help them drop). This kept my testicles from retracting. Then I pushed each ball separately thru the ring first. Finally I tuck my cock down and thru the ring. The mistake I read somewhere is to try and slide it over the ring over the cock first, then trying to get the balls in.
I don't see myself wearing the ring a night (yet). But I will during the day as the situation allows. That way I can monitor the fit for any issues. I'm going to go slow and stick with just the full cock ring at first. Then perhaps add a separate ball stretcher as things "relax" more.
I marked the region that needs to be trained here...
View attachment 37684501