So I was having lunch with a UTR provider/friend of mine not to long ago and something we talked about got me thinking.  I met this provider/friend last year after she had posted on eros for less than a week.  During that time she met a handful of gentlemen and a handful of those she has chosen to stay “in touch” with.

This woman truly is remarkable.  If you met her on the street it would never cross your mind that she had ever worked as an escort.  On top of that, a successful career, intelligent, beautiful, sweet and in fantastic shape to boot.

On the occasions where I feel I’ve developed a genuine rapport with someone I might feel comfortable asking the question, “so whatever made you decide to get into escorting?”  The most common answer I’ve gotten is that she worked as a dancer and “I finally accepted one of the customers propositions”, or “the other girls were making money at it, so I figured why not”.  Sometimes it's “my girlfriend convinced me it’s a great way to money…”  Other answers I’ve gotten were more reasoned where she deliberated needed to figure out a way to bring in an income that the hours could be very flexible around whatever, school, job, or project they had going.  Usually with a specific financial goal in mind.

However, this conversation I had struck me and it got me wondering if things like this happen more often than I realize.

After I asked the question she smiled and shared the following story with me:

About a year and half before she and I met, she was living in another state working in a customer service/account manager type position at a big company that shall remain nameless.  She had a serious boyfriend at the time and for the most part she was happy.

She spoke of a male customer who came in regularly to see her.  She described him as an attractive older gentleman, about 15 years her senior (she’s in her mid twenties), friendly, sweet and seemingly flirty.  

Now I admit, if I had this woman as an account manager for any thing, I would find every excuse I could to go down in person and flirt with her, just for fun.  I mean who wouldn’t, it’s an ego boost and usually harmless. But what she told me he did next floored me.

Apparently he ran into her outside of her job, (by chance or if he waited for her, I don’t know) and asked her if they could talk.  I think she said they went for coffee during which he proposed an arrangement.

Now I wish I know exactly WHAT he said and HOW he said it, because I am amazed he had the guts to do it and even more amazed that she responded positively.

Basically he proposed simple “sugar daddy” arrangement, where they would make arrangements at mutually convenient times in their schedules to spend evenings together.  Usually at least once a week, but sometimes more.  And each evening she “spent” with him he would reimburse her financially for her time.  He explained he had made this arrangement with other woman in the past and would like to set something up with her as well.  He gave her his email and asked her to think about it.

She said she was surprisingly not shocked or insulted by his proposal and actually felt complimented by his offer.  She said she thought about it briefly and ultimately emailed him back, accepted his offer and it began what she felt was a very mutual, very satisfying relationship between the two of them for the next year or so.  However, unfortunately, her then boyfriend (now ex-boyfriend) found out about the arrangement (after hacking her email) and told her family about it while also deleting any trace of him from her phone and computer.  Hence ending the arrangement.  

When she moved to NY to pursue a job offer she thought about how beneficial the arrangement had been both financially and even emotionally since she said he was a great emotional support for her at times.  But she didn’t think waiting for another generous gentleman to approach her with an offer was realistic, so she researched things a bit, posted a very brief ad on Eros and selected a handful of men to hang out with once in a while on her terms and schedule.  

I was amazed at her story.  Is this how it happens?  I’ve occasionally fantasized about approaching certain “out of reach” women I know with a business arrangements of sorts but always assumed that conversation would end with a slap or a scream for security.  

I guess it's all in whom and how you approach and couch the proposal... but is this one of those “nothing ventured, nothing gained” scenarios?  Perhaps it’s a numbers game and this guy has the guts to approach virtually every woman with whom he crosses paths with an arrangement and maybe 1 in a 100 accepts his offer.  The bravest I ever got was when I younger (and I used to spend some time in strip clubs) and I propositioned dancers once in awhile and on two occasions my offer was accepted, but I was by no means the first one to make such a proposal to them.

I’m curious if anyone has any thoughts or stories to share on this.  Am I missing out on what could be some great experiences and opportunities by not taking a chance?

it's illegal to proposition someone for sex for money.  So if you're not that special guy with a sparkling personality with deep pockets and she takes it the wrong way ... you could be jammed up.

Cash is king, just be careful.

