Welcome to Club Stogie, blacklagoon. I would like to echo the sentiment that you should post a introduction as well,
New Gorilla Forum
The question you ask is very similar to the following:
"I want to try wine for the first time, what do you recommend."
or
"I just got my drivers liciense what kinda of vehicle should I get."
Figure out what you might want to try. Do you want strong flavor or light? Do you something strong with nicotine strenght (ie. put you on the couch for an hour or two) or lighter? How long to want the cigar to last, as little 1 hour or up to 3?
The few people I know that just started or only smoke once or twice a year tend to go with light flavor and nicotine with about an hour or less for burn time. Macanuedo's seem to popular, though I don't care for them.
I would suggest one of two paths to start out with once you have an general area you want. Any good shop should be asking what you like before recommending anything.
1) Stop at a local store and see what they have. Buy one or two sticks.
2) Hit up some of the online sites like famous-smoke.com or cigarinternation.com for one of their samplers. I picked up the medium-Full from CI and like what I have tried from it. In the retail section of this forums there are some "codes" for cheap samplers from CI.