I have never dated a guy my age. The apple doesn’t fall far from the tree, though, as my mother has never dated a guy her own age either. In fact, she accepted and supported my choice in dating older men. Through this, I have learned much more than ever anticipated for my age. Because of this, people often confuse me for being much older, which I am thankful for, although it can be a double-edged sword. Friends are limited, as I fit in best with the older crowd and am shunned by the younger crowd for dating the older crowd. It works for me though; I have had a very fulfilling life thus far.
When I first started dating and having sex, my sights were set on someone who was experienced and could show me the ropes, and could make me feel comfortable, confident, and sexy. Guys my age could never peak my interest or turn me on; they were all too immature and juvenile. I wanted to be with a man, not help someone’s mother raise their son. I guess I have my mom to thank for this; she was good at sifting through the guys who were just a waste of time.
Unfortunately, she wasn’t with me in college every day. At that age, I was extremely sexually aggressive and often went straight for the jugular. Men, especially older men, absolutely loved (and still do) when I was sexually aggressive, taking charge and making the first, second, and often third move. It’s empowering and I needed a man who could handle it, who could handle me the way I was. It was during this time in my life that I briefly dated a 45-year-old married teacher who had a penchant for sex in daring places, a 39-year-old single biker, and a 43-year-old single Italian businessman. All of the men I’ve dated have helped shape me in one way or another with their wisdom, guidance, finances, and education. I am grateful for all of my experiences with them.
“Maestro,” the teacher, wasn’t my first older man, but he was the beginning of a whirlwind time in my life. I spent a lot of my formative years with Maestro in school, and it wasn’t too long before I made my intentions clear to him; I told him how I felt about him and what I’d like to do to him. As confident as I was, I never expected him to react the way he did…