My very first time was when I was very young. He was a former school mate of mine. He had gone to a different high school than me, but we stayed friends.
He was always kind of a kinky guy. He would moon me, flash me his dick and he was always talking about beating off and swallowing his own cum. Little did he know that I had a crush on him and I really wanted to suck his dick. When he would flash it at me, I would look at it and grin.
During a ......-over, and after showering, we started playing truth or dare. I kept picking dare. He dared me to suck his big toe. I did and he kept stepping it up. He dared me to suck his nipple, I did. I think he was impressed by how easily I was accepting his dares, lol.
When he dared me to kiss his ass, I surprised him. When he dropped his underwear to his ankles and bent over for me to kiss his ass, He was expecting me to kiss one of his butt cheeks, but instead, I kissed his butt hole.
Finally, after that, he dared me to suck his dick. I started sucking his dick and after just a few seconds he pulled his dick out of my mouth. He said "whoa that's going to make me cum." I told him that it was ok for him to cum in my mouth. He was surprised and asked "are you sure?" I started sucking his dick again and within a short time I heard him whispering that he was about to cum. I kept sucking, he started groaning and then felt the squirt of his cum against the back of my throat and then the taste of his cum. The taste of his cum didn't surprise me at all. But, the forse of his squirts and the amount of cum he was pumping into my mouth did surprise me. Nevertheless, I managed to swallow all of his cum.
He was very surprised that I swallowed his cum, but he told me that was the most intense orgasm he had ever had, lol.
From that point on, I was sucking his dick almost everyday. We would do ...... overs and I would suck his dick about 10 or more times over the course of the night, lol. This went on for about two years and it is one of my fondest memories.