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Try telling him, you like it when he is assertive and takes control, or that you like it when he is aggressive. By telling him you like it when he takes control, you will be encouraging him to take it further and giving him confidence boosts. The fact the he is a little shy, might be because he has never gone that far with girls, or just not that much, and you can give him signs that you want him to take you, such as lying on the bed, waiting for him, or telling him you want him.
As far as experience, it can be learned with time, and the first few times might suck, but remember even the great guys in bed, had to learn somehow, and your new guy, won't be inexperienced for too long.
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