TLDR: I followed the advice given by the members of this board, met a beautiful young woman and had an extended sexual encounter, for less than the cost of an escort.
Rather than offer a 'blow by blow', I thought that it would be more helpful to offer advice on what had worked for me. But, I realized that I'd simply be regurgitating the great advice that is already here. So, here is what I'd learned, from this site. And, trial and error. Followed by a summary of my first encounter:
1) Know precisely what you can offer (budget, gifts, outings, travel, advice, connections, etc. - coincidentally, a POT, with whom I'd had a failed first meeting, gave me this same advice)
2) Know what you want in an arrangement (besides hot, toe-curling sex - frequency of visits, dates, travel, confidant, pen pal, etc.)
3) Be your best self. But, always be true to yourself.
4) On your profile, and in on-site communication, be non-explicit, funny, engaged, honest and clear.
5) And maybe most important, when discussing allowance, always discuss it in terms of your budget, not her "worth". Keep in mind that your budget may need to cover date expenses (dinner, drinks, gifts, hotel, travel, etc.)
About 10 years ago, long before becoming a hobbyist, a friend shared his sugar bowl experience. He claimed that he was hooking up with an array of willing young things. At the time, it all sounded like bullshit. I was mistaken.
As a rule, on the site, I no longer message first. Mostly because most of the messages that I did initiate never received a response. Also because, I hoped that by waiting for POTs to contact me, they would have reviewed my profile, and "self-selected" after learning a little bit of what I offered and wanted. In many cases though, they did not read my profile. The other reason that I don't message first is because, I am a low volume SD. I don't have the means or schedule to juggle multiple SBs.
In this, my first arrangement, she contacted me, and right off the bat, offered PPM. I of course, thanked her for her directness and looked at her profile. I did not see any of my show-stoppers or red-flags (you'll have your own). I followed up by asking if she would be interested in getting lunch (a public coffee date is standard, but I like going out to eat). She accepted my invitation.
Up until this point, I kept all communication on the site (despite her asking for my number). On the day of, we kept in contact as the time approached. She got a little lost, so arrived late. Once we were seated, and exchanged pleasantries, I shared my number with her (I wanted to be sure that she matched her profile, and would actually show up). Over lunch I asked about her, her interests and plans and answered her questions about me. After we'd finished lunch, I asked whether she had had previous arrangements from the site. She indicated that she had, which lead me to ask what she had received for allowance. The number she stated was well within my budget (there might have been an opportunity to negotiate here, but the rate was very reasonable and I took it as an opportunity to appear 'generous'). I then made clear that our dates might include some combination of dinner, drinks, dancing, shows, etc. and the occasional gift. And that they would also include some "intimate one on one" time. She signaled that she understood and agreed. After a bit more chit-chat, I paid the bill and let her know that I had to leave. We parted, but both agreed that we'd like see one another again, on a formal date. A few minutes later, I sent her a text, thanking her for a lovely lunch. A couple of days after, I texted her, asking whether she might be available to meet for 6 hours on the coming weekend. She was, but then there was a bit of scheduling drama. We finally settled on a date that worked for both of us.
On the planned date, based on advice I'd received here, I proposed that we meet first for coffee. I got there early. I wanted to watch her arrival, to make sure that she was alone. We got our drinks and sat someplace discreet, so that I could lay out the plan for the day (one-on-one time to "explore our connection" and lunch). We went to our respective vehicles and she followed me to the room that I had secured. There, I gave her a gift that I had bought. I then initiated a discussion about expectations and limitations. I asked whether she thought of her self as sexual. I gave her the opportunity to talk about what she liked and what was out of bounds. I also shared what I enjoyed. I had planned the "one on one" time first, in the event that there was zero chemistry, we could both go our separate ways, with no harm done. But, the conversation when well, and the fun began. After a short while, she sheepishly asked about how we'd handle the "money", and I immediately handed over her allowance, plus a little extra for gas, etc. I let her know that she did not have to be reluctant about asking. And that it was my wish that we both be very clear and direct in communication about everything, including her allowance.
Throughout our time together, I was careful to always keep checking in with her, to make sure that she was comfortable with, and enjoying what was going on. All in all, our time together was great. But, it did lack the enthusiasm and initiative that I had become accustom to with escorts. I attribute this to the fact that she is young. However, she is also fit, beautiful, willing and tolerant of my awkward banter (iow - I was in heaven). After a couple of hours of "adult fun", we agreed that it was time for lunch. We drove together to lunch, had a lovely meal and there our date ended.
In all, we were together for 5 hours. My total investment being less than any of my two hour escort dates. As soon as my schedule allows, I look forward to seeing her again.
All in all, I feel as though the entire exchange went very smoothly. That is due to the excellent advice and support provided here. Thank you all (especially Herb).
Great recap of a great 1st SB date. Thank you for sharing your experience with us. And thank you for the shout out.
I'd like to say that if you find yourself looking for a new POT in the future, the processes you took will work as well as this. But that may not happen. Fortunately, the structure and process you used will help ensure you mitigate most serious risks.
