November 18, 2009

7 Tips On Meeting Older Women (And Where To Find Them)

How To 2 Comments
The Sexiest MILF on the Planet, Brenda James

The Sexiest MILF on the Planet, Brenda James

On my last diary post, a commenter asked for more on older women, specifically where to find them.

I personally believe potential cougars and MILF partners are everywhere and that it’s more about taking a situation to that level.

So before I get to the question of “where,” let’s list some basic tips:

Older Woman How To

  1. Scout’s Motto. Make sure this is what you want – that it is a fantasy you really want played out – and be prepared for an amazing time when it happens. Don’t get soft on her.
  2. Game Over. Many older woman are done playing the coy games we do in our twenties.  Be honest about what you want because she will be direct about about her desires.
  3. Listen. On that note of directness, listen to her words because she is still a classy woman who will expect you have some brains to read between her obvious lines.
  4. Play. She’s not flirting or initiating conversation to waste her or your time.  Flirt back because there’s an endgame that will leave you satisfied.
  5. Respect. If she has children, you must understand that she may not want you at her home, or at least when her kids are home. Don’t be pushy, be patient, it’s worth it.
  6. Foreplay. It may or may not happen (sometimes, she just wants it… and right now). Go with that flow and give your all if in foreplay mode.
  7. Endurance. She’s likely at a sexual peak unlike any before.  It might be a long, but awesome night.  You’re young (that’s part of the attraction) so make sure you’re hard for long enough! Expect to do it multiple times in a night.

Now, on to where to find a frisky kitty woman.  There’s no one answer to this. Here in Los Angeles, cougar dens, as they call them, can be found in suburbia.  Think The Southbay, Agoura Hills/Thousand Oaks, Orange County, Pasadena. That may sound a bit stereotypical but in my experience, the divorced women living here are feeling a bit sheltered so it’s your job to spice up her life.  Still, MILFs are everywhere:

  • Online: Whether it be MySpace or Facebook, does she list her self as single and looking? Does she have other younger guys as friends? If on a dating website, does she directly say she likes younger men.  Did she look at your profile? Remember, older women will be more upfront than younger women in most cases. If she’s flirting, follow through because, remember, she’s done with games.
  • The grocery store (or any store for this matter), art galleries, coffeeshop: Does she look your way often, make eye contact, did she throw you a smile? And if she asks you a dumb question about where the soy sauce is, the door is definitely open for you to engage.
  • At bars, on the casino floor, social situations: Things should be fairly obvious in these situations, but the drinking makes people more flirty  than usual, even if she’s not looking. But hey, in places like that, live it up, be yourself and have fun as that’s what a woman will find attractive.
  • On the sidewalk.  In all cases like this, it doesn’t hurt to throw a smile in when you make eye contact. You would be amazed how little people do this and how much such a small gesture can open things up.

Got questions, comments?  Ask, let it be known, etc.  You can also follow me on Twitter at @Arrow405.

Above photo of Brenda James via her website.

  • Zoey

    Mesa Lounge in Costa Mesa.

    It’s a cougar den in there!

  • Rocker

    And don’t forget the hot soccer mom’s in Valencia!


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