Contact e-mail should include a short description of yourself (6'4", 200, 40 yr. young, handsome), when you want to see her (Mon. afternoon at 5 pm), where (my hotel near the O'Hare airport), and how long (4 hr. dinner date).  You can call me at 317-222-4343 anytime since this is a private line or you can e-mail me back.  I'm a member of P411 under the name of John Doe.  Do not mention specific acts and/or money in any e-mail or phone call.

Don't just say "I'm a newbie and I want to fuck your brains out next week in Chicago.  Are you available?"

although you will need to mention that fact for any providers who want references.

Just be polite and somewhat business like.

Don't discuss activites or money.

Do suggest a specific date and time.

Also, make sure you have read that providers' sites thoroughly, and give any information that they request therein.  Providers respect that immensely.

Best of luck to you.

First, it seems you have done some good prepwork.  I trust you have read the newbie manual & this board until you can answer all the questions.  
Get a separate hobby e-mail not linked to your normal accounts.  Hobby phone.

Select a well reviewed provider. Read her web site.  I'd suggest a MILF with at least couple of years in the business.   Get VIP & read her reviews.

Know & expect the 2 call system...  where she gives to the approximate location (maybe a hotel name).  You call from outside, get lobby directions so you know where you are going.

I think the most important thing to convince her to see you, you need a date & approximate time frame.  
skb

don't ever forget this

I'm glad you're going ahead with this pleasure

I don't have anything to add to the other posts in terms of advice, except maybe if you decide to shave your balls I'd do it a couple days in advance in case you nick your sack, give it plenty of time to heal, she might freak out if she sees a "sore" down there

thanks for all the advice.  i have vip on here- that was part of my prep work.  all the info you gave me makes me feel safer and encouraged.  i'll also try to not nick my balls when shaving (that was hilarious by the way).  Hopefully I'll have reviews up soon.