SamSpring

https://rentmen.eu/Tatteduptyler  "I have a girlfriend and I'm definitely on the DL and really don't have time for games". 

No that’s not right, maybe I wasn’t clear. I’m very happy to discuss requirements. What I’m not happy to do (because it invariably goes nowhere) is to engage in sex chat. There’s a difference. One is establishing what the client wants and agreeing whether or not I’m ok to do it, and the other is just a fantasy that the client has no intention of seeing through, he’s just getting off on the chat. From experience I can quickly tell when a discussion about requirements etc becomes sex chat. I close down the discussion at that point. 

Just a side note to the beginners reading this…..this is WAY too much for you.
Take 1/2 of a 10 mg gummy and see how you feel. Wait at least 30 minutes
before you even consider taking more. An hour is even better. Then,
you can think about taking the other 1/2….but I’d still advise against it. 
Just trying to save you from a potentially very unpleasant experience.
I’m guessing @Axiom2001 is an experienced user.

I’d also say this hold true for Grindr, Scruff, etc. Often a guy’s pics are from their best days. 

Prefacing this by saying I don't go looking for red flags and many things that are red flags for others are not red flags for me. This, however, is a huge red flag. In fact, it is more than a red flag. It screams "He is grooming you to give him money that you will never see again."
You are falling for a trick that will burn you. Don't do it!
 
I understand how easy it is to get sucked into texting on a regular basis. To me, it is a very bad sign. 
A couple of things
If he seems busy/distracted, then he is. Hard as it may be, try laying off the texts for a couple of days.  IMO, the answer to the question "Are you falling victim again?" is "Yes." In my world, "being good to a provider" means "buying him a gift card as a token" or " driving him home from a playdate when his car is in the shop." It doesn't mean giving him money in advance of a date.
I applaud your desire to be nice and do a favor for this guy. That's very kind. It is also very risky. My advice is to 1) abandon the idea of giving him money in advance and 2) stop texting with him every day. You mentioned he seemed distracted (although sufficiently engaged to mention money problems). To me, the reason for texting or talking with someone is to develop a sense of engagement. I just don't see how you can develop that with someone who isn't engaged. 
It might be time to find someone else and let this guy ride off into the sunset.
 

Good.
Good.
And we’re off…..
That’s about 10 years away in "escort time"….just FYI.
Who didn’t see this coming?
You’re smarter than this…..don’t a moron
You are. Next question. 
All con artists "sound genuine". Again, just FYI. 
He is. He’s working 10 other John’s with the same scam and it’s hard work keeping all the lies straight. 
You’re making excuses for him. "Molly, you in danger girl." 
You are. Just keep stepping back. You’ll get the picture….eventually
There’s "being good" and there’s "being stupid". You are currently in the latter camp. "Snap out of it."
You got it. 

I cannot even believe this post. Yes, you’re being conned.

True. That seems maybe excessive for a provider. 5-6 times a day, for how many days now? Is that supposed to continue till you meet in person? Are you dating? That's a serious question, because unless it's a very elaborate session of time together that's being constructed and discussed... what are you talking about? While it's conceivable to become friends outside of the provider/client relationship, that takes time. 
How long was he talking about his money problems before you offered? How often/emphatically did he bring it up? How personal are the topics of conversation? 
Serious question to reflect on: how emotionally invested are you getting, and is that reciprocated? I've also set up session with providers far in advance before traveling to an area, though they were long established with solid reputations. I say that because, with that provider, all communication was almost explicitly regarding our time together and details regarding that. Is that the case with you currently?

and you've never met yet?...
it's always nice to be "good to providers", but you can do that at the end of your first meet......
 
 
 
 

I don’t understand why he is texting for 5 or 6 times a day. Stringing you along perhaps? 

My honest advice:  DO NOT DO IT….  This is a very heavy legal and emotional lift. I have done it. Worst experience of my life. (I had my head in the clouds. Thought I loved him. I was in love with idea of being in love).  And the main reason you should not go down this path: you do not love him. 

If you go down this road - you are 100% responsible for ALL of his needs until he becomes self-sufficient. Especially if you marry. Then during the marriage he has 100% access to everything you have. A prenup is only in case of breakup. 
 
I hope you fully understand all of the ramifications.  Please carefully consider all angles. 

Prenup. Prenup. Prenup. Prenup. 

