I have an almost but not quite story from around when I was 13 or so fooling around with two girls in a trailer. Ah, if I only knew then what I know now.
Anyway, my first time was in the living room of my college apartment after a party. All my roomates were there and had just gone to bed so it was a little odd. The next day she told me that she was complaining to her friend in class that she felt like she had been run through by a Mac truck (in a good way). That went a long way to boost my confidence.