My meditating has evolved slowly.
I started of with Wayne Dyers 'Meditations for Manifestation' and then got into a couple of Deepak Chopra cd's. I also like Bodhipaksa, a Scottish Buddhist living here in the US. Lovely gentle Scottish lilt to his voice that certainly trances me out
However, the one I love most is one I only got into recently and it's called 'Seven Masters One Path' by John Selby. I downloaded it from Audible.com and I think it was about 6 bucks as a member. Very clear explanations of not only what to do but why it works etc. It's about 65 minutes long but there is a condensed version of about 7 minutes at the end and each section is about 7 or 8 minutes long and can be used as a standalone.
Here's a couple of blogs that give you my take fwiw:
A Life Coach’s View Of Meditation Choose Wisely Grasshopper