True story, no shit as they AF says, yes I am this creepy, so reassure me, or laugh, or, eh, ugh.

First, I'm 53, avg ht weight, little belly but okay, been oversexed since 6 and hurt by women since 10.

Cutting right to chase, a MILF friend, recently divorced as I, but clearly out if my league; long straight red hair, easy laugh, talks of sx all the time (only downside, big ine, reeks of Marlboro's.

She had just, who knows why, gotten a boob job, while complaining of being broke, bitching about the (admittedly) dick soon to be ex. Descended into a teary hug, and yes, she said then, aloud, backing away, sniffing, "Guess I can always suck cock for money."

I know, know, know don't yell I know I was a bad friend, but rather than cmfort I teased back that I'd be her first customer.

So, days later, drunk. she left a message, giggly, that she wants to rent me somethng, "So long as ai know it's silly stuff."

Factoring un that smoke smell aside I have never and will never pass this amazing road again, and n actual price or number is discussed, if this happens, how do I, well, settle up with a friend? With pros I'm straight forard. Should I make her feel its her game, or stuff 300 in her purse? Or being former buddies dream wife should I toss in more to maybe get a fun revisit?

Lastly, she would never date me publicly.

Have fun roasting me, but the odd insightful remark would not hurt...

-- Modified on 1/6/2015 1:41:11 AM

... because it's usually a con story.

I've heard enough con stories from providers over the years that I have heard of this kind of story before. Maybe not exactly in the same manner as yours... but... it's still a con story to get more money out of YOU.  

that text message she sent you? how do you know she was drunk? maybe she's that way all the time!  

if you were you... I would not believe anything she says. you're better off that way.
 

and one of their hits was a song called What Do You Want from Life?

So, let me ask you, what do you want?

Do you want a strict P4P relationship with her?  If so, pay her what the going rate is all things considered, tell her that this is what you  want, and you are hoping that this is the start of a beautiful relationship.

On the other hand, do you want more of a SO relationship, then buy her a nice gift with the money (Maybe even something practical if you know what her needs are.)

In either case, she'll get the message and then she can start to think about what she wants.

The whole affair is bound to end up in flames, but that's true for 90% of these adventures.

No guts, no glory, after all.

Keep us posted.

Then fuck her or get your bj, whatever.  If she wants payment she'll let you know.  Unless you want to maintain a civvie relationship, which, from your post it doesn't seem so. Seems to me that she's into you. At least as a fuckbuddy if not a provider.

...I say run the other way. When she gets over her hurt and starts to get it together she will resent what happened and it will be all your fault. If you want to help a friend then help her but don't "be her first customer" don't be her customer at all.

If I were going to do this, and I am going to say I would not tho I damned well know that if she was sexy enough I would, my play would to be the dumb and reluctant one. Just keep asking her if she is sure she wants to do this, and what exactly she wants to do. Definitely do not treat her like a provider and do not let on in any way that you know anything about the business. Because, while this can go one of three ways for her - she actually becomes a provider, she recoils from the whole experience and is filled with regret, or she finds she kinda likes the OP and his money and thinks about them being rebound lovers, or at least SD/SB - the most likely outcome for any lady is that she does not like it, feels bad about it, and if she knows you, and now knows you hobby, that could come out.

So I would just play it coy, let her lead, be a little reluctant. Odds are she does not want "to be paid for sex," but would be okay with a "little help with some bills." And the odds she ever wants to be a provider are virtually zero. So after you dally, the question will be whether you want and can afford this little sugar baby.

So, yeah, I would do it if I wanted her. But my reply to her would be to meet her at her place or yours, have a drink and discuss it. If she shows, she will be prepared to do something and you just need to follow her lead, understanding she is thinking you might be a helpful sugar daddy, so she is prepared to "rent" it to you more than once, but at a far higher price than you really want to pay. Of course, when that becomes clear, you can fall back on the old standard, "Honey, I wish I could help, but I really do not have that kind of extra money." Then you leave with a sweet memory and a clean slate because she has less on you than you have on her. If she ever mentions it to anyone, she will leave out the part about the $$$s.

zig

...a P4P arrangement will end badly, but a friends-with-benefits deal might at least let you sample the goods with a chance of it going well.

In no case should you let on that you know anything about the hobby.  If she mentions money again, have a great "newbie" line ready -- "Uh, OK.  Will you take a check?"

all the fillies eventually need to leave the stable..

In the end, its your choice.  

She open that door for you ( People don't play) specially when they say: I was just kidding."  It's up to you to stay where your at, or walk in and deal with the consequences..  If you go play/pay what ever---make sure you know it might mess up your friendship. Or it might be beneficial for both. Never know.

   
Here's a simple question you somewhat already mentioned... Ask yourself this again.  
Would You date you? Then there you go. You have your answer.  

Shes looking for $, bottom line. Go back and read what you typed.  
Like that other person mentioned... "Never believe what you hear!" Actions always speaks volumes of a person's character. Breast enhanced, those are not cheap.

..and really come after you. No is the way to go.

