Dr. Carol Queen, who is the Staff Sexologist at Good Vibrations (what a job!) and has a doctorate in Human Sexuality, is kind of a legend in her field.
I met her for the first time at MomentumCon in April and asked her if she'd talk to me about the V Word. To my total delight, she ended up sharing her own 'First Time' story, including the part about nervously writing Dear Abby for advice. If you can't see the video, use this link! You can find her at carolqueen.com and goodvibes.com.