Maybe some of you are like me.  I've been lucky enough to be with some beautiful women, both in the hobby and in the civvie world.  At this stage of my life I'm basically resting on my laurels and staying on TER because some of the most interesting minds seems to be connected to the hobby.  

Then something comes along to shake up your world.  Like a 40 something female professional acquaintance who seems determined to start something. She's slender, blond and attractive.  She's married to a successful guy who I believe would be considered a hunk.  Let's face it, I'm past my prime. My assistant (a wonderful gal) says age and looks make much less of a difference to a woman.  Still, I'm perplexed how to respond and whether at this stage of my life I want to follow up. I'm also afraid I'm mis-reading the signals.  The "signals" are she keeps suggesting we go for drinks or a movie.  The last (I think it was the last) time we went for drinks she got pretty relaxed and keep coming back from the Ladies room more and more unbottoned until she blurted something like "so the most important thing to me is my family and my job."  

Where I'm at is does she view me as a mature confidant or does she want to play.  At my age I don't want to make a move and wind up looking like an old fool. (Maybe that's already happened!  LOL)

This has drama writ large all over it.

I'd cut off contact completely

Agreed. This could get messy beyond repair. She's looking for something and it'd be best to not be her means of experimentation.

You will never know if you don't ask...The next time you get together for a drink-and after the appropriate time has passed-read the moment-and ask if she is interested in taking things to the next level ?  The interesting thing is that she has asked if you'd like to catch a movie....that is different than a drink....she is sending you signals.....move on them !   (Please report back as to your success)!  (I would tell you I have used this approach very successfully for a long time -  if at any time she starts to back off - respect her wishes-don't force it in any way-let it be her call).

If you haven't tried the SD/SB World, maybe it's time. As far as this relationship, if it was me, I'd pass.

situation? Could you become her banker for a nice loan?

Tread lightly.

Said So Well !!!!! Exactly Right !!!  Now if the OP will just move on it-Things are perfectly aligned and I am willing to wager taking it to the next level is exactly what she has in mind,  but for the life of her can't figure out what is holding him back-or does he just not get it ?

"She's slender, blond and attractive.  She's married to a successful guy who I believe would be considered a hunk."

Every generation under us has a more open and sophisticated view of relationships and sexuality than we were allowed to embrace. It is completely possible that "seducing you" is part of a marital game between her and the husband. The problem is that it may only be a game where she goes "so far" with no intention of following through, gets herself all worked up into a puritanical lather of being "so naughty! tee hee!" and then goes home and shares the details with her husband to get his perverse jollies on and then they use that (you) to get their kinky little rocks off.

The problem here is that if she really isn't serious about following through and this is all just a game to see how far she can go or has to go to push your buttons, it could potentially leave you in a really awkward place if you move forward thinking (and rightly so) that she is interested when she is really only interested in using you for a game of mental masturbation.  

On the other hand - and this is also very true - one of the great appeals of older men "past their prime" by other folks standards is that they are safe in all the best ways and for some of us, it pushes our own kinky buttons because we have a bit of the gerontophile thing happening and anyone old enough to be someone's grandfather fits nicely into that category, regardless of actual age.  So, there could be THAT too but honestly, if she is all about you cause you are in her cross hairs for something sexier than tease and denial, because you ARE old enough to be considered safe and/or because she might have a bit of the gerontophile thing going... she will make an aggressive move and not continue playing clueless coquette. Trust me on this one. Rejection is not something we are typically afraid of when we are dealing with older men.

"Let's face it, I'm past my prime. My assistant (a wonderful gal) says age and looks make much less of a difference to a woman."

This is absolutely true. It doesn't matter how you dress up a pile of excrement, it still stinks and offends like excrement, no matter how nice it looks. Women are visual too but we also know that the downsides of dealing with selfish jerks are many and never ending and NEVER lead to an orgasm or being happy that you lowered your standards to someone who makes you feel like crap about yourself instead of masturbating with a vibrator that never disappoints or makes you feel like a loser.

"Still, I'm perplexed how to respond and whether at this stage of my life I want to follow up."

If you are enjoying this dance, sit back and enjoy the show while it plays out to its natural conclusion (she makes a clear advance or gets bored and goes away).

If your time has more value and you really do have better things to do with your energy, then just call her on it on your next "date".

"The last (I think it was the last) time we went for drinks she got pretty relaxed and keep coming back from the Ladies room more and more unbottoned until she blurted something like "so the most important thing to me is my family and my job."   ..."

Any time you get OBVIOUSLY conflicting messages like this, do not walk but RUN in the opposite direction as quickly as possible. Even if she isn't you, her internal conflict with what she is doing is going to turn this into a crap-fest of accusations, confusion and enough awkwardness later to make you feel like a middle school phys. ed. coach who got caught alone in the girls locker room during game time. Even if you did nothing wrong, you are still going to feel (and look) like the creep when this all shakes out. Its a bad set up and that never leads to a good ending.  

Hope this helps and let us know how it all plays out

The supportive posts are much appreciated. One thing every one here seems to agree on is that going to a movie is a DATE.  That puts the thing in perspective. She feels like she is going on a date.  

Okay. With that in mind I'm going to let her lead a bit, but she'll know I'm receptive to whatever she has in mind. The main thing is it's a date, so let's have fun and see where things go.  

I'll report back but this event is not around the corner.

Go For It !   If she is running a bluff-call it !

First, be certain that booze isn't her problem.

My own experience in situations like this leads me to believe that the bedroom is her problem. She wants to get laid, and she wants a man more mature than that hunk at home.  

But be careful who and what you might be putting at risk by taking her on an actual date. Your family? Her family (does she have kids at home)? The professional reputations of both of you?

If those risks are minimal, go for it. Use extreme discretion, both of you, as you test the waters.

I don't understand why this is even a question.

Her statement "so the most important thing to me is my family and my job."  tells me there's some type of conflicting baggage going on that might not be the best bedfellows. Sure it's monetarily free but what web are you spinning in the process. I'm not sure what your personal life situation is that could be in jeopardy .

Kisses Haley

There are so many great options in the hobby world, why take a chance on messing up your or her lives?  I'd just walk away.
As they say, you don't pay for sex.  You pay to be able to leave after the sex.

Perhaps you will just find this self serving, but consider the worst case scenario: you get involved and she goes psycho and ruins your life. Yikes! Hobbying has a MUCH higher safety rate and hopefully offers as much fun.
I would stay safe. Just my two cents worth.

The hobby is your sexual outlet.  Leave the married women alone.  This has disaster written all over it.  

 

and then see what happens. You can always say, oh so sorry that happened - we really should not have, that can't happen again, we need to be professional, blah blah blah. Then see what happens next - she might be a perfect situation for you. A discreet lady who just wants to play once in a while. I had a couple of those in my lifetime - but I was probably lucky. One was unhappily married - said her hubby had not done her in like 12 years (but who knows why - I didn't live with her for the past 20 years like he did). There is always a story in every relationship and both sides have baggage no matter what. She was mid 40's, very pretty blonde with nice tits, I was very happy to do her as often as I could - maybe once or twice a month and boy oh boy could she suck a dick - we had a nice thing. But to others comments here, if you want to play, you really should play with the pro's or try to find a Sugar Baby, it just easier and safer when your married.