Is his family part of the financial package you are offering~? Or… is he just leaving all that behind~? I’m asking because my Mom pulled a Karen Valentine: met a Greek guy, (Demetrius), who worked on a cruise ship~ She fell in love and moved to Greece without telling anyone~ (A close but, independent family).
  A neighbor informed me of this about a year and one half after she moved~
  She became the “financial helper” for this guy… and then his daughter… and then his son… and his mother… and then some friends of their family~
 He was pushing for marriage… she held off because my great aunt and I pointed out that if she were to marry him he would absorb all of her assets as his own property. That’s Greek law. This went on for years. They never live together and they were never exclusive. When she began to run out of money… He also began to run out of affection for her and went off to work for the Papandreou‘s family and started shagging his daughter.
 I can’t say that they didn’t have a relationship and didn’t share some sort of love but, it was also a very expensive relationship financially and emotionally on my mom. So, when entering a relationship like this that is financial it may also be important to consider that the investment is not merely monetary but also emotional and psychological… Best to have extra reserves in all three accounts~  
 Although this may seem negative, it’s really out of positive and genuine concern for you… I don’t know this other person at all~ It’s an appeal to step aside from yourself and view the circumstances outside of any personal need you may have by doing this~ I’m not saying things of this nature can’t or don’t work out… each situation is unique and there is no absolute rules here~ So, it may be beneficial to things in terms of your reality, his reality, your together reality… not Simply our assumed reality based on the little we know about the two of you~ Still… whatever that reality is: be real and keep it real~ 

It'll only take a couple of more clicks to find some other coincidences lol

Joined 5 hours ago, posted this 4 hours ago. Hmmmm

That's a good thing for escorts to remember:   If a client seems defensive or resistant to intimacy, it could simply be manifestations of anxiety. 

For the first time with a guy, I also try to keep it pretty simple. A typical 1 or maybe 2 hour meeting without trying to make any extraordinary demands and keeping to whatever donation he quotes. I usually wait until a few dates and we've established chemistry before I suggest a longer meeting or some kind of kinkier thing (unless the guys himself advertises those kind of services to begin with).
 
But yeah just be respectful. And also truly a best practice is to go with established guys that have a good reputation. Use the board, use reviews. Don't just go for some random guy. There are a few flakes, druggies and guys with off-putting attitudes (though not as many as you might think). But the real professionals are wonderful guys and if you treat them with respect, they will do likewise.

I agree with @maninsoma.  There's no reason to regret what you did.  There is reason, I'd say, to feel good that you learned things about yourself and don't feel a need to do something that doesn't work anymore.   I read what you wrote as a sort of declaration of independence.  If I am reading it correctly, congratulations.
That's the short version.  The longer version will be a few stories about what it feels like from the other side of the looking glass.  Which basically revolves around not feeling regret about doing what you did in order to grow.  Or even just to have fun.
There was a client who hired me for a handful of overnights who was an enigma.  Handsome, nice body, great sex, I'm guessing in his 30's, smart as a whip, beautiful house, professional career he loved.  He was driving me to an airport after our first "date" and I told him I had a great time.  But I was curious why he hired me.  Meaning why hire any escort? Whatever he said was brief and may have been "I don't know."  A few days later I got a long email pouring his heart out.  I don't remember the content but I remember the feelings.  Something about judgmental parents.  Something about shame.  Something about low self esteem about his body before he came out and set about to being a Gay gym rat.
Maybe six months later he was dating some guy who looked gorgeous in a photo he showed me.  A few years later, long after he'd stopped hiring me or anyone, he sent me a wedding photo of him and his hubby.  As happy endings go, it was a good one.  I'm not a psychologist.  But I know he did what he did in order to grow.  And he grew.  And you are correct @Andie40 that sticking to your gym routine helps.  It worked for him.
Based on my own relationships it works both ways.  I think most if not all escorts feel some version of regret.  Often in terms of trade offs that were made. 
This past week I had a really fun walk with a friend in town who I was very close to in my 30's.  Both from organizing work together, before I turned to escorting, and very bad Greek dancing on weekends.  I would have dated her and maybe fallen in love if she wasn't one of the first people I came out to.  So we spent hours exchanging this cascade of stories. 
My friend's version of your first paragraph is she felt enormous frustration after being in the center of maybe 10 years of organizing on same sex marriage, rather than 10 years of escorts.  I remember the California version of that as one of her volunteers.  We lost badly.  Again and again.  That kind of rejection sucks, too.  But who knew?  Fucking up is how you learn.  To make a very long story short, the happy ending is that after fuck up after fuck up after fuck up, she and others like her figured out how to do better.  When I regret not being some alternative version of myself, it's not the sex - good or bad.  It's that I would have spent my escort career running around the US like she did organizing for same sex marriage.  And beating my head against the wall.  Which turns out to be less satisfying than beating off.  I'm okay with just being able to thank her for what she did instead.
From reading the OP's comment and reactions about photos and Grindr, I think it largely works the same way on both sides of the looking glass.  From my perspective, the allure was almost irresistible - being an escort, or hiring one.  Why not touch bright shiny objects?  Or get hired because someone sees you as one?  And is it a shocker things are never quite as shiny or dazzling as you thought they might be?  When you feel that way, you move on.
I have a simple and happy and Gay go-to place on the subject of regret.  Another aging escort buddy and I love watching Dancing With The Stars together.  One week several years ago Cher was a guest judge.  She was asked if she could turn back time, where would she go?  She said hands down back to her 40's.  She said she had so much fun.  Almost too much fun.  I thought, "OMG.  I'm like Cher."  My 40's were a Gay romp.  
Ok.  But let's get real.  In order to get there Cher had to go through dumping one husband who she met when she was 16.  And then what seemed like a train wreck of a second marriage to Greg Allman.  If an escort you hired did not shoot up heroin on your first date, arguably you had better luck than Cher.  What's worse?  A bad 10 hour overnight or a bad 10 day marriage?  You get my point.  Cher did what she needed to do in order to grow.  Hell, she even won an Oscar for it.
My advice, @Andie40,  is don't regret what you did in order to get where you are today.  You're not in your 40's yet.  I hope you enjoy your next decade as much as Cher did.  You earned it. If you find a man you want to marry, now you can.  That is because a lot of people like my friend fucked things up for a long time, and learned from it.
Here's to being willing to learn and grow by fucking up.
 
