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I use plenty of 'wet' lube to get them on. It helps to be completely soft. Work the balls in one at a time and then push the head of your little dick inside of Your body and let it come out under the ring that is around your balls. It takes practice and time but you should be able to get everything thru. I know that I can with various devices. Eventually you will be able to. The smallest ring will never slip off bu will creat alot of pain when you do get hard and it will be impossible for you to cum thru all of the pain. At least that is my experience with the various devices out there and I have many of them.

Definitely balls first. Once they are through you can squeeze your cock through.

Those 2 answers are definitely correct - I have a CB2000. I use the ring that I can only just - and I do mean only just, push one of my balls through (the left seems to be bigger!!) so that one goes through first, and slowly, then the other, then my cock. I am essentially locked all the time with probably a few hours out every 7 days or so - and the ring is so tight I haven't bothered taking that off for a few weeks now...

Wow i like the look of that one, I wonder if they make it without a padlock...some of the new steelworx and mature metal devices are now making integrated locks

In answer to your question, you will never get into it that way...

You NEED a stocking SOCK, not a full length stocking....just a sock...buy a pair at your local supermarket....

Put one testicle through the ring then grab your skin and pull through some extra ball sack so your other testicle has somewhere to go....then push your other testicle through the ring so both are through....then get the stocking sock and put the open end over your penis, only enough sock to cover your penis, there will be plenty of sock hanging off the end of your dick....then push the closed end of the sock under the ring....you will find you can pull your penis through and into amazingly small rings....u can then repeat the stocking trick to get into the tube. Once you are practiced you can get them on very easily and you will no longer have the excuse of not being able to get any practical sized ring on...

The best way for this sissy to get into her steel chastity is in a hot bath. After soaking for about 10 minutes or so, the sissy bits soften up, stretch, and get more pliable. At that point you can slip one tessie at a time, sort of sideways one after the other, through the ring. Then, after shrinking up a bit, tuck the peenie through the ring, and voila, you're in!

Then, of course, you may attach the cage. In this sissies case, it's a 1.5" cage and a 1.75" ring. Think shrinking thoughts, then snap the lock shut and you're a locked sissy!
"Sissies don't get pussy, they ARE pussy!"