How to Bag a Cougar

You May Have a Dick, but You Don’t Have to Be One.

I recently had a tall, dark, and handsome man more than half my age attempt to woo me into bed. Like a surprising number of young men around his age, he fancies those of us with a little experience, shall we say. The problem is, however yummy these young folk may look, they’re wet behind the ears and have zero idea what they’re in for with an “older” woman.

Once upon a time, a MILF looked like someone old enough to have reproduced but not immediately after or instead of graduating from high school. Over time and for reasons I can’t explain although I can speculate about, the average age of the average MILF took a nosedive. While GMILFs are certainly a thing, there’s a huge span of time between the barely legal MILF and the Social Security GMILF.

So the Powers that Be determined that women of a certain age, especially those who actively welcome or pursue the attention of younger men, should be deemed Cougars. Growl. Meow. Since I know a lot of gay men, I’m familiar with terms like Bear, Cub, Wolf, and Otter. Women don’t get a lot of animal terms other than Fox or Dog, depending on whether you like how she looks or not. She can be a Chick, if you dig it, but nobody likes to be henpecked. Cougar is a special term reserved for those of us old enough to know it’s all a game but young enough to play it anyway.

For those foolish or courageous enough to hope to take on the task of courting, seducing, ravishing, or basically banging the living hell out of some woman old enough to be their Gen X or Late Boomer progenitor, I offer some insights and advice.

First off, if you’re connecting online, don’t lead with a dick pic unless you have the most beautiful dick in all of Dickland, that sprinkles magical dicksie dust. While most heterosexual or bisexual women can admire a good penis, very few like to have a conversation start off with one in their face. Get a nice face shot, at least. Sorry. At some point she’s going to need to see it, so the beginning is a good place for that to happen. It helps build trust, if nothing else.

Secondly, don’t start your conversation with something witty and urbane like, “Wanna fuck” or “Show me your pussy!” If there’s a mutual interest, there will be plenty of time to talk about how your genitals could fit into that of the Cougar’s. Also, for all that’s holy, don’t start a conversation with “hi.” Yes, it’s more polite than “I want to eat your ass,” but it’s not informative or enticing. Everyone can say “hi.” Make me want to respond, dude.

And there we have one of the challenges that our newer generations encounter when macking on the Cougar. They underestimate the extent to which they are done with the bullshit. They’re not opposed to being hit on or asked about sex but show some class while you’re doing it! And if you do nothing else right, take “no” for an answer. Especially in a club setting. The last thing a guy needs in a Lifestyle or BDSM context is a reputation for ignoring boundaries or refusing to back off.

This is where my tall, dark, and handsome 20-year-old blew it. He didn’t stop insisting. Even if I’d been inclined to fuck someone who isn’t even old enough to drink, by the 12^th time some configuration of “Can I please eat you out or screw you” came out of his mouth or his keyboard, I was totally over it. Yes, he asked nice. But he kept asking. And asking. And asking. Have some self-respect at the very least!

If you manage to successfully defeat the boss monster and bag a Cougar, remember that she’s probably had more sex than you have and she’ll know if you suck because she won’t get off. By the time women can see menopause on the horizon, they’re done having sex that doesn’t satisfy and ready for, I dunno, an orgasm. Young men can pop wood and stay hard forever, but that’s no guarantee of knowing the way around a woman’s body, especially her most intimate bits. Listen to what she says. Chances are good she has some idea what she’d like you to do and it may be something that never occurred to you.

Speaking of things that may never have occurred to you, make sure to have an STI talk. She may or may not be used to such frank and modern topics, but it’s important for both of you. If you’re going to be bagging a lot of Cougars (or even Babes and Chicks) it’s best to be tested at least every three months, if possible. The longer we’ve been in the saddle, the more chances a Cougar has of picking something up, herpes and HPV being among the most common. The more willing you are to wrap up that sterling example of raging manhood, the more likely you are to get to put it where it can do the most good. Within a sexual encounter context, of course.

There’s plenty more I could say, but let me leave you with this: open your eyes to the ways a woman’s body can change as she ages and how beautiful that can be even when it’s unconventional. Scars, stretch marks, smile lines, gray or white hair, reading glasses, and often a figure that has grown up to be plush and luxurious. You will encounter these and other so-called imperfections that you may not find in a younger woman. Don’t judge. And if you must judge, keep it to yourself. If you decide to share your opinion unkindly, do not be surprised if any woman who has any self-esteem tells you to go fuck yourself.

And if you must go fuck yourself, you probably shouldn’t start out with a dick pic.