 
 
 
 

I’d also say this hold true for Grindr, Scruff, etc. Often a guy’s pics are from their best days. 

Funny you say that. If you were hiring guys in their 20s I don't necessarily think they would struggle to fit in at a fancier hotel. From my observations of younger people who fly first class and stay in high end hotels, they dress pretty averagely. In fact when I've seen someone at an airport with designer luggage or clothing, they're more likely to turn right than left upon boarding.

It’s a very personal thing, extremely intimate. I always include it in my massages (and in escort sessions) unless my client specifically declines it. I love giving it so it’s no problem for me to include it (without charging extra). Mutual rimming is fine too although I think most people prefer to receive it than give. 
I think it fits very nicely into a sensual massage and can be a pleasant surprise if done with some teasing moves…as in “will he / won’t he go down there?”  I can also check my client’s responsiveness to it by briefly testing with a lick before going in deep so to speak.
Not everyone likes it or wants it (usually because of concerns about being clean etc or with guys who are anxious about anything anal) but I’ve found that most people do like it, especially before penetration. 
If it’s something that’s important to you and you definitely want it included in the session then ask your provider when booking, don’t leave it until the start of the session to ask. It can make the session awkward if at that point he has to say no. If he rules it out before you book the session then you can decide not to make a booking. 
If you make sure he knows it’s something you definitely want included then a good provider will ensure you get a rimming to die for 🙂 
 

Wow...  a lot of assumptions here.  
MOST escorts don't live in "the big city with the high life".   In fact I would venture a guess to say very few live the "high life".  All of the ones I know across a dozen cities are just normal guys who are not rich by any means. While some escorts are able to sustain their lifestyle through their work, I would venture a guess that MANY do it as a side gig to have extra spending cash or supplement their income.   You make the assumption that once you hit your mid 30's, it's all downhill and that their escorting days are over.  Some escorts just start hitting their stride in their 30-40's.  Not everyone is looking to hire an 18-25 year old.    There are several escorts that I know who have been able to make a pretty long run out of the activity with no signs of slowing down.   You're making the assumption the escort would not have made provisions for later in life. This is no different than someone in ANY field/career.  Some do and some don't.  As I noted, for many it's not even their primary income.  Those that do have it as their primary income typically are smarter about knowing it does not last forever and have something else they can do outside of escorting.  One started his own massage business...  another went into construction...  another is a motivational speaker.  There are a lot of career options outside of escorting!  

I don't think you can generalize the situation. Aging is a gradual process and while mid thirties is perhaps the peak of male powers in many ways, the descent into the 40's for many is a great time given the added experiences and skills one acquires.
I have hired providers up to around 50 or so and enjoyed the experience. At that age they still seem young to me.

I’ve been having sex with men for 40 years too. And I can assure you that I ALWAYS unload in a guy’s mouth while he is sucking me off. I‘m lazy and I don’t jerk off.
 
It may be because I’ve no interest in masturbation. Especially as I’m happy to feed a hot guy as I love kicking back and letting him do all the work.

I started hiring in my twenties, but I didn't hire very often back then not only because I had much less money and it was pre-internet but also because I got more of my needs met by dating which was much easier for me in my twenties and thirties (and even into my forties) than into my fifties and now sixties. To be honest, even when guys do match their descriptions that's no guarantee that the session will feel "worth it" since that's entirely objective.  Sounds like you've figured out that, at least at this point in your life, hiring isn't for you.  Don't get hung up on regretting your past choices; just most forward.