What Happened When I Agreed to a Date with a Rich Older Man I Met Online: Part 2

I kept my May-December rela­tion­ship with Brian a secret by sneak­ing out of the house to see him prob­a­bly five to 10 times a week. It was exhaust­ing, so one day, I finally approached Brian about meet­ing my mom. Because I still lived with my par­ents at that time and didn’t drive, I asked him if he felt com­fort­able with me dis­cussing things with my mom, or at least meet­ing her to make things easier—I was tired of sneak­ing out all the time. I assured him that she wasn’t judg­men­tal about the age dif­fer­ence due to her own expe­ri­ences, and it would make see­ing each other a lot eas­ier. He wasn’t com­fort­able with it at all because he was closer in age to my mom than to me. So, we never broached the sub­ject again.

Dur­ing the times I snuck out to see him, he would often be wait­ing in his pickup truck with that wily smile, beau­ti­ful brown eyes, and his large mus­cu­lar arms wait­ing to hold me tight. He was very fit with a shaved head and goa­tee, exactly what you’d expect for a typ­i­cal blue col­lar biker.

We would drive to his house where he always had lit­tle sur­prises for me.  It was always some­thing new and dif­fer­ent, because he wanted his girl to feel spe­cial and have nice things. Our rela­tion­ship was won­der­ful; it was based on us and every­thing else was just a bonus. We would dance, cook, make love, and just hang out. I could really be myself with him.

With­out any out­siders peer­ing in and judg­ing, it was very relaxed and just a happy time.  More than any­thing, he wanted a com­pan­ion, a sexy lit­tle friend who didn’t nag him, and a lover who was will­ing to try new things. I was all of those things for him; I did every­thing I could to make him happy.  I hon­estly gave him my all and was happy to do so. In his words, being with me dur­ing that time was like “hav­ing his own Play­boy play­mate.” Every­thing that made Brian happy, made me happy.

At one point, we decided to try hav­ing a cook­out at his house, invit­ing his friends and a few of mine. It was awk­ward to say the least. Between my younger friends and his middle-aged friends, there wasn’t much witty ban­ter, but thanks to the alco­hol, it was tol­er­a­ble. It was at that point that I real­ized this would be a norm for the rest of my life. The taboo stigma attached to dat­ing an older man, mesh­ing friends, and hav­ing par­ties would almost always be strained. It still both­ers me to this day, although it’s become much less notice­able as I’ve got­ten older.

  • Ash­ley Dempsey

    It was at that point that I real­ized this would be a norm for the rest of my life. The taboo stigma attached to dat­ing an older man, mesh­ing friends, and hav­ing par­ties would almost always be strained.“
    I know the feeling…