I got such great answers re the monthly question, that I wanted to collect some more wisdom from people here.

I am working through my first potential SB arrangement.  In the M&G, I got her explanation of what she is looking for, besides the obvious money piece.  Her lifestyle means a lot of travel, which combined with other factors causes her not to want a conventional dating relationship.  She doesn’t want to deal with the expectations and complications that go with that.

At the same time, she does not want to give up on male companionship, including intimacy.  She appears to want more than the cash and for the SD to be fixated just on the sex part.  I was surprised at how crisp and well thought out she was.  

I am 63 and she is 28.  During the meeting and afterwards, she was quite clear that she wants us to figure out if the arrangement can work.  I am not a typical 63 year old, in that I am founder and CEO of my own tech business, so I guess I should be more interesting than the average guy my age.  My life is very demanding, and with hers being the same, we would understand each other coming and going all the time.   Mutual comfort has come surprisingly fast.  

She is experienced on SA, but is on the verge of giving up on it, since she has not been able to achieve her goal.  She has apparently come across unreliable and in some cases, objectionable/dangerous people.  

Have you guys been able to satisfy the companionship part of these relationships with such a large age gap?  What do talk about and do, besides the sexual stuff?

-- Modified on 3/27/2018 12:43:44 PM

What caught your attention in the first place (besides the obvious)? Was it her interests? Activities? Line of work? Bubbly demeanor?

Since you are in business for yourself, I'm sure you made a lot of industry connections. Perhaps your potential SB would like to change gears professionally. Consider taking a cooking class together or attending a wine tasting. I'm sure you are well-traveled and been around the block. Expose your new sweetie to some of the things that interest you.  

Conversation starters: anything and everything! A lot of younger women love having conversations with seasoned men. The topics are endless. Just have fun with it. Screw the age difference.

A few things:

1. Zero bullshit - no games and to the point
2. Confidence - way beyond her years. I find that very attractive. Especially when she looks right at you and tells you what she wants.  
3. World travelled and knowledgeable. Super interesting.  

It doesn’t hurt that she is damn attractive as well.

You and your SB have a 35 year age difference, which is significant.  Me and my SBs have more like a 50 year age difference.  We tend to talk about the things that are universal and part of every human being's experience, no matter how long or how short that experience may be.  We talk a lot about dating, relationship issues, emotions, etc.  Usually my greater experience allows me to offer insights she has not considered, and it makes me look wise as well as sympathetic. We tell each other stories of adventures we've had and things we'd like to do.  My last date with my current #1 favorite lasted 4 hours, and only one of those hours was having sex. The rest of the time was conversation:  over wine preceding getting naked, in bed after 5 orgasms (4 for her, 1 for me) in a restaurant over dinner, and in the car going to and from venues.  I've been dating this girl for over a year and we always have interesting conversations.  Don't worry about it!  Relax, enjoy, and you will find common ground.

Great advice.

28, which is hardly the same thing as the younger ones still in college. She should be much more worldly and able to hold a conversation, even if it is not like what a 40 or 50-something woman would.  

Also, the way that you describe her indicates interests and experiences which will contribute to the relationship's quality.  

She sounds terrific and you sound like you are ready to light her up!

What sweetman said.

I have been lurking for a long time, and never expected to try the whole SA thing.  Based upon what I read here, I gave it a shot.   I placed the odds at about 5% of ever pursuing a meeting.    I owe you guys a MASSIVE thanks.

 
Just got back from a lunch with the POT described in this thread.  At the M&G, she was dressed down, and even kept her hat on.  She looked attractive, but so much was hidden, I could not get a complete read.  

 
Today was different, and she is mind-numbingly gorgeous.  Her profile provides no indication at all how attractive she is.  I have seen about 100 escorts, at the higher end of the spectrum, and she would be at the top of that list.   She explained what companionship means to her, and was precise, really articulate, and apparently sincere.  The match seems even better now.  

 
At the end of the lunch, she asked about getting together next week, at her place with some wine.   So it looks like I am going in.   I was dealing with quite the challenge in staying fully composed, once she made that suggestion.  

So again - thanks.  

-- Modified on 3/29/2018 4:12:17 PM

HIG, we have to have a come to jesus moment here man. It sounds to me like you're dating this woman, and she's costing you even more money than a normal girl with no real benefit.

 
  That and you've been on at least two dates and haven't gotten laid. I'm not 63, so perhaps my libido is more active than yours, but even with civvie relationships I'm at least getting it in by the second date. If not, odds are we're not on the same page and I'm not going to put effort into it because it's either A) not happening ever or B) going to mediocre when it does happen because she doesn't like sex that much (see: Starfish Missionary).

