Sex for the first time...!?

So I'm 14 almost 15 my boyfriend is 15 weve been together for 8 months. We decided it's time to go for it. I'm a virgin. He's not unfortunately. But I'm scared I'm gunna get hurt. I'm tight for a virgin you know, and I'm just scared it will hurt. He said no condom I said condom he said the first time no condom and he won't ( C U M ] in me. I told him sperm is still on his penis he Said he won't get me pregnant. That's the main 2 I'm worried about.. Hurting and pregnancy. But another question is when he inserts in my, how do I put this, rear-end .. Will it hurt? Help me please!!! And thank you !!!