Let's say that I've met a women IRL (whom I appreciate physically, emotionally and intellectually) who is not opposed to some intimate contact when accompanied with a financial gift.  But, she is not a professional and not, to my knowledge, someone actively looking for an SD (we're not in an declared sugar arrangement - just please operate under the assumption that what I'm saying is true).  However, I think there she may be a open to a (un)conventional sugar relationship, if I'm able to respectfully propose a P4P arrangement, while highlighting the mutually beneficial aspects (without making her feel like a prostitute).

 
Further, I perceive that if she's not interested in a full sugar arrangement, with all of the BCD benefits, she may be open to an arrangement with boundaries (cuddling, manual contact, oral contact) for which I would adjust a gift accordingly.

 
2 Questions:
    1) What advice would you give on how to respectfully initiate an offer for a sugar relationship?
    3) And more specifically, how I can propose that I am open to varying levels of intimacy?

 
P.S.  I already have in mind the various gift levels that would be offered based on whatever boundaries are discussed.

 
Thank you

Given all of the variables involved, including the ones too numerous to list here, there is no set approach defined for this.  

 
However, it is certainly possible to get a meeting of the minds, prior to a meeting of more tangible, fleshy bits.  

 
If you feel she is open to the idea, then here's one approach I might suggest. It's worked for me more times than it has failed. But some of those failures were epic disasters. At some time when you are talking to her, and the moment seems to flow naturally, let her know you have done sugar dating in the past. Don't give specifics on names, dates or amounts.  Just let her know that that you have some wonderful memories of fun dates, experiencing upscale moments and of course, helping each other meet their needs. Don't go head-on and ask her if she wants to do this.  (It's the soft-sell technique.)  

 
Again, don't go into details. Leave it somewhat vague. If she asks for names or details, demur and reinforce that a big part of this is discretion.  Her ask for specifics is a "shit test" to ensure you won't brag or blab about arrangements. Then just smile warmly while remembering the good times. That helps develop trust.  

 
IF she is really interested, she will keep asking questions. Take your cue from there. Answer questions truthfully, but not bluntly. If she remains interested and engaged, at some point you can ask her if she'd consider "something like that."  As long as she does not flat out reject the idea, you might suggest meeting or chatting somewhere away from where you are now, since presumably you are with other people you both know. If you can move on to a "private" meeting in public (say at a Starbucks) you can explore her needs and expectations like at any other M&G. As with any POT, don't be in a hurry, or try to pressure her to move forward. Stress that this is all about mutual consent.  

 
Please let us know how it works out.  

 
Life is good

 
The Cat

Exactly how do you know that she is interested in offering sex for renumeration?   For example, if you took her out for dinner and she let you hold her hand and gave you a peck on the cheek, then you're hardly on the scale yet.   On the other hand, if she balled the poop out of you and you paid her mortgage or rent that month and she said let's do this again soon, then you've hit a home run.   Just wash rinse and repeat.

 
So, details please before I can map a route for you.

 
Just remember, IRL sexual relationships can get very messy.   Maybe you want to go there, but that is antithecal to what TER is all about.    

 
You say that she is very attractive in terms of her intellect and emotional side.    Such people are rare.   If I was able to satisfy my sexual needs with others, but looking for someone who is as you describe for a Platonic relationship, then I would strongly suggest going that path.   In fact, I have one such relationship and value it very highly.   I tried to gently nudge in a P4P direction some years ago, but was gently rebuffed.   I'm very glad I was.  (The gal is someone I had met at an MP.)

Thanks Mr. Fisher.  Your request for more details is reasonable.  But, I'm afraid that I will have to disappoint you.  

 
For the purposes of my question, you can take on faith that when I say that she "is not opposed to some intimate contact when accompanied with a financial gift", it is fact.  All I will say is that in this case, 'intimate' would refer to heavy PG-13 contact and 'financial gift' would be well below that of a mortgage.

 
As for your advice concerning a platonic relationship, I would gladly have her as a friend, precisely because of her intellect and nature.  If, it weren't for the fact that there has been the aforementioned intimate contact.  And, the fact that I find her nearly irresistibly desirable.  That said, should any advances that I may make be rebuffed, I would be happy to come out of the experience with a friendship.

It is all up to her now.   She may decide to keep things at a low simmer, but may decide to turn the heat up a bit as well.

 
I would just go with the flow knowing that however she decides, you'll enjoy it one way or the other.

 
Making any kind of a forward move on your part may just push her away.

 
Relationships are like gossamer.

If your hopes are to have sex at some point, your odds are very low.  She clearly has you.pegged as a simp, can get away with simple fooling around for cash.  It's like the stripper who flirts.  Lap dances and touching for tips.  If you are.fine with just that forever go forward.  If you are wanting more. Relationship or sex.  You need to be clear now or cut it off.  Save yourself the pain.

Thanks Netnoy for playing the devil's advocate.  It's a necessary perspective.  I'm not at all offended by the proposition that she may view me as a 'simp'.  Although, I have not seen anything that would suggest that she has a scheme or is calculating.  But, if being a 'simp' means that I'm willing to let the lady decide what she wants out of the relationship, then that's me.

 
My intention, as suggested here, is to meet with her casually in public and mention that I'd been in sugar relationships (not a lie) and ask whether she had and let her guide the conversation from there.  I am fortunate enough that I am comfortable talking with her about nearly everything.  And, I'm hoping that I've shown her signals that she can safely do the same.

 
As mentioned, if what I get out of this is more of the same, I will be a happy guy.  But, you miss all of the shots that you don't take.