High & tight? Best way to get base ring on

You can push your balls through one at a time.
Push a bit harder if the ring diameter is smaller than they are.

 

Everyone has got a smaller ball, and a bigger one. So figure out which side has the big one and start there.

Get the big one through. Then pull all the scrotum you can through the ring towards the 'other ball. Then form a 'C' with your thumb and forefinger, and shove that smaller one through there with a POP. My base ring is tight enough you'd swear I'd never be able to get the shaft through but that's the easiest part. If you've done chastity for a while, all those amazing videos where the octopus squeezes through the bottle aren't nearly so amazing.

 

I try and pull through as much scrotal skin as I can through the ring first, then as @SubSnuggler said above, push through the bigger ball (for me, this is my right, it also hangs lower normally), re-do the skin thing and then the left. I hadn't thought about a "C" but if you push your testicle up against the ring then gently apply pressure so that it passes through the ring, keeping your fingers behind it to sort of trap it in place.

I tend to put the ring on in the shower when I am soaped up a bit, helps things slide through, especially the penis which goes through last. I once managed to push it back into my body far enough for it to just "pop out" in the ring, but usually it requires manhandlng the head through then pulling the rest through by the head. This looks (and sounds) worse than it actually is, and is why I do it when soapy

 

Subsnuggler hit the nail on the head with his advice, il just add using moisturiser will make it easier to.

 

My Miss has me unlock every night. As I result I have to cage up every morning.

I try to cage before my shower. For some reason If I lock in the shower or immediately after, I can wear it for an hour or two and then I get chafing like crazy. If I'm caged while I take a shower, I do fine. I have absolutely no idea why this happens.

I swim a lot while caged, and that doesn't bother me.

 

Says it all.
Which ever of your testes hangs the lowest normally put through first. Then pull as much scrotum as you comfortably can and put your other one through. Use lube and use a roughish towel to grip your scrotum with so your fingers dont keep sliding off.

If your ring is not too loose you will have have to apply a little pressure on that second testicle as you become more familiar with the practice u will come to realise that any discomfort is quite short lived and the quicker you get that second one through the better.

 

Press hard with both thumbs and it will pop through.

 

Pull your skin through first then pop one ball through at a time.

Then use a short stocking sock, cut the thick part off the top (only if you have to), Put your dick in the open end of the sock, then thread the closed end of the sock under the base ring. As you pull on the sock guide the head of your dick towards the ring, eventually the sock will close tighter on the head of your dick and you can pull it straight through under the base ring.

I do this even with the tetherspout inside and the ring is very tight. Ironically I cant get the cock out of the ring without a lot of difficulty even when unlocked so I pop my smaller testicle through the ring first then the larger one then remove the cock.

If your balls are falling out while locked the spacing between the ring and cage is wrong