I solved my problem after much trial and error. First I put some velcro on my 2" wide button leather ball stretcher, I put the other half of the velcro on my weights. For me, with my leather stretcher on, my weights that are 1 3/4" inner diameter, fit snuggly around the leather. The velcro helps with slippage. I have some weights that have a larger inner diameter that I put on last, or nearest the base of my penis. Even though they don't have velcro and would slip off if I only had them on, the weights with velcro hold in place and keep the others from pushing down on them.
Leather ball stretchers are cheap and you can have one customized for very little extra. Putting on the leather stretcher is a whole lot easier than trying to push your balls through a ring (I was never able to). In addition, I have several weights that are hinged and several that are held in place with a screw. I have put these on a million times, and because I am putting them on over the stretcher and not my actual sack, it is a simple matter to screw them in place. I have several allen wrenches, a couple in the car and around the house. I always put them back in their place when I finish so that I don't forget where I put them.
I added that third picture because stretching my sack is a complete turn on that never grows old. I'm up to 4lbs now, and I started with several ounces.