That Cougar Thing? Totally Legit!

Nearly a decade ago, I went through a divorce and started dating for the first time as an adult. When friends suggested I write about my experiences, I started a blog. I have been "revisiting" some of my former exploits lately, and decided to share, using my real name, for the first time.

"Cougar."

I’m not sure when I first heard the term, but I think that it started “trending” sometime after MILF – maybe in the mid-2000’s? Anne Bancroft is the most iconic cougar I can think of, but her tryst with a college-age Dustin Hoffman in “The Graduate” must predate the term by at least 35 years. Also, since Mrs. Robinson & Benjamin were a “May-December romance” made in Hollywood, Hoffman plays a 21-year-old, but at the time that the film was made, he was 30 years old and only six years younger than Bancroft in real life. That’s fiction for you, but the general idea of an older woman seducing a college-age man has long been the stuff of fantasy. Much the same is true of the older man and the nubile, young piece of tail, right?

If you look it up online, “cougar” seems to commonly refer to a woman over 40 who “preys” on younger men who are typically in their 20’s. Personally, I find that the term seems to be morphing into a new definition where “cougar” simply means a fuckable older woman. Maybe we have Courteney Cox to thank for that, but I don’t think that the word carries as much of a negative stigma as it may have five or ten years ago. If I mention my involvement with a younger man, many of my friends will say “oh, are you a cougar?” I don’t think that anyone means it in a bad way or is suggesting that I am “preying” on some poor young fool.

When I first made my profile on Plenty of Fish, I had a lot of advice from a single female friend of mine who is also in her early 40’s. I spoke to her right before I launched my profile and she said, “now you’re gonna have all the young guys hitting on you.” I was more than skeptical. I scoffed. She told me to wait & see – that the young guys love older women because there’s less drama. While I continued to be unconvinced, I thought about it a little bit more. Getting past my body image issues and general insecurity from not having dated in 20-some years, I could understand the appeal. Older women aren’t looking to settle down, get married, make babies, have someone pay their bills or take care of them. Most women over 40 are capable of taking care of themselves. Most older women don’t have the degree of angst, drama and maintenance that often comes with a woman in her 20’s. They don’t require a boyfriend to be available to them 24/7. They don’t get jealous if every minute isn’t spent with them. We have our own homes without roommates so we can “host” sexual escapades. Best of all, older women are experienced in the sack, near their sexual peak, and generally love to be physical. Many of us can’t even get pregnant, so that’s a bonus too. Yes, these are all generalizations, but they are also generally true, and I can certainly see the appeal. Still, I didn’t think that any young guys would be hitting me up. As it turned out, my friend’s “wait and see” didn’t have to wait long!

I was driving home from one of my first meetups with a POF guy. When my phone dinged telling me that I had a text, I assumed that it was my “safety friend” messaging to make sure I had made it home okay. It wasn’t. It was the 23-year-old son of some friends of mine who just happened to be texting me at 12:30 am to see what was up. Huh. That’s odd. This is a kid I’d known since he was about 13 and would consider a friend of the family. He briefly dated my niece, so I knew that the kid had a little bit of a kinky/exhibitionist streak from what she had shared with me. Because of that, I was slightly prepared for him to be a little risqué or flirtatious. He had messaged me on Facebook to chat from time to time, but sending a text – particularly so late, was new.

When I got in the house, he and I continued our conversation via Facebook chat. I mentioned that I had just come from a meet-up with someone and he asked how dating was going. I said it was very new and weird since I hadn’t dated in about as many years as he had been alive. He asked if I was doing online dating or how I was meeting people. He then made a comment that it was too bad that “my generation” didn’t just do what his does – hang out, hook up and chill. I said I had no idea what my generation does because it was all new to me. Then he said that if I wanted to do that with him sometime, he’d be down.

What?

Wait. What? Back it up…did he just…what? Please, followers, imagine me sitting in front of the computer, in the dark, at 1:30 in the morning, literally YELLING at the screen: “Shut the fuck up! Did that really just happen?” I was sure that Ashton Kutcher (a one-time cougar fan himself,) was going to jump out at any minute and tell me that I was being punked. Then my text notice bleeped again – with a photo from this guy. It’s him. Nearly naked – his bare torso covered with tattoos and his bedroom eyes staring pleadingly. The text said, “could you handle looking at this?”