This is much more a part of people's daily lives than most realize.  They don't call it the world's oldest profession for nothing!  I have had many friends tell me, when they find out about my 'secret life', that they have fantazised about being an escort or a Dom themselves, but haven't had the balls to actually do it.  It's a line that, once crossed, women realize just isn't that big of a deal.  Their self image doesn't change. Instead, they realize how small minded society is by making a mutually adventageous agreement between two consenting ADULTS (must be very clear on this) so taboo.
 Believe me, once you have had the ego boost, the freedom and the financial reward an arragement brings, it stays with you.  In a city like NY where it is soo expensive, and anonymous, I can see the lure.  
that doesn't mean you can start propping women randomly!  I would look for openings.  If boards and advertising sites are not the way you want to go, maybe try the sugardaddy sites.  Or, tell the story you told here to women you think might be intrigued, and see how she responds.  But be honest and do what you promise.  Don't play games, play safe.  xoClair Jordan

A curious thing happens when you get involved in any community of people: you get to assuming that "people in general" are just like the people in the group you know. If you only know Wall St guys, you get to thinking that all men are like they are; I grew up with artists and assumed everyone had creative passion, etc. When I entered the "hobby" world, it blew my mind to consider the prospect that so many people not only participate, but also so many people keep a secret life. Now that the dust has settled, I can see that even the wider pay-for-play community is actually quite small, and the women and men who participate in it are very much in the minority still. Our own confirmation bias tends to obscure that fact.

Your concern was whether you may be "missing out on some great experiences by not taking a chance" and propositioning civilian ladies into a pay-for-play situation. Perhaps, but I would guess that the failure rate on employing this tactic would be immense, and the repercussions could be incredibly damaging.

There are all types of women out there, sure. But I have trouble imagining a woman who would go for such a proposition. I'd venture to say that, if you took it upon yourself to develop the kind of brass balls it would take to start blatantly propositioning ladies you meet, you'd have more success bedding women for free than you would in inducing them to be paid. I'll even go so far as to say that, for women in this society, the stigma of being paid for sex is stronger than the stigma of promiscuity. I would guess you'd have far better chances finding a woman who was willing to make your day, sexually, than finding a woman who decides to cross the stigma line just for you, for a measly couple hundred dollars. When I was "just a civvie" woman myself, if someone had ever propositioned me, I would have been revolted, alarmed that an older man (i.e. predator taking advantage of his position; a gentleman should know better) would cross the line so far, and if I knew the offending man in any professional capacity, would have pushed it to the fullest extent that the law would allow, and would not have hesitated to bring in boyfriends, husbands, bosses, etc, to bolster retaliation. You never know how a woman will take your "well intentioned" advances. If I were a man, with a career, let alone a family, I probably wouldn't risk it.

Now, if you laid down a properly decent indecent proposal (i.e. backed with tons of cash) then maybe we'd have a story on our hands (wink)!

Don't forget you're not on an island without options. You're actually on an island that is teeming with payers-and-players! There is a thriving community of women who have already done the deciding for themselves. They've made their peace with the stigmas and pitfalls, and have simplified things by posting rates by which you may access their precious selves for a one-sided fantasy of your making. Consider yourself blessed!

What Clair says has been verified to me by other women I know in this business.

As far as propositioning a woman, it's really done on a bespoke basis.  You have to realize that not every woman is into this or open to this, but many are, without even realizing they are.

I met a woman recently outside a very popular Midtown restaurant that also turns into a lounge/club on some nights after hours.  If you've been there, you know what I'm talking about.  There is always a huge contingent of women there because that's where the moneyed guys hang out.  And a fair number of them are either outright pros or what my friends call "semi pro," meaning that they are looking for a guy to pay for stuff, but they don't quote an explicit rate.

The key is to find the girls who are semi-pro and who are essentially looking for a rich guy.  These women aren't looking for a boyfriend, but they are looking for a fun time, and they want the guy to take care of them.  That might take the form of a financial arrangement, or it just might be taking them to the exclusive parties, clubs, and events that they can't get into or afford.