 
 Again, you and I might be different. Maybe you're not that sexually oriented and paying this girl to be around you is what you'd like to do. I will tell you one thing though, her "crisp well thought out attitude" screams that she's a pro at this and you're probably not the only guy she's seeing. I don't buy the "I was about to quit SA" bullshit for one second. She has you all wrapped up, and if she's going to have you wrapped up she better be providing what you need to get out of this, otherwise you're just getting played with.

justsauce said everything I would have said and more
so many smart dudes on this site!

Think there is a misunderstanding.  Or you guys move at light speed compared to me.  We have had one M&G, which was for about half an hour.  Then one lunch, which caused us both to conclude that next time is BCD.  So I am out the cost of a lunch.  

 
We have worked out the comp, and I am seeing her next week.  Which is when comp starts   So in under two weeks I am going from a dead start, to intimacy.  I have no reason to believe she doesn’t like sex.  I also don’t really care if she is seeing others.  As long as I get treated fairly.  And there is zero chance I am not “sexually oriented”.  I have made it clear that sex is part of the deal, and by the looks of it, that is what is coming next.

 
Is what I am describing all that abnormal or slow?  I certainly don’t mind the two week investment, considering the payoff I see coming.  

-- Modified on 3/30/2018 9:09:39 PM

Some guys here leave no stone unrolled, to be sure....and BCD after one
M&G is the norm.....But l wouldn't be worried yet.
The upscale girls here, who could indeed turn into unicorns, are worth a
little extra time and effort; Sounds like you have a true stunner on your
hands, that warrants extra care and attention
To the gallery: Some guys, like HIG and myself, truly enjoy the pre-BCD
courting aspect of this dance; It's actually a very special and erotic time,  
savouring the delights to come, that can't be recreated after the fact....

Stunner is right, without the princess and ego baggage.  The other part of this, is that I spent 4 weeks on SA, before even paying and being able to read any messages.  I didn’t think I was ever going to pull the trigger.  Finally decided to have a look, and behind all the nonsense messages (“Hey”, “How’s it going”) was hers.  Well written and thoughtful.

 
Spent a bit of time messaging, and I eventually told her that SA was not for me, and that there was no chance I was doing anything after the M&G we had set up.  Gave her the option of canceling.  She suggested we keep the appointment, because I might end up liking her, and that the world works in strange ways sometimes.  Which I did, but I left the meeting, still non committal about meeting again.  

 
I finally decided to keep going,  but the other dynamic was that I needed her to host.  So here I was, a relative stranger possibly being invited to her place.  I wanted to make sure the comfort was there, before pushing on that.   GC - this is where you are bang on.  At the end of the lunch, when she started talking about me coming over, and now she wanted to be sure about being comfortable, it just got seriously erotic and special.  That night we got on email, and she emphatically made the point, that she has never been this comfortable right off the bat.    She was still silent on comp, which had not really been discussed.  I was the one that brought it up.  Either she is sincere, or simply a master at the subtle sales pitch.  

 
So a lot of the pace to this, is my doing.  At this point, I have zero belief that I am being played.  Since I have only met one POT, I have no basis to recognize a Unicorn if she was sitting there right in front of me.  Between the hobby life, and business I come across a ton of people.  Once in a while I encounter a woman I can’t get out of my head.  Last one was a customer rep in France,  but unfortunately I don’t think she is available .   This girl is in that category for me.  In the next week or so, I will know more about the outcome of this chase.  What I do know is that I would not even be in this chase, if I had not been lurking here and learning.  Which is why I wrote the thank you post in the first place.  

-- Modified on 3/31/2018 3:23:10 AM

Your approach seems perfectly fine to me.  And things are progressing nicely.  I don't see why some of the guys here see such a big difference between Dating and Sugar Dating.  Maybe they've had bad outcomes in the past.  But for me, and likely for you too, the biggest advantages of Sugar Dating are:

1. Meeting girls you would never, ever otherwise have a chance to meet.  Knowing in advance that they want you to approach them, otherwise they would not be on the site.

2. Getting things clearly discussed upfront!  None of this wining and dining for months shit before you find out you're never going to get laid. The time between first contact and first fuck is often very short.

3.  Boundaries! You agree not to interfere with each other's lives, which happens all too often in the civvy world with messy consequences.

Beyond that, there's little difference between Dating and Sugar Dating.  For me, the emotional connection is the same, my desire to have emotional connections with my SBs is very high, and I like to "catch feelings" as some call it easily and often.  Some SBs I've enjoyed are only about the money and the sex.  Hey, when the girl is stunning, I'll take it!  But when she wants to reciprocate my feelings it's extra special and nearly indistinguishable from civvy dating. So keep doing what you are doing and report back on how that first BCD date goes!  Good luck! I gotta sign off and hit the showers now so I can drive down to visit my favorite 22yo luscious blonde SB and see how many Os I can make her have this time!

