Would love some perspective from the girls and boys on this one. Sorry for the long post but it's complicated.

A month ago I made a 2 hr date with provider. Had good feelings from the pre-date email flirtations that wound up being spot on. Instant chemistry, great conversation, strong connection and some of the best sex ever. She encouraged me to try things I never had and didn't think I ever would. Some I liked, some not so much but no regrets. She stayed close to an hour over the agreed upon time and was really pushing to stay overnight but I declined because I had to get up early the next morning.
I then booked a four hour date, two weeks out. This time it was even better. Seriously, I didn't know sex could be like this and I started to feel like there were some real feelings developing and she did and said everything to support the fantasy. I didn't ask but she wound up staying through the night. Just the most amazing time I've ever had with another human being.

Booked another date two weeks out, this time for an overnight. Again, the most incredible experience. Deep emotional and physical connection, including some activity that was frankly irresponsible and dangerous, but we both had just completely lost control but we discussed it the next morning and agreed we needed to behave like adults regardless of the mutual feelings. I truly felt like I'd found a soulmate. She had come around 5p the previous evening and stayed through noon the next morning. So far so good.

Here is the problem. In between the 2nd & 3rd dates and after the overnight there was a lot of communication (email, text, calls, Facetime) and real sense of intimacy was developed. She shared her actual name and address, her children's names and pictures of them. We even met one time when she needed some help and then had a very nice dinner. There was even talk of me staying the night at her apartment, with her kids there (!) but we ultimately decided that wasn't such a great idea. I was having real hard time knowing what was fantasy and what was reality. During this time she indicated a couple times that what she was really looking for was a steady arrangement involving a monthly fee but, honestly it was more than I could do. Then she started hinting that maybe I "owed" her because she had stayed longer during our dates and was spending so much time communicating with me in between. This seemed odd since I had not asked her to stay over time and was often not the one initiating the communications.  

Then, I sent her an email asking if she would like to join me on a short business trip, including appropriate fee plus expenses. A day went by without a response and I had to leave, disappointed but realizing she is busy and has other clients. The next afternoon I hear from her saying she is ready to join me, she has cancelled all her appointments and just needs me to book her flight and send a car, immediately. At this point it's too late. She wouldn't have arrived until late evening and I already made plans to meet a business colleague for dinner. Now she is demanding that I direct deposit a significant cancellation fee into her account because she cancelled other appointments for me, even though she never confirmed and took over 24 hours to respond.  

Am I crazy? Is she? Are we both looney tunes? Am I getting played? I'm definitely not seeing clearly on this and will take any and all advice? Feel free to throw some shade, too. probably well-deserved, but this community has always been pretty candid which is why I love it. Thx.

Things spiraled so out of control! I think the first major red flag was her suggesting she stay overnight. She became too clingy too fast.

I know that's the right thing. It's just tough when you know how good it can be. Good advice. Thx.

-- Modified on 3/18/2017 3:40:48 PM

1.  Am I crazy?  
2.  Is she?  
3.  Are we both looney tunes?  
4.  Am I getting played?  
5.  advice?
6.  shade?  

How about :
7. she was feeling the effects of a Full Moon, at that time,  
and soon her brain will slide back to normal,  
as she starts feeling the effects of loss of fundage.

I don't know where to start. Maybe if I find the time I'll add on to this later. But to be short -

No. You don't owe her anything. You should expressly tell her that and I would also ask her to stop communicating with me.  

I guess you like her a lot, but don't be a wuss about this. You need to set the record straight.  

 And you included the word extortion in the post title so prayers up that nothing bad happens as a result of this scenario.  

This is why I don't do OTC time and minimize communication in between. People brag about it. I guess for some people it works out okay... but in my opinion.... Too many sticky situations can crop up.  
Some people are not built for this (also, a joke- crazy women always have the best sex lol)

She's showing major clinginess and transparently planting seeds for her next move. You see this and keep meeting her for (increasingly lengthy) appointments while exchanging sensitive info, increasing your emotional attachment, and engaging in physically risky behavior?!?!
Shes playing you, but you were inviting trouble in accepting the perks of her game and continuing on as you did. Shut it down now  and be glad if it ends quietly.

