In the Cougar’s jungle… the hunter becomes the hunted
Following a trail of breadcrumbs; I stumbled across an article here on Boston Magazine’s website which tells an updated version of a very old story – young guys on the prowl for older women. We’re called Cougars now – the older, successful, sexually aggressive woman who purloins encounters with eager young studs at will… no longer the sex kitten of her youth, but her grown up older sister who knows what she wants and knows how to get it; and if we’re to believe what this article proffers, the young studs who now hunt the Cougar claim to come to the game with an updated bag of tricks and with a slick new repertoire to try and bed the most elusive and cunning of feminine felines.
Now that I’ve stopped laughing… I think I’ll offer my own perspective!
(and I’ll try not to crush their egos too too much!) 
The article tells the story of two twenty-something guys who cruise Boston’s hottest Cougar hunting grounds (bars) in the hopes of getting lucky (laid). Boston is of course the perfect Cougar jungle – the city is filled with older successful professional women who are not only health conscious and physically active, but who are also in touch with our own sexuality and aren’t afraid of it either — and we look good and we know it too.
Without venturing too far into stereotypes – the Cougar is typically in her late thirties to early fifties, is financially secure, is professionally employed, has probably been married at least once, maybe twice, has an older child or two but isn’t tied down with little ones at home… so she can stay out at night and doesn’t need to worry about a babysitter, she looks good, she takes care of herself, and she wants to have fun, and that includes getting laid on some kind of regular basis, but she isn’t interested in being tied down either. Sometimes she wants romance and intimacy, but more often than not, she just wants to get seriously fucked silly stupid and doesn’t want the strings and responsibility of maintaining a relationship. She’s tried her hand at love and while she thinks that’s a wonderful sentiment – at this stage of the game, having good sex is a much better option — and believe me, we do have options.
Hmmm, sound like anyone we know? 
Aside from the fact that I’m happily married now and am monogamously bisexual – I could very well easily assume the role of Cougar if the circumstances fit – tho MILF tends to be a more accurate description of my role to play in life now – but I court the counsel of several Cougars from amongst my circle of friends.
So what’s wrong with the article?
Well – a few things.
“The cougars are out tonight,” says Davidson (his name has been changed for this story), eying the throngs of middle-aged ladies as he and Rosa belly up and order their drinks. “This could potentially be an epic night.” The bartender sees the same thing. Surveying the crowd, he sizes up his clientèle. “The women here are looking for one of two types: old and rich or young and handsome,” he says, taking an order for a cosmo. “And if it’s just a one-night thing, they’ll take young and handsome every time.”
As much as they like to wax poetic on what they do at night, Rosa and Davidson hate talking about what they do by day. Davidson says he works in the financial world, and prefers to leave it at that. Rosa does paralegal work and plays a lot of high-stakes poker—both of which he makes sound like side ventures. His real gig, he tells me, is “banging older chicks who pay for my stuff.” I laugh. He clears his throat. He’s not kidding.
LMFAO! Well, not to burst Rosa’s bubble – because if you can manage to finish this article without spitting your coffee out thru your nose – Rosa left the bar that night alone, because, as the article concludes:
Of course, that’s totally fine with Rosa and Davidson. As the crowd dwindles, phone numbers that will never be used are exchanged. Kisses are shared, but nothing more. As they leave the bar to hop into a cab, Rosa explains why they let the evening’s quarry get away. “Those chicks were too hammered, it was too much of a lay-up,” he says. “I just couldn’t do it.” He directs the cabbie to the Liberty Hotel, a place with “iffy cougar potential,” and looks back at a gaggle of cougars spilling blissfully out of the bar.
“Plus,” he says matter-of-factly, “they just weren’t that hot.”
There are a few dynamics at work here which one might be able to forgive Rosa’s ignorance of – he’s young and is likely inexperienced with the witchy ways of women and he hasn’t yet figured out that as much as he thinks he’s playing the Cougar for a fool – the reality is that the Cougar is toying with her mouse like the cunning cat that she is, and it’s always her decision about whether or not she’s in the mood to feed.
He assumes – as the articles goes on to tell us – that because he’s regularly fucking a female doctor on the South Shore who bought him an iPhone and pays his bill every month, as well as picking up the tab for his health club membership, that he’s somehow got her right where he wants her. It doesn’t occur to Rosa that these trinkets mean nothing to her, and aside from his ginormous ego which rivals Curt Schilling’s – Rosa is essentially a disposable piece of meat, and as soon as the good doctor gets bored with him or gets tired of trying to teach him how to give her head without causing serious injury to her clit… that bricked iPhone of his will be the only scrap the Cougar leaves untouched.
But it actually gets better, or worse? 
A pedigree also helps, whether invented or real. For the cougar hunter, dropping a home address on the flat of Beacon Hill or in parts of the Back Bay or the South End can suggest a certain It factor, especially with women from the suburbs. “I like to tell cougars that I bought Johnny Damon’s condo in Back Bay when he signed with the Yankees,” says Chris, 27, a banker. “I’m bullshitting, of course, but as a rule, cougars love Johnny Damon. And by the time they get back to your place, it’s pretty much a moot point.”
This is where I spit my tea. (sorry)
Do these young guys really think we believe this shit? lmao!
The rules of the jungle are this: we like the game and we know it’s a game, we like the idea of hot young guys paying attention to us, and it’s a fine thrill to take a young stud home and fuck his brains out – but it gets old quick.
I’ve dated younger guys – and while their energy and effort was enjoyable, as well as their stamina, the downside was trying to explain to them that my clitoris doesn’t work like a Playstation controller. 
Most young guys aren’t very good lovers. They’re much too consumed with the idea that they’ve actually managed to bed a woman who is way out of their league or their economic reach to stop and realize that when I’ve just told you that “no one has ever made me come like that before!” or “my god your cock is huge!” or “I’ve never done anything like this before!” when I let you fuck me in the ass… that you’ll never be any wiser as you’re staring into my lying eyes from across the pillows. You’ll believe every single lie thing I tell you… and you’ll have no clue that you are exactly where I want you.
Where’d you say you live again, slugger?
And whatever money I spend on you is an investment in my pleasure which serves the needs of my own ego – because let’s be honest here, fucking a younger guy is great for a Cougar’s ego – but don’t make the mistake of believing that you’re anything more than that — even tho for my needs it’s actually helpful if you do! 
In the jungle – the female is deadlier than the male. An attractive older woman – the Cougar – doesn’t typically have much difficulty in finding willing and eager pieces of hot young beefcake to roll around in the sheets with. And the one universal truth in this world is that the male always competes for female sexual energy – Kitten or Cougar.
These up and coming Cougar Hunters should remember; an older girl has had time to learn what makes men tick – it’s a skill we learn and start learning from the moment we grow breasts – but please continue… we love hearing about how a twenty-something guy who is probably making less than 50k a year and still living at home with his parents just bought Johnny Damon’s Back Bay condo!
Just make sure you’re gone in the morning, sweetie… you were a lot of fun… and please remember to put the seat back down before you leave!
OnEdit: Much love to my dear sweet Piper for offering her take on this topic here!
Mwah!
“…Following a trail of breadcrumbs;…”
Don’t you ever feed Moe, that poor poor cat? Ha!