You, sir are an inspiration.  I am with you on the emotional connection piece. I have come to believe there must be ass clowns galore, in the sugar world.  I have heard in the past that drop-dead-beautiful women sometimes have relationship trouble.  Most guys are intimidated and the balance can’t see past the exterior, and just want to bang them.  

 
I mention the ass clowns, because she is clearly frustrated with the sugar world.  She spent time explaining to me what she had to offer,  beyond the obvious physical part.  Someone that had to grow up quick due to her parents divorce, living in different countries,  lots of international travel, holding down two jobs (one as a part time nurse), and so on.  

 
It was sweet, but I didn’t need selling.  She seems hugely motivated to have a connection, and a relationship, on top of the sex.  I wonder if she has largely been exposed to guys who just can’t see past the exterior.  If so, they must be complete idiots.  Good for me though, because she seems really excited about our connection so far.  

 
I have nothing to compare what I am seeing with her, since this is the first interaction for me in the bowl.  But if this ends up going where all the signs are pointing, then I will be asking myself what took me so long.  

 
Enjoy the 22 year old blond.  Not that you needed reminding.  

Well, dating these days I've heard that bcd is pretty much expected by the third or fourth date. I just happen to have found a sexy peer, and we banged it out in her bed, multiples on the overnight, at about the fifth date.  

Here's the difference. If I'm "dating", I can be open about it with my family and friends. It's nice to tell others about how happy you are around a woman, isn't it? (whether the discussion is about getting down on it, or not!)  

Tell them about my Sugar Baby dating?? No way. But so wish that I could (;

I don’t think there needs to be any significant difference between dating and sugar dating. I treat sugar dating like dating accelerated and with some preset boundaries. I’ve picked up a civvie and had her start calling me sugar daddy the next morning when she realizes I was much older than her and wealthy enough to support her. With my favorite sugar baby, we even have made up story about how we met, so we don’t have to be strange talking to others. She has also introduced me to her family as her boyfriend.  

I think most of the interactions on SA are closer to p4p, but if you meet that special someone, why wouldn’t you take it further?  Some guys date prostitutes even while they’re still working, so what you’re suggesting seems much more normal.  

My only suggestion for this one might be to steer her towards favors instead of a fixed compensation amount for fixed number of visits.  Offer to pay her rent or car payments or whatever and sporadically gift her cash or other stuff. That might keep it feeling more real and less contractual.

So, after we decided to proceed, I deleted my account on SA.  Left money on the table with my premium membership.  In the last couple of days, something just started feeling off.

 
So this morning, I created a brand new profile, and viewed her.  Wondering if she would bite and message me.  Sure, enough a few hours later she did, using the very same come-on approach that she used with my old identity.  I am messaging her now, getting her to dig a deeper hole for herself.

 
This is after she has been telling me that she doesn’t want any other arrangements, since we are so compatible and clicking so well.   I am booked to see her twice this week, which is when the money is supposed to start flowing.  I played the dumb-ass agreeing to the monthly allowance, after the first of the two meetings.  

 
I think with my new identity, I am going to ask for a M&G that conflicts with my supposed second meeting.  That should be interesting.  

 
So while she is messaging the new me, she is emailing the old me, being all sweet and nice.
   

Sometime today, or tomorrow, she will know I am on to her.  That should be fun.   Wonder how many suckers have been blown away be her looks and have fallen for the same scam.  Dammit - I was hoping she was real.  At least I am only out the cost of a lunch.  

-- Modified on 4/3/2018 10:21:37 AM

If you start testing people, they will usually fail.

Stick with quid pro quo.  You'll get what you want and won't be disappointed as often.

Her tag line was “I want to drip with your seed” , I just looked and it’s now “make my Monday messy and release your stress in my guts”.  In her profile she talks about showing you all her holes, she will make one thing hard in your life and she will take care of that.  Etc.  
So I start messaging her, ask to switch to phone, no phone. Switch to email talk for a while.  I drop the convo.  
A month goes by she emails me.  We go back and forth ask if she got a phone, nope.  Ask for social media she says she has nothing.  Based on that, my spidey sense says ‘Here is another con’, I just said no thanks.  