Dear Ms. Love:
What you said has a lot of gravity, and is very lugubrious subject given that the poster does have a platonic relationship with the woman who is contemplating this.  However Ms. Love, one should examine closely the reasons why the woman got breast implants. Although we all have insecurities, when one goes to those economic extremes to compensate for that the issues seem to be much deeper than the ethereal.
With respect to the nature of the relationship to the poster, he should revisit it when she is sober. If this is the case then he would be at a crossroads with respect to the nature and scope of the relationship and could be forfeiting a good friend for hedonistic reasons.  The underlying question is that every action has a consequence.  Is he really ready to accept the fallout that would come out of it if he goes that route?

Looks like that circle has become a pin drop...err, drip?

There is still a stigma to providers & those who love them.  You can not let on that you really P4P.  I agree with others to not bring this up again.  If she brings it up...  deny.  Say you'd both been drinking or otherwise didn't mean it, thought she was joking so you played along.  Appologise.  

If she pursues you, maybe you end up with a F*ckBuddy.  Make her pursue you.  

You don't want to become her hobby expert...  or her pimp...   If she goes pro, you can occasionaly offer tips to keep her safe...  say you read it online or it was in a movie (& you checked it out) or something else with a cover story.

eom

END OF MESSAGE

Conan asked me to pass this along:
lu·gu·bri·ous
ləˈɡ(y)o͞obrēəs/
adjective
looking or sounding sad and dismal.
synonyms: mournful, gloomy, sad, unhappy, doleful, glum, melancholy, woeful, miserable, woebegone, forlorn, somber, solemn, serious, sorrowful, morose, dour, cheerless, joyless, dismal; More
antonyms: cheerful
Origin

early 17th century: from Latin lugubris (from lugere ‘mourn’) + -ous.
Translate lugubrious to
Use over time for: lugubriou

She was drunk, not sober, so that should be the first (and loudest) bell going off.

Personally, I would not even bring it up that the conversation ever took place.

Now if ~she~ brings it up while sober, while I agree you should not be her first "paid" one, there is no harm in letting her know your open to her practicing on you, or better yet, let her know where to start in the biz.  

Honestly, if she does decide to go this route and you are a helpful friend to her rather than a client; I can say from experience, there are benefits to being friends with ladies in the biz where not paying for their friendship and they know your trying to be with them physically.  Even though there is no sex involved, it is nice to have someone to talk to that is not judgmental.

make assumptions so readily.  

If you want her, you are both single and willing, then go get her. Take her on a public date and test your assumption. Totally safe option and better odds of something that lasts, with no effect if she decides it must be a SD/SB or "pro" arrangement.

Under no circumstances should you assume she is or wants to be a provider... this assumption is fraught with peril! If she tells you straight out that this is what she wants, then YOU get to decide how (or whether) to proceed.  

Play your own game, not someone else's or the one you are given by default assumptions.

.. I like this advice best of all, simply stated: What do you want out of life?

Look at it this way, every person has his or her own hopes fears and wants to some degree that adds up to “what’s in it for me.”

With that said, ask yourself; if I was down and out or struggling, would she be there for me? Does she care about me as a friend?

However (from what you say), it sounds like this isn’t the angle you’re concerned with and you desire her sexually, as you mentioned that you might not get the opportunity again. To add fire to that desire, she hinted to renting her body to you, even when you said she was drunk—And, you know, getting that boob job had not so much to do with lack of money, it has everything to do with her being noticed and looking attractive. With you nonchalantly saying you’d be her first client—you’re feeding her ego or narcissism (Sorry to put it that way, but humans do like attention.)

So, without playing a guessing game (as nobody knows your situation better than you), why not write it down. Write the pros and everything you like about her, even offering to pay for her companionship in one column, and then all the cons to doing it that may harm the friendship in a second column. Or to simplify, Column A: everything you like about her (Her sexiness and friendship, for example); Column B: everything you don’t like about her. (Her smelling like cigarettes and what it is like to kiss a woman with cigarette breath, for example--but if you say that’ her only down side, then what about her character?)  

Also, write everything down no matter how trivial.  Just do it. It may help you put things in better perspective in how you decide to go about it.

As far as all the other advice from pursuing cautiously to being coy, it has to do with finesse, style and timing, if waiting for her to be sober may make a difference. In any event, however you decide to go about the pursuit (if that’s your decision), prepare yourself to own up to the success or consequence of your actions.  

Hey, you say she’s a MILF, so she’s a big girl and like you, she should take responsibly for her actions. Even if you feel you planted the thought in her head by teasing her about it, it’s still her decision if she chooses to be a provider one time with you, or many times over with others. When all is said and done, everyone makes their own choices. What do you and your friend want out of life

She has dropped enough hints.   She is newly divorced and wants sex and to feel sexy.   If you don't give it to her some other guy will be happy to and then you will feel bad that you didn't act when you had the chance.   If she really wants to be paid she will let you know.   Good luck.   Hope it works out.   Don't agonize over this, go for it !!

then again, this isn't exactly "good friend advice" either, lol - I just want you to do it in order to be entertained by your followup story.

But I wouldn't pay if I were you.  No way I could pay someone for P4P if I knew them as a civvie first.