Should I Offer to Pay Her?

RichardG2020

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Nov 30, 2019
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I’m so excited, because I’m reconnecting with one of my all time faves tomorrow!

She’s pretty, with sexy, college co-ed looks, has a killer ass, plus a super chill vibe. We had instant chemistry the very first time we laid eyes on each other.

I first saw this former SP around 4 years ago. She was a rising star at her agency.

She had a Civvy job, and didn’t really need the money. The way she described it to me was that she was finally comfortable in her sexuality and thought it would be a thrill to escort. While it was a thrill, she also felt powerless and vulnerable because she had to sleep with whomever walked through the door - regardless of their appearance and attitude.

She couldn’t take it anymore, so she left the agency less than 8 months after she had started.

After she left, she continued to see a small handful of clients on the side, including me. I wouldn’t call her an Indy, because she didn’t market herself nor actively seek out new clients. Rather she would see a few clients every couple of months to scratch her itch.

Eventually, she stopped seeing other clients and would only make time for me.

However, she was also in a relationship, which started to get serious. Eventually, she moved in with her boyfriend.

She started making excuses about not being available anymore. I didn’t press, because I knew that she felt guilty about seeing me on the side.

As it turned out, I’ve only seen her once in the last two years.

She recently had a milestone birthday, so I reached out and offered her my well wishes and greetings. We got to chatting and I invited her out to lunch to celebrate her birthday.

She warmly accepted, and as we were finalizing the lunch date, our texts started to get a bit flirty, and then she unexpectedly suggested that we get a hotel room first.

I honestly thought that I would never be intimate with her again, but the few times we chattted over the past year or so, I made it a point to always be respectful and never needy, so that she would still feel comfortable with me.

With respect to tomorrow, we never spoke about money once. It feels like more of a hook up. I bought her a nice birthday gift, am paying for the room, and will be taking her out to lunch.

Would I offend her if I offered her cash? Or do I assume this is just a hook up? Or maybe it’s a SB/SD thing where I buy her stuff and take her out to lunch - and she’s happy with that type of arrangement?
 

Kracker

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Aug 20, 2001
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Don’t bring it up until after you’ve fucked, had lunch, had wine etc.

You’re going to want to see her again - after she’s cum, you’ve cum, you’re dressing or wrapping up, it seems like a real conversation.

We have something real here - it’s an adult conversation about the parameters of your relationship, including exclusivity and financial arrangements.

Just don’t do it beforehand. :)
 

Nathan 88

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Feb 1, 2017
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I would do as Jenesis said to have the money ready just in case.
However, when the issue of who’s gonna pay for the hotel room comes up, that could be an opportunity to discuss money right there.
 

escortsxxx

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I can see the confusion here. I would do everything like you are planning and if she asks for the money, just make sure you have it on you. If she doesn’t ask, you’re golden.

I would add that you should also have a physical gift. It is her birthday. Keeping in mind the situation
 
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Jenesis

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I would add that you should also have a physical gift. It is her birthday. Keeping in mind the situation
Yes. This is correct. I thought he said he was going to do that part anyway so I didn’t mention it.
 

RichardG2020

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Thanks for the suggestions everyone.

Yes, I do have a physical gift for her and I am paying for everything else. All in all, this date is going to be around $650 or $700 depending on how much lunch costs.

And yes, I will have cash ready in case she is expecting payment.

I’ll let you guys know how it goes…
 

stinkynuts

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Thanks for the suggestions everyone.

Yes, I do have a physical gift for her and I am paying for everything else. All in all, this date is going to be around $650 or $700 depending on how much lunch costs.

And yes, I will have cash ready in case she is expecting payment.

I’ll let you guys know how it goes…
AVOID cash, it's going to ruin everything, trust me.

Pay for dinner, and get her a very expensive gift. I'm thinking at least $800, the equivalent of what she'd probably charge yoiu if she were still escorting. A new iphone, eg.
 
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Jenesis

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AVOID cash, it's going to ruin everything, trust me.

Pay for dinner, and get her a very expensive gift. I'm thinking at least $800, the equivalent of what she'd probably charge yoiu if she were still escorting. A new iphone, eg.
Just going to say that women usually prefer cash over gifts. Then they can decide what they do with the money.
 

superman12

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I wouldn't bring up the discussion about cash since that might be offensive especially if she hasn't hinted at it or brought it up in anyway. Just pay for everything on the date and get her a nice gift since your celebrating her birthday. I wouldn't cheap out on the gift and get her something nice that you know she will like. I suppose you know her likes and dislikes. Give her the gift before you start to fuck and maybe when your out to lunch ask her if she wants anything special for her bday and at that point if she asks for cash or another gift she really wants then get it for her. This sounds more like a fwb relationship now and not a purely transactional escort relationship so your plan sounds fine.
 

primetimebob

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Nov 22, 2006
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AVOID cash, it's going to ruin everything, trust me.

Pay for dinner, and get her a very expensive gift. I'm thinking at least $800, the equivalent of what she'd probably charge yoiu if she were still escorting. A new iphone, eg.
Nooo and what happened if she ask for money after giving her that $800 gift? Just don’t give her anything and play along with it. Pay if she asks for money.
 

RichardG2020

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Nov 30, 2019
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Hey Everyone - thanks again for taking the time to provide advice. While I had a notion of what the situation was, I truthfully wasn’t wholly sure.

So, I’m happy to say that it was definitely a hook up!

Her fiancée (yup, she’s engaged) has been out of town for work, so she was feeling both lonely and horny. My reaching out to her when I did was fortuitous, because it was absolutely perfect timing.

When I was with her today, there was no talk of money or anything.

When we got to the room, there was chit chat for around a minute and then we couldn’t keep our hands and lips off of each other.

(Sorry to disappoint, but I’m not going to provide a review. Let’s just say that the passion was intense and we made up for lost time.)

We ended up staying in the room for around 3.5 hours. We didn’t even have a chance to go out for lunch.

Before we left, I gave her her birthday card and gift. She read the card and said thank you for the gift. It was a gift card for her favourite store, and she didn’t even look at the amount on the card or gift receipt. She didn’t care.

As we walked to our cars, she asked when we were going to see each other again.

I’m going to try and set something up for July.

She did tell me that when she does get married next year, then she’ll definitely stop seeing me.

I really don’t mind, because I ultimately want her to be in a happy marriage, so until then I’ll just savour the moments that we will have together.
 

Kracker

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Aug 20, 2001
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Thanks for the suggestions everyone.

Yes, I do have a physical gift for her and I am paying for everything else. All in all, this date is going to be around $650 or $700 depending on how much lunch costs.

And yes, I will have cash ready in case she is expecting payment.

I’ll let you guys know how it goes…
Yeah - sounding more and more like a marriage when the money creeps up to these levels.

Save yourself a bundle and go back to escorts.
 
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