Sending the mixed signals was the first red flag.

She probably has mixed emotions as well. She has an obligation to herself and her kids to make a living, and most likely wants to have it both ways. A guy she actually likes, but who is a complete "meal ticket" to boot.

The OP has already stated he can't/won't be her full time meal ticket, so putting the toothpaste back into the tube at this point is probably going to be VERY difficult to say the least.

There is always a risk when pushing or crossing boundaries in P4P, sometimes it works, other times it doesn't. This sounds like one of the times where it's not going to.

I suppose it's possible for the two of them to sit down rationally and get some ground rules straight that would allow them to be more than just hooker/john, but less than BF/GF maybe some kind of a negotiated SD/SB relationship where she keeps working, he keeps paying her, but the two of them spend more time together than they would if he were simply a client

I say it's "possible" for this to work, but how often do two people talk rationally about things like this?

Personally I think she wants to "retire" but can't give up the money. She has kids, so can you honestly blame her? BTW spending the night with the kids in the other room spells BOYFRIEND, or at least it should if she is any kind of a responsible parent.

END OF MESSAGE

Listen,

The lady likes you.  You like her.  You'll probably have a relationship of some sort with her for years to come if youre not an asshole and don't fck it up.  

Make it right with her.  Women are emotional and nutty.  Ask her what she wants and give it to her within reason.  Then go back to normal sessions if you're both getting to confused about what your relationship is, boundaries, or expectations.

One hint:  Always pay the woman.  Free time, free sessions, extra time, OTC etc is not really free.  

PAY THE WOMAN!

I have a slightly different take on this. At first she sounded like an experienced woman looking for a way to "retire" when in fact the woman in question is a relative newb.

She seems to be in rather high demand, rather high volume and I am sure she is knocking down some coin right now. I personally don't see this working at all. He is going to develop serious feelings for her, she is going to keep working and this love story is one that is going to have a rather unhappy ending.

I think he is best off just chalking this one up to experience

getting attach too soon is definitely not a good sign of a healthy relationship.

You booked 3 times, multiple hours & overnight in the first month. She recognized her opportunity...

Up to you to decide whether or not you owe her for the "cancelled appointments". You left the invitation open on the table, so perhaps you should compensate her.

If you do pay up, make sure it is "once and done". Then lose her number and email.

And about the direct deposit: remember those Nigerian princes? Find some other way to give her the cash...

Boy, oh boy... you are in a world of hurting...

One hour date the first night, OTC lunch the next. another paid date the very next day, leading up to overnight dates at the price of an hour within a week and within about ten days her declaring to me "I don't want your money, I want you to be my boyfriend"  

Our relationship lasted about a year and has been over for a few years now, but I have heard from her as recently as yesterday. So not all hooker/john relationships are fleeting or delusional.

It really sounds like she's trying to extort you in this case. Cancellation fees are appropriate for cancellations with one whatever time period that provider states is her cancelation fee period. This sounds just like it's a money grab; she made no attempt to confirm in a timely manner and it's her problem that she canceled her appointments.

I mean I would t have done that until I had an assurance that the trip was already arranged.... you can't enter into an agreement unless both parties are participating... she didn't participate.

You make a great point! I guess to me it's just strange if an escort wants to spend the night together OTC so soon before really getting to know eachother.  

It sound slides sd/sb relationship is what she'd benefit most from. The intimacy of bf/gf but with financial benefits.

You know what's up.  In my world, we acknowledged it.

First, you say she is hinting that you may owe her for the time she spent communicating and all the other extra time you both spent.  I don't think you owe her any more than she owes you.  You both agreed to a transaction, and after the agreed upon time you are two adults who are both capable of deciding whether you want to spend more time together in person or texting... or not.  

What I cannot tell on the second point is if you gave her a deadline for telling you if she could join you. Even if your trip was in progress I could see where she may have thought she could have done some of it with you. Some things needs to be spelled out concretely and this would be one of them as they stakes are high for both of you.  If she did not know when the 'drop dead' time was for her to inform you then I think you need to give her something (probably not all shes asking for if it's exorbitant and she has some responsibility too in asking for clarification from you) as she relied upon your offer (assuming that's true).  If you told her you needed to know by X and X passed, then she has to chalk it up as clearly she knew how to communicate with you all the other times, so if she knew she was rearranging things and was going to run beyond X in doing so she should have told you ahead of X.