I'm just thinking that from what you've said, there's no real proof she is conning you and you might offend her if she discovers you are being sneaky in your online research.  Maybe I'm too trusting, but let's take her at face value for a moment.  Maybe she's just like us, sending messages to as many Potential playmates as possible in order to find the best one or three.  Maybe she's using the same language and approach with all of them, maybe even cut and paste, in those conversations.  Maybe she would agree to a simple gift per visit arrangement, just at first until you get to know each other.  You've already indicated your willingness to give her a monthly allowance.  That's the carrot she's hoping for.  If she's legit she just might be willing to go for a gift per visit at first in order to get what she wants.  I wouldn't be so quick to declare her a scammer.  But do report back when you know more.

For better or worse, the situation is probably over.  She now knows that I did this.  Her explanation is that she lent her friend her account last night, so she could check out the talent, before jumping in.   So I am supposed to believe that it was her friend, messaging me, with the exact same language.  

Did she swear exclusivity to you? Did she get you to send her money on the pretext that she too was deactivating her account? Did she promise you true love? What exactly did this woman do to you except to make you feel special?

 
I don't mean to be harsh, but you might have just fucked up a good thing. I don't see where she did anything wrong, it was YOUR insecurity that fucked this up. If it were me I would have already fucked her by now and too busy enjoying her company during the time we had together to be obsessed about what she is doing when the two of us aren't together.

 
You are 63 she is 28, but it sounds like of the two of you, she is by far the more mature one. I ALWAYS assume my SB's are seeing or at least talking to other guys, not all of them are, but that is my default assumption and that way I never end up butt hurt like you appear to be.

I don’t care about exclusivity, but I care about honesty.  Yesterday, when we were finalizing our first meeting, stuff started to change.  We went from an extended BCD meeting, to her wanting a quick cocktail meeting.  Where I bring the money, and then leave.  That change bothered me, and I pushd back.  We ended up in a quasi compromise.  

 
And yes, she has continually told me that she was done with SA, and that she wanted to focus on just me.  And that she had stopped messaging everyone else.  Which I never asked for. She volunteered it.  

 
So my spidey sense was going off.  So I put up a new profile.  Viewed her after noting she was on the site 8 hours ago, but did not message her.  Within an hour or two she is messaging me, telling me that she only wants one arrangement, and that it is hard to find honest people on the site.  The day after she is telling me we are all set.  

 
Maybe I fucked up a good thing, but to me this situation is off.  

-- Modified on 4/3/2018 11:52:37 AM

About 5 months ago. Pretty picture,  be rey sexual innuendos in her profile, and I was going to be in her town soon. Several messages later she ghosted and I gave up on her.

You failed to mention the change from an "extended BCD" meeting to a "paid" public M&G. That changes thinks completely.  I don't much care about the rest of your story, I rarely take the various stories told to me by POT SB's seriously anyhow, but this part of your story changes EVERYTHING.  

 
I am well on record about how I feel about "paid" public only dates. I absolutely REFUSE to do it and evidently so do you, or at least now you do. Congratulations, you are starting to catch on, or at least I hope you are, You say you came up with a "quasi compromise" I hope that compromise doesn't entail you giving her money before going BCD with her. If you give her a single penny, knowing she's a liar I might add, I hereby sentence you to write "No intimacy, No allowance" a hundred times on the chalk board. lol

After all the goofing around, yesterday I told her to forget the whole thing.  I just cannot convince her to accept the concept that payment comes with intimacy.  She seems really hung up on this not looking like a paid escort thing.  She is trying to change my mind, but I am not budging.  

Which is really frustrating.  This girl is literally the most attractive woman I can recall seeing in months.   Absolutely stunning, but with what I know now, I am just not going there.  She must have a lot of guys wrapped around her finger.  

Go find the hottest hooker you can find, and even better, one that looks similar to the POT you just blew off. Fuck her brains out, get this no sex, gold digging cunt out of your mind and start all over again with another girl. I know you think/thought this girl was something special, but just like hookers there are a thousand more just like her waiting in the wings.

 
BTW You say she is "absolutely stunning" have you actually met her in person?

Ya, I met her in person twice.  The second time I bought her lunch.  Her one and only pic on SA, gives no idea what she actually looks like.  And walking around in the street, she keeps herself really low key, so she kind of flies under the radar.  But when she sat down at lunch, that cover was gone.    

 
So I got the full impression of her including intellect,  confidence, and looks.  You see a ton more women than me, but I have been with many high end escorts.   LA, London, Toronto, Tokyo etc.    And I have not yet been with someone that is off the charts like her. I know I sound like a star struck kid, but she is jaw dropping.  Just having her across the table, looking straight at me and telling what she wants in an arrangement, seriously got me hard at lunch.  And she never even touched me.   It had the potential to be embarrassing.  

 
But then she started changing the understanding, and I felt like I was getting played, so end of story.   I have a screen shot up of Margaret Thatcher on my PC.  Staring at that is my therapy.