What the?!? Okay, okay…I guess I didn’t misread that.

The next message from him contained an apology for being so forward and said that he hoped that he didn’t make me feel uncomfortable. I finally managed to find some words and type a response saying that I was pretty stunned but not uncomfortable. He went on to say that he was looking through my photos and came upon a particularly voluptuous one of me in a certain dress and that I was really hot. He said that he wouldn’t mind fucking me in that dress. Okay, yeah. Message received. That was pretty direct. Yikes.

My mind was scrambling. I was still dying to have sex at that time and here was a young, hard-bodied guy who was offering it. However, this is also someone that I still imagined riding a Razor scooter around the neighborhood. I know this kid’s parents and siblings; he knows my kids and my ex and he once slept with my niece. I could certainly imagine, but I couldn’t possibly imagine…!

Finally, I said thank you. I told him that his was the best offer that I had had in about six months, and I really appreciated him being so sex positive. I joked that I couldn’t imagine having sex with him and then looking his mom in the eye. He said “well, don’t tell my mom.” Jesus. He was tempting, to be sure, but I wasn’t willing to risk friendships or have my kids be the butt of scandalous jokes just so that I could get laid. We had a sweet, brief flirtation and ended the conversation…at least for then. We did exchange some dirty texts a few weeks later, but nothing that would have rocked the gossip network in the town where I used to live.

I still doubt that his mom would approve…

But wait! There’s more!

That particular week had been a tough one for me, emotionally. My ex and I had been going through the worst of the nastiness that goes with separating. I was finding the online dating scene to be daunting and a little bit weird. I felt detached from everything that I had once held dear – my home, my family – even my dog.

So, I went to the casino. And I met this guy. And I will blog about him later. He was Bar Buddy and twice the age of Scooter the guy who made me my first official cougar offer. Bar Buddy bought me dinner and got my number and boy, wasn’t I having a better week with all this attention?

The next night, I was on Facebook again and received a message from a totally different 23-year-old!! This guy is also the son of friends, though I haven’t known him since he was a pup like I did the other young guy. This guy would send me “pokes” on FB almost daily, but I never thought much about that. Some folks do that stuff. That particular night, however, he was more chatty than usual, and I found myself once again on the receiving end of some serious flirtation with a very young guy. This one wasn’t as smooth or direct as the other, but he finally managed to get around to telling me that having sex with an older woman had always been on his bucket list. He followed that with “which reminds me, incidentally, I haven’t seen your new place yet. Heh.”

Holy shit! Have I just had three guys hit on me in the course of four days? And were two of them under 25?

Yep.

I told this guy that he was the second 23-year-old to “hit me up” that week and that I told the first that I would keep it in mind, but wasn’t sure about fucking my friends’ kids. He then asked if I had come up with a policy about fucking my friends’ kids yet because he wanted to fuck me. Well jeezo man!

Admittedly, I was much more intrigued with youngster #2, (whom we’ll call Derp,) and even went so far as to call his bluff a few times over the next few weeks of text messaging, flirting and a little bit of dirty talk. Mostly I think he enjoyed the texting and suggestive talk. He never took me up on it – even when I offered to pick him up. In retrospect, I’m glad. Months of no sex may have impaired my judgment. As it turned out, I started having pretty regular sex within a few weeks of the 23-year-old spree, so I am glad that I didn’t do anything foolish or embarrassing.

In general, while I would consider any adult, I’m not particularly interested in most people under the age of 30. The youngest that I have slept with in the past 6 months was 28, and he was pretty lame in the sack. Brad Pitt was 29, gorgeous, fantastic, generous, dirty & delightful and I would see him again in a hot minute! Soup Can Man is 30, sweet, and amazing in bed and someone that I am currently seeing. I’ve turned down offers from “men” as young as 18 and dated as old as 48. The average age of my post-marital lovers is 38, however – with 2/3 of them being younger than I, and three of them being at least a dozen years younger.

So yes, I guess I am a cougar, but I’m not an ageist and I am willing to consider all shapes, sizes, races, and ages…just maybe not my friends’ kids, huh?