My first time hurt like hell, so did the second. But by the third time, it was quite pleasurable. I guess it was a combo of nerves, and him being not on the small size. I was 27, but my first sexual encounter was when I was 17. My "cherry" was popped during some digital stimulation by a boy, and after that, my sexual desire was awakened. Not by the popping, but by the encounter itself. It was also the first time I gave a hand job.