friends with benefits for first time?

I'm a virgin on account of a penis has never been inside me but I've done plenty and I'm pretty comfortable. I'm currently not on birth control, but I'm thinking about sleeping with a good friend of mine. We've made it to 2nd base before but didn't make it all the way before. I think I'm ready, but I don't know much about the "first time" esp. when I'm not on birth control yet. Any tips? Is it a good idea for your first time to be a casual friend?