Tips for loosing your virginity and being more confident

My previous boyfriend and I went as far as oral. We were both virgins however and were both very nieve about things. Now, I'm pretty sure my current, whom is not a virgin,  and I will most likely lead to more.I hate the way I look naked. That may sound dumb, but I'm pretty sure it will be more pleasurable if I'm not constantly worrying about how I look. How do I over come that? Also, what should I do to prepare myself? He is also about 9-10 inches, so will it hurt?