I lucked out, big time. My boyfriend has been my best friend for over 5 years, was the first person I really came out to..Biggest thing I can say really is make sure whoever you're gonna do it with knows you. Really knows you. Because the biggest thing that makes me so comfortable with B, as far as sex is concerned, is that he just knows what's okay and what isn't. Don't try screwing someone who's going to make you feel ever more self-conscious and sick with yourself, I did that for 7 years, and I still feel like a jackass sometimes.