That said, I see you have two choices with her: continue with her but work this out as grown up and communicate better in the future.  Choice #2, if you don't like the first, is to do what's right based on the above, and then just move on.  

Good luck.

-- Modified on 3/18/2017 5:54:51 PM

END OF MESSAGE

It doesn't happen often but it does happen and I might add it doesn't always lead to ANYTHING more than a fun filled night. Sometimes it's just getting caught up in the moment and then coming to your senses in the morning and realizing great sex doesn't necessarily translate into anything more than that.

My first thought was that a SD/SB relationship was what would be best for her, but she appears to be QUITE popular and at a very healthy rate, so getting one guy to replace all that income looks to be a pipe dream unless she hooks a whale, and the OP is admittedly not a whale

There ain't no such thing as a free lunch. But if a provider gives me OTC time spontaneously, she's paying for it, not me.  

Don't pay unless there's an agreement beforehand, or you feel like it.

This is just wrong. Deadline or no, in order for him to be obligated they'd have to have an agreement beforehand. No agreement, no need to give her anything.  

She's responsible for not canceling other appointments until she knows she can go. He's responsible for compensating her for her lost time IF he does so after they've already agreed she's going. That's the way you spell things out correctly.

... state the expiration date/time of his offer.  It appears he didn't do that. She accepted his offer before he left on the trip.

It was on him to make it clear when he made the offer that she needed to let him know within a specific timeframe if she wanted to go or not.  One could argue that the provider should have waited to free her schedule until she responded to the guy.  But his mistake was bigger, because he made the offer.

I think he should offer her some compensation, but she should also make every effort to find other clients for that time.

She did not accept his offer until after he had already left town.

You can still make the argument that he didn't tell her "sorry, I didn't hear from you so I have already left town" but it's clear from his post that she did NOT accept his offer before he left on his trip.

... about how this travel arrangement would work.

And it means he made another big mistake. When he hadn't heard from her before he had to leave, he should have dashed off a follow up to his previous message ala, "Since I haven't heard from you, I assume you can't join me. I have to leave for the airport now so I may not be reachable for awhile. Maybe next time blah blah..."  Then I'd argue he wouldn't owe her any compensation.

Technically he probably has a good case against paying.  Nevertheless there is an emotional timebomb out there and it may be worth it in the long run to pay it to defuse.

To touch on the latter point, for her to email you back a day late is kind of suspicious.  You mentioned earlier in the post that the two of you had spoken via FaceTime, phone, text, etc.  So my question to you would be why not call her and get an immediate response as to whether or not she could join you.  To her I'd ask why would she not (after seeing that the email was from the previous day) contact you to see if the offer was still valid, I am assuming that you dated when and for how long she would be joining you since she would have to arrange for her kids to be cared for.  For her to go from there to demanding a direct deposit seems like it was planned to say the least.

Without getting into the weeds of what all happened on the previous dates, if she decided to stay longer than payed for then she should understand that that is considered OTC time.  From the perspective of a client, if i were to pay for a 2 hour session with a lady and tip her the amount for an hour session, could I then call her again and request a free visit because I tipped her the last time? I wouldn't say that either of you are crazy, although she may be more on the side of manipulation rather than mutual feelings.  

I'd be worried more about other things than her being pregnant. Hope he got tested

I think he should have given her a deadline, yes. That's the courteous thing to do. But it has nothing to do with whether he owes her money.  

You only have to pay if you've already set the date. If you haven't, and it's up in the air, it's on her to set the date before clearing her schedule if she wants compensation.  

I don't get all huffy when I have an up-in-the-air maybe with a provider and she bails out. (I usually don't get huffy when she wants to reschedule after we have a set date, either, but that's neither here nor there.) We have to have an actual date first before there are obligations.

Yes, he should have done that too, but I don't see why not doing so obligated him to pay one red cent. Because she should have actually confirmed the date before canceling other appointments. That's on her.

