Anal. Anal?. Anal!

So 2 days ago I asked my boyfriend if we could try anal after like months or oral and "hands-on" work... So he agreed... But now he tried putting it in, it ddnt go in... So he tried pushing it in more... I then felt like the edge of my Crack was about to tear... And we stop immediately. But continued doing what we usually do. My question is how do you go about having anal.. I really need help. I read online that you should wear a condom to protect yourself from infections... And be lubricated. Okay I get that, but does it feel good. For both of you guys or just the guy?. BTW I haven't had sex ever... So this is a big step for me in the penetration field..so I'm super excited and afraid. Please help