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Hey man I'v got a similair situation, two older woman both married have been talking to me at the gyn, I was introduced to one of their brother in laws and he was a real dick saying she had a competition coming up and to let her work out. Both are married the other woman i see constantly almost every day we work out I have not done anything more than give her a hug. She came over one day because i helped her get pot, she smoked a small amount with me and left. I just feel like a sleezy person trying to go in for a kiss or make the situation uncomfortable, there has to be a way i can use my words for everything to happen the way i would like it too. I have both womans numbers but the woman i work out with everyday texts me back and is very direct with me. This is part of the reason i would need to do this in a some what respectful manner.
I generally try to feel a woman out by asking if she is adventurous, and then slip into the conversation that adults should be able to do what they want and not be limited by what society expects them to do. This generally gets them to open up and if their responses are positive, you can be pretty sure that they are DTF.
As for teh kiss, I've found that unless you are a position / location to proceed, that it can backfire if you kiss and then have to stop. I kino like crazy under the table when sitting together (and am damn good at it too). If you are looking for a safe way to kino in public, you can always thumb-wrestle (I know it sounds silly, and it is, but as a professional in my 40's girls appreciate a man who can be silly). This gets you to holding each other's hands in an innocuous way in public, which then allows you to step up your kino efforts.
If the one woman is direct and already DTF - tell her to meet you at a coffee shop near your house or her's after a workout, get her worked up, and then LEAD her back to the location (don't ask her if she wants to go, just say "let's go to my place, I want to show you ________________" get up, and go to your car. She will follow you, and it will happen if you've calibrated correctly.
Go forth and close and report back with the lay ...