I expect that as you see your new SB going forward, the sex will get better, as long as you are consistently delivering on your commitments (frequency, occasional gifts, respect, etc.) and as long as you remember to ensure she gets as much (or more) pleasure as you do. We've said it before: A new SB will come (no pun intended) for the allowance, but she will come back (pun definitely intended) for the cunnilingus. One thing that successful SD's do is give better, longer, and more enthusiastic head than any BF, Hubby, or rando douchebag she may meet in a bar ever has (or will).
Over the last 18 months, my Latina spinner has more than once texted me that she wants to see me while she is parked in front of her BF's home after fucking him. He just doesn't get the job done, and she knows I will get her there (after a shower lol). She doesn't even ask for additional allowance on these occasions. In the last 3 months, she tells me she is not even having sex with the BF; she's just not interested. Then we fuck like bunnies, and I spend the last 30 minutes using my tongue (and lately my new Rose toy) on her until she's had 5, 6, or up to 10 O's. She leaves exhausted, and verry happy. I'm sure this is NOT typical. But it does demonstrate what providing mind-blowing orgasms to your SB will do her desire to see you again. (Yeah... that's my own humble brag.)
One thing you mentioned in your report is worth noting:
"The number she stated was well within my budget (there might have been an opportunity to negotiate here, but the rate was very reasonable and I took it as an opportunity to appear 'generous')."
This was a smart decision. She's already in your budget so you will be happy to deliver that allowance. If you can avoid talking her down to a lower amount, you avoid any potential for her to see you as "cheap" (known as a "Salt Daddy" or "Cheap Charlie") or that you don't think she has "worth." Instead, you "validate her" and all that other psyco-babble bullshit that women like.
In the times before FOSTA/SETSA, when Seeking was still "Seeking Arrangement" and they were all about promoting Sugar Relationships, they had section in the SB profiles for "support expectations" (not sure of the exact words). This allowed a POT SB to check a box on a range of desired monthly allowances. I'm sure each POT went through psychological gymnastics trying to pick this range; too low and you under-sell yourself, too high and you scare away too many POT SD's by looking like a Gold Digger, etc. But at least it provided the POT SD's with a reasonable starting point to make an initial offer that was likely to be accepted. Those days are gone. So know we must use other techniques to achieve a successful win-win negotiation, as you did. Again, well done!
Have fun with your new SB!
Life is good
The Cat 
Thanks for the recap! Seeking works great, when it works! My own procedure is nearly identical to yours, but here are a few differences.
1. I do exchange phone numbers before our first coffee date. It makes staying in touch on the day of the meeting easier, and also because,
2. I like to discuss allowance amounts before the first coffee date. I want to know that we are at least in the same ball park before spending time on a lunch date. I have 3 reasons for this. Firstly, if our expectation$ are totally out of sync there's little point in wasting each others' time, and secondly, nearly all my dates are in the city an hour drive away, so It's best to get a feel for the allowance amount before wasting hours driving to a pointless meeting. And thirdly, Seeking is so sensitive to avoid the impression of promoting prostitution that nearly any reference to payment for services , no matter how disguised or oblique, can result in getting banned from the site. If a SB asks me whether I'm ok with PPM or asks what her allowance will be I immediately say I'm very happy to discuss that but suggest we take the conversation offsite. No exceptions.
3. I initiate the conversation on Seeking much more frequently than the potential SBs do. Mostly because in my locale (aka Pussy Siberia) the worthy potentials are so few I feel I'm more likely to succeed if I message them as soon as their profiles pop up. I envy you guys who have thousands to choose from!
4. And as for Herb's comments about DATY, yes, it's true! If you know how to lick a pussy properly you are soooo much more likely to get invited back for seconds, thirds, etc. But every rule has it's exceptions! My most recent first time BCD was with a lovely thin 21yo Latina who surprised the hell outa me by declining my offer to lick her pussy! Said she doesn't like it, feels weird. But she was a tigress in bed in most other ways, and her enthusiasm was delightful. Go figure.
Anyway Dude, thanks for sharing your experiences with us and best of luck with your continued success in the sugar Bowl!
Thanks for the reply.
1. The part that I omitted about my experience is that at the time that she messaged me, my profile basically said, "Message me if you want to meet for lunch." I had adopted the attitude that I wasn't going to invest so much in forcing an arrangement. That I was going to "go with the flow". Consequently, I'm happy to see how things go before sharing my number.
2. (See above) Because I had adopted a zen attitude about finding an arrangement, if a beautiful lady is willing to come to my area for lunch, I am happy to enjoy her company, regardless of whether our expectations are compatible. It is also a bit of a GPS test. If she isn't willing to invest a bit of effort, to explore a possible arrangement, in exchange for a nice lunch, then she probably isn't the girl for me. As for your third point, I was surprised that there weren't some consequences to her offering PPM so explicitly. But, too late now, the proverbial cat is out of the bag.
3. I acknowledge the enormous benefit of having a broad array of POTS from which to choose. I recognize that were that not the case, I could not adopt such a casual attitude about finding a connection. However, as mentioned, my "lassez faire" approach is also a function of the fact that I only need to find one at a time. I am grateful that (so far) I don't need to rely on sending messages to die in the great chasm of entitlement and detachment.
4. In my "yout", an older friend gave me this advice: "Eat that pussy to the bone, and she will be yours forever." It remains one of the great truths of my life. Maybe your Latina will come around.