We’ve all seen American Pie a hundred times. Stiffler’s Mom is pretty damn hot, right? And we’ve probably all at least fantasized about banging a hot older chick. Personally, my infatuation with Cougars started when I was 18 and dating a girl that had a very attractive 40-something mother. As sick as it might seem, I would fantasize about her mom while I was having sex with my girlfriend. Later in life, I told my ex-girlfriend about this and she laughed.
When I was in College and single, I got the idea that I would like to find a Cougar to hookup with. This was a few years after American Pie became popular, so that helped fuel my fantasy of hooking up with a MILF. Of course, I didn’t know where I was going to meet one. I had enough problems attracting girls on campus. How was I going to find a 40-something hottie to hookup with?
Despite my inability to attract many chicks on campus, I had this fantasy of doing a Cougar stuck in my head and so I was going to find some way to make it happen. I didn’t actually “find” a way to make it happen. I got a bit lucky and a Cougar sort of just came to me. This very attractive 40-something woman moved into the unit next to me. She was single and lived alone. She was very flirty and came over to introduce herself. Right away, I figured she would make a good target but I had no idea if she was into younger men…or me.
As it turns out, she ONLY gets with younger men!
She invited me over for dinner one night. It seemed like just a friendly gesture from a new neighbor. She cooked up a delicious steak and we had a great conversation over dinner. But I wasn’t really on my game. I didn’t so much as ask her if she would date a younger man. I didn’t need to. Out of the blue, she straight up asked me if I would ever hookup with an older woman.
I nearly peed myself in excitement when she asked that. Here I was sitting in her apartment, alone with her and she asked me the question I was too afraid to ask her. It was almost like a dream situation. When she asked the question, I knew she wanted to have sex. Why else would she ask me that? I didn’t answer with a “yes”. I answered with a “fuck yeah I do!”
She then went into story telling mode. She told me her entire life story. She had been married twice to men her age or older. She said that she lost out on enjoying her 20’s because she was married. But when I knew for sure I was going to hit it was when she told me she was fed up with men her age. She likes younger men because they’re more fun and have a higher sex drive.
As you may have guessed, I did get laid that night. And the next night, the night after that, and probably a dozen times the following week. My relationship with her – which was only sexual – continued for about 3 months. It was AWESOME sex. Older women are the best because they are more experienced and really want to let loose in bed. They know they’re coming towards the end of their sexual peak so they want to get it as often as possible while they still can.