My first time was last spring (at the age of 23). It was pretty good. I mean, I was more than ready and was lucky enough to have a good guy who was very patient with me and left all choices up to me. For me, it hurt only the first time he got all the way in, and of course the blood wasn't fun, but its the way it goes. The next time with him was much better. I don't know about any tips tho... Other than using condom + lube = good. Make sure you are relaxed and want to do it, if you don't relax, it ends up hurting a little more 'cause you are tense.