Hay 40, other than dental work is there any other area of your appearance that might need work? Are you happy with your hair? Do you have a respectable wardrobe? Do you wear Coke bottle or other style of birth control glasses?
The first thing I would do is do the best I could with what I have. Maybe think about joining a gym and getting yourself in shape. Not only will these things make you more attractive but they will give you confidence as well.
I know you hear over and over that these things aren't important but believe me, even if a woman believes this is the case, her subconcious will over rule her opinons every time.
One good first step though is to try to portray yourself in a more positive light and try to understand that what women respond to and what they tell you they like are far different. Advertising the fact that you have been waiting for true love will get you praise from women on this board, but it will also ensure that you remain a vergin.
Most guys I know who are successful with women have the basic philosophy that you should ask women what they like in a man and do the opposite. Look at that thread about "Women are a Conquest" or whatever it's called. Beautifull woman madly in love with major a-hole cheeting duche bag. Proof positive.
As for prostitues, I personally would rather earn it, but if you do decide to pay for services, do your research. I'd think Vegas girls are probably expensive. You might try Canada or save for a trip to Thailand and get 2 for $50. By the way, Thailand has excellent dentists for a fraction of what they cost in the US. You might be able to kill 2 birds with one bone.