The first time for me was that I was picked up in a bar and then seduced into bed. The guy did not know I was a virgin and I was reluctant to say so. He was not suprised that I was wareing panties and this maybe reinforced the fact that I was a bottom. I was not fucked on that night but was made love to, he did what he wanted to do but made sure I was happy, a very good introduction to anal sex.
He just doesn't know how to get that cherry, do what my first BBC did which was lay me flat on my stomach and straddle my ass. He had control of his cock and my asspussy, and he stretched me out as he slid his big cock in me then he lifted my hips up and pounded my ass senseless dodggystyle.