Rules of Cougar Dating: When to Have Sex

Does dating younger men change the rule of when to have sex for the first time? Find out from an experienced Cougar, an expert in older women dating younger men.

Photograph: istock photo

There comes a time in every woman’s life when she has to ask herself, does it really matter how long after the first date you wait before having sex with a new guy? What if that guy is say 10 or even 19 years younger than you—how do the rules change then? 

After careful albeit brief thought, all I can say is, good grief, is that really a question? Even when I was a younger woman, I never paid attention to the three-date rule—you know, wait three dates before jumping into bed. In fact, it’s a saintly day if I abide by the three-minute rule. Bill Maher had his “New Rules” and I have my, “SeasonedSex Rules.” Here’s the first one. Regardless of timing, if it looks right and feels right, it’s probably worth sitting on. I know, I’m bad but you’re allowed to be when people start calling you an “older woman” (that’s SeasonedSex Rule No. 2).

So, I’m joking. I’m not that bad. In fact, I waited over a year before I had sex with my “cub,” Michael. He’s19 years younger than me and his youthfulness exuberance initially threw me off my game. I tried to walk away but the sexual chemistry would keep sneaking up on me, pulling me back in like a magnet.

Michael eventually became the accidental cub. What I mean by that is I consciously decided to unconsciously have sex with him. As ridiculous as that sounds, it’s easier to manage than you’d think. A few martinis are all you need.

Now don’t get me wrong here, I’m not an advocate of drunken sex. I’ve only done that about 712 times in my life. But it does open up one’s perspective. And damn if it doesn’t ease the nerves. And, boy, I was nervous.

Michael had asked me out on a dinner date with some business people he knows with a text message. Can you believe it? A text message. It was a first for me and it went something like:

Michael: cum dinner fri?
Pamela: who, where?
Michael: scotts. 8.
Pamela: you and me?
Michael: others 2
Pamela:  is this a date?
Michael: yes
Pamela: will I be your date?
Michael: yes
Pamela: oh. LOL. ok

I don’t know why I put the, LOL. I must have just learned what it meant and wanted to seem cool. Can you say, “generation gap?”

By the time Friday rolled around my anxiety was peaking. As I drove to meet him at the restaurant (another generational thing, this taking your own car), a slew of scenarios ran through my head. What if he wants to have sex later? I was 45 at the time. He was 26. What if he wants to stay over and all I want to do is fart in my sleep because I ate too much and the digestion ain’t what it used to be? What if I get tired and can’t make it past 10 PM? It’d been known to happen?

You can understand why I downed a few cocktails the second my rear end hit the chair. At least I remember the appetizer. Some crab cake thing. Then I remember riding him like a cowgirl, screaming and laughing like an idiot who’d totally forgotten the big 5-0 was watching from another room. I vaguely remembering him spanking me, too, but oddly have no recollection of worrying about the cellulite jiggle.

Funny how age can suddenly became so irrelevant.

So here’s my bottom line. If the sexual chemistry is there and you like the guy and feel good with him, why not go for it? I mean, isn’t that the only honest thing to do? Because once the vibe takes over, it doesn’t matter how old he is, how old you are, how fat you feel, it’s just going happen. And it’s going to be great. Trust me, the worst that can happen is he won’t stop calling you.

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