I don't really think you are asking the board for "permission" on breaking your cherry with a hooker, or if it's the "right thing" to do, and for that I commend you, nothing is more pathetic than asking complete strangers on the internet to make a moral decision for you, kudos for not being "that guy"
It seems like you are more asking the how best to do this and not if you should do this in the first place.
If I am reading you correctly, let me offer you this advice. Younger providers are probably not the best choice to "deflower" you. You have said yourself that you would like a more experienced woman to guide you through your first time and I think that's probably the best thing for you. I don't know where you are located, but since you are going to have some issues with screening, which is why I asked you about "getting caught" doing this, I think a good approach would be to make this very same post on your regional board, make sure you get VIP so the ladies who think they might be a good fit can contact you privately and be prepared to provide some personal information about yourself so the provider you end up picking feels comfortable seeing you. I am sure that in every major market there will be at least a couple of mature providers willing to be your first.
I would have suggested joining P 411, but until and unless you decide this is something you want to continue doing, I don't think the investment into joining P 411 can be justified.
I will offer you one word of caution if you choose to embark on this as a "lifestyle" however. A lot of guys here have been burned with civvie relationships and now have sworn off regular dating in their 40's 50's or even 60's, but most of us/them have at least tried civvie dating before swearing it off. I think you would be doing yourself a great disservice if you went straight to fucking hookers for the rest of your life without at least trying conventional relationships, seeing no one but hookers can leave a person lonely, bitter and without the ability to interact with the opposite sex if you allow it to. I personally saw my first hooker at age 15, and I have been seeing hookers off and on, mainly "on" for my entire life, but I did take a few years off to get married, and I have had several LTR's in my life, i think you owe it to yourself to at least try both way before deciding one way or the other is the kind of sex life you are going to engage in for the rest of your life.