Any way to make your first time more pleasurable/less awkward?

I'm a college student and I think I'm ready to have sex with my boyfriend for the first time [first time myself as well as with him]. I want to really make it as pleasurable as possible, as well as least awkward as possible. Does anyone have any suggestions?

Also, I'm kind of insecure about my intimate areas [boobs and vagina]. I feel as though they don't look right. Like, unsmooth and just awkward in general. I'm worried I won't look good enough.

Along with the fact that I'm worried I'll regret it. He's a wonderful guy who isnt pressuring me into anything, I just have so many doubts in my mind.

One other thing; I'm not quite sure how or when to tell him I'm ready?

Thank you to everyone who comments.