Yesterday I was at my boyfriends house and we tried to have sex but it didnt really happen. We've been together 10 months but he's been one of my best friends for almost 2 years. I'm a virgin but he has had sex before. While I was at his house we fooled around for about an hour and he asked if I was ready and I told him yes. He put a condom on and tried to put it in but he couldn't. We tried changing positions a few times but he could only get the tip inside which hurt like hell. He didn't make a huge deal about it, we just joked about but it was still frustrating. After that we decided to wait and try another time since I was sore and bleeding a little. I honestly think I was nervous and tensed up, making it difficult for him, but I'm not sure. Is there anything we can do to make it easier/more comfortable next time?