So… You Want an Older Woman?

It seems to be every guys fantasy to sleep with an older woman. I’m 28 now so an older woman for me is a lady in her fourties. For some of you young lads you might consider a woman in her thirties “older” anyway you look at it though there is something extremely appealing about banging a girl during her prime fucking years.

I remember being 19 in college and making out with a woman close to 50. I actually was on a bus heading back to her hotel but do to a friends reluctance to take one for the team and do her equally old, but not nearly as hot friend my opportunity was ruined.. I will never forgive him.

Now adays banging older women is pretty damn easy. My friend Tad cleans up with women in their thirties and fourties on Adult FriendFinder. He gets guilt free no strings sex. Back in my days as a Real Estate agent I had a little thing with one of my clients. She was a single mom 42, hot, but unfortanately she wanted a little more from Bobby then he was willing to give. I do miss her and her short jean skirts and her unquenchable thirst for sex.

Anyway, here is a question and answer with Christian Hudson about how to sleep with older women. I agree with him and thougth I would post this for those who want a Couger..

How to Fuck Older Women by Christian Hudson?


I was wondering what your thoughts were in regards to the
approaches you recommend and their compatibility with different
age groups. Do you find the basic methods transcend various ages
or do they tend to work best on a specific demographic? I am 42
and still single and feel some of the examples to which I have
listened just don’t work with woman over 30. This, of course,
could explain why I am still single but my experience has been
(aside from being limited) that woman closer to my age are more
on guard and far more careful with whom they will strike up a
conversation. They also seem to have a more specific image of
what they are looking for after having gone through a marriage
or two and not wanting to repeat past mistakes. Alternatively, I
am in need of incredible assistance to overcome my
interpretations of all of this and the woman are just fine.
Either way, any input would be greatly appreciated.

Hi Christoph, thanks for writing. So will the stuff you hear
work on older women? Yes – in principal. The techniques behind
what you’re hearing are solid, but the way they’ve been
implemented on Master the Vibe is of course with some younger

But I don’t want to lead you astray and suggest that there are
no differences. There are a lot of caveats here and your
interpretation of this scene is not off.

You bring up some great points. Women who have been through a
divorce are typically very selective about the men they let into
their lives. Women who are somewhat older and haven’t yet been
married can be a mixed bag – either they’ve accepted that they
won’t get married, or they’re remarkably unselective. In all
cases, older womens’ desires are often tempered by the cynicism
of one or many failed previous relationships. It is not so easy
to sweep them off their feet and into a fantasy land.

With that said: I’m friends with one particular older woman who
is really attractive. She is always telling me how direct men
are with her. It seems that older men think that being
successful and experienced, they can cut past all the BS of
courtship. But she is always turned off by this, as are her
single girlfriends. Women of all ages love to feel the tingle
of a new love interest, so never lose sight of that, no matter
how jaded a particular woman may seem.

A few thoughts regarding meeting them…

First, what venues are you frequenting? 80% of the time I’ve
met an older woman (35 ) with whom I’ve connected, its usually
been through a social circle, at a party, or a fundraiser, or
something like that. In venues like these, there’s a common
reason you’re there, so you’re “pre-selected”, unlike in a
bookstore or a bar. If you want to greatly increase your
success ratio with older women, one of the first things you can
do is to start putting community and/or group events on your
social calendar. And your opener in these situations is easy –
“Hey, so how did you get involved with Charity:water/Ballroom
Dancing/The History Museum?” After she tells you, start talking
about your interest, and you’re off to an easy start.

For that other 20% of times when I’ve met them at bars, here’s
your primary focus: be a cool, masculine guy, and make her feel
like a real woman. Too many men joke around and don’t take
women seriously. Smile. Be warm. And show her that you’re a
real man.

I went back and listened to some of the audio I’ve recorded that
you’ve heard, and thought about how it compares to my delivery
when I’m talking to an older woman. The content is going to be
very similar. But rather than an excited “oh my God, this is
sooo much fun” playful vibe, there’s more of a “I’m impressed,
its great that we connect” thing going on. My word choice is
also more mature. I back of my boyish energy about 30%.

Now to get to your very first question: what approaches work
with older women? A sincere complement will go a long way.
They’re not getting complemented the way they were when they
were twenty, and they will appreciate it. You can also use
situational openers to good effect: “what’s taking you to
Budapest?” at the airport or “The last time I felt this flexible
was when I was five” as you’re walking out of Yoga class.

I’d recommend that you stay away from anything like indirect
opinion openers. These are meant to capture a young girl’s
attention at a club, and are going to come across as insincere
to a woman with a good disingenuousness radar.

And here’s a secret weapon: tell older women that they are
“hot.” It is a great word because again, its usually reserved
for younger girls. Say it with strength and with commitment –
with this one word, you can go a long ways towards sweeping them
off their feet and making them feel young again.

I’ve recorded a two minute clip of a tonality example. You can
check it out here:

And hey, it’s August 1, which means that my birthday is right
around the corner. As I’ve been alluding to, we’ve got some
really cool stuff planned, so keep your eyes peeled.


Read our review of Master the Vibe

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About Bobby Rio I'm Bobby Rio, one of the founders of TSB. I tend to write about what is on my mind so you'll find a mix of self development, social dynamics and dating articles/experiences.  For a collection of some of my favorite articles check them out.

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