The Most Valuable Lesson a Mother Can Teach Her Daughter About Dating a Rich Older Man: Part 1

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…