I’d Rather Have Sex With Your Mom

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Something strange happened to me when a woman—nearly twice my age—leaned into my ear and whispered: “Let’s fuck.”

I got off.

I love older women: They’re direct and to the point. They’ve been there, done that, and are in NO mood for small talk. They want you to take them, ravage them and, if you’re lucky, won’t even ask you for your number when the smoke clears.

Did I mention that most of the time they’re not wearing any underwear?

Now for me, this was all a novelty, because up until I was 28, I had been dating in my age bracket and had become accustomed to the endless first-date banter (jobs, family, blah blah) with girls who seemed to be looking for a good time but were really just trying to nail down a husband so they could fulfill that childhood fantasy of wearing a dumb wedding dress and experiencing the joys of child-rearing before their biological clocks took their final tick.

So imagine my surprise when, while downing my sixth vodka-seven at Thursday’s, I spot a 50-something woman off the corner of my eye sipping a glass of wine like some Tuscan vineyard aristocrat—looking like a complete and utter bombshell—and whom I found myself staring at every three seconds.

She had it all: The curves, the look, and the attitude—all tied up nicely in a barely-there black mini dress that was as flimsy as it was classy. It almost seemed like some weird, Happy Hour mirage to have that much woman in the room.

True, this was Thursday’s after all: Montreal’s notorious meat-market for the more “mature” clientele. But the real shocker was that she actually stood out so effortlessly from the crowd (i.e. the women half her age) and she knew it. She knew that every man was checking her out, evident in every subtle look and gesture she made. She seemed to be nonchalant but deep down was in total control of her surroundings. She had all the power.

And in that one magical moment, I finally understood the appeal of older women:

There’s a sexiness about them, a confidence that seeps out of their pores, and a certain stride in their walk that tells every other young chick in the room to get the fuck out of her way. It was intimidating, for sure, for even a guy like me, who had practically hit on every girl in the room at some point in the past 10 years, found it difficult to approach this blonde enchantress for fear that she, with all her experience, would be two steps ahead.

Turns out her name was Catherine. And within the first five minutes of introducing ourselves, she had revealed to me that she was twice divorced, had a son my age and was just out looking for fun. She made no secret of the fact that men her age didn’t interest her; they’re apparently boring, unattractive, and pretty much only have money to offer, which she claimed to already have plenty of.

After a few minutes of my awkward, let-me-try-to-sound-older repartee, she told me I had kissable lips and before I had time to respond, her tongue was down my throat. Knowing that the entire room was looking at two people with 25 years between them make out like two insatiable beasts was enough to get my adrenaline skyrocketing (I was never one to shy away from publicity).

By the end of our first hour together, she had offered to drive me home. And in case you were wondering, it was a Benz convertible.

That was it. No pick-up lines. No romancing. No obligatory first date.

It was shaping up to be a quintessential one-night stand. Except this time it was all new, different…exciting. So much so that I actually found myself taken aback by her aggressiveness. She was the leader, the mistress of ceremonies. And from the time she kicked off her heels and sashayed into my dark apartment, she was calling all the shots.

Never before had I been with a woman who made the first moves, but there we were, standing at the foot of my bed, her hand pulling the hair on the back of head, whispering the kind of filth in my ear that no twenty-something could have ever dreamt of. I couldn’t make every word out, but I knew the gist was that she wanted me to smash her against the wall.

It was the kind of sexual—and sensual— experience I thought only existed on TV, where I could actually hear my heart pulsating through my ears while still on a high from doing something that seemed so wrong yet felt so, so right.

In the darkness, everything was normal: her body, her moves, the way she moaned, the way she felt. I had pretty much blocked out the reality that the woman riding me was a mother to a 30-year-old–and a Three Finger Girl to boot. All that seemed to matter at that point was that, for the first time, I was with a W-O-M-A-N who was a true professional, and who didn’t fake an orgasm; she made you work for it. This was most apparent at the grand finale; I hadn’t sprootz’d that hard in a while.

Then it was over. She gathered her stuff, blew me a kiss and left. She didn’t say much, other than she hoped to “see me around.” She didn’t even want me to walk her to her car. I just went to bed, scratching my head, wondering what the hell just happened.

I still can’t pinpoint the exact science of man’s attraction to cougars. But it’s definitely real. So much so that since my encounter with Fifty (the first of seven to date, FYI), I often find myself unable to enjoy the company of a girl under 40, for fear that younger girls come with too much excess baggage—or shyness, or insecurity, or anything else that could detract my libido.

Maybe cougars and younger bachelors just want the same thing: Sex, straight up…no dinner, no poems, no bullshit.

Maybe a younger man and an older woman are both simply at their sexual peak. Maybe it’s the wealth of experience that she brings to the table (or bed, or shower, or public restroom as the case may be). Whatever the reason, the attraction is real and genuine, and aside from a few mortified female friends of mine who looked at me like I had leprosy, most of my entourage agreed that 50 could be the new 25. Some even confessed to having tried it themselves.

Of course, when I am out courting women closer to my demographic (which doesn’t happen much anymore, I must say), I don’t mention that my track record includes MILFs born in the mid-1950s; some might find that a turn-off. But truth be told: Women my age just don’t seem to stoke my fire, so to speak, since my now-infamous rendez-vous with Fifty.

I’m not saying 30-somethings will always be unfulfilling, but it’s such a warm and comforting thought knowing that the perfect one-night-stand is just a cocktail, and a few extra wrinkles, away!

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  • dario

    This is TOO good!

  • JerryAZ

    This blog fucking rocks!!!!!!!!!!!!!!!!!!!!!!!!!!!

    • http://bacheloruncut.com/ Bachelor Uncut

      Enjoy the ride. This is only the beginning ;)

  • Brett_M_79

    Dude, just landed here from Reddit. Too funny. New fan ;)

    • http://bacheloruncut.com/ Bachelor Uncut

      Welcome to the party. New post tomorrow!!!

  • CanadianGuy

    I haven’t exactly gotten near 25 years in the difference, but I too have come to realize my strange attraction to older women. Many older women have a certain sophistication, and as you said, a sexy confidence about them.

    All in all, this is my first time reading your blog, and I consider myself a fan already! Hopefully there are more entries here I can relate to! Great times for all :)

    • http://bacheloruncut.com/ Bachelor Uncut

      Thanks! There are no shortage of great reads! Consider this your new guilty pleasure lol.