I am a (M23) and getting with a older woman has been a goal of mine for as long as I can remember. By “getting with” I ultimately just mean sleeping with (‘Milf’ has always been a favorite category.) When I say older I mean like mid-late 30’s maybe even 40’s depending. I hear stories of guys my age or even younger than me sleeping with women who are 10+ yrs older than them and it just intrigues me so much on how they were able to pull a woman who could be their mom’s age. I’d be lying if I said I don’t get hit with a bit of envy sometimes, when I hear a young buck around my age smashing cougars.

I don’t have many “notches” under my belt but the few I’ve been with were all around my age. And while they were great, I’ve always wondered what it would be like to get with a woman far more experienced than me.

I also think it must be a major confidence push in one’s self, knowing you pulled a woman who’s supposedly more mature than you. Yet the amount of game or seduction or whatever it is you have, made her drop the draws, regardless of her age, who she is (your boss, higher-up, neighbor, teacher, etc.) OR if she’s even single, married in some cases.

So my question is; How does one obtain such abilities, such game, such seduction, such presence? And I’m mainly asking the ones who did the pursuing of this ‘mature’ woman, not so much the ones that got pursued (though that insight is still very much welcomed to be shared.)