he might be using the wrong size. you can get different sizes in condoms he must be wearing one thats to small, OR sex might be a bit to rough?
Does it break while in use, or does it break when he puts it on? If the latter, he might be trying to unroll it upside-down.
ps -- get on the pill
while in use . and i was on the pill but i stopped taking them .
Given the breaking problem, unless you are in fact trying to get pregnant, I'd go back onto the pill. Change the brand of condom, and maybe the size. Good luck!