Ruff,
I found your post to be, at once, insightful, probably admirably honest, and somewhat disturbing. Your dilemmas are many for such a young man and I wish peace of mind for you, wherever you eventually find it.
I don’t know you except through your posts (many delightful and insightful posts by the way) and hesitate to put my two cents in, being that I’m a newbie to the site and to the mongering experience. But hey what the hell, I figure you wouldn’t have laid your soul out there, if you hadn’t wanted input from others.
I’m older (50ish), widowed after 30 years with one woman (and I mean “one woman†in every respect). I emphasize the fact that I stayed faithful to one woman for that length of time, not to pat myself on the back (my wife deserves all the credit), but to give response to your “fidelity†statements. Perhaps it’s a generational thing, but I’m aware of several men, in my small sphere of knowledge, that have stayed true (physically, if not mentally) to wives of 20, 30 or more years. It is difficult, but not impossible and, as I’ve said, probably is more due to the wife’s love, understanding and intellect, than the mans.
I’m going to have to side more with Prolijo on the two negatives don’t make a positive theory. IMHO, I believe, that while a solid relationship is certainly possible between a client and a provider, the ifs and what ifs to such a relationship are innumerably more complex than the more traditional one of the “untamed†male being smitten to such an extent that he is willing to “harness†his inner beast. When you have two “untamed†libidos (sexual or monetary) to contend with, who is going to do the taming? The love, understanding and forgiveness required would need to be of godlike proportions. Again, not impossible, but improbable.
For myself, I figure that the best part of my life is gone. I’ve had the best woman and relationship a man could have hoped for, unparalleled love, devotion, beauty and intellect rolled into one package. Yes, I’m bragging.
After not wanting to bother with women on any level for a couple of years, I’ve gotten to a point where I want some company. I’ve dated a few women, being totally honest up front, that I only wanted activity partners, but I found that after a couple of dates, they want to get serious. I’m not looking to replace my wife, as if that were possible, so I’m checking out the CR “scene†for temporary, no-strings company.
I have tremendous respect for the girls that offer themselves. More respect perhaps than I should, but perhaps being raised in the south and being of my generation accounts for this. Maybe respect isn’t the right word. Admiration perhaps is the better choice. Admiration for their guts, their acting ability and grace in the presence of some of the a**holes they certainly come in contact with and for providing a service that offers lost gringos, like myself, an ear, those eyes (O lord don’t let me drown in those eyes) and a few moments of intimacy without the prospect of them trying to sink a ring in your nose. I’ll take their lies over most others, because I know they’re lies and because the lies are so sweet. Unlike you though, I wish they weren’t so damned young. Makes an old fart like me feel guilty.
Your self-questioning has the ring that you have either found a provider that you consider mate material or you feel that you have ruined a chance at real love with your wife or someone else and are taking the total blame on yourself and your lifestyle. Let me offer this. It is surely a cliche, but in personal and intimate relationships honesty is the “only†plausible policy. It’s not easy to be honest, but it is respectful to be honest. I’ve found that it’s usually not the truth that ends up destroying relationships, but the lack of respect of another’s intellect you show to someone by lying to them. It’s the deceit and the perceived arrogance of the liar that he, or she, is smarter that the deceived party that is the relationship killer. Be honest with yourself (you seem to be off to a good start) and with your mate, potential or otherwise, provider or otherwise, and you will avoid 95% of the shit most couples get themselves into. You present yourself as an intellectual and deeply thoughtful sort of guy so I’m sure I’m preaching to the choir here. If I were your age and found someone that I couldn't live without, provider or not, I'd tell her everything about everything and if she is still sitting there, I'd tell the rest of the world to go ph*ck itself and hang on to her for dear life.
In any case, I enjoy your postings and trust you will continue to share your thoughts.
P.S. I’ve read in here that “the business†is sometimes a family affair and that the girls begin to have hijos at young ages. That would mean that there are possibly some fine forty something provider’s mothers out there somewhere who might still be in the business. Maybe I’ll stumble across one once in a while.

Feel free to steer them my way if they are over your age limit.