I saw my first escort when I was under 30. I never hid or lied about my age. I never had an issue with agency providers or independents. As long as you treat the SP like you would any other woman in your bed, I don't see what the problem is. The only difference is that an SP is generally more open to your sexual advances and desire for experimentation. Some SP's post age preferences on their pages, and if I don't qualify I simply do not seek to spend time with them. Montreal has far too many options available to get hung up on not meeting a handful of SPs.
I never really asked any of them how they want to be pleased. I kept trying several things patiently, and I took their responses at face value. I am certain there is acting going on, but I don't really dwell on that. This is mainly because I don't like being asked about details about how I like being pleased. I am afraid that if I am too specific, I will miss out on a great talent the SP might possess. Ultimately I just stick with the one(s) I feel I enjoy a good time with and experiment with new ones from time to time.
With agencies this is a non-issue, since the SP does not know anything about the person she is going to see. If you are e-mailing an independent, just be respectful - she will use your writing to figure out what kind of person you are (this is an assumption on my part). Also be sure to tell her a bit about yourself.
I have been told by various people that young men should seek women in a more conventional manner. The fact is I do both, and I never see an SP while dating someone (I don't want to lie or keep secrets). SP's tend to be more open and talented sexually, and I don't want to wait until I am old man and wonder what something would have been like had I been younger and had more energy to do it.
Edit: Just wanted to add that from my experience, SPs are very open to suggestion, except for things they explicitly say they will not do (e.g. Greek or CIM). It may not be acceptable to treat her like a tramp, but it is acceptable to say it is your fantasy to completely debase a woman in bed, and then she can agree/disagree to play the role you want her to.