Here's that video I mentioned. It's of one our models (and friend) who did a video where he went into a local shop here in Toronto in our Gay Village and they discuss cock rings and demonstrate how to wear them.
There's a trick to getting a solid ring on: you generally get your balls through first then you get your cock through. The other trick is to try to do this all before you cock gets to hard from all the fondling, lol!
Here's the video, sorry I can't upload it as it's too big but it's on our server so you should be able to just click the link to see it:
https://www.jockstrapcentral.com/video/RYANTIME-cockring.mp4