There’s a woman who often comes into my workplace. She has let me know she’s very interested and I think she’s gorgeous. However, I know she’s hesitant to do anything with me because I’m married, and it wouldn’t be right for me just to “nail her” and leave her hanging because she really needs a man. She’s a single mom who just lost her job a few months ago, so she’s having some financial problems. So what if I approach her and offer her some compensation? I’d pay her just like any other escort (and I pay well); all she’d really have to do is spend 3 or 4 hours with me at dinner and her place and I know she already would like to do that. She’s definitely no prude; she always talks and jokes very candidly. So I don’t think she’ll be offended if I make the offer – but I’m not too sure. Is a good idea?
In a word: no. Most amateur women are so brainwashed into seeing sex work as “dirty” and “bad” that they will instantly and stupidly perceive the offer of money as an insult, even if they see the request that they give it up for free as a reasonable one. Take a look at some of the mental gymnastics halfway whores perform in order to avoid admitting the truth; Cirque du Soleil has nothing on these gals. Nor is it ever a good idea for a married man to become involved with an amateur, especially not one who’s attracted to him and “needs” a man, because those are exactly the characteristics that will drive her to cause trouble. I’m sure it’s a great boost to your ego for a hot chick to come on to you, but emotional involvement is inevitably a spanner in the spokes of extramarital activity unless you actually want a divorce. Women who only want small amounts of money in exchange for small amounts of sex are safe partners for a married man; those who want love, fun, companionship or a lifetime of support are disasters waiting to happen.
The only way this could possibly work is if she turns pro. You could try bringing up the subject half-jokingly, telling her that she really ought to consider escorting in order to make ends meet; if she seems offended just blow it off as an idle suggestion, ending with something like “I don’t see anything wrong with a woman using her natural abilities to prosper.” Then never bring it up again, and give up on the whole idea of boinking her. If, on the other hand, she seems intrigued, point her to this website; there are plenty of mentoring posts she can read to help her decide. You absolutely do not want her to think that you’re offering to be her pimp or anything like that, and if she gets that idea anyway and seems open to it, you need to insist that she do it on her own (see the last sentence of the preceding paragraph). If she takes up sex work on her own and then offers you a compensated date without any hinting on your part, it’s a horse of a different color from your offering her money outright; though you still need to be extremely careful since you know she’s attracted to you, the fact that she’s doing sex work will show you she at least has the ability to view the situation pragmatically, and the money will provide a buffer. Furthermore, if she’s hooking and you know it, you have a secret to counterbalance her knowledge of your infidelity. You may call that calculus cold-blooded if you like; I prefer the word “realistic”.