I loved Jeffery Gitomer's Little Red Book of Selling. I was still going through it the week before I closed my biggest sale so far against two competitors with lower prices. His follow-up, the Sales Answers book, also has a lot of useful tips. These books are good because as you're going through this with different customers, you can re-read short parts to identify solutions to the problems you're currently facing and then put them into practice.
I don't think it's that hard to start selling, everything gets easier as you go along. What people usually recommend is to start on an easier task so you can get yourself started, but you might not always have that option. I my case, I wrote to about 60-80 people who were interested in my kind of service before I started to get consistent results; even in the beginning someone has to bite so that's your chance to do everything you can to prove that people should buy from you.
There's no good substitute for failing a lot of times. You get used to it after a bit; if you don't make a strong impression and someone ignores you or turns you down, it's quickly forgotten on both sides when there's lots of other people to do business with. You should try an approach 15-20 times with only minor variations to get a feel for how well it works; if it doesn't work (or even if it does), change your approach.
An example of this is when I started off writing formal letters that were a bit long. After trying that for a bit I was only getting occasional results, but when I saw another example and started writing short, friendly letters that directly lay out why I'm qualified and ask a few questions about the buyer I got much better results.
At the start it certainly feels better to just fill in the blanks (I do most selling using email), whereas the Little Red Books are more about the general ideas, so it might help if you can find real examples of things you could write or say (just make sure you modify them so they not only fit the situation but show you took the time to understand the customer).
Gitomer's ideas are based on selling something of value and quality, which is one of the things I like about them. If you focus on benefitting the customer you'll feel good about it and find that it helps with selling. There's definitely some people who are born to make shady deals using pressure and manipulation, but in a good sales position you should focus on the customer at least as much as you focus on your company. You can even represent them within the company when they point out that something is wrong, and sell changes to the management to make the transaction better for everyone.
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