Did anal hurt even after lube

So I've had anal before with my ex and he ended up ripping my asshole from not being lubricated (or from the actual action of it) and I'm so scared to do anal with my new boyfriend but he really wants to so he can cum in me so since I love sex with him and I always get off I figure I should do what I can to make him cum/enjoy it also. He said he'll use loads of lube to make it enjoyable for me but I'm not sure lube would even work. Like I said last time I had anal my asshole literally split and bled for a week.