When is the ideal time to discuss arrangement terms?  I ask, because going BCD this week with a SB and neither of us has discussed financial terms of the arrangement.  She is 32 (I know...too old for many of you), petite, blonde, killer body with a sweet southern accent.  Claims to have had 1 previous arrangement with a gentleman from out of town who visited her regularly.  The only logistics that we've discussed is frequency of visit.  She wants 3 to 4 times/month and I countered with probably twice monthly.

My current plan is to proceed with BCD activities and offer my standard donation of $$$$.  I've had good success in the DC metro region with this amount.  Sure, a few pot SB's laughed at this offer as way insufficient, but many have gladly accepted.

Open to suggestions and strategies.

I recall a couple of situations where I had no idea what to leave, so I went to my usual given all the circumstances at hand.

Only twice did the gal balk:  Both times they said I was being too generous.   Oh, the horrors.

here on this forum, so I won't try and repeat it all.  But I do try to discuss $ early in the conversation rather than later.  If not online, then certainly at the first coffee meet. What I try to avoid at all costs is meeting a SB in a private setting, when I'm all primed up and medicated, ready and eager for some action, only then to have her ask for more $ than I'm comfortable with.  I truly hate being in that position, and the few times I've let it happen, I've gone way over budget because the thinking was controlled by the little head not the big one. My advice is to discuss $ before going BCD. Having a hard on with a willing but overpriced  pussy in front of you is not a strong bargaining position!

As Sweet points out, you may not necessarily want to receive the 'bill for services' after the act lol, but when faced with such a scenario, I usually just say yes, pay it and then wait for her to text me for another meeting.  Then I mention she was a bit high.  otoh, discussing $$$ before you meet seems to rarely work.  If nothing else the girl is simply auctioning herself off to the current highest bidder, and assuredly there will be others in the future.  My first meeting and BCD are typically the same, so I just time it prior to the panties coming off!  Hopefully she's a bit eager (and more or less drunk), making for much easier negotiations.

I am the exact opposite where it comes to discussing money. I am NEVER am the one to initiate the topic of money, I have actually had a couple of PYTs flat out tell me over dinner how "the last guy" made her feel like a prostitute (many SB's HATE the idea of being a prostitute, but can quite easily rationalize fucking for money. lol) by talking about PPM to them.  

 
Yes, I have had a couple of SB's spring an unreasonable "ask" on me at the last minute, but OTOH I have had a few where the discussion of money NEVER came up. One of my absolute faves was an "old girl" of about 29 who just wanted to taken to nice places and to be fucked well. (She honestly loved to fuck for HOURS, our first date we fucked for about 90 minutes and she seemed a bit disappointed when I came, our second date we fucked for THREE fucking hours, until i just couldn't fuck a single second longer. lol) We didn't actually have a conversation about money until our third or fourth date. I am completely convinced that if I had broached the subject of money before going BCD, that there never would have been an "afterwards"

 
I have to agree that for most guys, your advice is probably spot on, but I am going to stick to letting the woman bring up the topic of "allowance" instead of bringing it up myself.  

 
I guess this just proves that there is no one single approach to the sugar bowl that is the "correct one" You do as well at this as anyone else on this board, and so do I, even though we have many completely different approaches. You and I are also proof that we can disagree without being disagreeable. I am sure that would SHOCK posters on the GD and P&R boards who have seen the "other side" of me. lol

I don't want to blow a block of time only to get nothing out if it, so I'll always get the money agreement early.  I probably do lose a high percentage by stating early on that I am mostly about the sex.  However, anyone who responds positively is usually open to discussing ppm. I try to shoot for an hourly rate that's half of the midscale local pro rate. In other words about $150/$175 hour.

I live a couple of hours outside of Dallas and I often see SB's in Dallas, I certainly don't want to end up two hours from home with my dick in my hand if things don't go well with a new SB so I always put in a call to my favorite K-girl agency to make sure they have someone working that night that I can book on short notice if my SB date turns out to be a pig, either in looks, or in greed. lol  

 
When I am at home I don't bother because I can always call up one of the other girls in my rotation so I always have options. Having options tends to allow a guy to make better decisions where it comes to pussy.

Went BCD with the new SB.  Had a mind blowing time with no discussion of money.  As she dressed to leave, gave her my usual donation and thanked her for a lovely evening.  She deposited in her purse without counting.

The next afternoon received an enthusiastic email message thanking me for a wonderful time and looking forward to our next visit...which occurred yesterday.  

So, perhaps I overpaid.  However, as the amount tendered was my usual and customary...I am comfortable with our ppm arrangement.  And now that I have 2 SB's comfortably on the roster, I will look for a value proposition in the next SB.

Now you are stuck at four bills per meet.  You HAVE to find out what their expectation is.  If she said $250, and you gave her $300, she would have been just as happy as she was with the $400, and you would know you are saving $100 every time you fuck her compared to one of your other $400 girls.  How sweet is THAT?

But he is happy, she is happy, I don't see any losers here.

 
One suggestion I might make is when you just give an SB an amount of your own choosing, you might consider saying something like "I know we never talked about what your needs are, and we can talk about what you need on an ongoing basis, but I had a good time tonight and this is for you" as you give her the money.