Is not putting a deadline on the "offer."  When I invite someone on an extended session/trip, I always end it my saying, "If I don't hear from you by XX:XXpm on (day) I will construe it to mean you can't make it and I will withdraw the offer and make other plans."  This would absolutely have prevented what happened to you.  If she doesn't get back to you with a "yes" or some other kind of confirmation by the deadline you set, then the offer is cancelled, so any clearing of her schedule after the deadline is on her, not you.  

An offer that can result in a provider losing other business should have an expiration date/time.  With that said, I would still say you are getting played.  Most reasonable providers would have given you a heads-up that they were "working on it" before you left, so you could let them know the deadline.  

There was no agreement, only an offer. The woman is bull shitting her way to your money. She already has pulled the "you owe me for all of the extra time I gave you" crap. There was zero arrangement there.  

No agreement, zero obligation.  

You are being manipulated, played, extorted. Call it whatever you want.

It's all very unprofessional on her part. You don't owe her for the times that she stayed or the trip. She's planted girlfriend seeds and is trying to get as much out of you as she can. Just move on and cease contact. The point of seeing us is for the GFE to last the agreed on amount of time, not to deal with the crazy loose cannon behavior weeks afterword.

First you have to decide if you are a trick sugar daddy boyfriend or husband.Having gone thru similar thing where one hour sessions turning to overnites,
Not knowing all the details She may not have wanted to leave some nites maybe she was tired or had been drinking idk.
Realize you started with multi hour apps so she knows you have deep pockets..
She probably knows if you are married or single and you both sound a little codependent.
Do not feel guilty about the trip she never responded to confirm.Her wanting money is bs she is pissed you did not want to make special arrangement.Remember you met on line for sex so both parties knew what they were doing.
I imagine she is a very nice woman but what do you really know about her .
I know there are hobbiests that seek bareback services I know all the lines how it feels better.
Are you willing to accept the consequences of have unprotected sex with a escort.
She is mad about her cancelled appointments and not making special arrangement next she is going to say you knocked her up .
You have to decide if you want to keep seeing this woman or not.
Nothing worse than a angry hooker that has dirt on you and thinks you have done her wrong.
You clearly have money if you think she can do anything to hurt or embarrass you pay her off and move on or put a ring on her finger

abrupt, but I shall be for the instance at hand....

You are a "Client" to her, regardless of her amorous
   affections, behaviors, or actions.  

This is a Business!
  {last I checked, this is not a "Seeking A Soulmate" site!}

She is a Provider, and one whom knows how to "work it",  
  to her advantage and make you, "the Client",
  think you're "in love".

She faultered big-time regarding a few aspects;

She made the #1 mistake of  
  a)revealing her true identity
  b)introducing you to her children! {just WOW!??}

{These two actions played on your emotions
   and increased your level of trust.}
     
c)Her other mistake was being just too endearing
    and unprofessional"  {in and out of the boudoir},
    to further encourage you to think, you weren't  
    simply  just "another Client".
    {ouch!  I had to say it 😑 }

There is a delicate balance between actually a
   "GFE" {a "job" which a Provider "performs", and  
    being a "GFR"! {Girlfriend For Real}.
    The two should never twine. {imho}

Angelina Jones 💋💋

Oh, and P.S.   Do Not, I Repeat,  
Do Not Pay Her!!

She did not respond to your business trip  
request in a timely manner!  {End of story}

Who in the World would think that they
would be "owed", for THEIR lack of responding
to your offer of the business trip "gig"?

That's quite simply her assuming she's got
you tightly wrapped around her ring finger,
and p****~whipped!  
Now that you've met her kids, {in her mind},
you are emotionally tied to almost thinking if you
don't pay her, or stop seeing her, that indeed,
her kids may starve.  {what a ploy!} smdh!

EOM

She MAY have feelings for you;  She may not have.  Professional ladies are people too.  MAYBE she is smitten with you and really did dump everything because you called.... And she does have bills that need to be paid. Or maybe she just decided that an email or two would be a good way to make the rent this month.   You will never be able to know that - so don't determine what YOU are going to do based on what you think HER motivation is.  

From your description - it seems like your "relationship" is toxic.  Lack of communication; different expectations... yada yada yada.... You said yourself that you can't afford her full time - or even just as a time share....

So - regardless of HER motives - my opinion is that you need to be done with her.