I have been keeping rays for over 9 years and my rays have had many litters over those years but never once have I caught them in the act, until today and I had my camera in hand.
That male there is at least 4-5 years old and the female is about 4 years as well. Been finding that all my female Leo's are usually at least 4 years they produce any pups. I only have grown out one male Leo from a pup and he had fully developed clasper at 2 years and he beat the crap out of my girls for almost 2 years until successfully breeding with them. Now my males are super gentle, only a little nip near the back of the disc.
I have found that when the males start coming of age, they pretty much start trying but it seem they are not very good at first and takes some time till they are stealthy at it. Lots of separating I had to do to give the girls a chance to recover.