"and be able to look back and not feel some regret about having paid someone for sex?"
Do you mean if I met a man who actually disclosed he had feelings for me and it was reciprocated, and then I told him I went through a lengthy period of time in my life when I missed sex enough to pay for a professional to have sex with me on a purely transactional basis, and then that man decided I was not for him?
I think its fair enough, in the same way women might be turned off by the idea that men have had sex with prostitutes in their history.
But if I was a man, I would be equally turned off to find out that a woman has led men on in the past, used them for money,used them for "perks" (eg sugar daddies) and misled them as to where it might ultimately go. There are men who are genuinely cool with that, but there will also be men who are aggrieved in hind sight and I would think that was fair enough to feel that way.
I think I'd have a problem with a man who implied I had not "kept myself pure" because I paid for sex. Paying cash for sex is not ok but sleeping around with lots of different men (but it never going anywhere) is ok?
I actually think it comes down to the man more than the woman to be honest in this situation. There will be a fair number of men who will in retrospect get the ick from the idea that a woman is giving him cold hard cash for professional no strings sex. There might even be men who cannot actually perform on that basis. All of which is fair enough and unlike female prostitutes for that reason I would say its a far better position for men to do this than women. I cannot see a man saying "even tho I paid you I now want a relationship with you inspite of the terms at the start" - can you?
Some men are actually doing this on a serious level (instagram following, keep themselves in top condition etc) so I don't think I am the only woman who has asked herself this question, its just finding where these men are.