 
I don't know your budget, but you said you normally give $400. Her total expectations for doing this might be $2,000 a month, and she might have two free nights a week. You could easily enter into an arrangement where you give her $500 a week and get to see her twice a week for doing so. She gets more money, you get more pussy. WiN WIN. lol

 
Contrary to popular belief you can negotiate "down" from the "gift" you give her the first time you go BCD. It's all in the way that you phrase it. As long as she enjoys your company and doesn't consider it to be "work" to be with you, a lot of women are more than happy to accept less per visit as long as they end up getting at least as much money if not more at the end of each month. To put this into perspective, at $15 hr a girl would have to be working fulltime OVER 40 hours a week to earn $2,000 in take home pay. You aren't taking advantage of her at all, you are making her life a thousand times easier.

If she says, say, $300 PPM I'll agree to once a week. After the first time, if I enjoy her, I'll offer $400 for twice a week or $300 for once. I'll say "depends on your and my schedule".  They always agree, and if sometimes I give $200 and the second meet in the week doesn't occur for some reason there are no refunds!

You give them the "opportunity" for more money, and ensure that you get "better value" at the same time. Win Win.

 
One other negotiating ploy you can use if you get pushback on this kind of negotiation, sometimes an SB will whine that she is "Doing more work" under this kind of arrangement. The best counter is to compare her to a hooker if that's the way she feels. SB's HATE being compared to hookers, and if you counter with something like "Do you REALLY consider spending time with me WORK???. I don't want you doing anything you don't really want to do, maybe we should reconsider this whole arrangement if that's the way you feel?" Either she has to make a claim that "time is money" IOW either she admits that shes a hooker, which 90% of SB's will NEVER do, or she has no comeback to your offer.

I used to use that sliding scale based on time spent. For instance $X for an hour visit at my place, 2x$X for a whole evening and 3x$X for an all-nighter. Her choice !  

Eventually I didn't want any more all-nighters as I like to wake up alone with my coffee so I modified the system to the weekly schedules

"most" hookers will leave right after "morning sex" which is perfect for me as I am the type of guy who really likes to sleep next to a nice warm body, I also REALLY like morning sex, especially if we got too drunk the night before to "finish what we started", but then I REALLY like to be left the fuck alone for the rest of the morning, unless of course we are simply going to roll over, grab another hours worth of sleep, have more morning sex and THEN she gets up and leaves me alone for the rest of the day. lol

 
SB's can sometimes act like GF's and some of them think that spending the night together means that the next day will be spent doing BF/GF kind of stuff like SHOPPING, UGH. lol So yes I do understand your aversion to all nighters even though I don't share it. But yes, I completely agree with your sliding scale for one hour, multi hour and all night dates. I do much the same

is spot on and reflects my own experience in doing overnights with both SB's and hookers.  

Slightly off topic, but this week have been approached by two different sets of twosomes - yeah, life can be hard sometimes!   So is the tradition to do 2X, although I'm thinking more 1.5X since they will be enjoying each other equally?

I only did twosomes twice. I'm not a twosome guy. The first time I doubled up and ended up dry. They spent most of the time giggling in the bathroom and eventually just split. I got scammed.

The second time one girl that I was seeing pestered me about involving her roommate that she wanted to fuck herself. I told her I wasn't interested and that I would not pay double anyway. She asked me if she could invite her roommate anyway and I said okay. The three of us had a decent time together but it wasn't that great. Very mechanical. Just going through various positions with no real feeling.  I paid for one only. Later she texted me that she had expected me to be more generous. So I never saw her again

If you're "not a twosome guy", then you are saying you're a masturbator and I don't think that's what you mean.  Lol

 
The key to a great threesome for me is when the girls are bisexual, and are willing to engage in some girl-on-girl sex.  Let's face it, most guys can't cum, then pull out and immediately plunge heir now-softening dick into the other girl, so we require a refractory period between pops.  (IME, About eight-ten minutes up until about 55 yo, and a little longer as I get older.  At 61, it takes about 15-20 min.)   So what to do while we are recovering?  A sexy girl-on-girl DFK, pussy-licking, ass-fingering, toy-insertion round is pretty hot to watch, since (unless you got these girls off the street) you're paying for time and not  just for a pop, its great entertainment, and the side benefit is, it may reduce the refractory period because we guys are "visual" and you may be ready to go again sooner than if you were just sitting around chatting.  

 
So I think its incumbent on us guys to lay everything out on the table when setting up a threesome.  The thing you did right was to let the girl you know pick a girl that she is comfortable with.  Not every women can be naked, having sex with a guy in front of their friends.  However,  you should have clarified that she has done doubles with her before, finds her attractive, and has no aversion to engaging sexually WITH HER as well as you.  The other mistake was not to clarify how much the second girl is getting.  In most threesomes, the girls will expect the same amount, but I have had a few where the price was quoted by the primary girl I knew and she said she would pay the other girl out of that, but if I wanted to give her a tip separately,, she would appreciate it, which gives me the opening to say, "That depends on how hot she is with me AND with you" (reinforcing that I have an expectation of girl-on-girl action during the session).

 
Without the girl-on-girl action, you are basically paying two girls to do half the work in pleasing you, but you are still paying each one full price for the time.  I don't know how others feel, but in my book, THAT is NOT a good deal.  

 
Not every girl is up for girl-on-girl pussy-licking and DFK, so you MUST clarify that you want this up front, before you commit, IMO.  Always tip something if you think you are going to repeat. (Not everyone here agrees with me on that - Lol).   Follow these suggestions and your next experience should be much better.