I met a woman outside this place, and we shared a cigarette as I was waiting for my other associates to arrive.  In that five minutes I learned that she was working in a creative position that didn't pay any money and that she was basically out of her league as far as spending money at this place.  In other words, this was a girl who was down to meet a guy who was gonna pay for her drinks that whole night, and who was gonna pay for dinner possibly, and then take her out to other cool places.

I got her number, told about what I did for a living, and then set up a date with her a few nights later.  We agreed to stop by her apartment in the UES first, and then figure out what to do from there.  But basically we ended up smoking weed and she mentioned that she had worked in a high-end, fancy salon where a lot of finance guys and attorneys go (if I mentioned the name, you would know it).

Turns out that she was more broke than I thought, and she mentioned that she just got a text from a guy who wanted to come over to get his hair cut (she was a stylist at this place and when she left, she kept a few regular clients for her freelance work).  Of course, I was wondering if "haircut" was code for "he's my client, and you have to leave because he's one of THOSE clients."  Well, she said I could stay, so I figured it was a real haircut, but I used the opportunity to segue into talking about whether she would take on another haircut client and perhaps whether she would ever consider doing it in the nude.  Remember, we were high, so it didn't come across as totally obnoxious.

She said, "Well, I don't do haircuts in the nude," so I tried another approach, asking her if she did massage while she worked at the old establishment (I know they offer massage there, legit only).  She said she didn't, but that she might be more open to doing a sensual massage for the right amount of money.

And that, my friend, is where it all started.

Had she done this before?  Probably.  But I basically met a civilian or a semi pro and then turned it into a regular thing.

Well, until she showed how batshit crazy she was.

But that's how my last one started...

Please come back to reality...above all, think of the infinitesimal chance that it might work, compared with the overwhelming risks.

I was made an offer when I was in my early 20s, by a work supervisor 45ish years my senior. Out of mutual respect and trust, we both agreed to forget that conversation forever, and that was the end of it. However, I was TOTALLY repulsed, insulted...everything you'd expect. It goes without saying that there were grounds for an ugly SH suit. I'd known him for years, so our situation was a bit unusual...if he ever tries again with another girl, I doubt he'll be so lucky.

At that time I was not yet ready to think about pay for play in any form. When I was ready, I took it upon myself to find sites such as this one, and make myself available under my own terms. I would still be horrified at a p4p approach from someone in my personal or professional life. Here in the hobby, I am a commodity by choice...in my personal life, I do not expect people to view me that way. It's one thing to advertise yourself on Eros or SugarDaddy.com as a pretty blonde nympho, and be paid for that...it's another to present yourself in the civvy world as a bachelorette/girlfriend/mom/wife/nun/careerwoman/dreamer/romantic/poet/athlete/whatever and have someone assume that their money can supersede those things...or that they even have a right to ask. The most obvious thing, though, which you already know but which can't be said enough,  is that most civvy women dislike sexual attention from men they don't want to date, and would be repulsed at the $ angle - and most of them would badmouth you for asking in a hot second.  

I also question whether the story is true. Is it possible that she wants such an arrangement with you, and used that little narrative to make the suggestion?

Anka, a very thought provoking post and very well written. I, not for one I would suspect would never in a million years "proposition" a women out of the blue. I am just not that bold or frankly not that stupid to do something like that. I have much higher opinion of myself and certainly would never do that. Thank you for your very interesting post and ironically before reading this, coincentally I just sent you a private email. Thank you again for your candor and honesty

Let's get the original story straight. The man did not proposition her out of the blue!  They had known each other in a businesss relationship for sometime and had flirted. That's a totally different scenario than just approaching a lady in a bar or a store and asking her for sex for money.

They already knew one another and were comfortable going for coffee.  She decided to sleep with him and also to accept cash for future dates.  Why? who knows what her financial situation was.  

Carly, you said it! I could not agree with you more.

Your analysis is totally on target. Forwarding such a proposition to any woman is not only insulting, potentially illegal, and uncouth, but it also signifies an egotism that belies reality. Having said that, is it the case that the women who have "made their peace with the stigmas and pitfalls" of providing always consider their liaisons "a one-sided fantasy?" Is there any room for mutuality, or are we, the "hobbyists," deluding ourselves into thinking that is possible?

Anka-your post is really well written. I compliment you. Smart and beautiful is super sexy!