My best friend growing up and I spent a lot of time together. His dad was well-to do and they had a nice house so we spent most of his time there. His mom was named Nancy, but I always called her Ms. Nancy. She was super sexy. What we today would call a milf, but we had no such word back then.
At night, I would frequently jerk off while fantasizing about her, whether I was staying at his house or mine. His sister was pretty sexy too, a couple of years older than me, and I wouldn't have minded spending some "quality time" with her.
The summer following our senior year in High School, we had just turned 18 and were each about to go away to college. We decided to play golf together (we were both golf crazy). Afterward he asked his sexy mom if I could stay the night. She always said yes, so we hung out all evening in his family room, I ate dinner with the family, and we had the usual chit-chat of a family meal, but I mostly spent my time fantasizing about what was underneath her sweater.
That evening I found it difficult to go to sleep because I was thinking about her. 11 o'clock came and went, then midnight, then 1 a.m., and I realized that I had to do something or I would never fall asleep.