1, Good choice. MILF's can be much more accommodating for newbies.
2. Join a referral service like P411 or Date Check.
3. Read the Newbie Manual (top right near the red & white life preserver) and several pages here to get an idea of how this game is played.
4. Newbies should only see well-reviewed ladies meaning ladies with at least 5-6 reviews from well established reviewers with at least that many reviews over time
Not to make assumptions, but you did say that you are unemployed. You should plan to spend a few hundred dollars if you want a good experience. I agree with all of the advice above and I think a MILF is an excellent idea. P411 providers are best but will cost a little more. Be careful of BackPage ads, unless the provider has TER reviews.
Don't worry about the ladies working with someone your age. You're of legal age so to most it won't matter. If it does matter to any of them you simply move on to another provider.
As for their age and experience it depends on what you're looking for. Do you want someone who can extend this experience as long as possible and teach you a few tricks in the process, or are you just looking to get this milestone done and over with? Either way, my suggestion is that you spend a lot of time reading up on any info you can find here, get any questions you have answered, get VIP access here and read the reviews of various ladies, get verified, pick your ideal candidate, and (assuming you can pass her screening process) make sure she knows this is your first time with any woman, not just a provider.
Additional tips? It's hard to say because my first time was when I was considerably younger, but I would imagine that the typical "issues" would be valid for you at your age also. If so, expect it to be over before you want it to be, so you might want to make sure the lady allows multiple "pops." If she does, and you're up for it (pun intended) your second attempt will likely last longer and be more enjoyable than the first one.
Also, you said you're unemployed, and I don't know your financial situation, but I would suggest you don't get tempted to spend less by approaching high volume providers running BP specials. You could easily end up with a woman looking to get things done ASAP so she can move on to the next John (though that would be the least of your worries because you could also end dealing with LE or unsavory characters looking to part you from your money).
Lastly, you need to be thinking with the right head when you figure out how much risk you're willing to take (in terms of STIs). When you're horny and about to get it done (esp. for the first time) it's the worst possible time to decide if you're willing to take a certain risk or not. Of course this isn't entirely up to you because the lady you'll be with will have her dos and don'ts, but if she allows any part without cover you need to know beforehand if you're good with that, and you need to stick to it (remember, you'll be fighting your urges, not hers).
Hope this helps
